View source for Cyproterone acetate

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{{Short description|Chemical compound}}{{Use vanc name-list-style|date=December 2023}}{{cs1 config|name-list-style=vanc}}
{{Use dmy dates|date=December 2023}}
{{Drugbox
| verifiedrevid = 460111438
| IUPAC_name = (2a''R'',3a''S'',3b''S'',3c''S'',5a''S'',6''R'',8a''S'',8b''R'')-6-acetyl-10-chloro-3b,5a-dimethyl-2-oxo-2,2a,3,3a,3b,3c,4,5,5a,6,7,8,8a,8b-tetradecahydrocyclopenta[''a'']cyclopropa[''g'']phenanthren-6-yl acetat
| image = Cyproterone acetate.svg
| width = 230px
| image2 = Cyproterone-acetate-from-xtal-view-1-Mercury-3D-balls-thin.png
| width2 = 235px

<!--Clinical data-->
| tradename = Androcur, Androcur Depot, Cyprostat, Siterone, others
| Drugs.com = {{drugs.com|CONS|cyproterone}}
| pregnancy_category = X
| legal_status = Rx-only
| routes_of_administration = [[Oral administration|By mouth]], [[intramuscular injection]]
| class = [[Steroidal antiandrogen]]; [[Progestogen (medication)|Progestogen]]; [[Progestin]]; [[Progestogen ester]]; [[Antigonadotropin]]

<!--Pharmacokinetic data-->
| bioavailability = Oral: 68–100%<ref name="pmid16112947" /><ref name="pmid2977383">{{cite journal | vauthors = Huber J, Zeillinger R, Schmidt J, Täuber U, Kuhnz W, Spona J | title = Pharmacokinetics of cyproterone acetate and its main metabolite 15 beta-hydroxy-cyproterone acetate in young healthy women | journal = Int J Clin Pharmacol Ther Toxicol | volume = 26 | issue = 11 | pages = 555–61 | date = November 1988 | pmid = 2977383 }}</ref>
| protein_bound = [[Human serum albumin|Albumin]]: 93%<br />Free: 7%<ref name="pmid26327902">{{cite journal | vauthors = Bińkowska M, Woroń J | title = Progestogens in menopausal hormone therapy | journal = Przegla̜d Menopauzalny = Menopause Review | volume = 14 | issue = 2 | pages = 134–43 | date = June 2015 | pmid = 26327902 | doi = 10.5114/pm.2015.52154 | pmc=4498031}}</ref><ref name="pmid14670641">{{cite journal | vauthors = Schindler AE, Campagnoli C, Druckmann R, Huber J, Pasqualini JR, Schweppe KW, Thijssen JH | title = Classification and pharmacology of progestins | journal = Maturitas | volume = 46 | issue = Suppl 1 | pages = S7–S16 | date = December 2003 | pmid = 14670641 | doi = 10.1016/j.maturitas.2003.09.014 | quote = Since there is no binding of CPA to SHBG and CBG in the serum, 93% of the compound is bound to serum albumin. }}</ref><ref name="Wakelin-2002-quote-1">{{cite book|vauthors=Wakelin SH, Maibach HI, Archer CB|title=Systemic Drug Treatment in Dermatology: A Handbook|url=https://books.google.com/books?id=F1ZiAgAAQBAJ&pg=PA32|date=1 June 2002|publisher=CRC Press|isbn=978-1-84076-013-2|pages=32–|quote=It is almost exclusively bound to plasma albumin.|access-date=27 September 2016|archive-date=14 January 2023|archive-url=https://web.archive.org/web/20230114143141/https://books.google.com/books?id=F1ZiAgAAQBAJ&pg=PA32|url-status=live}}</ref><ref name="pmid6215538">{{cite journal | vauthors = Hammond GL, Lähteenmäki PL, Lähteenmäki P, Luukkainen T | title = Distribution and percentages of non-protein bound contraceptive steroids in human serum | journal = Journal of Steroid Biochemistry | volume = 17 | issue = 4 | pages = 375–80 | date = October 1982 | pmid = 6215538 | doi = 10.1016/0022-4731(82)90629-X }}</ref>
| metabolism = [[Liver|Hepatic]] ([[CYP3A4]])<ref name="Dickman-2012">{{cite book| vauthors = Dickman A | title = Drugs in Palliative Care|url=https://books.google.com/books?id=LKrZINavapAC&pg=PA138|date=27 September 2012|publisher=OUP Oxford|isbn=978-0-19-966039-1|pages=137–138}}</ref><ref name="Boarder-2010">{{cite book|vauthors=Boarder M, Newby D, Navti P|title=Pharmacology for Pharmacy and the Health Sciences: A Patient-centred Approach|url=https://books.google.com/books?id=KVicAQAAQBAJ&pg=PA632|date=25 March 2010|publisher=OUP Oxford|isbn=978-0-19-955982-4|pages=632–|access-date=27 September 2016|archive-date=6 July 2024|archive-url=https://web.archive.org/web/20240706162108/https://books.google.com/books?id=KVicAQAAQBAJ&pg=PA632#v=onepage&q&f=false|url-status=live}}</ref>
| metabolites = • {{abbrlink|15β-OH-CPA|15β-Hydroxycyproterone acetate}} (major)<ref name="pmid16112947" /><ref name="pmid3160716">{{cite journal | vauthors = Frith RG, Phillipou G | title = 15-Hydroxycyproterone acetate and cyproterone acetate levels in plasma and urine | journal = J. Chromatogr. | volume = 338 | issue = 1 | pages = 179–86 | year = 1985 | pmid = 3160716 | doi = 10.1016/0378-4347(85)80082-7}}</ref><br /> • [[Cyproterone]] (minor)<ref name="Weber-2015">{{cite book| vauthors = Weber GF |title=Molecular Therapies of Cancer|url=https://books.google.com/books?id=dhs_CgAAQBAJ&pg=PA316|date=22 July 2015|publisher=Springer|isbn=978-3-319-13278-5|pages=316–|quote=The terminal half-life is about 38 h. A portion of the drug is metabolized by hydrolysis to cyproterone and acetic acid. However, in contrast to many other steroid esters hydrolysis is not extensive, and much of the pharmacological activity is exerted by the acetate form. Excretion is about 70% in the feces, mainly in the form of glucuronidated metabolites, and about 30% in the urine, predominantly as non-conjugated metabolites.}}</ref><br />• [[Acetic acid]] (minor)<ref name="Weber-2015" />
| elimination_half-life = Oral: 1.6–4.3 days<ref name="Weber-2015" /><ref name="pmid7919640" /><ref name="BradfordKaye1998">{{cite book|title=AAPL Newsletter|year=1998|publisher=The Academy|url=http://courtpsychiatrist.com/pdf/pharmacological%20treatment%20sex%20offenders.pdf|quote=CPA is 100% bioavailable when taken orally with a half life of 38 hours. The injectable form reaches maximum plasma levels in 82 hours and has a half life of about 72 hours.|access-date=16 August 2016|archive-date=30 August 2017|archive-url=https://web.archive.org/web/20170830021818/http://courtpsychiatrist.com/pdf/pharmacological%20treatment%20sex%20offenders.pdf|url-status=live}}</ref><br />{{abbr|IM|Intramuscular injection}}: 3–4.3 days<ref name="pmid2977383" /><ref name="Weber-2015" /><ref name="BradfordKaye1998" />
| excretion = [[Feces]]: 70%<ref name="Weber-2015" /><br />[[Urine]]: 30%<ref name="Weber-2015" />

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 427-51-0
| CAS_supplemental = <br />2098-66-0 ([[Cyproterone|free alcohol]])
| ATC_prefix = G03
| ATC_suffix = HA01
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 139835
| PubChem = 9880
| IUPHAR_ligand = 2865
| DrugBank_Ref =
| DrugBank = DB04839
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 9496
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4KM2BN5JHF
| KEGG_Ref =
| KEGG = D01368
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 50743
| synonyms = SH-80714; SH-714; NSC-81430; 1α,2α-Methylene-6-chloro-17α-hydroxy-δ<sup>6</sup>-progesterone acetate; 1α,2α-Methylene-6-chloro-17α-hydroxypregna-4,6-diene-3,20-dione acetate

<!--Chemical data-->
| C=24 | H=29 | Cl=1 | O=4
| SMILES = CC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C=C(C4=CC(=O)[C@@H]5C[C@@H]5[C@]34C)Cl)C)OC(=O)C
| StdInChI = 1S/C24H29ClO4/c1-12(26)24(29-13(2)27)8-6-16-14-10-20(25)19-11-21(28)18(15)23(19,4)17(14)5-7-22(16,24)3/h10-11,14-18H,5-9H2,1-4H3/t14-,15+,16-,17-,18-,22-,23-,24-/m0/s1
| StdInChIKey = UWFYSQMTEOIJJG-FDTZYFLXSA-N

<!--Physical data-->
| melting_point = 200
| melting_high = 201
}}
<!-- Definition and medical uses -->
'''Cyproterone acetate''' ('''CPA'''), sold alone under the brand name '''Androcur''' or [[Ethinylestradiol/cyproterone acetate|with ethinylestradiol]] under the brand names '''Diane''' or '''Diane-35''' among others, is an [[antiandrogen]] and [[progestin]] medication used in the treatment of [[androgen-dependent condition]]s such as [[acne]], [[hirsutism|excessive body hair growth]], [[precocious puberty|early puberty]], and [[prostate cancer]], as a component of [[feminizing hormone therapy]] for [[Transgender|transgender individuals]], and in [[oral contraceptive|birth control pill]]s.<ref name="pmid16112947">{{cite journal | vauthors = Kuhl H | title = Pharmacology of estrogens and progestogens: influence of different routes of administration | journal = Climacteric | volume = 8 | issue = Suppl 1 | pages = 3–63 | year = 2005 | pmid = 16112947 | doi = 10.1080/13697130500148875| s2cid = 24616324 }}</ref><ref name="pmid7919640">{{cite journal | vauthors = Barradell LB, Faulds D | title = Cyproterone. A review of its pharmacology and therapeutic efficacy in prostate cancer | journal = Drugs Aging | volume = 5 | issue = 1 | pages = 59–80 | date = July 1994 | pmid = 7919640 | doi = 10.2165/00002512-199405010-00006 | s2cid = 260845477 }}</ref><ref name="pmid8005205">{{cite journal | vauthors = Neumann F | title = The antiandrogen cyproterone acetate: discovery, chemistry, basic pharmacology, clinical use and tool in basic research | journal = Exp. Clin. Endocrinol. | volume = 102 | issue = 1 | pages = 1–32 | year = 1994 | pmid = 8005205 | doi = 10.1055/s-0029-1211261 | doi-access = free }}</ref><ref name="pmid66176">{{cite journal | vauthors = Neumann F | title = Pharmacology and potential use of cyproterone acetate | journal = Horm. Metab. Res. | volume = 9 | issue = 1 | pages = 1–13 | date = January 1977 | pmid = 66176 | doi = 10.1055/s-0028-1093574 | s2cid = 7224893 }}</ref><ref name="pmid2949114">{{cite journal | vauthors = Neumann F, Töpert M | title = Pharmacology of antiandrogens | journal = Journal of Steroid Biochemistry | volume = 25 | issue = 5B | pages = 885–95 | date = November 1986 | pmid = 2949114 | doi = 10.1016/0022-4731(86)90320-1}}</ref> It is formulated and used both alone and in combination with an [[estrogen (medication)|estrogen]]. CPA is taken [[Oral administration|by mouth]] one to three times per day.

<!-- Side effects and mechanism -->
Common [[side effect]]s of high-dose CPA in men include [[gynecomastia]] (breast development) and [[feminization (biology)|feminization]]. In both men and women, possible side effects of CPA include [[hypogonadism|low sex hormone levels]], reversible [[infertility]], [[sexual dysfunction]], [[fatigue (medical)|fatigue]], [[depression (mood)|depression]], [[weight gain]], and [[elevated transaminases|elevated liver enzymes]]. At very high doses in older individuals, significant [[cardiovascular]] complications can occur. Rare but serious adverse reactions of CPA include [[blood clot]]s, [[hepatotoxicity|liver damage]] and [[brain tumor]]s. CPA can also cause [[adrenal insufficiency]] as a [[drug withdrawal|withdrawal]] effect if it is discontinued abruptly from a high dosage. CPA blocks the effects of [[androgen]]s such as [[testosterone]] in the body, which it does by preventing them from interacting with their [[biological target]], the [[androgen receptor]] (AR), and by reducing their [[biosynthesis|production]] by the [[gonad]]s, hence their concentrations in the body.<ref name="pmid16112947" /><ref name="pmid8005205" /><ref name="Berek-2007">{{cite book | vauthors = Berek JS |title=Berek & Novak's Gynecology |url=https://books.google.com/books?id=P3erI0J8tEQC&pg=PA1085 |year=2007 |publisher=Lippincott Williams & Wilkins |isbn=978-0-7817-6805-4 |page=1085}}</ref> In addition, it has [[progesterone]]-like effects by activating the [[progesterone receptor]] (PR).<ref name="pmid16112947" /><ref name="pmid8005205" /> It can also produce weak [[cortisol]]-like effects at very high doses.<ref name="pmid16112947" />

<!-- History, society and culture -->
CPA was discovered in 1961.<ref name="pmid9476091">{{cite journal | vauthors = Pucci E, Petraglia F | title = Treatment of androgen excess in females: yesterday, today and tomorrow | journal = Gynecol. Endocrinol. | volume = 11 | issue = 6 | pages = 411–33 | date = December 1997 | pmid = 9476091 | doi = 10.3109/09513599709152569 }}</ref> It was originally developed as a progestin.<ref name="pmid9476091" /> In 1965, the antiandrogenic effects of CPA were discovered.<ref name="pmid5989926" /> CPA was first marketed, as an antiandrogen, in 1973, and was the first antiandrogen to be introduced for medical use.<ref name="Wakelin-2002-Systemic Drug Treatment">{{cite book |vauthors=Wakelin SH |title=Systemic Drug Treatment in Dermatology: A Handbook |url=https://books.google.com/books?id=F1ZiAgAAQBAJ&pg=PA32 |date=1 June 2002 |publisher=CRC Press |isbn=978-1-84076-013-2 |page=32 |access-date=27 September 2016 |archive-date=14 January 2023 |archive-url=https://web.archive.org/web/20230114143141/https://books.google.com/books?id=F1ZiAgAAQBAJ&pg=PA32 |url-status=live }}</ref> A few years later, in 1978, CPA was introduced as a progestin in a birth control pill.<ref name="Plewig-2012" /> It has been described as a "first-generation" progestin<ref name="pmid27616670" /> and as the prototypical antiandrogen.<ref name="Jameson-2015">{{cite book|vauthors=Jameson JL, De Groot LJ|url=https://books.google.com/books?id=xmLeBgAAQBAJ&pg=PA2293|title=Endocrinology: Adult and Pediatric E-Book|date=25 February 2015|publisher=Elsevier Health Sciences|isbn=978-0-323-32195-2|pages=2293, 2464, 2479, 6225|access-date=2 August 2018|archive-date=6 July 2024|archive-url=https://web.archive.org/web/20240706162108/https://books.google.com/books?id=xmLeBgAAQBAJ&pg=PA2293#v=onepage&q&f=false|url-status=live}}</ref> CPA is available widely throughout the world.<ref name="Drugs.com-Cyproterone" /><ref name="IndexNominum2000" /> An exception is the [[United States]], where it is not approved for use.<ref name="Schechter-2016" /><ref name="y1">{{cite book |doi=10.1016/B978-0-12-387817-5.00030-3 |chapter=Cancer Chemotherapy |title=Drug-Induced Liver Disease |year=2013 | vauthors = Deleve LD |pages=541–567 |publisher=Academic Press |isbn=9780123878175 }}</ref> 

{{TOC limit|3}}

==Medical uses==
CPA is used as a [[progestin]] and [[antiandrogen]] in [[hormonal birth control]] and in the treatment of [[androgen-dependent condition]]s.<ref name="pmid8005205" /> Specifically, CPA is used in [[combined birth control pill]]s, in the treatment of androgen-dependent [[dermatological condition|skin and hair condition]]s such as [[acne]], [[seborrhea]], [[hirsutism|excessive hair growth]], and [[scalp hair loss]], [[hyperandrogenism|high androgen levels]], in [[transgender hormone therapy]], to treat [[prostate cancer]], to reduce [[sex drive]] in [[sex offender]]s or men with [[paraphilia]]s or [[hypersexuality]], to treat [[precocious puberty|early puberty]], and for other uses.<ref name="Maggi-2011">{{cite book | vauthors = Maggi M |title=Hormonal Therapy for Male Sexual Dysfunction |url=https://books.google.com/books?id=in_DuQFgcJMC&pg=PA104 |date=17 November 2011 |publisher=John Wiley & Sons |isbn=978-1-119-96380-6 |page=104}}</ref> Treatment dosages range from 2mg or less, to 100mg or more daily.<ref name=":0">EMA. European Medicines Agency. Assessment report cyproterone. 13 February 2020. https://www.ema.europa.eu/en/documents/referral/cyproterone-article-31-referral-prac-assessment-report_en.pdf. Accessed 9 Apr 2020.</ref>

In the United States, where CPA is not available, other medications with antiandrogenic effects are used to treat androgen-dependent conditions instead.<ref name="Duker-2013">{{cite book | vauthors = Duker M, Malsch M | title = Incapacitation: Trends and New Perspectives |url=https://books.google.com/books?id=OfGlANwlHAEC&pg=PT77 |date=28 January 2013 |publisher=Ashgate Publishing, Ltd. |isbn=978-1-4094-7151-6 |page=77}}</ref> Examples of such medications include [[gonadotropin-releasing hormone modulator]]s (GnRH modulators) like [[leuprorelin]] and [[degarelix]], [[nonsteroidal antiandrogen]]s like [[flutamide]] and [[bicalutamide]], the [[diuretic]] and [[steroidal antiandrogen]] [[spironolactone]], the [[progestin]] [[medroxyprogesterone acetate]], and the [[5α-reductase inhibitor]]s [[finasteride]] and [[dutasteride]].<ref name="Duker-2013" /> The steroidal antiandrogen and progestin [[chlormadinone acetate]] is used as an alternative to CPA in [[Japan]], [[South Korea]], and a few other countries.{{citation needed|date=May 2021}}

In 2020, the [[European Medicines Agency|European Medicine Agency]] issued a warning that high doses of cyproterone acetate may contribute to risk of meningioma, and recommended physicians use alternative treatment for most indications (or the minimum effective dose where no alternatives were available) with the exception of [[Prostate cancer|prostate carcinoma]].<ref name=":0" />

===Birth control===
CPA is used with [[ethinylestradiol]] as a [[combined birth control pill]] to prevent [[pregnancy]]. This birth control combination has been available since 1978.<ref name="Plewig-2012">{{cite book| vauthors = Plewig G, Kligman AM |title=ACNE and ROSACEA|url=https://books.google.com/books?id=0cD-CAAAQBAJ&pg=PA685|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-59715-2|pages=662, 685}}</ref> The formulation is taken once daily for 21&nbsp;days, followed by a 7-day free interval.<ref name="Diane-35-Label">{{cite web |title=PrDIANE® -35 |url=https://omr.bayer.ca/omr/online/diane-35-pm-en.pdf |archive-url=https://web.archive.org/web/20160508183945/https://omr.bayer.ca/omr/online/diane-35-pm-en.pdf |archive-date=May 8, 2016 |date=September 2, 2015 |url-status=dead}}</ref> CPA has also been available in combination with [[estradiol valerate]] (brand name Femilar) as a combined birth control pill in [[Finland]] since 1993.<ref name="pmid22468839">{{cite journal | vauthors = Fruzzetti F, Trémollieres F, Bitzer J | title = An overview of the development of combined oral contraceptives containing estradiol: focus on estradiol valerate/dienogest | journal = Gynecol. Endocrinol. | volume = 28 | issue = 5 | pages = 400–8 | date = May 2012 | pmid = 22468839 | pmc = 3399636 | doi = 10.3109/09513590.2012.662547 }}</ref><ref name="pmid20004267">{{cite journal | vauthors = Fruzzetti F, Bitzer J | title = Review of clinical experience with estradiol in combined oral contraceptives | journal = Contraception | volume = 81 | issue = 1 | pages = 8–15 | year = 2010 | pmid = 20004267 | doi = 10.1016/j.contraception.2009.08.010 }}</ref> High-dose CPA tablets have a contraceptive effect and can be used as a form of birth control, although they are not specifically licensed as such.<ref name="pmid23078975">{{cite journal | vauthors = Gourdy P, Bachelot A, Catteau-Jonard S, Chabbert-Buffet N, Christin-Maître S, Conard J, Fredenrich A, Gompel A, Lamiche-Lorenzini F, Moreau C, Plu-Bureau G, Vambergue A, Vergès B, Kerlan V | title = Hormonal contraception in women at risk of vascular and metabolic disorders: guidelines of the French Society of Endocrinology | journal = Ann. Endocrinol. (Paris) | volume = 73 | issue = 5 | pages = 469–87 | date = November 2012 | pmid = 23078975 | doi = 10.1016/j.ando.2012.09.001 }}</ref>

===Skin and hair conditions===

====Females====
CPA is used as an antiandrogen to treat [[androgen-dependent condition|androgen-dependent]] [[cutaneous condition|skin and hair condition]]s such as [[acne]], [[seborrhea]], [[hirsutism]] (excessive hair growth), [[scalp hair loss]], and [[hidradenitis suppurativa]] in women.<ref name="pmid14583927">{{cite journal | vauthors = Van der Spuy ZM, le Roux PA | title = Cyproterone acetate for hirsutism | journal = Cochrane Database Syst Rev | issue = 4 | pages = CD001125 | date = 2003 | volume = 2010 | pmid = 14583927 | doi = 10.1002/14651858.CD001125 | pmc = 8955083 }}</ref><ref name="pmid28447864">{{cite journal | vauthors = Bitzer J, Römer T, Lopes da Silva Filho A | title = The use of cyproterone acetate/ethinyl estradiol in hyperandrogenic skin symptoms - a review | journal = Eur J Contracept Reprod Health Care | volume = 22 | issue = 3 | pages = 172–182 | date = June 2017 | pmid = 28447864 | doi = 10.1080/13625187.2017.1317339 | doi-access = free }}</ref><ref name="pmid9557250">{{cite journal | vauthors = Beylot C, Doutre MS, Beylot-Barry M | title = Oral contraceptives and cyproterone acetate in female acne treatment | journal = Dermatology (Basel) | volume = 196 | issue = 1 | pages = 148–52 | date = 1998 | pmid = 9557250 | doi = 10.1159/000017849 | s2cid = 46763689 }}</ref><ref name="pmid2941191">{{cite journal | vauthors = Miller JA, Jacobs HS | title = Treatment of hirsutism and acne with cyproterone acetate | journal = Clin Endocrinol Metab | volume = 15 | issue = 2 | pages = 373–89 | date = May 1986 | pmid = 2941191 | doi = 10.1016/S0300-595X(86)80031-7
 }}</ref><ref name="pmid26443004">{{cite journal | vauthors = Ingram JR, Woo PN, Chua SL, Ormerod AD, Desai N, Kai AC, Hood K, Burton T, Kerdel F, Garner SE, Piguet V | title = Interventions for hidradenitis suppurativa | journal = Cochrane Database Syst Rev | issue = 10 | pages = CD010081 | date = October 2015 | volume = 2017 | pmid = 26443004 | doi = 10.1002/14651858.CD010081.pub2 | pmc = 6464653 }}</ref><ref name="pmid26370643">{{cite book | vauthors = Ioannides D, Lazaridou E | title = Alopecias - Practical Evaluation and Management | chapter = Female pattern hair loss | journal = Curr. Probl. Dermatol. | volume = 47 | pages = 45–54 | date = 2015 | pmid = 26370643 | doi = 10.1159/000369404 | series = Current Problems in Dermatology | isbn = 978-3-318-02774-7 }}</ref><ref name="pmid15832490" /> These conditions are worsened by the presence of androgens, and by suppressing androgen levels and blocking their actions, CPA improves the symptoms of these conditions. CPA is used to treat such conditions both at low doses as a birth control pill and on its own at higher doses.<ref name="pmid14583927" /><ref name="pmid28447864" /><ref name="pmid9557250" /><ref name="pmid2941191" /><ref name="pmid22786490">{{cite journal | vauthors = Arowojolu AO, Gallo MF, Lopez LM, Grimes DA | veditors = Arowojolu AO | title = Combined oral contraceptive pills for treatment of acne | journal = Cochrane Database Syst Rev | issue = 7 | pages = CD004425 | date = July 2012 | pmid = 22786490 | doi = 10.1002/14651858.CD004425.pub6 | pmc = 11437354 }}</ref> A birth control pill containing low-dose CPA in combination with [[ethinylestradiol]] to treat acne has been found to result in overall improvement in 75 to 90% of women, with responses approaching 100% improvement.<ref name="pmid10495361">{{cite journal | vauthors = Diamanti-Kandarakis E | title = Current aspects of antiandrogen therapy in women | journal = Curr. Pharm. Des. | volume = 5 | issue = 9 | pages = 707–23 | date = September 1999 | doi = 10.2174/1381612805666230111201150 | pmid = 10495361 | url = https://books.google.com/books?id=9rfNZL6oEO0C&pg=PA707 | access-date = 18 December 2018 | archive-date = 11 January 2023 | archive-url = https://web.archive.org/web/20230111121904/https://books.google.com/books?id=9rfNZL6oEO0C&pg=PA707 | url-status = live }}</ref> High-dose CPA alone likewise has been found to improve symptoms of acne by 75 to 90% in women.<ref name="pmid25627824">{{cite journal | vauthors = Bettoli V, Zauli S, Virgili A | title = Is hormonal treatment still an option in acne today? | journal = Br. J. Dermatol. | volume = 172 | issue = Suppl 1 | pages = 37–46 | year = 2015 | pmid = 25627824 | doi = 10.1111/bjd.13681 | s2cid = 35615492 | doi-access =  }}</ref> Discontinuation of CPA has been found to result in marked recurrence of symptoms in up to 70% of women.<ref name="pmid2976627">{{cite journal | vauthors = Reed MJ, Franks S | title = Anti-androgens in gynaecological practice | journal = Baillière's Clin Obstet Gynaecol | volume = 2 | issue = 3 | pages = 581–95 | date = September 1988 | pmid = 2976627 | doi = 10.1016/S0950-3552(88)80045-2 }}</ref> CPA is one of the most commonly used medications in the treatment of hirsutism, hyperandrogenism, and polycystic ovary syndrome in women throughout the world.<ref name="pmid15151716" /><ref name="Nikolaou-2005" />

Higher dosages of CPA are used in combination with an estrogen specifically at doses of 25 to 100&nbsp;mg/day cyclically in the treatment of hirsutism in women.<ref name="Nikolaou-2005" /><ref name="pmid9111556">{{cite journal | vauthors = Rittmaster RS | title = Hirsutism | journal = Lancet | volume = 349 | issue = 9046 | pages = 191–5 | date = January 1997 | pmid = 9111556 | doi = 10.1016/S0140-6736(96)07252-2 | s2cid = 208789457 }}</ref><ref name="pmid10950156">{{cite journal | vauthors = Azziz R, Carmina E, Sawaya ME | title = Idiopathic hirsutism | journal = Endocrine Reviews | volume = 21 | issue = 4 | pages = 347–62 | date = August 2000 | pmid = 10950156 | doi = 10.1210/edrv.21.4.0401 | doi-access = free }}</ref> The efficacy of such dosages of CPA in the treatment of hirsutism in women appear to be similar to that of [[spironolactone]], [[flutamide]], and [[finasteride]].<ref name="pmid9111556" /><ref name="pmid10950156" /><ref name="pmid15151716" /><ref name="Nikolaou-2005" /> [[Randomized controlled trial]]s have found that higher dosages of CPA (e.g., 20&nbsp;mg/day or 100&nbsp;mg/day) added cyclically to a [[birth control pill]] containing [[ethinylestradiol]] and 2&nbsp;mg/day CPA were no more effective or only marginally more effective in the treatment of severe hirsutism in women than the birth control pill alone.<ref name="Nikolaou-2005" /><ref name="pmid10950156"/><ref name="pmid15151716">{{cite journal | vauthors = Sahin Y, Kelestimur F | title = Medical treatment regimens of hirsutism | journal = Reproductive Biomedicine Online | volume = 8 | issue = 5 | pages = 538–46 | date = May 2004 | pmid = 15151716 | doi = 10.1016/S1472-6483(10)61100-5 | doi-access = free }}</ref><ref name="pmid10469088">{{cite journal | vauthors = Liew SH | title = Unwanted body hair and its removal: a review | journal = Dermatologic Surgery | volume = 25 | issue = 6 | pages = 431–9 | date = June 1999 | pmid = 10469088 | doi = 10.1046/j.1524-4725.1999.08130.x }}</ref><ref name="pmid2946604">{{cite journal | vauthors = Belisle S, Love EJ | title = Clinical efficacy and safety of cyproterone acetate in severe hirsutism: results of a multicentered Canadian study | journal = Fertility and Sterility | volume = 46 | issue = 6 | pages = 1015–20 | date = December 1986 | pmid = 2946604 | doi = 10.1016/S0015-0282(16)49873-0 | doi-access = free }}</ref><ref name="pmid1832346">{{cite journal | vauthors = Barth JH, Cherry CA, Wojnarowska F, Dawber RP | title = Cyproterone acetate for severe hirsutism: results of a double-blind dose-ranging study | journal = Clinical Endocrinology | volume = 35 | issue = 1 | pages = 5–10 | date = July 1991 | pmid = 1832346 | doi = 10.1111/j.1365-2265.1991.tb03489.x | s2cid = 27293697 }}</ref> Maintenance therapy with lower doses of CPA, such as 25&nbsp;mg/day, has been found to be effective in preventing relapse of symptoms of hirsutism.<ref name="pmid2976627" /> CPA has typically been combined with ethinylestradiol, but it can alternatively be used in combination with [[hormone replacement therapy]] dosages of [[estradiol (medication)|estradiol]] instead.<ref name="Nikolaou-2005">{{cite journal| vauthors = Nikolaou D, Gilling-Smith C |title=Hirsutism|journal=Current Obstetrics & Gynaecology|volume=15|issue=3|year=2005|pages=174–182|issn=0957-5847|doi=10.1016/j.curobgyn.2005.03.006}}</ref> CPA at a dosage of 50&nbsp;mg/day in combination with 100&nbsp;μg/day transdermal estradiol patches has been found to be effective in the treatment of hirsutism similarly to the combination of CPA with ethinylestradiol.<ref name="pmid10950156"/><ref name="pmid1826278">{{cite journal | vauthors = Jasonni VM, Bulletti C, Naldi S, Di Cosmo E, Cappuccini F, Flamigni C | title = Treatment of hirsutism by an association of oral cyproterone acetate and transdermal 17 beta-estradiol | journal = Fertility and Sterility | volume = 55 | issue = 4 | pages = 742–5 | date = April 1991 | pmid = 1826278 | doi = 10.1016/S0015-0282(16)54240-X | doi-access =  }}</ref>

The efficacy of the combination of an estrogen and CPA in the treatment of hirsutism in women appears to be due to marked suppression of total and free [[androgen]] levels as well as additional blockade of the [[androgen receptor]].<ref name="pmid15151716" /><ref name="Nikolaou-2005" /><ref name="Hammerstein-1990" />

====Males====
CPA has been found to be effective in the treatment of acne in males, with marked improvement in symptoms observed at dosages of 25, 50, and 100&nbsp;mg/day in different studies.<ref name="pmid6235105">{{cite journal | vauthors = Ward A, Brogden RN, Heel RC, Speight TM, Avery GS | title = Isotretinoin. A review of its pharmacological properties and therapeutic efficacy in acne and other skin disorders | journal = Drugs | volume = 28 | issue = 1 | pages = 6–37 | date = July 1984 | pmid = 6235105 | doi = 10.2165/00003495-198428010-00002 }}</ref><ref name="Rasmusson-1986">{{cite book| vauthors = Rasmusson GH |title=Chapter 18. Chemical Control of Androgen Action|volume=21|year=1986|pages=179–188|issn=0065-7743|doi=10.1016/S0065-7743(08)61128-8|series=Annual Reports in Medicinal Chemistry|publisher=Academic Press |isbn=9780120405213}}</ref><ref name="Cormane-1981">{{cite journal| vauthors = Cormane RH, van der Meeren HL |title=Cyproteronacetate in the management of severe acne in males|journal=Archives of Dermatological Research |volume=271 |issue=2 |year=1981 |pages=183–187|issn=0340-3696|doi=10.1007/BF00412545|s2cid=12153042}}</ref><ref name="pmid2945742">{{cite journal | vauthors = Misch KJ, Dolman WF, Neild V, Rhodes EL | title = Response of male acne to antiandrogen therapy with cyproterone acetate | journal = Dermatologica | volume = 173 | issue = 3 | pages = 139–42 | date = 1986 | pmid = 2945742 | doi = 10.1159/000249236 }}</ref> It can also halt further progression of scalp hair loss in men.<ref name="Simpson-1989">{{cite book| vauthors = Simpson NB |title=Pharmacology of the Skin II|volume=87 / 2|year=1989|pages=495–508|issn=0171-2004|doi=10.1007/978-3-642-74054-1_37|series=Handbook of Experimental Pharmacology|isbn=978-3-642-74056-5|chapter=The Effect of Drugs on Hair|publisher=Springer }}</ref><ref name="Unger-1995">{{cite book| vauthors = Unger WP |chapter=Androgenetic alopecia and its treatment. A historical overview|pages=1–33|title=Hair Transplantation, Third Edition|url=https://books.google.com/books?id=_KxsAAAAMAAJ|date=1 February 1995|publisher=Taylor & Francis|isbn=978-0-8247-9363-0}}</ref><ref name="pmid6376557">{{cite journal | vauthors = Coskey RJ | title = Dermatologic therapy: December, 1982, through November, 1983 | journal = Journal of the American Academy of Dermatology | volume = 11 | issue = 1 | pages = 25–52 | date = July 1984 | pmid = 6376557 | doi = 10.1016/S0190-9622(84)80163-2 }}</ref> Increased head hair and decreased body hair has been observed with CPA in men with scalp hair loss.<ref name="pmid1838080" /><ref name="pmid8005205" /> However, its side effects in men, such as [[demasculinization]], [[gynecomastia]], [[sexual dysfunction]], [[bone mineral density|bone density]] loss, and reversible [[infertility]], make the use of CPA in males impractical in most cases.<ref name="Simpson-1989" /><ref name="Unger-1995" /><ref name="Rasmusson-1986" /><ref name="Cormane-1981" /><ref name="pmid19297634">{{cite journal | vauthors = Giltay EJ, Gooren LJ | title = Potential side effects of androgen deprivation treatment in sex offenders | journal = The Journal of the American Academy of Psychiatry and the Law | volume = 37 | issue = 1 | pages = 53–8 | date = 2009 | pmid = 19297634 }}</ref><ref name="Lam-2012">{{cite book| vauthors = Lam SM, Hempstead BR, Williams EF |title=Aesthetic Medicine|chapter=Medical Management Options for Hair Loss|year=2012|pages=529–535|publisher=Springer |doi=10.1007/978-3-642-20113-4_41|isbn=978-3-642-20112-7}}</ref><ref name="Neumann-1996" /> In addition, lower dosages of CPA, such as 25&nbsp;mg/day, have been found to be better-tolerated in men.<ref name="Cormane-1981" /> But such doses also show lower effectiveness in the treatment of acne in men.<ref name="pmid6235105" />

===High androgen levels===
CPA is used as an antiandrogen to treat [[hyperandrogenism|high androgen levels]] and associated [[symptom]]s such as [[masculinization]] due to conditions like [[polycystic ovary syndrome]] (PCOS) and [[congenital adrenal hyperplasia]] (CAH) in women.<ref name="pmid28447864" /><ref name="pmid15832490">{{cite journal | vauthors = Wiegratz I, Kuhl H | title = Managing cutaneous manifestations of hyperandrogenic disorders: the role of oral contraceptives | journal = Treat Endocrinol | volume = 1 | issue = 6 | pages = 372–86 | date = 2002 | pmid = 15832490 | doi = 10.2165/00024677-200201060-00003 | s2cid = 71806394 }}</ref><ref name="pmid28463030">{{cite journal | vauthors = Ruan X, Kubba A, Aguilar A, Mueck AO | title = Use of cyproterone acetate/ethinylestradiol in polycystic ovary syndrome: rationale and practical aspects | journal = Eur J Contracept Reprod Health Care | volume = 22 | issue = 3 | pages = 183–190 | date = June 2017 | pmid = 28463030 | doi = 10.1080/13625187.2017.1317735 | doi-access = free }}</ref><ref name="pmid10969925" /><ref name="pmid22846529">{{cite book | vauthors = Catteau-Jonard S, Cortet-Rudelli C, Richard-Proust C, Dewailly D | title = Pediatric and Adolescent Gynecology | chapter = Hyperandrogenism in adolescent girls | journal = Endocr Dev | volume = 22 | pages = 181–93 | date = 2012 | pmid = 22846529 | doi = 10.1159/000326688 | series = Endocrine Development | isbn = 978-3-8055-9336-6 }}</ref><ref name="pmid19689407">{{cite journal | vauthors = Reismann P, Likó I, Igaz P, Patócs A, Rácz K | title = Pharmacological options for treatment of hyperandrogenic disorders | journal = Mini Rev Med Chem | volume = 9 | issue = 9 | pages = 1113–26 | date = August 2009 | pmid = 19689407 | doi = 10.2174/138955709788922692 }}</ref> It is almost always combined with an estrogen, such as [[ethinylestradiol]], when it is used in the treatment of PCOS in women.<ref name="pmid9856417">{{cite journal | vauthors = Diamanti-Kandarakis E | title = How actual is the treatment with antiandrogen alone in patients with polycystic ovary syndrome? | journal = J. Endocrinol. Invest. | volume = 21 | issue = 9 | pages = 623–9 | date = October 1998 | pmid = 9856417 | doi = 10.1007/BF03350788 | s2cid = 46484837 }}</ref>

===Menopausal hormone therapy===
CPA is used at low doses in [[menopausal hormone therapy]] in combination with an estrogen to provide [[endometrial protection]] and treat [[menopausal symptoms]].<ref name="Husmann-1997">{{cite book| vauthors = Husmann F |title=Women's Health and Menopause|volume=11|year=1997|pages=257–261|issn=0928-9550|doi=10.1007/978-94-011-5560-1_38|series=Medical Science Symposia Series|isbn=978-94-010-6343-2|chapter=Clinical Experiences with a Combination of Estradiol Valerate and Cyproterone Acetate for Hormone Replacement|publisher=Springer }}</ref><ref name="pmid16112947" /><ref name="pmid14644837">{{cite journal | vauthors = Schneider HP | title = Androgens and antiandrogens | journal = Ann. N. Y. Acad. Sci. | volume = 997 | issue = 1| pages = 292–306 | date = November 2003 | pmid = 14644837 | doi = 10.1196/annals.1290.033 | bibcode = 2003NYASA.997..292S | s2cid = 8400556 }}</ref><ref name="pmid11379383">{{cite journal | vauthors = Schneider HP | title = The role of antiandrogens in hormone replacement therapy | journal = Climacteric | volume = 3 | issue = Suppl 2 | pages = 21–7 | date = December 2000 | pmid = 11379383 }}</ref> It is used in menopausal hormone therapy under the brand name Climen, which is a sequential preparation that contains 2&nbsp;mg [[estradiol valerate]] and 1&nbsp;mg CPA.<ref name="Husmann-1997" /><ref name="pmid14644837" /><ref name="pmid11379383" /> Climen was the first product for use in menopausal hormone therapy containing CPA to be marketed.<ref name="pmid14644837" /> It is available in more than 40&nbsp;countries.<ref name="Husmann-1997" />

===Transgender hormone therapy===
CPA is widely used as an [[antiandrogen]] and [[progestogen (medication)|progestogen]] in [[feminizing hormone therapy]] for [[Transgender|transgender individuals]].<ref name="pmid17986639">{{cite journal | vauthors = Gooren LJ, Giltay EJ, Bunck MC | title = Long-term treatment of transsexuals with cross-sex hormones: extensive personal experience | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 93 | issue = 1 | pages = 19–25 | date = January 2008 | pmid = 17986639 | doi = 10.1210/jc.2007-1809 | doi-access =  }}</ref><ref name="pmid28945902">{{cite journal | vauthors = Hembree WC, Cohen-Kettenis PT, Gooren L, Hannema SE, Meyer WJ, Murad MH, Rosenthal SM, Safer JD, Tangpricha V, T'Sjoen GG | display-authors = 6 | title = Endocrine Treatment of Gender-Dysphoric/Gender-Incongruent Persons: An Endocrine Society Clinical Practice Guideline | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 102 | issue = 11 | pages = 3869–3903 | date = November 2017 | pmid = 28945902 | doi = 10.1210/jc.2017-01658 | doi-access = free }}</ref><ref name="pmid29514975">{{cite journal | vauthors = Chew D, Anderson J, Williams K, May T, Pang K | title = Hormonal Treatment in Young People With Gender Dysphoria: A Systematic Review | journal = Pediatrics | volume = 141 | issue = 4 | pages = e20173742 | date = April 2018 | pmid = 29514975 | doi = 10.1542/peds.2017-3742 | doi-access = free }}</ref><ref name="Deutsch-2016">{{citation |vauthors=Deutsch M |title=Guidelines for the Primary and Gender-Affirming Care of Transgender and Gender Nonbinary People |date=17 June 2016 |edition=2nd |publisher=Center of Excellence for Transgender Health |location=University of California, San Francisco |page=28 |url=http://transhealth.ucsf.edu/pdf/Transgender-PGACG-6-17-16.pdf |access-date=2 August 2018 |archive-date=22 May 2019 |archive-url=https://web.archive.org/web/20190522074651/http://transhealth.ucsf.edu/pdf/Transgender-PGACG-6-17-16.pdf |url-status=live }}</ref><ref name="Barrett-2017">{{cite book|vauthors=Barrett J|title=Transsexual and Other Disorders of Gender Identity: A Practical Guide to Management|url=https://books.google.com/books?id=P803DwAAQBAJ&pg=PT216|date=29 September 2017|publisher=CRC Press|isbn=978-1-315-34513-0|pages=216–217, 221|access-date=2 August 2018|archive-date=6 July 2024|archive-url=https://web.archive.org/web/20240706162108/https://books.google.com/books?id=P803DwAAQBAJ&pg=PT216#v=onepage&q&f=false|url-status=live}}</ref><ref name="Ettner-2016">{{cite book|vauthors=Ettner R, Monstrey S, Coleman E|title=Principles of Transgender Medicine and Surgery|url=https://books.google.com/books?id=LwszDAAAQBAJ&pg=PA169|date=20 May 2016|publisher=Routledge|isbn=978-1-317-51460-2|pages=169, 171, 216|access-date=2 August 2018|archive-date=6 July 2024|archive-url=https://web.archive.org/web/20240706162109/https://books.google.com/books?id=LwszDAAAQBAJ&pg=PA169#v=onepage&q&f=false|url-status=live}}</ref><ref name="Israel-2001">{{cite book|vauthors=Israel GE|title=Transgender Care: Recommended Guidelines, Practical Information, and Personal Accounts|url=https://books.google.com/books?id=IlPX6E5glDEC&pg=PA66|date=March 2001|publisher=Temple University Press|isbn=978-1-56639-852-7|pages=66–|access-date=2 August 2018|archive-date=6 July 2024|archive-url=https://web.archive.org/web/20240706162110/https://books.google.com/books?id=IlPX6E5glDEC&pg=PA66#v=onepage&q&f=false|url-status=live}}</ref> It has been historically used orally at a dosage of 10 to 100&nbsp;mg/day and by intramuscular injection at a dosage of 300&nbsp;mg once every 4&nbsp;weeks.<ref name="Winkler-CrepazMüller2017_">{{cite journal | vauthors = Winkler-Crepaz K, Mueller A, Boettcher B, Wildt L |title=Hormonbehandlung bei Transgenderpatienten|trans-title=Hormone treatment of transgender patients|journal=Gynäkologische Endokrinologie|volume=15|issue=1|year=2017|pages=39–42|issn=1610-2894|doi=10.1007/s10304-016-0116-9|s2cid=12270365}}</ref><ref name="Urdl2009_">{{cite journal| vauthors = Urdl W |title=Behandlungsgrundsätze bei Transsexualität|trans-title=Therapeutic principles in transsexualism|journal=Gynäkologische Endokrinologie|volume=7|issue=3|year=2009|pages=153–160|issn=1610-2894|doi= 10.1007/s10304-009-0314-9|s2cid=8001811}}</ref> Many transgender individuals seeking feminizing hormone therapy have breast growth as one of the goals for undergoing feminizing hormone therapy, making this particular side effect of CPA generally viewed as a beneficial outcome rather than an issue.<ref name="Unger-1995" />

Studies have found that 10, 25, 50, and 100&nbsp;mg/day CPA in combination with estrogen all result in equivalent and full testosterone suppression in [[Trans woman|transgender women]].<ref name="pmid34125226">{{cite journal | vauthors = Kuijpers SM, Wiepjes CM, Conemans EB, Fisher AD, T'Sjoen G, den Heijer M | title = Toward a Lowest Effective Dose of Cyproterone Acetate in Trans Women: Results From the ENIGI Study | journal = J Clin Endocrinol Metab | volume = 106 | issue = 10 | pages = e3936–e3945 | date = September 2021 | pmid = 34125226 | pmc = 8571811 | doi = 10.1210/clinem/dgab427 | url = }}</ref><ref name="pmid34176757">{{cite journal | vauthors = Even Zohar N, Sofer Y, Yaish I, Serebro M, Tordjman K, Greenman Y | title = Low-Dose Cyproterone Acetate Treatment for Transgender Women | journal = J Sex Med | volume = 18 | issue = 7 | pages = 1292–1298 | date = July 2021 | pmid = 34176757 | doi = 10.1016/j.jsxm.2021.04.008 | s2cid = 235660315 | url = }}</ref><ref name="pmid31751300">{{cite journal | vauthors = Meyer G, Mayer M, Mondorf A, Fluegel AK, Herrmann E, Bojunga J | title = Safety and rapid efficacy of guideline-based gender affirming hormone therapy: an analysis of 388 individuals diagnosed with gender dysphoria | journal = European Journal of Endocrinology | volume =  182| issue =  2| date = November 2019 | pages = 149–156 | pmid = 31751300 | doi = 10.1530/EJE-19-0463 | doi-access = free }}</ref><ref name="Fung-2017">{{cite journal| vauthors = Fung R, Hellstern-Layefsky M, Lega I |title=Is a lower dose of cyproterone acetate as effective at testosterone suppression in transgender women as higher doses?|journal=International Journal of Transgenderism|volume=18|issue=2|year=2017|pages=123–128|issn=1553-2739|doi=10.1080/15532739.2017.1290566|s2cid=79095497}}</ref> In light of risks of CPA such as [[fatigue (medical)|fatigue]], [[venous thromboembolism|blood clot]]s, [[benign tumor|benign]] [[brain tumor]]s, and [[hepatotoxicity|liver damage]], the use of lower dosages of CPA may help to minimize such risks.<ref name="Fung-2017" /> As a result, a CPA dosage of 10{{nbsp}}mg/day and no greater is now recommended by the [[World Professional Association for Transgender Health]] (WPATH) ''[[Standards of Care for the Health of Transgender and Gender Diverse People, Version 8]]'' (SOC8).<ref name="pmid36238954">{{cite journal | vauthors = Coleman E, Radix AE, Bouman WP, Brown GR, de Vries AL, Deutsch MB, Ettner R, Fraser L, Goodman M, Green J, Hancock AB, Johnson TW, Karasic DH, Knudson GA, Leibowitz SF, Meyer-Bahlburg HF, Monstrey SJ, Motmans J, Nahata L, Nieder TO, Reisner SL, Richards C, Schechter LS, Tangpricha V, Tishelman AC, Van Trotsenburg MA, Winter S, Ducheny K, Adams NJ, Adrián TM, Allen LR, Azul D, Bagga H, Başar K, Bathory DS, Belinky JJ, Berg DR, Berli JU, Bluebond-Langner RO, Bouman MB, Bowers ML, Brassard PJ, Byrne J, Capitán L, Cargill CJ, Carswell JM, Chang SC, Chelvakumar G, Corneil T, Dalke KB, De Cuypere G, de Vries E, Den Heijer M, Devor AH, Dhejne C, D'Marco A, Edmiston EK, Edwards-Leeper L, Ehrbar R, Ehrensaft D, Eisfeld J, Elaut E, Erickson-Schroth L, Feldman JL, Fisher AD, Garcia MM, Gijs L, Green SE, Hall BP, Hardy TL, Irwig MS, Jacobs LA, Janssen AC, Johnson K, Klink DT, Kreukels BP, Kuper LE, Kvach EJ, Malouf MA, Massey R, Mazur T, McLachlan C, Morrison SD, Mosser SW, Neira PM, Nygren U, Oates JM, Obedin-Maliver J, Pagkalos G, Patton J, Phanuphak N, Rachlin K, Reed T, Rider GN, Ristori J, Robbins-Cherry S, Roberts SA, Rodriguez-Wallberg KA, Rosenthal SM, Sabir K, Safer JD, Scheim AI, Seal LJ, Sehoole TJ, Spencer K, St Amand C, Steensma TD, Strang JF, Taylor GB, Tilleman K, T'Sjoen GG, Vala LN, Van Mello NM, Veale JF, Vencill JA, Vincent B, Wesp LM, West MA, Arcelus J | display-authors = 6 | title = Standards of Care for the Health of Transgender and Gender Diverse People, Version 8 | journal = International Journal of Transgender Health | volume = 23 | issue = Suppl 1 | pages = S1–S259 | date = 19 August 2022 | pmid = 36238954 | pmc = 9553112 | doi = 10.1080/26895269.2022.2100644 | doi-access = free }}</ref>

CPA has an advantage over [[spironolactone]] as an antiandrogen in transgender people, as the combination of estrogen and CPA consistently suppresses [[testosterone]] levels into the normal female range whereas estrogen with spironolactone does not.<ref name="pmid36596713">{{cite journal | vauthors = Defreyne J, Vander Stichele C, Iwamoto SJ, T'Sjoen G | title = Gender-affirming hormonal therapy for transgender and gender-diverse people-A narrative review | journal = Best Pract Res Clin Obstet Gynaecol | volume = 86 | issue = | pages = 102296 | date = February 2023 | pmid = 36596713 | doi = 10.1016/j.bpobgyn.2022.102296 | s2cid = 254818114 | url = | pmc = 11197232 }}</ref><ref name="pmid34081614">{{cite journal | vauthors = Glintborg D, T'Sjoen G, Ravn P, Andersen MS | title = MANAGEMENT OF ENDOCRINE DISEASE: Optimal feminizing hormone treatment in transgender people | journal = Eur J Endocrinol | volume = 185 | issue = 2 | pages = R49–R63 | date = June 2021 | pmid = 34081614 | doi = 10.1530/EJE-21-0059 | s2cid = 235335361 | url = | doi-access = free }}</ref><ref name="pmid32926454">{{cite journal | vauthors = Angus LM, Nolan BJ, Zajac JD, Cheung AS | title = A systematic review of antiandrogens and feminization in transgender women | journal = Clin Endocrinol (Oxf) | volume = 94 | issue = 5 | pages = 743–752 | date = May 2021 | pmid = 32926454 | doi = 10.1111/cen.14329 | hdl = 11343/276405 | s2cid = 221724686 | url = | hdl-access = free }}</ref><ref name="pmid36403287">{{cite journal | vauthors = Sudhakar D, Huang Z, Zietkowski M, Powell N, Fisher AR | title = Feminizing gender-affirming hormone therapy for the transgender and gender diverse population: An overview of treatment modality, monitoring, and risks | journal = Neurourol Urodyn | volume = 42| issue = 5| pages = 903–920| date = November 2022 | pmid = 36403287 | doi = 10.1002/nau.25097 | s2cid = 253707685 | url = http://knowledge.uchicago.edu/record/5421}}</ref><ref name="pmid34274044">{{cite journal | vauthors = Burinkul S, Panyakhamlerd K, Suwan A, Tuntiviriyapun P, Wainipitapong S | title = Anti-Androgenic Effects Comparison Between Cyproterone Acetate and Spironolactone in Transgender Women: A Randomized Controlled Trial | journal = J Sex Med | volume = 18 | issue = 7 | pages = 1299–1307 | date = July 2021 | pmid = 34274044 | doi = 10.1016/j.jsxm.2021.05.003 | s2cid = 236092532 | url = }}</ref><ref name="pmid33471679">{{cite journal | vauthors = Sofer Y, Yaish I, Yaron M, Bach MY, Stern N, Greenman Y | title = Differential Endocrine and Metabolic Effects of Testosterone Suppressive Agents in Transgender Women | journal = Endocr Pract | volume = 26 | issue = 8 | pages = 883–890 | date = August 2020 | pmid = 33471679 | doi = 10.4158/EP-2020-0032 | s2cid = 225334013 | url = }}</ref><ref name="pmid31234145">{{cite journal | vauthors = Angus L, Leemaqz S, Ooi O, Cundill P, Silberstein N, Locke P, Zajac JD, Cheung AS | title = Cyproterone acetate or spironolactone in lowering testosterone concentrations for transgender individuals receiving oestradiol therapy | journal = Endocr Connect | volume = 8 | issue = 7 | pages = 935–940 | date = July 2019 | pmid = 31234145 | pmc = 6612061 | doi = 10.1530/EC-19-0272 | url = }}</ref> Spironolactone is the most widely used antiandrogen in transgender women in the United States, whereas CPA is widely used in Europe and throughout the rest of the world.<ref name="pmid34081614" /><ref name="pmid36238954" />

Aside from adult transgender people, CPA has also been used as a [[puberty blocker]] and hence as an antiandrogen and [[antiestrogen]] to suppress [[puberty]] in [[Transgender youth|transgender adolescents]], although [[GnRH modulator]]s are primarily used and more effective for this purpose.<ref name="pmid30112593">{{cite journal | vauthors = Panagiotakopoulos L | title = Transgender medicine - puberty suppression | journal = Reviews in Endocrine & Metabolic Disorders | volume = 19 | issue = 3 | pages = 221–225 | date = September 2018 | pmid = 30112593 | doi = 10.1007/s11154-018-9457-0 | s2cid = 52009542 }}</ref><ref name="pmid25140398">{{cite journal | vauthors = Rosenthal SM | title = Approach to the patient: transgender youth: endocrine considerations | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 99 | issue = 12 | pages = 4379–89 | date = December 2014 | pmid = 25140398 | doi = 10.1210/jc.2014-1919 | doi-access = free }}</ref><ref name="pmid29514975" /><ref name="pmid28546095">{{cite journal | vauthors = Mahfouda S, Moore JK, Siafarikas A, Zepf FD, Lin A | title = Puberty suppression in transgender children and adolescents | journal = The Lancet. Diabetes & Endocrinology | volume = 5 | issue = 10 | pages = 816–826 | date = October 2017 | pmid = 28546095 | doi = 10.1016/S2213-8587(17)30099-2 | s2cid = 10690853 }}</ref><ref name="pmid28499525">{{cite journal | vauthors = Tack LJ, Heyse R, Craen M, Dhondt K, Bossche HV, Laridaen J, Cools M | title = Consecutive Cyproterone Acetate and Estradiol Treatment in Late-Pubertal Transgender Female Adolescents | journal = The Journal of Sexual Medicine | volume = 14 | issue = 5 | pages = 747–757 | date = May 2017 | pmid = 28499525 | doi = 10.1016/j.jsxm.2017.03.251 | s2cid = 31089247 }}</ref>

===Prostate cancer===
CPA is used as an antiandrogen monotherapy and means of [[androgen deprivation therapy]] in the [[palliative]] treatment of [[prostate cancer]] in men.<ref name="pmid7919640" /><ref name="pmid16372511">{{cite journal | vauthors = Torri V, Floriani I | title = Cyproterone acetate in the therapy of prostate carcinoma | journal = Archivio Italiano di Urologia, Andrologia | volume = 77 | issue = 3 | pages = 157–63 | date = June 2005 | pmid = 16372511 | citeseerx = 10.1.1.663.9458 }}</ref><ref name="Schröder-1996">{{cite book| vauthors = Schröder FH |title=Antiandrogens in Prostate Cancer|year=1996|pages=45–51|doi=10.1007/978-3-642-45745-6_4|isbn=978-3-642-45747-0|chapter=Cyproterone Acetate — Results of Clinical Trials and Indications for Use in Human Prostate Cancer|series=ESO Monographs }}</ref><ref name="pmid8252496">{{cite journal | vauthors = Schröder FH | title = Cyproterone acetate--mechanism of action and clinical effectiveness in prostate cancer treatment | journal = Cancer | volume = 72 | issue = 12 Suppl | pages = 3810–5 | date = December 1993 | pmid = 8252496 | doi = 10.1002/1097-0142(19931215)72:12+<3810::AID-CNCR2820721710>3.0.CO;2-O | s2cid = 221762 | doi-access = free }}</ref><ref name="pmid1533452">{{cite journal | vauthors = de Voogt HJ | title = The position of cyproterone acetate (CPA), a steroidal anti-androgen, in the treatment of prostate cancer | journal = The Prostate. Supplement | volume = 4 | pages = 91–5 | date = 1992 | pmid = 1533452 | doi = 10.1002/pros.2990210514 | s2cid = 22747185 }}</ref><ref name="pmid1825143">{{cite journal | vauthors = Goldenberg SL, Bruchovsky N | title = Use of cyproterone acetate in prostate cancer | journal = The Urologic Clinics of North America | volume = 18 | issue = 1 | pages = 111–22 | date = February 1991 | doi = 10.1016/S0094-0143(21)01398-7 | pmid = 1825143 }}</ref> It is used at very high doses by mouth or by intramuscular injection to treat this disease. Antiandrogens do not cure prostate cancer, but can significantly extend life in men with the disease.<ref name="Lemke-2008">{{cite book| vauthors = Lemke TL, Williams DA |title=Foye's Principles of Medicinal Chemistry|url=https://books.google.com/books?id=R0W1ErpsQpkC&pg=PA1288|year=2008|publisher=Lippincott Williams & Wilkins|isbn=978-0-7817-6879-5|pages=1288–}}</ref><ref name="pmid10744594">{{cite journal | vauthors = Seidenfeld J, Samson DJ, Hasselblad V, Aronson N, Albertsen PC, Bennett CL, Wilt TJ | title = Single-therapy androgen suppression in men with advanced prostate cancer: a systematic review and meta-analysis | journal = Annals of Internal Medicine | volume = 132 | issue = 7 | pages = 566–77 | date = April 2000 | pmid = 10744594 | doi = 10.7326/0003-4819-132-7-200004040-00009 | s2cid = 23128641 }}</ref><ref name="pmid16372511" /> CPA has similar effectiveness to [[GnRH modulator]]s and [[surgical castration]], [[high-dose estrogen]] therapy (e.g., with [[diethylstilbestrol]]), and high-dose [[nonsteroidal antiandrogen]] monotherapy (e.g., with [[bicalutamide]]), but has significantly inferior effectiveness to [[combined androgen blockade]] with a GnRH modulator and a nonsteroidal antiandrogen (e.g., with bicalutamide or [[enzalutamide]]).<ref name="pmid16372511" /><ref name="pmid10744594" /><ref name="Mydlo-2015">{{cite book | vauthors = Mydlo JH, Godec CJ |title=Prostate Cancer: Science and Clinical Practice |url=https://books.google.com/books?id=292cBAAAQBAJ&pg=PA530 |date=29 September 2015 |publisher=Elsevier Science |isbn=978-0-12-800592-7 |pages=516–521, 534–540 |url-status=live |archive-url= https://web.archive.org/web/20170908222331/https://books.google.com/books?id=292cBAAAQBAJ&pg=PA530 |archive-date=8 September 2017 }}</ref><ref name="pmid15389811">{{cite journal | vauthors = Miyamoto H, Messing EM, Chang C | title = Androgen deprivation therapy for prostate cancer: current status and future prospects | journal = The Prostate | volume = 61 | issue = 4 | pages = 332–53 | date = December 2004 | pmid = 15389811 | doi = 10.1002/pros.20115 | s2cid = 22300358 | doi-access = free }}</ref><ref name="pmid17007995">{{cite journal | vauthors = Wirth MP, Hakenberg OW, Froehner M | title = Antiandrogens in the treatment of prostate cancer | journal = European Urology | volume = 51 | issue = 2 | pages = 306–13; discussion 314 | date = February 2007 | pmid = 17007995 | doi = 10.1016/j.eururo.2006.08.043 }}</ref> In addition, the combination of CPA with a GnRH modulator or surgical castration has not been found to improve outcomes relative to a GnRH modulator or surgical castration alone, in contrast to nonsteroidal antiandrogens.<ref name="pmid10637363">{{cite journal | vauthors = Singh SM, Gauthier S, Labrie F | title = Androgen receptor antagonists (antiandrogens): structure-activity relationships | journal = Current Medicinal Chemistry | volume = 7 | issue = 2 | pages = 211–47 | date = February 2000 | pmid = 10637363 | doi = 10.2174/0929867003375371 | quote = When compared to flutamide, [cyproterone acetate] has significant intrinsic androgenic and estrogenic activities. [...] The effects of flutamide and the steroidal derivatives, cyproterone acetate, chlormadinone acetate, megestrol acetate and medroxyprogesterone acetate were compared in vivo in female nude mice bearing androgen-sensitive Shionogi tumors. All steroidal compounds stimulated tumor growth while flutamide had no stimulatory effect [51]. Thus, CPA due to its intrinsic properties stimulates androgen-sensitive parameters and cancer growth. Cyproterone acetate added to castration has never been shown in any controlled study to prolong disease-free survival or overall survival in prostate cancer when compared with castration alone [152-155]. }}</ref> Due to its inferior effectiveness, [[tolerability]], and [[drug safety|safety]], CPA is rarely used in the treatment of prostate cancer today, having largely been superseded by GnRH modulators and nonsteroidal antiandrogens.<ref name="pmid18506331">{{cite journal | vauthors = Kaliks RA, Del Giglio A | title = Management of advanced prostate cancer | journal = Revista da Associação Médica Brasileira | volume = 54 | issue = 2 | pages = 178–82 | year = 2008 | pmid = 18506331 | doi = 10.1590/S0104-42302008000200025 | url = http://www.scielo.br/pdf/ramb/v54n2/a25v54n2.pdf | url-status = live | archive-url = https://web.archive.org/web/20170510112152/http://www.scielo.br/pdf/ramb/v54n2/a25v54n2.pdf | df = dmy-all | archive-date = 10 May 2017 | doi-access = free }}</ref><ref name="Chabner-2010">{{cite book |vauthors=Chabner BA, Longo DL |title=Cancer Chemotherapy and Biotherapy: Principles and Practice |url=https://books.google.com/books?id=WL4arNFsQa8C&pg=PA680 |date=8 November 2010 |publisher=Lippincott Williams & Wilkins |isbn=978-1-60547-431-1 |pages=679–680 |quote=From a structural standpoint, antiandrogens are classified as steroidal, including cyproterone [acetate] (Androcur) and megestrol [acetate], or nonsteroidal, including flutamide (Eulexin, others), bicalutamide (Casodex), and nilutamide (Nilandron). The steroidal antiandrogens are rarely used. |access-date=12 September 2018 |archive-date=10 January 2023 |archive-url=https://web.archive.org/web/20230110224032/https://books.google.com/books?id=WL4arNFsQa8C&pg=PA680 |url-status=live }}</ref> CPA is the only steroidal antiandrogen that continues to be used in the treatment of prostate cancer.<ref name="pmid10744594" />

[[Dose-ranging study|Dose-ranging studies]] of CPA for prostate cancer were not performed, and the optimal dosage of CPA for the treatment of the condition has not been established.<ref name="Horwich-2010">{{cite book| vauthors = Horwich A |title=Systemic Treatment of Prostate Cancer|url=https://books.google.com/books?id=MR-vVpipynUC&pg=PT44|date=11 February 2010|publisher=OUP Oxford|isbn=978-0-19-956142-1|pages=44–}}</ref><ref name="pmid12603397">{{cite journal | vauthors = Anderson J | title = The role of antiandrogen monotherapy in the treatment of prostate cancer | journal = BJU International | volume = 91 | issue = 5 | pages = 455–61 | date = March 2003 | pmid = 12603397 | doi = 10.1046/j.1464-410X.2003.04026.x | s2cid = 8639102 | doi-access = free }}</ref> A dosage range of oral CPA of 100 to 300&nbsp;mg/day is used in the treatment of prostate cancer, but generally 150 to 200&nbsp;mg/day oral CPA is used.<ref name="Dalesio-2000">{{cite journal|vauthors=Dalesio O, van Tinteren H, Clarke M, Peto R, Schroder F, Dechering I, Evans V, Godwin J, Blumenstein B, Crawford E, Denis L, Hall R, Hill C, Iversen P, Shipley W, Soloway M, Sylvester R | display-authors = 6 |title=Maximum androgen blockade in advanced prostate cancer: an overview of the randomised trials|journal=The Lancet|volume=355|issue=9214|year=2000|pages=1491–1498|issn=0140-6736|doi=10.1016/S0140-6736(00)02163-2|s2cid=25366526}}</ref><ref name="Denis-2012">{{cite book|vauthors=Denis L|title=Antiandrogens in Prostate Cancer: A Key to Tailored Endocrine Treatment|url=https://books.google.com/books?id=jqZDBQAAQBAJ&pg=PT70|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-45745-6|pages=70–|access-date=25 September 2018|archive-date=6 July 2024|archive-url=https://web.archive.org/web/20240706074500/https://books.google.com/books?id=jqZDBQAAQBAJ&pg=PT70#v=onepage&q&f=false|url-status=live}}</ref> Schröder (1993, 2002) reviewed the issue of CPA dosage and recommended a dosage of 200 to 300&nbsp;mg/day for CPA as a monotherapy and a dosage of 100 to 200&nbsp;mg/day for CPA in [[combined androgen blockade]] (that is, CPA in combination with [[surgical castration|surgical]] or [[medical castration]]).<ref name="Schröder-2009">{{cite book | vauthors = Schröder FH, Radlmaier A | date = 2009 | chapter = Steroidal Antiandrogens | pages = [https://archive.org/details/hormonetherapybr00crai/page/n328 325]–346 | doi = 10.1007/978-1-59259-152-7_15 | title = Hormone Therapy in Breast and Prostate Cancer | series = Cancer Drug Discovery and Development | url = https://archive.org/details/hormonetherapybr00crai | url-access = limited | editor1 = V. Craig Jordan | editor2 = Barrington J. A. Furr | publisher = Humana Press | isbn = 978-1-60761-471-5}}</ref><ref name="pmid8252496" /> However, the combination of CPA with castration for prostate cancer has been found to significantly decrease [[overall survival]] compared to castration alone.<ref name="pmid17956709">{{cite journal | vauthors = Chodak G, Gomella L, Phung DH | title = Combined androgen blockade in advanced prostate cancer: looking back to move forward | journal = Clinical Genitourinary Cancer | volume = 5 | issue = 6 | pages = 371–8 | date = September 2007 | pmid = 17956709 | doi = 10.3816/CGC.2007.n.019 }}</ref> Hence, the use of CPA as the antiandrogen component in combined androgen blockade would appear not to be advisable.<ref name="pmid17956709" /> When used by intramuscular injection to treat prostate cancer, CPA is used at a dosage of 300&nbsp;mg once a week.<ref name="Neumann-1996">{{cite book| vauthors = Neumann F |title=Antiandrogens in Prostate Cancer|year=1996|pages=31–44|doi=10.1007/978-3-642-45745-6_3|isbn=978-3-642-45747-0|chapter=Pharmacology of Cyproterone Acetate — A Short Review|series=ESO Monographs }}</ref>

The combination of CPA with an estrogen such as [[ethinylestradiol sulfonate]] or low-dose [[diethylstilbestrol]] has been used as a form of combined androgen blockade and as an alternative to the combination of CPA with surgical or medical castration.<ref name="Schröder-2009" /><ref name="pmid7500443" /><ref name="pmid8677581" /><ref name="pmid2973529" /><ref name="Hinkelbein-2013">{{cite book|vauthors=Hinkelbein W, Miller K, Wiegel T|title=Prostatakarzinom — urologische und strahlentherapeutische Aspekte: urologische und strahlentherapeutische Aspekte|trans-title=Prostate carcinoma — urological and radiotherapeutic aspects: urological and radiotherapeutic aspects|url=https://books.google.com/books?id=wdTLBgAAQBAJ&pg=PA99|date=7 March 2013|publisher=Springer-Verlag|isbn=978-3-642-60064-7|pages=99–|access-date=27 December 2018|archive-date=12 January 2023|archive-url=https://web.archive.org/web/20230112173056/https://books.google.com/books?id=wdTLBgAAQBAJ&pg=PA99|url-status=live}}</ref>

===Sexual deviance===
CPA is used as an antiandrogen and form of [[chemical castration]] in the treatment of [[paraphilia]]s and [[hypersexuality]] in men.<ref name="pmid25692326">{{cite journal | vauthors = Khan O, Ferriter M, Huband N, Powney MJ, Dennis JA, Duggan C | title = Pharmacological interventions for those who have sexually offended or are at risk of offending | journal = Cochrane Database Syst Rev | issue = 2 | pages = CD007989 | date = February 2015 | volume = 2015 | pmid = 25692326 | doi = 10.1002/14651858.CD007989.pub2 | pmc = 6544815 }}</ref><ref name="pmid26428645">{{cite journal | vauthors = Silvani M, Mondaini N, Zucchi A | title = Androgen deprivation therapy (castration therapy) and pedophilia: What's new | journal = Arch Ital Urol Androl | volume = 87 | issue = 3 | pages = 222–6 | date = September 2015 | pmid = 26428645 | doi = 10.4081/aiua.2015.3.222 | doi-access = free | hdl = 11568/1073189 | hdl-access = free }}</ref><ref name="pmid10986575">{{cite journal | vauthors = Reilly DR, Delva NJ, Hudson RW | title = Protocols for the use of cyproterone, medroxyprogesterone, and leuprolide in the treatment of paraphilia | journal = Can J Psychiatry | volume = 45 | issue = 6 | pages = 559–63 | date = August 2000 | pmid = 10986575 | doi = 10.1177/070674370004500608 | doi-access = free }}</ref><ref name="pmid1838080">{{cite journal | vauthors = Neumann F, Kalmus J | title = Cyproterone acetate in the treatment of sexual disorders: pharmacological base and clinical experience | journal = Exp. Clin. Endocrinol. | volume = 98 | issue = 2 | pages = 71–80 | date = 1991 | pmid = 1838080 | doi = 10.1055/s-0029-1211103 }}</ref><ref name="pmid7006321">{{cite journal | vauthors = Freund K | title = Therapeutic sex drive reduction | journal = [[Acta Psychiatr Scand Suppl]] | volume = 287 | pages = 5–38 | date = 1980 | pmid = 7006321 | doi = 10.1111/j.1600-0447.1980.tb10433.x | s2cid = 21981060 }}</ref><ref name="pmid18996306">{{cite journal | vauthors = Codispoti VL | title = Pharmacology of sexually compulsive behavior | journal = Psychiatr. Clin. North Am. | volume = 31 | issue = 4 | pages = 671–9 | date = December 2008 | pmid = 18996306 | doi = 10.1016/j.psc.2008.06.002 }}</ref> It is used to treat [[sex offender]]s.{{citation needed|date=March 2022}} The medication is approved in more than 20&nbsp;countries for this indication and is predominantly employed in [[Canada]], [[Europe]], and the [[Middle East]].<ref name="pmid24877704" /> CPA works by decreasing [[sex drive]] and [[sexual arousal]] and producing [[sexual dysfunction]]. CPA can also be used to reduce sex drive in individuals with inappropriate sexual behaviors, such as people with [[intellectual disability]] and [[dementia]].<ref name="pmid19161930">{{cite journal | vauthors = Guay DR | title = Inappropriate sexual behaviors in cognitively impaired older individuals | journal = Am J Geriatr Pharmacother | volume = 6 | issue = 5 | pages = 269–88 | date = December 2008 | pmid = 19161930 | doi = 10.1016/j.amjopharm.2008.12.004 }}</ref><ref name="pmid2526280">{{cite journal | vauthors = Clarke DJ | title = Antilibidinal drugs and mental retardation: a review | journal = Med Sci Law | volume = 29 | issue = 2 | pages = 136–46 | date = April 1989 | pmid = 2526280 | doi = 10.1177/002580248902900209 | s2cid = 37808515 }}</ref> The medication is also used to reduce sexual behavior diagnosed as self-harmful, such as [[sadomasochism|masochism]].<ref name="pmid3895195">{{cite journal | vauthors = Hucker SJ | title = Self-harmful sexual behavior | journal = Psychiatr. Clin. North Am. | volume = 8 | issue = 2 | pages = 323–37 | date = June 1985 | pmid = 3895195 | doi = 10.1016/s0193-953x(18)30698-1}}</ref> CPA has comparable effectiveness to [[medroxyprogesterone acetate]] in suppressing sexual urges and function but appears to be less effective than [[GnRH modulator]]s like [[leuprorelin]] and has more [[side effect]]s.<ref name="pmid26428645" />

High-dose CPA significantly decreases [[sexual fantasy|sexual fantasies]] and [[sexual activity]] in 80 to 90% of men with paraphilias.<ref name="pmid24877704">{{cite journal | vauthors = Assumpção AA, Garcia FD, Garcia HD, Bradford JM, Thibaut F | title = Pharmacologic treatment of paraphilias | journal = Psychiatr. Clin. North Am. | volume = 37 | issue = 2 | pages = 173–81 | date = June 2014 | pmid = 24877704 | doi = 10.1016/j.psc.2014.03.002 }}</ref> In addition, it has been found to decrease the rate of reoffending in sex offenders from 85% to 6%, with most of the reoffenses being committed by individuals who did not follow their CPA treatment prescription.<ref name="pmid24877704" /> It has been reported that in 80% of cases, 100&nbsp;mg/day CPA is adequate to achieve the desired reduction of sexuality, whereas in the remaining 20% of cases, 200&nbsp;mg/day is sufficient.<ref name="pmid1177426">{{cite journal | vauthors = Laschet U, Laschet L | title = Antiandrogens in the treatment of sexual deviations of men | journal = J. Steroid Biochem. | volume = 6 | issue = 6 | pages = 821–6 | date = June 1975 | pmid = 1177426 | doi = 10.1016/0022-4731(75)90310-6 }}</ref> When only a partial reduction in sexuality is desired, 50&nbsp;mg/day CPA can be useful.<ref name="pmid1177426" /> Reduced sexual desire and erectile function occurs with CPA by the end of the first week of treatment, and becomes maximal within three to four weeks.<ref name="pmid1177426" /><ref name="Neumann-1996" /> The dosage range is 50 to 300&nbsp;mg/day.<ref name="Neumann-1996" /><ref name="pmid1177426" />

===Early puberty===
CPA is used as an antiandrogen and antiestrogen to treat [[precocious puberty]] in boys and girls.<ref name="pmid8005205" /><ref name="pmid10969925">{{cite journal | vauthors = Laron Z, Kauli R | title = Experience with cyproterone acetate in the treatment of precocious puberty | journal = J. Pediatr. Endocrinol. Metab. | volume = 13 | issue = Suppl 1 | pages = 805–10 | date = July 2000 | pmid = 10969925 | doi = 10.1515/JPEM.2000.13.S1.805 | s2cid = 25398066 }}</ref><ref name="pmid18345393">{{cite journal | vauthors = Brito VN, Latronico AC, Arnhold IJ, Mendonça BB | title = Update on the etiology, diagnosis and therapeutic management of sexual precocity | journal = Arq Bras Endocrinol Metabol | volume = 52 | issue = 1 | pages = 18–31 | date = February 2008 | pmid = 18345393 | doi = 10.1590/S0004-27302008000100005 | doi-access = free }}</ref> However, it is not fully satisfactory for this indication because it is not able to completely suppress puberty.<ref name="Sachdeva-2012">{{cite book|vauthors=Sachdeva A, Dutta AK|title=Advances in Pediatrics|url=https://books.google.com/books?id=I2FHFyCaDeIC&pg=PA1202|date=31 August 2012|publisher=JP Medical Ltd|isbn=978-93-5025-777-7|pages=1202–|access-date=27 August 2018|archive-date=13 January 2023|archive-url=https://web.archive.org/web/20230113004839/https://books.google.com/books?id=I2FHFyCaDeIC&pg=PA1202|url-status=live}}</ref> For this reason, CPA has mostly been superseded by [[GnRH agonist]]s in the treatment of precocious puberty.<ref name="pmid10969925" /> CPA is not satisfactory for [[gonadotropin-independent precocious puberty]].<ref name="pmid1903104">{{cite journal | vauthors = Holland FJ | title = Gonadotropin-independent precocious puberty | journal = Endocrinol. Metab. Clin. North Am. | volume = 20 | issue = 1 | pages = 191–210 | date = March 1991 | pmid = 1903104 | doi = 10.1016/s0889-8529(18)30288-3}}</ref> CPA has been used at dosages of 50 to 300&nbsp;mg/m<sup>2</sup> to treat precocious puberty.<ref name="Neumann-1996" /><ref name="pmid8005205" />

===Other uses===
CPA is useful in the treatment of [[hot flash]]es, for instance due to [[androgen deprivation therapy]] for prostate cancer.<ref name="Mydlo-2015" /><ref name="pmid19962840">{{cite journal | vauthors = Frisk J | title = Managing hot flushes in men after prostate cancer--a systematic review | journal = Maturitas | volume = 65 | issue = 1 | pages = 15–22 | date = January 2010 | pmid = 19962840 | doi = 10.1016/j.maturitas.2009.10.017 | doi-access = free }}</ref><ref name="pmid15334868">{{cite journal | vauthors = Spetz AC, Zetterlund EL, Varenhorst E, Hammar M | title = Incidence and management of hot flashes in prostate cancer | journal = J Support Oncol | volume = 1 | issue = 4 | pages = 263–6, 269–70, 272–3; discussion 267–8, 271–2 | date = 2003 | pmid = 15334868 }}</ref><ref name="pmid2149457">{{cite journal | vauthors = Radlmaier A, Bormacher K, Neumann F | title = Hot flushes: mechanism and prevention | journal = Prog. Clin. Biol. Res. | volume = 359 | pages = 131–40; discussion 141–53 | date = 1990 | pmid = 2149457 }}</ref>

CPA is useful for suppressing the testosterone flare at the initiation of GnRH agonist therapy.<ref name="pmid16986003">{{cite journal | vauthors = Thompson IM | title = Flare Associated with LHRH-Agonist Therapy | journal = Rev Urol | volume = 3 | issue = Suppl 3 | pages = S10–4 | date = 2001 | pmid = 16986003 | pmc = 1476081 }}</ref><ref name="Mydlo-2015" /><ref name="Denis-1999">{{cite book|vauthors=Denis LJ, Griffiths K, Kaisary AV, Murphy GP|title=Textbook of Prostate Cancer: Pathology, Diagnosis and Treatment: Pathology, Diagnosis and Treatment|url=https://books.google.com/books?id=GreZlojD-tYC&pg=PA308|date=1 March 1999|publisher=CRC Press|isbn=978-1-85317-422-3|pages=308–|access-date=12 September 2018|archive-date=6 July 2024|archive-url=https://web.archive.org/web/20240706074500/https://books.google.com/books?id=GreZlojD-tYC&pg=PA308#v=onepage&q&f=false|url-status=live}}</ref><ref name="pmid7919640" /><ref name="pmid10969925" /><ref name="pmid15711607">{{cite journal |vauthors=Sugiono M, Winkler MH, Okeke AA, Benney M, Gillatt DA |title=Bicalutamide vs cyproterone acetate in preventing flare with LHRH analogue therapy for prostate cancer—a pilot study |journal=Prostate Cancer and Prostatic Diseases |volume=8 |issue=1 |pages=91–4 |year=2005 |pmid=15711607 |doi=10.1038/sj.pcan.4500784|s2cid=9151853 |doi-access= }}</ref><ref name="pmid2144596">{{cite journal | vauthors = Schulze H, Senge T | title = Influence of different types of antiandrogens on luteinizing hormone-releasing hormone analogue-induced testosterone surge in patients with metastatic carcinoma of the prostate | journal = J. Urol. | volume = 144 | issue = 4 | pages = 934–41 | date = October 1990 | pmid = 2144596 | doi = 10.1016/S0022-5347(17)39625-8 }}</ref><ref name="pmid2949980">{{cite journal | vauthors = Boccon-Gibod L, Laudat MH, Dugue MA, Steg A | title = Cyproterone acetate lead-in prevents initial rise of serum testosterone induced by luteinizing hormone-releasing hormone analogs in the treatment of metastatic carcinoma of the prostate | journal = Eur. Urol. | volume = 12 | issue = 6 | pages = 400–2 | date = 1986 | pmid = 2949980 | doi = 10.1159/000472667 }}</ref><ref name="Klosterhalfen-1988">{{cite book | vauthors = Klosterhalfen H, Jacobi GH | veditors = Klosterhalfen H |chapter=Long-term results of an LH-RH agonist monotherapy in patients with carcinoma of the prostate and reflections on the so-called total androgen blockade with pre-medicated cyproterone acetate |title=Endocrine Management of Prostatic Cancer |publisher=De Gruyter |date=1988 |pages=127–137 |doi=10.1515/9783110853674-014|isbn=9783110853674 }}</ref> It has been used successfully both alone and in combination with [[estrogen (medication)|estrogen]]s such as [[diethylstilbestrol]] for this purpose.<ref name="pmid16986003" /><ref name="pmid7688656">{{cite journal | vauthors = Bruchovsky N, Goldenberg SL, Akakura K, Rennie PS | title = Luteinizing hormone-releasing hormone agonists in prostate cancer. Elimination of flare reaction by pretreatment with cyproterone acetate and low-dose diethylstilbestrol | journal = Cancer | volume = 72 | issue = 5 | pages = 1685–91 | date = September 1993 | pmid = 7688656 | doi = 10.1002/1097-0142(19930901)72:5<1685::AID-CNCR2820720532>3.0.CO;2-3 | s2cid = 21824595 | doi-access = free }}</ref>

===Available forms===
{{See also|Estradiol valerate/cyproterone acetate|Ethinylestradiol/cyproterone acetate}}

CPA is available in the form of [[oral administration|oral]] [[tablet (pharmacy)|tablet]]s alone (higher-dose; 10&nbsp;mg, 50&nbsp;mg, 100&nbsp;mg) or in combination with [[ethinylestradiol]] or [[estradiol valerate]] (low-dose; 1 or 2&nbsp;mg CPA) and in the form of [[ampoule]]s for [[intramuscular injection]] (higher-dose; 100&nbsp;mg/mL, 300&nbsp;mg/3&nbsp;mL; brand name Androcur Depot).<ref name="Rabe-2015">{{cite journal | vauthors = Rabe T, Albring C, Blume-Peytavi U, Egarter C, Geisthövel F, König K, Kuhl H, Merkle E, Mueck AO, Reisch N, Schüring A, Stute P, Toth B, Wildt L, Zouboulis CC | title = Hirsutismus – Medikamentöse Therapie Gemeinsame Stellungnahme der Deutschen Gesellschaft für Gynäkologische Endokrinologie und Fortpflanzungsmedizin e.V. und des Berufsverbands der Frauenärzte e.V. | trans-title = Hirsutism – Medicinal treatment. Joint statement of the German Society of Gynaecological Endocrinology and Reproductive Medicine and the Professional Association of Gynaecologists | journal = Journal für Reproduktionsmedizin und Endokrinologie | year = 2015 | volume = 12 | issue = 3 | pages = 102–149 | language = de | issn = 1810-2107 | url = https://www.kup.at/journals/summary/12989.html | access-date = 22 December 2018 | archive-date = 5 December 2020 | archive-url = https://web.archive.org/web/20201205085747/https://www.kup.at/journals/summary/12989.html | url-status = live }}</ref><ref name="Engel-2014" /><ref name="Muller-1998">{{cite book|vauthors=Muller NF, Dessing RP|title=European Drug Index: European Drug Registrations, Fourth Edition|url=https://books.google.com/books?id=2HBPHmclMWIC&pg=PA79|date=19 June 1998|publisher=CRC Press|isbn=978-3-7692-2114-5|pages=79–|access-date=29 November 2017|archive-date=6 July 2024|archive-url=https://web.archive.org/web/20240706074500/https://books.google.com/books?id=2HBPHmclMWIC&pg=PA79#v=onepage&q&f=false|url-status=live}}</ref><ref name="Bolognia-2012">{{cite book|vauthors=Bolognia JL, Jorizzo JL, Schaffer JV|title=Dermatology E-Book|url=https://books.google.com/books?id=A78BaiEKnzIC&pg=PA557|date=8 June 2012|publisher=Elsevier Health Sciences|isbn=978-0-7020-5182-1|pages=557–|access-date=29 November 2017|archive-date=6 July 2024|archive-url=https://web.archive.org/web/20240706074500/https://books.google.com/books?id=A78BaiEKnzIC&pg=PA557#v=onepage&q&f=false|url-status=live}}</ref><ref name="Altmeyer-2013">{{cite book|vauthors=Altmeyer P|title=Therapielexikon Dermatologie und Allergologie|url=https://books.google.com/books?id=f-WzBgAAQBAJ&pg=PA27|date=2 July 2013|publisher=Springer-Verlag|isbn=978-3-662-10498-9|pages=27–|access-date=20 September 2018|archive-date=6 July 2024|archive-url=https://web.archive.org/web/20240706074529/https://books.google.com/books?id=f-WzBgAAQBAJ&pg=PA27#v=onepage&q&f=false|url-status=live}}</ref>

The higher-dose formulations are used to treat prostate cancer and certain other androgen-related indications while the low-dose formulations which also have an estrogen are used as [[combined oral contraceptive pill|combined]] [[birth control pill]]s and are used in [[menopausal hormone therapy]] for the treatment of [[menopause|menopausal]] [[symptom]]s.<ref name="Bolognia-2012" /><ref name="Kassirer-1997">{{cite book|vauthors=Kassirer JP, Greene HL|title=Current Therapy in Adult Medicine|url=https://books.google.com/books?id=XqBLAQAAIAAJ|year=1997|publisher=Mosby|isbn=978-0-8151-5480-8|page=174|access-date=29 November 2017|archive-date=6 July 2024|archive-url=https://web.archive.org/web/20240706074501/https://books.google.com/books?id=XqBLAQAAIAAJ|url-status=live}}</ref>

==Contraindications==
[[Contraindication]]s of CPA include:<ref name="AndrocurLabel">{{cite web | title = Androcur Label | url = http://www.bayerresources.com.au/resources/uploads/PI/file9701.pdf | access-date = 23 December 2018 | archive-date = 8 March 2017 | archive-url = https://web.archive.org/web/20170308062025/http://www.bayerresources.com.au/resources/uploads/PI/file9701.pdf | url-status = live }}</ref><ref name="Mylan-Cyproterone Label">{{cite web | title = Mylan-Cyproterone Label | url = https://pdf.hres.ca/dpd_pm/00011374.PDF | access-date = 2 August 2018 | archive-date = 26 January 2021 | archive-url = https://web.archive.org/web/20210126094105/https://pdf.hres.ca/dpd_pm/00011374.PDF | url-status = live }}</ref><ref name="Hammerstein-1990">{{cite book| vauthors = Hammerstein J |title=Hair and Hair Diseases|year=1990|pages=827–886|doi=10.1007/978-3-642-74612-3_35|isbn=978-3-642-74614-7|chapter=Antiandrogens: Clinical Aspects|publisher=Springer }}</ref>
* [[Hypersensitivity]] to CPA or any of the other components of the medication
* [[Pregnancy]], [[lactation]], and [[breastfeeding]]
* [[Puberty]] (except if being used to treat precocious puberty or delay puberty)
* [[Liver disease]]s and [[liver dysfunction]]
* [[Chronic kidney disease]]
* [[Dubin–Johnson syndrome]] and [[Rotor syndrome]]
* [[Intrahepatic cholestasis of pregnancy|History of jaundice or persistent pruritus during pregnancy]]
* History of [[herpes]] during pregnancy
* Previous or existing [[liver tumor]]s (only if not due to [[metastasis|metastases]] from prostate cancer)
* Previous or existing [[meningioma]], [[hyperprolactinemia]], or [[prolactinoma]]
* [[Wasting syndrome]]s (except in inoperable prostate cancer)
* Severe [[depression (mood)|depression]]
* Previous or existing [[thromboembolism|thromboembolic processes]], as well as [[stroke]] and [[myocardial infarction]]
* Severe [[diabetes]] with [[vascular]] changes
* [[Sickle-cell anemia]]

When CPA is used in combination with an estrogen, contraindications for [[birth control pill]]s should also be considered.<ref name="Hammerstein-1990" />

==Side effects==
{{Main|Side effects of cyproterone acetate}}

CPA is generally well-[[tolerability|tolerated]] and has a mild [[side effect|side-effect]] profile regardless of dosage when it is used in combination with an estrogen in women.<ref name="pmid20096826">{{cite journal | vauthors = Bachelot A, Chabbert-Buffet N, Salenave S, Kerlan V, Galand-Portier MB | title = Anti-androgen treatments | journal = Ann. Endocrinol. (Paris) | volume = 71 | issue = 1 | pages = 19–24 | date = February 2010 | pmid = 20096826 | doi = 10.1016/j.ando.2009.12.001 }}</ref><ref name="pmid394887">{{cite journal | vauthors = Burton JL | title = Anti-androgen therapy in dermatology: a review | journal = Clin. Exp. Dermatol. | volume = 4 | issue = 4 | pages = 501–7 | date = December 1979 | pmid = 394887 | doi = 10.1111/j.1365-2230.1979.tb01648.x | s2cid = 29236094 }}</ref> Side effects of CPA in general include [[hypogonadism]] (low sex-hormone levels) and associated [[symptom]]s such as [[demasculinization]], [[sexual dysfunction]], [[infertility]], and [[osteoporosis]] (fragile bones); [[breast]] changes such as [[breast tenderness]], [[breast enlargement]], and [[gynecomastia]] (breasts in men); [[emotional disorder|emotional]] changes such as [[fatigue (medical)|fatigue]] and [[depression (mood)|depression]]; and other side effects such as [[vitamin B12 deficiency]], weak [[glucocorticoid]] effects, and [[elevated liver enzymes]].<ref name="Hammerstein-1990" /> [[Weight gain]] can occur with CPA when it is used at high doses.<ref name="pmid10352926">{{cite journal | vauthors = Rittmaster RS | title = Antiandrogen treatment of polycystic ovary syndrome | journal = Endocrinol. Metab. Clin. North Am. | volume = 28 | issue = 2 | pages = 409–21 | date = June 1999 | pmid = 10352926 | doi = 10.1016/S0889-8529(05)70077-3 }}</ref><ref name="pmid2946604"/> Some of the side effects of CPA can be improved or fully prevented if it is combined with an estrogen to prevent [[estrogen deficiency]].<ref name="pmid9856417" /><ref name="pmid10495361"/> Few [[quantitative data]] are available on many of the potential side effects of CPA.<ref name="pmid19243704">{{cite journal | vauthors = Guay DR | title = Drug treatment of paraphilic and nonparaphilic sexual disorders | journal = Clin Ther | volume = 31 | issue = 1 | pages = 1–31 | date = January 2009 | pmid = 19243704 | doi = 10.1016/j.clinthera.2009.01.009 | quote = No quantitative data on these adverse events are available, even in the product prescribing information and data sheets.}}</ref> Pooled tolerability data for CPA is not available in the literature.<ref name="pmid10673793">{{cite journal | vauthors = Migliari R, Muscas G, Murru M, Verdacchi T, De Benedetto G, De Angelis M | title = Antiandrogens: a summary review of pharmacodynamic properties and tolerability in prostate cancer therapy | journal = Arch Ital Urol Androl | volume = 71 | issue = 5 | pages = 293–302 | date = December 1999 | pmid = 10673793 }}</ref> Cyproterone is also known to suppress adrenocortical function.<ref name="y2">Mylan-Cypersterone Monograph at 4. https://pdf.hres.ca/dpd_pm/00011374.PDF {{Webarchive|url=https://web.archive.org/web/20210126094105/https://pdf.hres.ca/dpd_pm/00011374.PDF |date=26 January 2021 }}</ref>

At very high doses in aged men with prostate cancer, CPA can cause [[cardiovascular]] side effects. Rarely, CPA can produce [[blood clot]]s, [[hepatotoxicity|liver toxicity]] (including [[hepatitis]], [[liver failure]], and [[liver cancer]]), [[hyperprolactinemia|excessively high prolactin level]]s, and certain [[benign tumor|benign]] [[brain tumor]]s including [[meningioma]]s (tumors of the [[meninge]]s) and [[prolactinoma]]s ([[prolactin]]-secreting tumors of the [[pituitary gland]]). Upon [[drug discontinuation|discontinuation]] from high doses, CPA can produce [[adrenal insufficiency]] as a [[drug withdrawal|withdrawal]] effect.

{{Side effects of high-dose cyproterone acetate}}

==Overdose==
CPA is relatively safe in acute [[overdose]].<ref name="Mylan-Cyproterone Label" /> It is used at very high doses of up to 300&nbsp;mg/day by mouth and 700&nbsp;mg per week by intramuscular injection.<ref name="Mylan-Cyproterone Label" /><ref name="Saleh-2009">{{cite book| vauthors =  Saleh FM, Grudzinskas AJ, Bradford JM |title=Sex Offenders: Identification, Risk Assessment, Treatment, and Legal Issues|url=https://books.google.com/books?id=df0RDAAAQBAJ&pg=PA197|date=11 February 2009|publisher=Oxford University Press, USA|isbn=978-0-19-517704-6|pages=197–}}</ref> For comparison, the dose of CPA used in birth control pills is 2&nbsp;mg/day.<ref name="Fritz-2011">{{cite book|vauthors=Fritz MA, Speroff L|title=Clinical Gynecologic Endocrinology and Infertility|url=https://books.google.com/books?id=Ll73ZsBKLkwC&pg=PA1091|year=2011|publisher=Lippincott Williams & Wilkins|isbn=978-0-7817-7968-5|pages=1091–|access-date=23 November 2018|archive-date=6 July 2024|archive-url=https://web.archive.org/web/20240706074501/https://books.google.com/books?id=Ll73ZsBKLkwC&pg=PA1091#v=onepage&q&f=false|url-status=live}}</ref> There have been no deaths associated with CPA overdose.<ref name="Mylan-Cyproterone Label" /> There are no specific [[antidote]]s for CPA overdose, and treatment should be [[symptom]]-based.<ref name="Mylan-Cyproterone Label" /> [[Gastric lavage]] can be used in the event of oral overdose within the last 2 to 3&nbsp;hours.<ref name="Mylan-Cyproterone Label" />

==Interactions==
[[Enzyme inhibitor|Inhibitor]]s and [[enzyme inducer|inducer]]s of the [[cytochrome P450]] [[enzyme]] [[CYP3A4]] may [[drug interaction|interact]] with CPA.<ref name="Mylan-Cyproterone Label" /> Examples of strong CYP3A4 inhibitors include [[ketoconazole]], [[itraconazole]], [[clotrimazole]], and [[ritonavir]], while examples of strong CYP3A4 inducers include [[rifampicin]], [[rifampin]], [[phenytoin]], [[carbamazepine]], [[phenobarbital]], and [[St. John's wort]].<ref name="Mylan-Cyproterone Label" /> Certain [[anticonvulsant]] medications can substantially reduce levels of CPA, by as much as 8-fold.<ref name="pmid2941191" />

==Pharmacology==

===Pharmacodynamics===
{{Main|Pharmacology of cyproterone acetate#Pharmacodynamics}}

CPA has [[antiandrogen]]ic activity,<ref name="pmid16112947" /><ref name="Figg-2010">{{cite book |vauthors=Figg W, Chau CH, Small EJ |title=Drug Management of Prostate Cancer |url=https://books.google.com/books?id=4KDrjeWA5-UC&pg=PA71 |date=14 September 2010 |publisher=Springer |isbn=978-1-60327-829-4 |page=71 |access-date=27 September 2016 |archive-date=10 January 2023 |archive-url=https://web.archive.org/web/20230110224030/https://books.google.com/books?id=4KDrjeWA5-UC&pg=PA71 |url-status=live }}</ref> [[progestogen (medication)|progestogen]]ic activity,<ref name="pmid16112947" /><ref name="Figg-2010" /> weak [[partial agonist|partial]] [[glucocorticoid]] activity,<ref name="pmid12695529">{{cite journal | vauthors = Honer C, Nam K, Fink C, Marshall P, Ksander G, Chatelain RE, Cornell W, Steele R, Schweitzer R, Schumacher C | display-authors = 6 | title = Glucocorticoid receptor antagonism by cyproterone acetate and RU486 | journal = Molecular Pharmacology | volume = 63 | issue = 5 | pages = 1012–20 | date = May 2003 | pmid = 12695529 | doi = 10.1124/mol.63.5.1012 | s2cid = 23872584 }}</ref> weak [[steroidogenesis inhibitor]] activity,<ref name="pmid2956461">{{cite journal | vauthors = Ayub M, Levell MJ | title = Inhibition of rat testicular 17 alpha-hydroxylase and 17,20-lyase activities by anti-androgens (flutamide, hydroxyflutamide, RU23908, cyproterone acetate) in vitro | journal = Journal of Steroid Biochemistry | volume = 28 | issue = 1 | pages = 43–7 | date = July 1987 | pmid = 2956461 | doi = 10.1016/0022-4731(87)90122-1 }}</ref> and [[agonist]] activity at the [[pregnane X receptor]].<ref name="Han-2010">{{cite book | vauthors = Han C, Davis CB, Wang B | title = Evaluation of Drug Candidates for Preclinical Development: Pharmacokinetics, Metabolism, Pharmaceutics, and Toxicology|url=https://books.google.com/books?id=2TsQKxRdRVEC&pg=PA92|date=6 January 2010|publisher=John Wiley & Sons|isbn=978-0-470-57488-1|pages=92–}}</ref><ref name="pmid9727070">{{cite journal | vauthors = Lehmann JM, McKee DD, Watson MA, Willson TM, Moore JT, Kliewer SA | title = The human orphan nuclear receptor PXR is activated by compounds that regulate CYP3A4 gene expression and cause drug interactions | journal = The Journal of Clinical Investigation | volume = 102 | issue = 5 | pages = 1016–23 | date = September 1998 | pmid = 9727070 | pmc = 508967 | doi = 10.1172/JCI3703 }}</ref><ref name="pmid16863430">{{cite journal | vauthors = Christians U, Schmitz V, Haschke M | title = Functional interactions between P-glycoprotein and CYP3A in drug metabolism | journal = Expert Opinion on Drug Metabolism & Toxicology | volume = 1 | issue = 4 | pages = 641–54 | date = December 2005 | pmid = 16863430 | doi = 10.1517/17425255.1.4.641 | s2cid = 17742146 }}</ref> It has no [[estrogen (medication)|estrogen]]ic or [[antimineralocorticoid]] activity.<ref name="pmid16112947" /> In terms of [[potency (pharmacology)|potency]], CPA is described as a highly potent progestogen, a moderately potent antiandrogen, and a weak glucocorticoid.<ref name="Hammerstein-1990" /><ref name="pmid10352926" /><ref name="pmid10495361" /> Due to its progestogenic activity, CPA has [[antigonadotropic]] effects, and is able to suppress [[fertility]] and [[sex hormone|sex-hormone]] levels in both males and females.<ref name="pmid16112947" /><ref name="pmid8005205" /><ref name="Hammerstein-1990" />

===Pharmacokinetics===
{{Main|Pharmacology of cyproterone acetate#Pharmacokinetics}}

CPA can be taken [[oral administration|by mouth]] or by [[intramuscular injection|injection into muscle]].<ref name="pmid8005205" /> It has near-complete oral [[bioavailability]], is highly and exclusively bound to [[human serum albumin|albumin]] in terms of [[plasma protein binding]], is [[metabolism|metabolized]] in the [[liver]] by [[hydroxylation]] and [[conjugation (biochemistry)|conjugation]], has [[15β-hydroxycyproterone acetate]] (15β-OH-CPA) as a single major [[active metabolite]], has a long [[elimination half-life]] of about 2 to 4&nbsp;days regardless of route of administration, and is [[excretion|excreted]] in [[feces]] primarily and to a lesser extent in [[urine]].<ref name="pmid16112947" /><ref name="pmid14670641" /><ref name="BradfordKaye1998" />

==Chemistry==
{{See also|List of progestogens|Progestogen ester|List of progestogen esters|Steroidal antiandrogen|List of steroidal antiandrogens}}

CPA, also known as 1α,2α-methylene-6-chloro-17α-acetoxy-δ<sup>6</sup>-progesterone or as 1α,2α-methylene-6-chloro-17α-hydroxypregna-4,6-diene-3,20-dione acetate, is a [[synthetic compound|synthetic]] [[pregnane]] [[steroid]] and an [[acetyl group|acetylated]] [[chemical derivative|derivative]] of [[17α-hydroxyprogesterone]].<ref name="Graf-1974">{{cite book| vauthors = Gräf KJ, Brotherton J, Neumann F |chapter=Clinical Uses of Antiandrogens |title=Androgens II and Antiandrogens / Androgene II und Antiandrogene|series=Handbuch der experimentellen Pharmakologie/Handbook of Experimental Pharmacology |year=1974|pages=485–542|publisher=Springer |doi=10.1007/978-3-642-80859-3_7|isbn=978-3-642-80861-6}}</ref><ref name="Knaus-2012">{{cite book| vauthors = Knaus JV, Isaacs JH |title=Office Gynecology: Advanced Management Concepts|url=https://books.google.com/books?id=dgnpBwAAQBAJ&pg=PA150|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-1-4612-4340-3|pages=150–}}</ref> It is structurally related to other 17α-hydroxyprogesterone derivatives such as [[chlormadinone acetate]], [[hydroxyprogesterone caproate]], [[medroxyprogesterone acetate]], and [[megestrol acetate]].<ref name="Knaus-2012" />

===Synthesis===
[[Chemical synthesis|Chemical syntheses]] of CPA have been published.<ref name="Engel-2014">{{cite book|vauthors=Engel J, Kleemann A, Kutscher B, Reichert D|title=Pharmaceutical Substances: Syntheses, Patents and Applications of the most relevant APIs|edition=5th|url=https://books.google.com/books?id=4lCGAwAAQBAJ&pg=PA351|date=14 May 2014|publisher=Thieme|isbn=978-3-13-179275-4|pages=351–352|access-date=7 September 2018|archive-date=6 July 2024|archive-url=https://web.archive.org/web/20240706162111/https://books.google.com/books?id=4lCGAwAAQBAJ&pg=PA351|url-status=live}}</ref><ref name="Publishing2013">{{cite book|author=William Andrew Publishing|title=Pharmaceutical Manufacturing Encyclopedia|url=https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA1182|date=22 October 2013|publisher=Elsevier|isbn=978-0-8155-1856-3|pages=1182–1183}}</ref><ref name="y3">{{cite patent | inventor = Buddhasukh D, Maier R, Manosroi A, Manosroi J, Sripalakit P, Werner R | country = EP | number = 1359154A1 | title = Further syntheses of cyproterone acetate | url = https://patents.google.com/patent/EP1359154A1 | pubdate = 5 November 2003 }} {{Webarchive|url=https://web.archive.org/web/20210208015651/https://patents.google.com/patent/EP1359154A1 |date=8 February 2021 }}</ref> The following is one such synthesis:<ref name="DE1189991B">{{Cite web | url=https://patents.google.com/patent/DE1189991B | title=Verfahren zur Herstellung von 1, 2alpha-Methylen-delta-17alpha-hydroxy-progesteronen | access-date=20 September 2018 | archive-date=8 February 2021 | archive-url=https://web.archive.org/web/20210208015752/https://patents.google.com/patent/DE1189991B | url-status=live }}</ref><ref name="US3234093A">{{Cite web | url=https://patents.google.com/patent/US3234093A | title=6-chloro-1, 2alpha-methylene-delta6-17alpha-hydroxyprogesterone compounds and compositions | access-date=20 September 2018 | archive-date=8 February 2021 | archive-url=https://web.archive.org/web/20210208032819/https://patents.google.com/patent/US3234093A | url-status=live }}</ref>

[[File:Cyproterone acetate synthesis.png|thumb|center|500px|[https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-03-0271 Thieme] [[Partial synthesis]] of CPA, using [[hydroxyprogesterone acetate]] as a starting material, by Wiechert & Neumann (1965) and Wiechert (1966).<ref name="DE1189991B" /><ref name="US3234093A" />]]

The dehydrogenation of [[17α-hydroxyprogesterone acetate]] [302-23-8] ('''1''') with [[chloranil]] (tetrachloro-p-benzoquinone) gives a compound that has been called melengestrol acetate [425-51-4] ('''2'''). Dehydrogenation with selenium dioxide gives 17-acetoxy-1,4,6-pregnatriene-3,20-dione [2668-75-9] ('''3'''). Reacting this with diazomethane results in a 1,3-dipolar addition reaction at C1–C2 of the double bond of the steroid system, which forms a derivative of dihydropyrazole, [https://pubchem.ncbi.nlm.nih.gov/compound/134990386 CID:134990386] ('''4'''). This compound cleaves when reacted with [[perchloric acid]],<ref name="y4">Rudolf Wiechert, {{US patent|3127396}} (1964).</ref> releasing nitrogen molecules and forming a cyclopropane derivative, 6-deschloro cyproterone acetate [2701-50-0] ('''5'''). Selective oxidation of the C6=C7 olefin with benzoyl peroxide gives the epoxide, i.e. 6-deschloro-6,7-epoxy cyproterone [15423-97-9] ('''6'''). The penultimate step involves a reaction with hydrochloric acid in acetic acid, resulting in the formation of chlorine and its subsequent dehydration, and a simultaneous opening of the cyclopropane ring giving 1α-(chloromethyl) chlormadinone acetate [17183-98-1] ('''7'''). The heating of this in collidine reforms the cyclopropane ring, completing the synthesis of CPA ('''8''').

==History==
CPA was first [[chemical synthesis|synthesized]] in 1961 by [[:de:Rudolf Wiechert|Rudolf Wiechert]], a [[Schering AG|Schering]] employee, and together with [[:de:Friedmund Neumann|Friedmund Neumann]] in [[Berlin]], they filed for a patent for CPA as "progestational agent" in 1962.<ref name="pmid9476091" /><ref name="US3234093">{{US Patent|3234093}}</ref> The antiandrogenic activity of CPA was discovered serendipitously by Hamada, Neumann, and Karl Junkmann in 1963.<ref name="pmid14071315">{{cite journal | vauthors = Hamada H, Neumann F, Junkmann K | title = Intrauterine Antimaskuline Beeinflussung von Rattenfeten Durch ein Stark Gestagen Wirksames Steroid | language = de | journal = Acta Endocrinologica | volume = 44 | issue = 3 | pages = 380–8 | date = November 1963 | pmid = 14071315 | doi = 10.1530/acta.0.0440380 | trans-title = Intrauterine antimasculine influence of Rat Fetuses by Birtue of a Powerful Steroid Acting as a Progestogen }}</ref><ref name="Neumann-1996" /> Along with the steroidal antiandrogens [[benorterone]] (17α-methyl-''B''-nortestosterone; SKF-7690), [[cyproterone]], [[BOMT]] (Ro 7–2340), and [[trimethyltrienolone]] (R-2956) and the [[nonsteroidal antiandrogen]]s [[flutamide]] and [[DIMP (antiandrogen)|DIMP]] (Ro 7–8117), CPA was one of the first antiandrogens to be discovered and researched.<ref name="pmid10495361" /><ref name="Mann-2012">{{cite book| vauthors = Mann T, Lutwak-Mann C |title=Male Reproductive Function and Semen: Themes and Trends in Physiology, Biochemistry and Investigative Andrology|url=https://books.google.com/books?id=cezjBwAAQBAJ&pg=PA352|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-1-4471-1300-3|pages=352–}}</ref><ref name="Norman-2014">{{cite book| vauthors = Norman AW, Litwack G |title=Hormones|url=https://books.google.com/books?id=AORRAwAAQBAJ&pg=PA508|date=28 June 2014|publisher=Elsevier Science|isbn=978-1-4832-5810-2|pages=508–}}</ref><ref name="Mainwaring-2012">{{cite book| vauthors = Mainwaring WI |title=The Mechanism of Action of Androgens|url=https://books.google.com/books?id=rrDoCAAAQBAJ&pg=PA53|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-88429-0|pages=53–}}</ref>

CPA was initially developed as a progestogen for the prevention of [[threatened abortion]].<ref name="Neumann-1996" /> As part of its development, it was assessed for androgenic activity to ensure that it would not produce [[teratogen]]ic effects in female [[fetus]]es.<ref name="Neumann-1996" /> The drug was administered to [[pregnancy|pregnant]] rats and its effects on the rat fetuses were studied.<ref name="Neumann-1996" /> To the surprise of the researchers, all of the rat pups born appeared to be female.<ref name="Neumann-1996" /> After 20&nbsp;female rat pups in a row had been counted, it was clear that this could not be a chance occurrence.<ref name="Neumann-1996" /> The rat pups were further evaluated and it was found that, in terms of [[karyotype]], about 50% were actually males.<ref name="Neumann-1996" /> The male rat pups had been feminized, and this resultant finding constituted the discovery of the powerful antiandrogenic activity of CPA.<ref name="Neumann-1996" /> A year after patent approval in 1965, Neumann published additional evidence of CPA's antiandrogenic effect in rats; he reported an "organizational effect of CPA on the brain".<ref name="pmid5989926">{{cite journal | vauthors = Neumann F, Elger W |year=1966 |title=Permanent changes in gonadal function and sexual behaviour as a result of early feminization of male rats by treatment with an antiandrogenic steroid |journal=Endokrinologie |volume=50 |issue=5 |pages=209–225|pmid=5989926 }}</ref> CPA started being used in animal experiments around the world to investigate how antiandrogens affected fetal [[sexual differentiation]].<ref name="pmid4949979">{{cite journal | vauthors = Jost A | title = Use of androgen antagonists and antiandrogens in studies on sex differentiation | journal = Gynecol Invest | volume = 2 | issue = 1 | pages = 180–201 | date = 1971 | pmid = 4949979 | doi = 10.1159/000301861 }}</ref>

The first clinical use of CPA in the treatment of [[sexual deviance]] and [[prostate cancer]] occurred in 1966.<ref name="pmid66176" /><ref name="pmid20459370">{{cite journal | vauthors = Thibaut F, De La Barra F, Gordon H, Cosyns P, Bradford JM | title = The World Federation of Societies of Biological Psychiatry (WFSBP) guidelines for the biological treatment of paraphilias | journal = The World Journal of Biological Psychiatry | volume = 11 | issue = 4 | pages = 604–55 | date = June 2010 | pmid = 20459370 | doi = 10.3109/15622971003671628 | s2cid = 14949511 }}</ref><ref name="pmid2462132">{{cite journal | vauthors = Namer M | title = Clinical applications of antiandrogens | journal = Journal of Steroid Biochemistry | volume = 31 | issue = 4B | pages = 719–29 | date = October 1988 | pmid = 2462132 | doi = 10.1016/0022-4731(88)90023-4 }}</ref> It was first studied in the treatment of androgen-dependent skin and hair symptoms, specifically acne, hirsutism, seborrhea, and scalp hair loss, in 1969.<ref name="pmid4304873">{{cite journal | vauthors = Hammerstein J, Cupceancu B | title = [Management of hirsutism using cyproterone acetate] | language = de | journal = Deutsche Medizinische Wochenschrift | volume = 94 | issue = 16 | pages = 829–34 | date = April 1969 | pmid = 4304873 | doi = 10.1055/s-0028-1111126 | s2cid = 71214286 | trans-title = Management of hirsutism using cyproterone acetate }}</ref> CPA was first approved for medical use in 1973 in [[Europe]] under the brand name Androcur.<ref name="Publishing2013" /><ref name="Tobias-2014">{{cite book | vauthors = Tobias JS, Hochhauser D | title = Cancer and its Management |url=https://books.google.com/books?id=CXjDBAAAQBAJ&pg=PA379 |date=3 October 2014 |publisher=Wiley |isbn=978-1-118-46871-5 |pages=379–}}</ref> In 1977, a formulation of CPA was introduced for use by intramuscular injection.<ref name="Jacobi-1982">{{cite book | vauthors = Jacobi GR, Tunn UW, Senge TH | chapter = Clinical experience with cyproterone acetate for palliation of inoperable prostate cancer | veditors = Jacobi GH, Hohenfellner R | title = Prostate Cancer | chapter-url = https://books.google.com/books?id=4HNrAAAAMAAJ | date = 1 December 1982 | publisher = Williams & Wilkins | isbn = 978-0-683-04354-9 | pages = 305–319 | access-date = 10 July 2019 | archive-date = 6 July 2024 | archive-url = https://web.archive.org/web/20240706075014/https://books.google.com/books?id=4HNrAAAAMAAJ | url-status = live }}</ref> CPA was first marketed as a birth control pill in 1978 in combination with ethinylestradiol under the brand name Diane.<ref name="Plewig-2012" /> Following [[Phases of clinical research#Phase III|phase III]] [[clinical trial]]s, CPA was approved for the treatment of prostate cancer in Germany in 1980.<ref name="Jacobi-1982" /><ref name="pmid7000222">{{cite journal | vauthors = Jacobi GH, Altwein JE, Kurth KH, Basting R, Hohenfellner R | title = Treatment of advanced prostatic cancer with parenteral cyproterone acetate: a phase III randomised trial | journal = British Journal of Urology | volume = 52 | issue = 3 | pages = 208–15 | date = June 1980 | pmid = 7000222 | doi = 10.1111/j.1464-410X.1980.tb02961.x }}</ref> CPA became available in [[Canada]] as Androcur in 1987, as Androcur Depot in 1990, and as Diane-35 in 1998.<ref name="Androcur-HC">{{Cite web | title = Androcur | url = https://health-products.canada.ca/dpd-bdpp/info.do?lang=en&code=7394#fn1 | work = Drug Product Database Online Query | publisher = Health Canada | date = 25 April 2012 | access-date = 2 January 2019 | archive-date = 3 December 2020 | archive-url = https://web.archive.org/web/20201203170453/https://health-products.canada.ca/dpd-bdpp/info.do?lang=en&code=7394#fn1 | url-status = live }}</ref><ref name="AndrocurDepot-HC">{{Cite web | title = Androcur Depot | url = https://health-products.canada.ca/dpd-bdpp/info.do?lang=en&code=11880#fn1-rf | work = Drug Product Database Online Query | publisher = Health Canada | date = 25 April 2012 | access-date = 2 January 2019 | archive-date = 3 December 2020 | archive-url = https://web.archive.org/web/20201203160911/https://health-products.canada.ca/dpd-bdpp/info.do?lang=en&code=11880#fn1-rf | url-status = live }}</ref><ref name="Diane-HC">{{Cite web | title = DIANE-35 | url = https://health-products.canada.ca/dpd-bdpp/info.do?lang=en&code=53444 | work = Drug Product Database Online Query | publisher = Health Canada | date = 25 April 2012 | access-date = 2 January 2019 | archive-date = 3 December 2020 | archive-url = https://web.archive.org/web/20201203155956/https://health-products.canada.ca/dpd-bdpp/info.do?lang=en&code=53444 | url-status = live }}</ref> Conversely, CPA was never introduced in any form in the [[United States]].<ref name="Schechter-2016" /><ref name="Duker-2013" /> This was reportedly due to concerns about [[breast tumor]]s observed with high-dose [[pregnane]] progestogens in beagle dogs as well as concerns about potential [[teratogenicity]] in pregnant women.<ref name="Becker-2001">{{cite book| vauthors = Becker KL |title=Principles and Practice of Endocrinology and Metabolism|url=https://books.google.com/books?id=FVfzRvaucq8C&pg=PA1004|year=2001|publisher=Lippincott Williams & Wilkins|isbn=978-0-7817-1750-2|pages=1004–}}</ref> Use of CPA in [[transgender women]], an [[off-label]] indication, was reported as early as 1977.<ref name="Steinbeck-1977">{{cite journal| vauthors = Steinbeck AW |title=Of Homosexuality: The Current State of Knowledge|journal=Journal of Christian Education|volume=os-20|issue=2|year=1977|pages=58–82|issn=0021-9657|doi=10.1177/002196577702000204 |s2cid=149168765}}</ref><ref name="Zingg-1980">{{cite journal | vauthors = Zingg E, König MP, Cornu F, Wildholz A, Blaser A |title=Transsexualismus: Erfahrungen mit der operativen Korrektur bei männlichen Transsexuellen|trans-title=Transsexualism: Experience with surgical correction in male transsexuals|journal=Aktuelle Urologie|volume=11|issue=2|year=1980|pages=67–77|issn=0001-7868|doi=10.1055/s-2008-1062961|s2cid=56512058 }}</ref> The use of CPA in transgender women was well-established by the early 1990s.<ref name="Asscheman-1993">{{cite journal| vauthors = Asscheman H, Gooren LJ |title=Hormone Treatment in Transsexuals|journal=Journal of Psychology & Human Sexuality|volume=5|issue=4|year=1993|pages=39–54|issn=0890-7064|doi=10.1300/J056v05n04_03|s2cid=144580633 }}</ref>

The history of CPA, including its discovery, development, and marketing, has been reviewed.<ref name="pmid2967500">{{cite journal | vauthors = Neumann F, Wiechert R | title = Das Antiandrogen Cyproteronacetat Seine Geschichte von der Entdeckung bis zur Marktreife | trans-title = The antiandrogen cyproterone acetate. Its history from discovery to marketing | language = de | journal = Pharmazie in unserer Zeit | volume = 17 | issue = 2 | pages = 33–50 | date = March 1988 | issn = 0048-3664 | pmid = 2967500 | doi = 10.1002/pauz.19880170202 }}</ref><ref name="pmid8005205" />

==Society and culture==

===Generic names===
The [[English language|English]] and [[generic drug|generic name]] of CPA is ''cyproterone acetate'' and this is its {{abbrlink|USAN|United States Adopted Name}}, {{abbrlink|BAN|British Approved Name}}, and {{abbrlink|JAN|Japanese Accepted Name}}.<ref name="Drugs.com-Cyproterone" /><ref name="IndexNominum2000" /><ref name="Elks-2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA339|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=339–}}</ref><ref name="Morton-2012">{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA89|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=89–}}</ref> The English and generic name of unacetylated [[cyproterone]] is ''cyproterone'' and this is its {{abbrlink|INN|International Nonproprietary Name}} and {{abbrlink|BAN|British Approved Name}},<ref name="Elks-2014" /><ref name="Morton-2012" /><ref name="Zink-1988">{{cite book | vauthors = Zink C |title=Dictionary of Obstetrics and Gynecology|url=https://books.google.com/books?id=EQlvzV9V7xIC&pg=PA61|date=1 January 1988|publisher=Walter de Gruyter|isbn=978-3-11-085727-6|pages=61–}}</ref> while ''cyprotérone'' is the {{abbrlink|DCF|Dénomination Commune Française}} and [[French language|French]] name and ''ciproterone'' is the {{abbrlink|DCIT|Denominazione Comune Italiana}} and [[Italian name|Italian]] name.<ref name="Drugs.com-Cyproterone" /><ref name="IndexNominum2000" /> The name of unesterified cyproterone in [[Latin language|Latin]] is ''cyproteronum'', in [[German language|German]] is ''cyproteron'', and in [[Spanish language|Spanish]] is ''ciproterona''.<ref name="Drugs.com-Cyproterone" /><ref name="IndexNominum2000" /> These names of cyproterone correspond for CPA to ''acétate de cyprotérone'' in French, ''acetato de ciproterona'' in Spanish, ''ciproterone acetato'' in Italian, ''cyproteronacetat'' in German, ''siproteron asetat'' in Turkish, and ''cyproteronacetaat'' in [[Dutch language|Dutch]]. CPA is also known by the developmental code names ''SH-80714'' and ''SH-714'', while unacetylated cyproterone is known by the developmental code names ''SH-80881'' and ''SH-881''.<ref name="Drugs.com-Cyproterone" /><ref name="IndexNominum2000" /><ref name="Elks-2014" /><ref name="Morton-2012" />

===Brand names===
CPA is marketed under brand names including Androcur, Androcur Depot, Androcur-100, Androstat, Asoteron, Cyprone, Cyproplex, Cyprostat, Cysaxal, Imvel, and Siterone.<ref name="Drugs.com-Cyproterone">{{Cite web | url=https://www.drugs.com/international/cyproterone.html | title=Cyproterone | access-date=1 December 2016 | archive-date=9 September 2018 | archive-url=https://web.archive.org/web/20180909222231/https://www.drugs.com/international/cyproterone.html | url-status=live }}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA289|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=289–}}</ref> When CPA is formulated in combination with ethinylestradiol, it is also known as ''co-cyprindiol'', and brand names for this formulation include Andro-Diane, Bella HEXAL 35, Chloe, Cypretil, Cypretyl, Cyproderm, Diane, Diane Mite, Diane-35, Dianette, Dixi 35, Drina, Elleacnelle, Estelle, Estelle-35, Ginette, Linface, Minerva, Vreya, and Zyrona.<ref name="Drugs.com-Cyproterone" /><ref name="IndexNominum2000" /> CPA is also marketed in combination with [[estradiol valerate]] as Climen, Climene, Elamax, and Femilar.<ref name="Drugs.com-Cyproterone" />

===Availability===
[[File:Cyproterone acetate availability.png|thumb|right|300px|Availability of CPA in countries throughout the world (as of March 2018). Turquoise is combined with an estrogen at a low dose, dark blue is alone at a high dose, and light blue is both available.]]

CPA is widely available throughout the world, and is marketed in almost every developed country,<ref name="Danby-2015">{{cite book | vauthors = Danby FW |title=Acne: Causes and Practical Management|url=https://books.google.com/books?id=Z1yFBQAAQBAJ&pg=PA142|date=27 January 2015|publisher=John Wiley & Sons|isbn=978-1-118-23277-4|pages=142–}}</ref> with the notable major exceptions of the [[United States]] and [[Japan]].<ref name="Drugs.com-Cyproterone" /><ref name="IndexNominum2000" /><ref name="Schechter-2016">{{cite book|vauthors=Schechter LS|title=Surgical Management of the Transgender Patient|url=https://books.google.com/books?id=eGkgDQAAQBAJ&pg=PP26|date=22 September 2016|publisher=Elsevier Health Sciences|isbn=978-0-323-48408-4|pages=26–|access-date=30 October 2016|archive-date=6 July 2024|archive-url=https://web.archive.org/web/20240706075014/https://books.google.com/books?id=eGkgDQAAQBAJ&pg=PP26#v=onepage&q&f=false|url-status=live}}</ref><ref name="Micromedex">http://www.micromedexsolutions.com/micromedex2/{{dead link|date=July 2018 |bot=MutchyMan112 |fix-attempted=yes }}</ref><ref name="Pharmaceutical Press-2009">{{cite book |editor=Sweetman, Sean C. |chapter=Sex hormones and their modulators |title=Martindale: The Complete Drug Reference |edition=36th |year=2009 |page=2082 |publisher=Pharmaceutical Press |location=London |isbn=978-0-85369-840-1 |chapter-url=https://www.medicinescomplete.com/mc/martindale/2009/9034-b.htm |access-date=11 March 2018 |archive-date=6 July 2024 |archive-url=https://web.archive.org/web/20240706075023/https://www.medicinescomplete.com/log-in/#/ |url-status=live }}</ref> In almost all countries in which CPA is marketed, it is available both alone and in combination with an estrogen in birth control pills.<ref name="Drugs.com-Cyproterone" /><ref name="Micromedex" /><ref name="Pharmaceutical Press-2009" /> CPA is marketed widely in combination with both [[ethinylestradiol]] and [[estradiol valerate]].<ref name="Drugs.com-Cyproterone" /><ref name="IndexNominum2000" /><ref name="Micromedex" /><ref name="Pharmaceutical Press-2009" /> CPA-containing birth control pills are available in [[South Korea]], but CPA as a standalone medication is not marketed in this country.<ref name="Drugs.com-Cyproterone" /><ref name="IndexNominum2000" /><ref name="Micromedex" /><ref name="Pharmaceutical Press-2009" /> In Japan and South Korea, the closely related antiandrogen and progestin [[chlormadinone acetate]], as well as other medications, are used instead of CPA.<ref name="Mydlo-2003">{{cite book|vauthors=Mydlo JH, Godec CJ|title=Prostate Cancer: Science and Clinical Practice|url=https://books.google.com/books?id=EIXDBJj6H4wC&pg=PA437|date=11 July 2003|publisher=Academic Press|isbn=978-0-08-049789-1|pages=437–|access-date=11 March 2018|archive-date=6 July 2024|archive-url=https://web.archive.org/web/20240706075017/https://books.google.com/books?id=EIXDBJj6H4wC&pg=PA437#v=onepage&q&f=false|url-status=live}}</ref> Specific places in which CPA is marketed include the [[United Kingdom]], elsewhere throughout [[Europe]], [[Canada]], [[Australia]], [[New Zealand]], [[South Africa]], [[Latin America]], and [[Asia]].<ref name="Drugs.com-Cyproterone" /><ref name="IndexNominum2000" /><ref name="Micromedex" /><ref name="Pharmaceutical Press-2009" /> CPA is not marketed in most of [[Africa]] and the [[Middle East]].<ref name="Drugs.com-Cyproterone" /><ref name="IndexNominum2000" /><ref name="Micromedex" /><ref name="Pharmaceutical Press-2009" />

It has been said that the lack of availability of CPA in the United States explains why there are relatively few studies of it in the treatment of androgen-dependent conditions such as hyperandrogenism and hirsutism in women.<ref name="pmid20096826"/>

===Generation===
Progestins in birth control pills are sometimes grouped by generation.<ref name="Unzeitig-2000">{{cite book| vauthors = Unzeitig V, van Lunsen RH |title=Contraceptive Choices and Realities: Proceedings of the 5th Congress of the European Society of Contraception|url=https://books.google.com/books?id=-FliV0TxtEEC&pg=PA73|date=15 February 2000|publisher=CRC Press|isbn=978-1-85070-067-8|pages=73–}}</ref><ref name="World Health Organization-2007">{{cite book |author1=IARC Working Group on the Evaluation of Carcinogenic Risks to Humans |author2=World Health Organization |author3=International Agency for Research on Cancer |title=Combined Estrogen-progestogen Contraceptives and Combined Estrogen-progestogen Menopausal Therapy |url=https://books.google.com/books?id=aGDU5xibtNgC&pg=PA437 |year=2007 |publisher=World Health Organization |isbn=978-92-832-1291-1 |pages=44,437}}</ref> While the [[19-nortestosterone]] progestins are consistently grouped into generations, the [[pregnane]] progestins that are or have been used in birth control pills are typically omitted from such classifications or are grouped simply as "miscellaneous" or "pregnanes".<ref name="Unzeitig-2000" /><ref name="World Health Organization-2007" /> In any case, CPA has been described as a "first-generation" progestin similarly to closely related progestins like [[chlormadinone acetate]], [[medroxyprogesterone acetate]], and [[megestrol acetate]].<ref name="pmid27616670">{{cite journal | vauthors = Louw-du Toit R, Storbeck KH, Cartwright M, Cabral A, Africander D | title = Progestins used in endocrine therapy and the implications for the biosynthesis and metabolism of endogenous steroid hormones | journal = Mol. Cell. Endocrinol. | volume = 441 | pages = 31–45 | date = February 2017 | pmid = 27616670 | doi = 10.1016/j.mce.2016.09.004 | s2cid = 38582443 }}</ref><ref name="Gordon-2007">{{cite book| vauthors = Gordon JD |title=Obstetrics, Gynecology & Infertility: Handbook for Clinicians|url=https://books.google.com/books?id=2JLC6yiA7fcC&pg=PA228|year=2007|publisher=Scrub Hill Press, Inc.|isbn=978-0-9645467-7-6|pages=228–}}</ref>

==Research==
CPA has been studied and used in combination with low-dose [[diethylstilbestrol]] in the treatment of [[prostate cancer]].<ref name="pmid7500443">{{cite journal | vauthors = Cox RL, Crawford ED | title = Estrogens in the treatment of prostate cancer | journal = The Journal of Urology | volume = 154 | issue = 6 | pages = 1991–1998 | date = December 1995 | pmid = 7500443 | doi = 10.1016/S0022-5347(01)66670-9 }}</ref><ref name="pmid2973529">{{cite journal | vauthors = Goldenberg SL, Bruchovsky N, Rennie PS, Coppin CM | title = The combination of cyproterone acetate and low dose diethylstilbestrol in the treatment of advanced prostatic carcinoma | journal = The Journal of Urology | volume = 140 | issue = 6 | pages = 1460–1465 | date = December 1988 | pmid = 2973529 | doi = 10.1016/S0022-5347(17)42073-8 }}</ref><ref name="pmid8677581">{{cite journal | vauthors = Goldenberg SL, Bruchovsky N, Gleave ME, Sullivan LD | title = Low-dose cyproterone acetate plus mini-dose diethylstilbestrol--a protocol for reversible medical castration | journal = Urology | volume = 47 | issue = 6 | pages = 882–884 | date = June 1996 | pmid = 8677581 | doi = 10.1016/S0090-4295(96)00048-9 }}</ref> The combination results in suppression of testosterone levels into the [[castration|castrate]] range, which normally cannot be achieved with CPA alone.<ref name="pmid2973529" /> CPA has been studied as a form of [[androgen deprivation therapy]] for the treatment of [[benign prostatic hyperplasia]] (enlarged prostate).<ref name="pmid1702565">{{cite journal | vauthors = Matzkin H, Braf Z | title = Endocrine treatment of benign prostatic hypertrophy: current concepts | journal = Urology | volume = 37 | issue = 1 | pages = 1–16 | date = January 1991 | pmid = 1702565 | doi = 10.1016/0090-4295(91)80069-j }}</ref><ref name="pmid7516371">{{cite journal | vauthors = Tenaglia R, Nicolai M, Di Federico G, Iantorno R, Zezza A, Lombardi G | title = [Androgen deprivation in benign prostatic hypertrophy] | language = fr | journal = Journal d'Urologie | volume = 99 | issue = 6 | pages = 296–298 | date = 1993 | pmid = 7516371 }}</ref><ref name="pmid7516378">{{cite journal | vauthors = Di Silverio F, D'Eramo G, Flammia GP, Buscarini M, Frascaro E, Mariani M, Sciarra A | title = [Pharmacological combinations in the treatment of benign prostatic hypertrophy] | language = fr | journal = Journal d'Urologie | volume = 99 | issue = 6 | pages = 316–320 | date = 1993 | pmid = 7516378 }}</ref> The medication has been studied in the treatment of [[breast cancer]] as well.<ref name="pmid9767736">{{cite journal | vauthors = Locker GY | title = Hormonal therapy of breast cancer | journal = Cancer Treatment Reviews | volume = 24 | issue = 3 | pages = 221–240 | date = June 1998 | pmid = 9767736 | doi = 10.1016/S0305-7372(98)90051-2 }}</ref><ref name="pmid2968261">{{cite journal | vauthors = Willemse PH, Dikkeschei LD, Mulder NH, van der Ploeg E, Sleijfer DT, de Vries EG | title = Clinical and endocrine effects of cyproterone acetate in postmenopausal patients with advanced breast cancer | journal = European Journal of Cancer & Clinical Oncology | volume = 24 | issue = 3 | pages = 417–421 | date = March 1988 | pmid = 2968261 | doi = 10.1016/S0277-5379(98)90011-6 }}</ref>

CPA has been studied for use as a potential [[male contraceptive|male hormonal contraceptive]] both alone and in combination with [[testosterone (medication)|testosterone]] in men.<ref name="pmid20933120">{{cite journal | vauthors = Nieschlag E | title = Clinical trials in male hormonal contraception | journal = Contraception | volume = 82 | issue = 5 | pages = 457–70 | date = November 2010 | pmid = 20933120 | doi = 10.1016/j.contraception.2010.03.020 | url = http://www.kup.at/kup/pdf/10172.pdf | access-date = 29 January 2019 | archive-date = 5 December 2020 | archive-url = https://web.archive.org/web/20201205082822/https://www.kup.at/kup/pdf/10172.pdf | url-status = live }}</ref><ref name="Nieschlag-2012">{{cite book| vauthors = Nieschlag E, Behre HM, Nieschlag E, Behre HM, Nieschlag S | veditors = Nieschlag E, Behre HM, Nieschlag S |title=Testosterone|chapter=The essential role of testosterone in hormonal male contraception |year=2012 |pages=470–493| publisher = Cambridge University Press |doi=10.1017/CBO9781139003353.023 |isbn=9781139003353}}</ref> CPA was under development by Barr Pharmaceuticals in the 2000s for the treatment of [[hot flash]]es in prostate cancer patients in the [[United States]].<ref name="AdisInsight">{{Cite web | url=http://adisinsight.springer.com/drugs/800015250 | title=Cyproterone acetate - Barr Laboratories - AdisInsight | access-date=11 December 2017 | archive-date=2 August 2018 | archive-url=https://web.archive.org/web/20180802193342/https://adisinsight.springer.com/drugs/800015250 | url-status=live }}</ref> It reached [[Phases of clinical research#Phase III|phase III]] [[clinical trial]]s for this indication and had the tentative brand name CyPat but development was ultimately discontinued in 2008.<ref name="AdisInsight" /> CPA is not satisfactorily effective as [[topical medication|topical]] antiandrogen, for instance in the treatment of [[acne]].<ref name="Graf-1974" /> CPA has been used to treat [[estrogen hypersensitivity vulvovaginitis]] in women.<ref name="pmid28718897">{{cite journal | vauthors = Nguyen Y, Bradford J, Fischer G | title = Cyproterone acetate in the treatment of oestrogen hypersensitivity vulvovaginitis | journal = The Australasian Journal of Dermatology | volume = 59 | issue = 1 | pages = 52–54 | date = February 2018 | pmid = 28718897 | doi = 10.1111/ajd.12657 | s2cid = 22365089 }}</ref>

CPA has been investigated for use in reducing [[aggression]] and [[self-harm|self-injurious behavior]] via its antiandrogenic effects in conditions like [[autism spectrum disorder]]s, [[dementia]]s like [[Alzheimer's disease]], and [[psychosis]].<ref name="pmid22508080">{{cite journal | vauthors = Geier DA, Kern JK, King PG, Sykes LK, Geier MR | title = An evaluation of the role and treatment of elevated male hormones in autism spectrum disorders | journal = Acta Neurobiol Exp (Wars) | volume = 72 | issue = 1 | pages = 1–17 | year = 2012 | doi = 10.55782/ane-2012-1876 | pmid = 22508080 | s2cid = 11909534 | doi-access = free }}</ref><ref name="pmid19942637">{{cite journal | vauthors = Bolea-Alamanac BM, Davies SJ, Christmas DM, Baxter H, Cullum S, Nutt DJ | title = Cyproterone to treat aggressivity in dementia: a clinical case and systematic review | journal = J. Psychopharmacol. (Oxford) | volume = 25 | issue = 1 | pages = 141–5 | year = 2011 | pmid = 19942637 | doi = 10.1177/0269881109353460 | s2cid = 11479701 }}</ref><ref name="pmid8309650">{{cite journal | vauthors = Albert DJ, Walsh ML, Jonik RH | title = Aggression in humans: what is its biological foundation? | journal = Neurosci Biobehav Rev | volume = 17 | issue = 4 | pages = 405–25 | date = 1993 | pmid = 8309650 | doi = 10.1016/S0149-7634(05)80117-4 | s2cid = 28557481 }}</ref><ref name="pmid1837749">{{cite journal | vauthors = Thibaut F, Kuhn JM, Colonna L | title = A possible antiaggressive effect of cyproterone acetate | journal = Br J Psychiatry | volume = 159 | issue = 2| pages = 298–9 | date = August 1991 | pmid = 1837749 | doi = 10.1192/bjp.159.2.298b | doi-access = free }}</ref> CPA may be effective in the treatment of [[obsessive–compulsive disorder]] (OCD).<ref name="pmid31814547">{{cite journal | vauthors = Nomani H, Mohammadpour AH, Moallem SM, YazdanAbad MJ, Barreto GE, Sahebkar A | title = Anti-androgen drugs in the treatment of obsessive-compulsive disorder: a systematic review | journal = Curr Med Chem | date = December 2019 | volume = 27 | issue = 40 | pages = 6825–6836 | pmid = 31814547 | doi = 10.2174/0929867326666191209142209 | s2cid = 208956450 }}</ref><ref name="Rapoport-1989">{{cite book | vauthors = Rapoport JL |title=Obsessive-compulsive Disorder in Children and Adolescents |url=https://archive.org/details/obsessivecompuls0000rapo |url-access=registration |date=1 January 1989 |publisher=American Psychiatric Pub |isbn=978-0-88048-282-0 |pages=[https://archive.org/details/obsessivecompuls0000rapo/page/229 229]–231}}</ref><ref name="pmid20623923">{{cite journal | vauthors = Kellner M | title = Drug treatment of obsessive-compulsive disorder | journal = Dialogues in Clinical Neuroscience | volume = 12 | issue = 2 | pages = 187–97 | year = 2010 | doi = 10.31887/DCNS.2010.12.2/mkellner | pmid = 20623923 | pmc = 3181958 }}</ref><ref name="Lopez Ibor-2004">{{cite book | vauthors = López Ibor JJ, Cercós CL, Masiá CC | title = Images of Spanish Psychiatry |url=https://books.google.com/books?id=wNIJ4rs7cnEC&pg=PA376 |year=2004 |publisher=Editorial Glosa, S.L. |isbn=978-84-7429-200-8 |pages=376–}}</ref> CPA has been studied in the treatment of [[cluster headache]]s in men.<ref name="pmid3366500">{{cite journal | vauthors = Sicuteri F | title = Antiandrogenic medication of cluster headache | journal = Int J Clin Pharmacol Res | volume = 8 | issue = 1 | pages = 21–4 | year = 1988 | pmid = 3366500 }}</ref>

==See also==
* [[Estradiol valerate/cyproterone acetate]]
* [[Ethinylestradiol/cyproterone acetate]]

==References==
{{Reflist}}

==Further reading==
{{Refbegin|30em}}
* {{cite journal | vauthors = Neumann F | title = Use of cyproterone acetate in animal and clinical trials | journal = Gynecol Invest | volume = 2 | issue = 1 | pages = 150–79 | date = 1971 | pmid = 4949823 | doi = 10.1159/000301860 }}
* {{cite book| vauthors = Neumann F, Steinbeck H |chapter=Antiandrogens |title=Androgens II and Antiandrogens / Androgene II und Antiandrogene |series=Handbuch der experimentellen Pharmakologie/Handbook of Experimental Pharmacology |year=1974|pages=235–484|publisher=Springer |doi=10.1007/978-3-642-80859-3_6|isbn=978-3-642-80861-6}}
* {{cite book| vauthors = Gräf KJ, Brotherton J, Neumann F |chapter=Clinical Uses of Antiandrogens |title=Androgens II and Antiandrogens / Androgene II und Antiandrogene|series=Handbuch der experimentellen Pharmakologie/Handbook of Experimental Pharmacology |year=1974|pages=485–542|publisher=Springer |doi=10.1007/978-3-642-80859-3_7|isbn=978-3-642-80861-6}}
* {{cite book| vauthors = Horn HJ |title=Androgens II and Antiandrogens / Androgene II und Antiandrogene|year=1974|pages=543–562|doi=10.1007/978-3-642-80859-3_8|isbn=978-3-642-80861-6|chapter=Administration of Antiandrogens in Hypersexuality and Sexual Deviations|series=Handbuch der experimentellen Pharmakologie/Handbook of Experimental Pharmacology |publisher=Springer }}
* {{cite journal | vauthors = Hammerstein J, Meckies J, Leo-Rossberg I, Moltz L, Zielske F | title = Use of cyproterone acetate (CPA) in the treatment of acne, hirsutism and virilism | journal = J. Steroid Biochem. | volume = 6 | issue = 6 | pages = 827–36 | date = June 1975 | pmid = 126335 | doi = 10.1016/0022-4731(75)90311-8 }}
* {{cite journal | vauthors = Neumann F | title = Pharmacology and potential use of cyproterone acetate | journal = Horm. Metab. Res. | volume = 9 | issue = 1 | pages = 1–13 | date = January 1977 | pmid = 66176 | doi = 10.1055/s-0028-1093574 | s2cid = 7224893 }}
* {{cite book | vauthors = Neumann F | title = Hormonal Steroids | chapter = Pharmacological basis for clinical use of antiandrogens | journal = J. Steroid Biochem. | volume = 19 | issue = 1A | pages = 391–402 | date = July 1983 | publisher = Pergamon | pmid = 6224971 | doi = 10.1016/B978-0-08-030771-8.50055-3 | isbn = 9780080307718 }}
* {{cite journal | vauthors = Hammerstein J, Moltz L, Schwartz U | title = Antiandrogens in the treatment of acne and hirsutism | journal = J. Steroid Biochem. | volume = 19 | issue = 1B | pages = 591–7 | date = July 1983 | pmid = 6224974 | doi = 10.1016/0022-4731(83)90223-6 }}
* {{cite journal | vauthors = Miller JA, Jacobs HS | title = Treatment of hirsutism and acne with cyproterone acetate | journal = Clin Endocrinol Metab | volume = 15 | issue = 2 | pages = 373–89 | date = May 1986 | pmid = 2941191 | doi = 10.1016/S0300-595X(86)80031-7 }}
* {{cite journal | vauthors = Neumann F, Wiechert R | title = Das Antiandrogen Cyproteronacetat: Seine Geschichte von der Entdeckung bis zur Marktreife | trans-title = The Antiandrogen Cyproterone Acetate: Its History from Discovery to Marketing | language = de | journal = Pharm unserer Zeit | volume = 17 | issue = 2 | pages = 33–50 | date = March 1988 | pmid = 2967500 | doi = 10.1002/pauz.19880170202 }}
* {{cite journal | vauthors = Tunn UW | title = Cyproterone acetate in the management of prostatic cancer | journal = Prog. Clin. Biol. Res. | volume = 303 | pages = 105–10 | date = 1989 | pmid = 2528734 }}
* {{cite book| vauthors = Hammerstein J |title=Hair and Hair Diseases|year=1990|pages=827–886|doi=10.1007/978-3-642-74612-3_35|isbn=978-3-642-74614-7|chapter=Antiandrogens: Clinical Aspects|publisher=Springer }}
* {{cite journal | vauthors = Mowszowicz I | title = Les antiandrogènes. Mécanismes et effets paradoxaux | trans-title = Antiandrogens. Mechanisms and paradoxical effects | language = fr | journal = Annales d'Endocrinologie (Paris) | volume = 50 | issue = 3 | pages = 189–99 | date = January 1989 | issn = 0003-4266 | pmid = 2530930 }}
* {{cite journal | vauthors = Schindler AE | title = [Anti-androgen therapy in the female] | language = de | journal = Geburtshilfe Frauenheilkd | volume = 50 | issue = 10 | pages = 749–53 | date = October 1990 | pmid = 1704865 | doi = 10.1055/s-2008-1026359 | s2cid = 260156319 }}
* {{cite journal | vauthors = de Voogt HJ | title = Cyproterone acetate as monotherapy in prospective randomized trials | journal = Prog. Clin. Biol. Res. | volume = 359 | pages = 85–91; discussion 105–7 | date = 1990 | pmid = 2149459 }}
* {{cite journal | vauthors = Namer M | title = Clinical applications of antiandrogens | journal = J. Steroid Biochem. | volume = 31 | issue = 4B | pages = 719–29 | date = October 1988 | pmid = 2462132 | doi = 10.1016/0022-4731(88)90023-4 }}
* {{cite journal | vauthors = Goldenberg SL, Bruchovsky N | title = Use of cyproterone acetate in prostate cancer | journal = Urol. Clin. North Am. | volume = 18 | issue = 1 | pages = 111–22 | year = 1991 | doi = 10.1016/S0094-0143(21)01398-7 | pmid = 1825143 }}
* {{cite journal | vauthors = Neumann F, Kalmus J | title = Cyproterone acetate in the treatment of sexual disorders: pharmacological base and clinical experience | journal = Exp. Clin. Endocrinol. | volume = 98 | issue = 2 | pages = 71–80 | year = 1991 | pmid = 1838080 | doi = 10.1055/s-0029-1211103 }}
* {{cite journal | vauthors = de Voogt HJ | title = The position of cyproterone acetate (CPA), a steroidal anti-androgen, in the treatment of prostate cancer | journal = Prostate Suppl | volume = 4 | pages = 91–5 | date = 1992 | pmid = 1533452 | doi = 10.1002/pros.2990210514| s2cid = 22747185 }}
* {{cite journal | vauthors = Schröder FH | title = Cyproterone acetate--mechanism of action and clinical effectiveness in prostate cancer treatment | journal = Cancer | volume = 72 | issue = 12 Suppl | pages = 3810–5 | year = 1993 | pmid = 8252496 | doi = 10.1002/1097-0142(19931215)72:12+<3810::aid-cncr2820721710>3.0.co;2-o| s2cid = 221762 | doi-access = free }}
* {{cite journal | vauthors = Barradell LB, Faulds D | title = Cyproterone. A review of its pharmacology and therapeutic efficacy in prostate cancer | journal = Drugs Aging | volume = 5 | issue = 1 | pages = 59–80 | year = 1994 | pmid = 7919640 | doi = 10.2165/00002512-199405010-00006| s2cid = 260845477 }}
* {{cite journal | vauthors = Neumann F | title = The antiandrogen cyproterone acetate: discovery, chemistry, basic pharmacology, clinical use and tool in basic research | journal = Exp. Clin. Endocrinol. | volume = 102 | issue = 1 | pages = 1–32 | year = 1994 | pmid = 8005205 | doi = 10.1055/s-0029-1211261 | url = https://www.thieme-connect.com/products/ejournals/pdf/10.1055/s-0029-1211261.pdf | access-date = 18 October 2016 | archive-date = 3 April 2022 | archive-url = https://web.archive.org/web/20220403071939/https://www.thieme-connect.com/products/ejournals/pdf/10.1055/s-0029-1211261.pdf | url-status = live }}
* {{cite journal | vauthors = Mahler C, Verhelst J, Denis L | title = Clinical pharmacokinetics of the antiandrogens and their efficacy in prostate cancer | journal = Clin Pharmacokinet | volume = 34 | issue = 5 | pages = 405–17 | date = May 1998 | pmid = 9592622 | doi = 10.2165/00003088-199834050-00005 | s2cid = 25200595 }}
* {{cite journal | vauthors = Schröder FH | title = Antiandrogens as monotherapy for prostate cancer | journal = European Urology | volume = 34 | issue = Suppl 3 | pages = 12���7 | year = 1998 | pmid = 9854190 | doi = 10.1159/000052291 | s2cid = 24831338 }}
* {{cite journal | vauthors = Diamanti-Kandarakis E | title = How actual is the treatment with antiandrogen alone in patients with polycystic ovary syndrome? | journal = J. Endocrinol. Invest. | volume = 21 | issue = 9 | pages = 623–9 | date = October 1998 | pmid = 9856417 | doi = 10.1007/BF03350788 | s2cid = 46484837 }}
* {{cite journal | vauthors = Diamanti-Kandarakis E | title = Current aspects of antiandrogen therapy in women | journal = Curr. Pharm. Des. | volume = 5 | issue = 9 | pages = 707–23 | date = September 1999 | doi = 10.2174/1381612805666230111201150 | pmid = 10495361 | url = https://books.google.com/books?id=9rfNZL6oEO0C&pg=PA707 | access-date = 18 December 2018 | archive-date = 11 January 2023 | archive-url = https://web.archive.org/web/20230111121904/https://books.google.com/books?id=9rfNZL6oEO0C&pg=PA707 | url-status = live }}
* {{cite journal | vauthors = Migliari R, Muscas G, Murru M, Verdacchi T, De Benedetto G, De Angelis M | title = Antiandrogens: a summary review of pharmacodynamic properties and tolerability in prostate cancer therapy | journal = Arch Ital Urol Androl | volume = 71 | issue = 5 | pages = 293–302 | date = December 1999 | pmid = 10673793 }}
* {{cite journal | vauthors = Laron Z, Kauli R | title = Experience with cyproterone acetate in the treatment of precocious puberty | journal = J. Pediatr. Endocrinol. Metab. | volume = 13 | issue = Suppl 1 | pages = 805–10 | year = 2000 | pmid = 10969925 | doi = 10.1515/jpem.2000.13.s1.805| s2cid = 25398066 }}
* {{cite journal | vauthors = Reilly DR, Delva NJ, Hudson RW | title = Protocols for the use of cyproterone, medroxyprogesterone, and leuprolide in the treatment of paraphilia | journal = Can J Psychiatry | volume = 45 | issue = 6 | pages = 559–63 | date = August 2000 | pmid = 10986575 | doi = 10.1177/070674370004500608 | doi-access = free }}
* {{cite journal | vauthors = Anderson J | title = The role of antiandrogen monotherapy in the treatment of prostate cancer | journal = BJU Int. | volume = 91 | issue = 5 | pages = 455–61 | date = March 2003 | pmid = 12603397 | doi = 10.1046/j.1464-410X.2003.04026.x | s2cid = 8639102 | doi-access = free }}
* {{cite journal | vauthors = Van der Spuy ZM, le Roux PA | title = Cyproterone acetate for hirsutism | journal = Cochrane Database Syst Rev | issue = 4 | pages = CD001125 | year = 2003 | volume = 2010 | pmid = 14583927 | doi = 10.1002/14651858.CD001125 | pmc = 8955083 }}
* {{cite journal | vauthors = Zouboulis CC | title = Therapie der Akne mit Antiandrogenen – Eine evidenzbasierte Übersicht | trans-title = Treatment of acne with antiandrogens--an evidence-based review | language = de | journal = J Dtsch Dermatol Ges | volume = 1 | issue = 7 | pages = 535–46 | date = July 2003 | pmid = 16295039 | doi = 10.1046/j.1610-0387.2003.03011.x | s2cid = 71005143 }}
* {{cite journal | vauthors = Thole Z, Manso G, Salgueiro E, Revuelta P, Hidalgo A | title = Hepatotoxicity induced by antiandrogens: a review of the literature | journal = Urol. Int. | volume = 73 | issue = 4 | pages = 289–95 | date = 2004 | pmid = 15604569 | doi = 10.1159/000081585 | s2cid = 24799765 }}
* {{cite journal | vauthors = Sciarra A, Cardi A, Di Silverio F | title = Antiandrogen monotherapy: recommendations for the treatment of prostate cancer | journal = Urol. Int. | volume = 72 | issue = 2 | pages = 91–8 | date = 2004 | pmid = 14963347 | doi = 10.1159/000075960 | hdl = 11573/9907 | s2cid = 24203925 }}
* {{cite journal | vauthors = Torri V, Floriani I | title = Cyproterone acetate in the therapy of prostate carcinoma | journal = Arch Ital Urol Androl | volume = 77 | issue = 3 | pages = 157–63 | year = 2005 | pmid = 16372511 | citeseerx = 10.1.1.663.9458 }}
* {{cite book | vauthors = Schröder FH, Radlmaier A | chapter = Steroidal Antiandrogens | pages = [https://archive.org/details/hormonetherapybr00crai/page/n328 325]–346 | doi = 10.1007/978-1-59259-152-7_15 | title = Hormone Therapy in Breast and Prostate Cancer | series = Cancer Drug Discovery and Development | url = https://archive.org/details/hormonetherapybr00crai | url-access = limited | editor1 = V. Craig Jordan | editor2 = Barrington J. A. Furr | year = 2009 | publisher = Humana Press | isbn = 978-1-60761-471-5 }}
* {{cite journal | vauthors = Gillatt D | title = Antiandrogen treatments in locally advanced prostate cancer: are they all the same? | journal = J. Cancer Res. Clin. Oncol. | volume = 132 | issue = Suppl 1 | pages = S17–26 | date = August 2006 | pmid = 16845534 | doi = 10.1007/s00432-006-0133-5 | s2cid = 23888640 }}
* {{cite journal | vauthors = Bachelot A, Chabbert-Buffet N, Salenave S, Kerlan V, Galand-Portier MB | title = Anti-androgen treatments | journal = Ann. Endocrinol. (Paris) | volume = 71 | issue = 1 | pages = 19–24 | date = February 2010 | pmid = 20096826 | doi = 10.1016/j.ando.2009.12.001 }}
* {{cite journal | vauthors = Zouboulis CC, Rabe T | title = Hormonelle Antiandrogene in der Aknetherapie | trans-title = Hormonal antiandrogens in acne treatment | language = de | journal = J Dtsch Dermatol Ges | volume = 8 | issue = Suppl 1 | pages = S60–74 | date = March 2010 | pmid = 20482693 | doi = 10.1111/j.1610-0387.2009.07171.x | s2cid = 196375064 }}
* {{cite journal | vauthors = Bolea-Alamanac BM, Davies SJ, Christmas DM, Baxter H, Cullum S, Nutt DJ | title = Cyproterone to treat aggressivity in dementia: a clinical case and systematic review | journal = J. Psychopharmacol. (Oxford) | volume = 25 | issue = 1 | pages = 141–5 | date = January 2011 | pmid = 19942637 | doi = 10.1177/0269881109353460 | s2cid = 11479701 }}
* {{cite journal | vauthors = Kim JH, Yoo BW, Yang WJ | title = Hepatic failure induced by cyproterone acetate: A case report and literature review | journal = Can Urol Assoc J | volume = 8 | issue = 5–6 | pages = E458–61 | date = May 2014 | pmid = 25024808 | pmc = 4081269 | doi = 10.5489/cuaj.1753 }}
* {{cite journal | vauthors = Bitzer J, Römer T, Lopes da Silva Filho A | title = The use of cyproterone acetate/ethinyl estradiol in hyperandrogenic skin symptoms - a review | journal = Eur J Contracept Reprod Health Care | volume = 22 | issue = 3 | pages = 172–182 | date = June 2017 | pmid = 28447864 | doi = 10.1080/13625187.2017.1317339 | doi-access = free }}
* {{cite journal | vauthors = Ruan X, Kubba A, Aguilar A, Mueck AO | title = Use of cyproterone acetate/ethinylestradiol in polycystic ovary syndrome: rationale and practical aspects | journal = Eur J Contracept Reprod Health Care | volume = 22 | issue = 3 | pages = 183–190 | date = June 2017 | pmid = 28463030 | doi = 10.1080/13625187.2017.1317735 | doi-access = free }}
{{refend}}

==External links==
* [http://www.arznei-telegramm.de/html/1994_09/9409084_02.html <nowiki>Die Geschichte des Wirkstoffs Cyproteronazetat: Von der "Pille für den Mann" zum "Hautpflegemittel mit Empfängnisschutz" [The History of Cyproterone Acetate: From the "Pill for Men" to the "Skin Care Product and Contraceptive"]</nowiki> - Arznei-Telegramm] {{in lang|de}} [https://translate.google.com/translate?hl=en&sl=auto&tl=en&u=https%3A%2F%2Fwww.arznei-telegramm.de%2Fhtml%2F1994_09%2F9409084_02.html <nowiki>[</nowiki>Google Translate<nowiki>]</nowiki>]

{{Cyproterone acetate}}
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