Cabazitaxel: Difference between revisions
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Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL', 'StdInChI', 'CAS_number'). |
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{{Short description|Chemical compound}} |
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{{Drugbox |
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{{Use mdy dates|date=August 2024}} |
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{{cs1 config |name-list-style=vanc |display-authors=6}} |
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{{Infobox drug |
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| verifiedrevid = |
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| IUPAC_name = (1''S'',2''S'',3''R'',4''S'',7''R'',9''S'',10''S'',12''R'',15''S'')-4-(Acetyloxy)-15-{[(2''R'',3''S'')-3-{[(tert-butoxy)carbonyl]amino}-2-hydroxy-3-phenylpropanoyl]oxy}-1-hydroxy-9,12-dimethoxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0<sup>3,10</sup>.0<sup>4,7</sup>]heptadec-13-ene-2-yl benzoate |
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| image = Cabazitaxel.png |
| image = Cabazitaxel.png |
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| alt = |
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| caption = |
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<!--Clinical data--> |
<!--Clinical data--> |
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| tradename = Jevtana |
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| Drugs.com = {{drugs.com|CDI|cabazitaxel}} |
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| Drugs.com = {{drugs.com|monograph|cabazitaxel}} |
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| MedlinePlus = a611009 |
| MedlinePlus = a611009 |
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| DailyMedID = Cabazitaxel |
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| licence_EU = Jevtana |
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| pregnancy_AU = D |
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| licence_US = Cabazitaxel |
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| pregnancy_AU_comment = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = D |
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| pregnancy_category = |
| pregnancy_category = |
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| routes_of_administration = [[Intravenous]] |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| ATC_supplemental = |
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| legal_status = |
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| routes_of_administration = Intravenous |
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| legal_AU = S4 |
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| bioavailability = |
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| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F --> |
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| metabolism = |
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| legal_BR_comment = |
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| elimination_half-life = |
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| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| excretion = |
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| legal_CA_comment = |
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| legal_DE = <!-- Anlage I, II, III or Unscheduled --> |
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| legal_DE_comment = |
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| legal_NZ = <!-- Class A, B, C --> |
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| legal_NZ_comment = |
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| legal_UK = POM |
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| legal_UK_comment = |
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| legal_US = Rx-only |
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| legal_US_comment = <ref name="Jevtana FDA label">{{cite web | title=Jevtana- cabazitaxel kit | website=DailyMed | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=de3d9c26-572b-4ea4-9b2d-dd58a2b3e8fa | access-date=December 30, 2021}}</ref> |
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| legal_EU = Rx-only |
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| legal_EU_comment = <ref>{{cite web | title=Jevtana EPAR | website=European Medicines Agency (EMA) | date=March 17, 2011 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/jevtana | access-date=August 10, 2024}}</ref> |
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| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV --> |
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| legal_UN_comment = |
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| legal_status = <!-- For countries not listed above --> |
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<!-- |
<!----> |
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| bioavailability = |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| protein_bound = |
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| CAS_number = <!-- blanked - oldvalue: 183133-96-2 --> |
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| metabolism = |
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| ATC_prefix = None |
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| onset = |
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| elimination_half-life = |
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| duration_of_action = |
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| excretion = |
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<!-- Identifiers --> |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = 183133-96-2 |
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| CAS_supplemental = |
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| PubChem = 9854073 |
| PubChem = 9854073 |
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| IUPHAR_ligand = 6798 |
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| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB06772 |
| DrugBank = DB06772 |
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| ChemSpiderID_Ref = {{chemspidercite| |
| ChemSpiderID_Ref = {{chemspidercite||chemspider}} |
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| ChemSpiderID = 8029779 |
| ChemSpiderID = 8029779 |
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| UNII_Ref = {{fdacite| |
| UNII_Ref = {{fdacite||FDA}} |
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| UNII = 51F690397J |
| UNII = 51F690397J |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG = D09755 |
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| KEGG2 = D10452 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 63584 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = |
| ChEMBL = 1201748 |
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| NIAID_ChemDB = |
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| PDB_ligand = |
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| synonyms = XRP-6258 |
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<!-- Chemical and physical data --> |
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| IUPAC_name = (1''S'',2''S'',3''R'',4''S'',7''R'',9''S'',10''S'',12''R'',15''S'')-4-(Acetyloxy)-15-<nowiki/>{[(2''R'',3''S'')-3-<nowiki/>{[(tert-butoxy)carbonyl]amino}-2-hydroxy-3-phenylpropanoyl]oxy}-1-hydroxy-9,12-dimethoxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0<sup>3,10</sup>.0<sup>4,7</sup>]heptadec-13-en-2-yl benzoate |
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| C=45 | H=57 | N=1 | O=14 |
| C=45 | H=57 | N=1 | O=14 |
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| SMILES = CO[C@H]1C[C@H]2OC[C@@]2(OC(C)=O)[C@H]2[C@H](OC(=O)c3ccccc3)[C@]3(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)c4ccccc4)C(C)=C([C@@H](OC)C(=O)[C@]12C)C3(C)C |
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| molecular_weight = 835.93 g/mol |
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| smiles = CC1=C2C(C(=O)C3(C(CC4C(C3C(C(C2(C)C)(CC1OC(=O)C(C(C5=CC=CC=C5)NC(=O)OC(C)(C)C)O)O)OC(=O)C6=CC=CC=C6)(CO4)OC(=O)C)OC)C)OC |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C45H57NO14/c1-24-28(57-39(51)33(48)32(26-17-13-11-14-18-26)46-40(52)60-41(3,4)5)22-45(53)37(58-38(50)27-19-15-12-16-20-27)35-43(8,36(49)34(55-10)31(24)42(45,6)7)29(54-9)21-30-44(35,23-56-30)59-25(2)47/h11-20,28-30,32-35,37,48,53H,21-23H2,1-10H3,(H,46,52)/t28-,29-,30+,32-,33+,34+,35-,37-,43+,44-,45+/m0/s1 |
| StdInChI = 1S/C45H57NO14/c1-24-28(57-39(51)33(48)32(26-17-13-11-14-18-26)46-40(52)60-41(3,4)5)22-45(53)37(58-38(50)27-19-15-12-16-20-27)35-43(8,36(49)34(55-10)31(24)42(45,6)7)29(54-9)21-30-44(35,23-56-30)59-25(2)47/h11-20,28-30,32-35,37,48,53H,21-23H2,1-10H3,(H,46,52)/t28-,29-,30+,32-,33+,34+,35-,37-,43+,44-,45+/m0/s1 |
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| StdInChI_comment = |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = BMQGVNUXMIRLCK-OAGWZNDDSA-N |
| StdInChIKey = BMQGVNUXMIRLCK-OAGWZNDDSA-N |
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| density = |
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| solubility = |
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| specific_rotation = |
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}} |
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'''Cabazitaxel''' |
'''Cabazitaxel''' name '''Jevtana''' is a semi-synthetic derivative of a natural [[taxoid]].<ref>http://www.cancer.gov/drugdictionary/?CdrID=534131 U.S. of , It is a microtubule inhibitor<ref>{{ |
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| title = Jevtana (cabazitaxel) Injection Approved by U.S. FDA After Priority Review |
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| publisher = sanofi-aventis |
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| date = 2010-06-17 |
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| url = http://sanofi-aventis.mediaroom.com/index.php?s=43&item=288 |
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| accessdate = June 17, 2010 |
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}}</ref> |
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Cabazitaxel was developed by [[Sanofi-Aventis]] and was approved by the US [[Food and Drug Administration]] (FDA) for the treatment of hormone-refractory [[prostate cancer]] in June 2010.<ref>{{cite web | title=Drug Approval Package: Jevtana (Cabazitaxel) NDA #201023 | website=U.S. [[Food and Drug Administration]] (FDA) | date=July 8, 2013 | url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2010/201023s000TOC.cfm | access-date=December 30, 2021 }}</ref><ref>{{cite press release | title=Jevtana (cabazitaxel) Injection Approved by U.S. FDA After Priority Review | publisher=Sanofi Aventis | via=PR Newswire | date=June 17, 2010 | url=https://www.prnewswire.com/news-releases/jevtana-cabazitaxel-injection-approved-by-us-fda-after-priority-review-96589609.html | access-date=December 30, 2021}}</ref><ref>{{cite press release | title=Jevtana (cabazitaxel) Injection Approved by U.S. FDA After Priority Review - Jun 17, 2010 | publisher=Sanofi | date=June 17, 2010 | url=https://www.news.sanofi.us/press-releases?item=118525 | access-date=December 30, 2021}}</ref> It is available as a [[generic medication]].<ref>{{cite web | title=Cabazitaxel: FDA-Approved Drugs | website=U.S. [[Food and Drug Administration]] (FDA) | url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=207949 | access-date=December 30, 2021}}</ref><ref>{{cite web | title=First Generic Drug Approvals | website=U.S. Food and Drug Administration | date=October 17, 2022 | url=https://www.fda.gov/drugs/drug-and-biologic-approval-and-ind-activity-reports/first-generic-drug-approvals | access-date=November 28, 2022}}</ref> |
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Cabazitaxel in combination with [[prednisone]] is a treatment option for [[hormone-refractory prostate cancer]] following or during [[docetaxel]]-based treatment. |
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== Medical uses == |
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Cabazitaxel is [[Indication (medicine)|indicated]] in combination with [[prednisone]] for the treatment of metastatic castration-resistant [[prostate cancer]] following [[docetaxel]]-based treatment.<ref name="Jevtana FDA label" /> |
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== Mechanism of action == |
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Taxanes enhance microtubule stabilization and inhibit cellular mitosis and division.<ref>{{cite journal | vauthors = Jordan MA, Wilson L | title = Microtubules as a target for anticancer drugs | journal = Nature Reviews. Cancer | volume = 4 | issue = 4 | pages = 253–65 | date = April 2004 | pmid = 15057285 | doi = 10.1038/nrc1317 | s2cid = 10228718 }}</ref> Moreover, taxanes prevent androgen receptor (AR) signaling by binding cellular microtubules and the microtubule-associated motor protein dynein, thus averting AR nuclear translocation.<ref>{{cite journal | vauthors = Darshan MS, Loftus MS, Thadani-Mulero M, Levy BP, Escuin D, Zhou XK, Gjyrezi A, Chanel-Vos C, Shen R, Tagawa ST, Bander NH, Nanus DM, Giannakakou P | title = Taxane-induced blockade to nuclear accumulation of the androgen receptor predicts clinical responses in metastatic prostate cancer | journal = Cancer Research | volume = 71 | issue = 18 | pages = 6019–29 | date = September 2011 | pmid = 21799031 | pmc = 3354631 | doi = 10.1158/0008-5472.CAN-11-1417 }}</ref> |
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==Clinical trials== |
==Clinical trials== |
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In people with metastatic castration-resistant prostate cancer (mCRPC), overall survival (OS) is markedly enhanced with cabazitaxel versus mitoxantrone after prior docetaxel treatment. FIRSTANA (ClinicalTrials.gov identifier: NCT01308567) assessed whether cabazitaxel 20 mg/m<sup>2</sup> (C20) or 25 mg/m<sup>2</sup> (C25) is superior to docetaxel 75 mg/m<sup>2</sup> (D75) in terms of OS in patients with chemotherapy-naïve mCRPC. However, C20 and C25 did not demonstrate superiority for OS versus D75 in people with chemotherapy-naïve mCRPC. Cabazitaxel and docetaxel demonstrated different toxicity profiles, and C20 showed the overall lowest toxicity.<ref name="ascopubs.org">{{cite journal | vauthors = Oudard S, Fizazi K, Sengeløv L, Daugaard G, Saad F, Hansen S, Hjälm-Eriksson M, Jassem J, Thiery-Vuillemin A, Caffo O, Castellano D, Mainwaring PN, Bernard J, Shen L, Chadjaa M, Sartor O | title = Cabazitaxel Versus Docetaxel As First-Line Therapy for Patients With Metastatic Castration-Resistant Prostate Cancer: A Randomized Phase III Trial-FIRSTANA | journal = Journal of Clinical Oncology | volume = 35 | issue = 28 | pages = 3189–3197 | date = October 2017 | pmid = 28753384 | doi = 10.1200/JCO.2016.72.1068 }}</ref> |
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In a phase III trial with 755 men for the treatment of [[hormone-refractory prostate cancer]], median survival was 15.1 months for patients receiving cabazitaxel versus 12.7 months for patients receiving mitoxantrone. Cabazitaxel was associated with more grade 3-4 neutropenia (81.7%) than mitoxantrone (58%).<ref>{{cite web |url=http://professional.cancerconsultants.com/oncology_main_news.aspx?id=44709 |title=Cabazitaxel Effective for Hormone Refractory Prostate Cancer After Failure of Taxotere }}</ref> |
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In a [[Phases of clinical research#Phase III|phase III trial]] with 755 men for the treatment of [[castration-resistant prostate cancer]], median survival was 15.1 months for participants receiving cabazitaxel versus 12.7 months for participants receiving [[mitoxantrone]]. Cabazitaxel was associated with more grade 3–4 [[neutropenia]] (81.7%) than mitoxantrone (58%).<ref>{{cite web |url=http://professional.cancerconsultants.com/oncology_main_news.aspx?id=44709 |title=Cabazitaxel Effective for Hormone Refractory Prostate Cancer After Failure of Taxotere }}{{Dead link|date=November 2018 |bot=InternetArchiveBot |fix-attempted=yes }}</ref> Common adverse effects with cabazitaxel include neutropenia (including febrile neutropenia) and GIT side effects appeared mainly in diarrhea, whereas, neuropathy was rarely detected.<ref name="ncbi.nlm.nih.gov">{{cite journal | vauthors = Paller CJ, Antonarakis ES | title = Cabazitaxel: a novel second-line treatment for metastatic castration-resistant prostate cancer | journal = Drug Design, Development and Therapy | volume = 5 | pages = 117–24 | date = March 2011 | pmid = 21448449 | pmc = 3063116 | doi = 10.2147/DDDT.S13029 | doi-access = free }}</ref> |
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== Pharmacokinetics == |
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==References== |
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Cabazitaxel administration causes a decrease in plasma concentrations showing triphasic kinetics: a mean half life (t<sub>1/2</sub>) of 2.6 min in the first phase, a mean t<sub>1/2</sub> of 1.3 h in the second phase, and a mean t<sub>1/2</sub> of 77.3 h in the third phase.<ref>{{cite journal | vauthors = Mita AC, Denis LJ, Rowinsky EK, Debono JS, Goetz AD, Ochoa L, Forouzesh B, Beeram M, Patnaik A, Molpus K, Semiond D, Besenval M, Tolcher AW | title = Phase I and pharmacokinetic study of XRP6258 (RPR 116258A), a novel taxane, administered as a 1-hour infusion every 3 weeks in patients with advanced solid tumors | journal = Clinical Cancer Research | volume = 15 | issue = 2 | pages = 723–30 | date = January 2009 | pmid = 19147780 | doi = 10.1158/1078-0432.CCR-08-0596 | doi-access = free }}</ref> |
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=== Metabolism === |
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Cabazitaxel is metabolized in the liver by [cytochrome P<sub>450</sub> (CYP)3A4/5 > CYP2C8], which result in seven plasma metabolites and excreted 20 metabolites. During 14 days after administration, 80% of cabazitaxel is excreted: 76% in the feces and 3.7% as a renal excretion.<ref name=":0">{{cite journal | vauthors = Tsao CK, Cutting E, Martin J, Oh WK | title = The role of cabazitaxel in the treatment of metastatic castration-resistant prostate cancer | journal = Therapeutic Advances in Urology | volume = 6 | issue = 3 | pages = 97–104 | date = June 2014 | pmid = 24883107 | pmc = 4003844 | doi = 10.1177/1756287214528557 }}</ref> |
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== References == |
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{{reflist}} |
{{reflist}} |
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== External links == |
== External links == |
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* {{ClinicalTrialsGov|NCT00417079|XRP6258 Plus Prednisone Compared to Mitoxantrone Plus Prednisone in Hormone Refractory Metastatic Prostate Cancer (TROPIC)}} |
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* [http://www.jevtana.com Cabazitaxel] - Official web site of manufacturer. |
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* {{ClinicalTrialsGov|NCT01308580|Cabazitaxel at 20 mg/m² Compared to 25 mg/m² With Prednisone for the Treatment of Metastatic Castration Resistant Prostate Cancer (PROSELICA)}} |
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* [http://products.sanofi-aventis.us/jevtana/jevtana.html Cabazitaxel Prescribing Information] - Official prescribing information. |
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* {{ClinicalTrialsGov|NCT02485691|Cabazitaxel Versus the Switch to Alternative AR-targeted Agent (Enzalutamide or Abiraterone) in Metastatic Castration-resistant Prostate Cancer (mCRPC) Patients Previously Treated With Docetaxel and Who Rapidly Failed a Prior AR-targeted Agent (CARD)}} |
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* [http://druginfo.nlm.nih.gov/drugportal/dpdirect.jsp?name=Cabazitaxel U.S. National Library of Medicine: Drug Information Portal - Cabazitaxel] |
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{{Chemotherapeutic agents}} |
{{Chemotherapeutic agents}} |
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{{Portal bar | Medicine}} |
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{{Authority control}} |
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[[Category:Microtubule inhibitors]] |
[[Category:Microtubule inhibitors]] |
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[[Category:Mitotic inhibitors]] |
[[Category:Mitotic inhibitors]] |
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[[Category:Carbamates]] |
[[Category:Carbamates]] |
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[[Category: |
[[Category:]] |
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[[Category:Acetate esters]] |
[[Category:Acetate esters]] |
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[[Category:Taxanes]] |
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[[Category:Tert-Butyl esters]] |
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{{antineoplastic-drug-stub}} |
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[[de:Cabazitaxel]] |
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[[nl:Cabazitaxel]] |
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[[ja:カバジタキセル]] |
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[[pt:Cabazitaxel]] |