Pitolisant

{{chembox-lat | Verifiedfields = | verifiedrevid = 464208162 |ImageFile=BF2649_structure.png |ImageSize=200px |IUPACName=1-{3-[3-(4-hlorofenil)propoksi]propil}piperidin |OtherNames= BF2.649 |Section1=! colspan=2 style="background: #f8eaba; text-align: center;" |Identifikacija

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CAS broj

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903576-44-3^Y

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3D model (Jmol)

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interaktivna slika

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| ChemSpider

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8123714^Y

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PubChem^[1]^[2] C ID

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9948102

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SMILES

Clc1ccc(cc1)CCCOCCCN2CCCCC2

|- |Section2=! colspan=2 style="background: #f8eaba; text-align: center;" |Svojstva

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Hemijska formula

| C₁₇H₂₆ClNO

|- | Molarna masa

| 295,846 g/mol

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Pitolisant (INN) ili tiprolisant (USAN) je inverzni agonist/antagonist histaminskog receptora koji je selektivan za H₃ receptor.^[3] On ima stimulantne i nootropne efekte u životinjskim studijama,^[4] i može da ima nekoliko potencijalnih medicinskih primena. Istražen je za tretman narkolepsije, i za tu indikaciju mu je odobren status orfan leka u EU i SAD.^[5]^[6] On je u kliničkim ispitivanjima za šizofreniju i Parkinsonova bolest.^[6]^[7]^[8]

Pitolisant je razvijen nakon otkrića H3 receptora.^[9] Pitolisant je prvi inverzni agonist H3 receptora sa kliničkom primenom.

Reference

^ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today. 15 (23-24): 1052—7. PMID 20970519. doi:10.1016/j.drudis.2010.10.003. уреди
^ Evan E. Bolton; Yanli Wang; Paul A. Thiessen; Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry. 4: 217—241. doi:10.1016/S1574-1400(08)00012-1.
^ Celanire S, Wijtmans M, Talaga P, Leurs R, de Esch IJ (2005). „Keynote review: histamine H3 receptor antagonists reach out for the clinic”. Drug Discov. Today. 10 (23-24): 1613—27. PMID 16376822. doi:10.1016/S1359-6446(05)03625-1.
^ -{Ligneau X, Perrin D, Landais L, Camelin JC, Calmels TP, Berrebi-Bertrand I, Lecomte JM, Parmentier R, Anaclet C, Lin JS, Bertaina-Anglade V, la Rochelle CD, d'Aniello F, Rouleau A, Gbahou F, Arrang JM, Ganellin CR, Stark H, Schunack W, Schwartz JC. BF2.649 [13-[3-(4-Chlorophenyl)propoxy]propyl}piperidine, hydrochloride], a nonimidazole inverse agonist/antagonist at the human histamine H3 receptor: Preclinical pharmacology. Journal of Pharmacology and Experimental Therapeutics. 320 (1): 365—75. јануар 2007. PMID 17005916. Недостаје или је празан параметар |title= (помоћ)
^ Lin JS, Dauvilliers Y, Arnulf I, Bastuji H, Anaclet C, Parmentier R, Kocher L, Yanagisawa M, Lehert P, Ligneau X, Perrin D, Robert P, Roux M, Lecomte JM, Schwartz JC (април 2008). „An inverse agonist of the histamine H(3) receptor improves wakefulness in narcolepsy: studies in orexin-/- mice and patients”. Neurobiology of Disease. 30 (1): 74—83. PMID 18295497.
^ ^а ^б Prous Science: Molecule of the Month September 2011
^ Ligneau, X.; Landais, L.; Perrin, D.; Piriou, J.; Uguen, M.; Denis, E.; Robert, P.; Parmentier, R.; Anaclet, C.; Lin, J. S.; Burban, A.; Arrang, J. M.; Schwartz, J. C. (април 2007). „Brain histamine and schizophrenia: Potential therapeutic applications of H3-receptor inverse agonists studied with BF2.649.” (PDF). Biochemical Pharmacology. 73 (8): 1215—24. PMID 17343831. doi:10.1016/j.bcp.2007.01.023.
^ Stocking EM, Letavic MA (2008). „Histamine H3 antagonists as wake-promoting and pro-cognitive agents”. Current Topics in Medicinal Chemistry. 8 (11): 988—1002. PMID 18673168. doi:10.2174/156802608784936728.
^ Schwartz, Jean-Charles (2011). „The histamine H3 receptor: From discovery to clinical trials with pitolisant”. British Journal of Pharmacology. 163 (4): 713—721. PMC 3111674 . PMID 21615387. doi:10.1111/j.1476-5381.2011.01286.x.

Spoljašnje veze

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today. 15 (23-24): 1052—7. PMID 20970519. doi:10.1016/j.drudis.2010.10.003. уреди

[2] Evan E. Bolton; Yanli Wang; Paul A. Thiessen; Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry. 4: 217—241. doi:10.1016/S1574-1400(08)00012-1.

[pmid16376822-3] Celanire S, Wijtmans M, Talaga P, Leurs R, de Esch IJ (2005). „Keynote review: histamine H3 receptor antagonists reach out for the clinic”. Drug Discov. Today. 10 (23-24): 1613—27. PMID 16376822. doi:10.1016/S1359-6446(05)03625-1.

[4] -{Ligneau X, Perrin D, Landais L, Camelin JC, Calmels TP, Berrebi-Bertrand I, Lecomte JM, Parmentier R, Anaclet C, Lin JS, Bertaina-Anglade V, la Rochelle CD, d'Aniello F, Rouleau A, Gbahou F, Arrang JM, Ganellin CR, Stark H, Schunack W, Schwartz JC. BF2.649 [13-[3-(4-Chlorophenyl)propoxy]propyl}piperidine, hydrochloride], a nonimidazole inverse agonist/antagonist at the human histamine H3 receptor: Preclinical pharmacology. Journal of Pharmacology and Experimental Therapeutics. 320 (1): 365—75. јануар 2007. PMID 17005916. Недостаје или је празан параметар |title= (помоћ)

[5] Lin JS, Dauvilliers Y, Arnulf I, Bastuji H, Anaclet C, Parmentier R, Kocher L, Yanagisawa M, Lehert P, Ligneau X, Perrin D, Robert P, Roux M, Lecomte JM, Schwartz JC (април 2008). „An inverse agonist of the histamine H(3) receptor improves wakefulness in narcolepsy: studies in orexin-/- mice and patients”. Neurobiology of Disease. 30 (1): 74—83. PMID 18295497.

[Prous-6] а ^б Prous Science: Molecule of the Month September 2011

[7] Ligneau, X.; Landais, L.; Perrin, D.; Piriou, J.; Uguen, M.; Denis, E.; Robert, P.; Parmentier, R.; Anaclet, C.; Lin, J. S.; Burban, A.; Arrang, J. M.; Schwartz, J. C. (април 2007). „Brain histamine and schizophrenia: Potential therapeutic applications of H3-receptor inverse agonists studied with BF2.649.” (PDF). Biochemical Pharmacology. 73 (8): 1215—24. PMID 17343831. doi:10.1016/j.bcp.2007.01.023.

[pmid18673168-8] Stocking EM, Letavic MA (2008). „Histamine H3 antagonists as wake-promoting and pro-cognitive agents”. Current Topics in Medicinal Chemistry. 8 (11): 988—1002. PMID 18673168. doi:10.2174/156802608784936728.

[9] Schwartz, Jean-Charles (2011). „The histamine H3 receptor: From discovery to clinical trials with pitolisant”. British Journal of Pharmacology. 163 (4): 713—721. PMC 3111674 . PMID 21615387. doi:10.1111/j.1476-5381.2011.01286.x.

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