15β-Hydroxycyproterone acetate

Chemical compound (1R,3aS,3bR,8bS,8cS,10aS)-1-acetyl-5-chloro-3-hydroxy-8b,10a-dimethyl-7-oxo-1,2,3,3a,3b,7,7a,8,8a,8b,8c,9,10,10a-tetradecahydrocyclopenta[a]cyclopropa[g]phenanthren-1-yl acetate 15β-Hydroxycyproterone acetate.svg skin-invert-image 225px correct CAS 65423-26-9 114884-50-3 (non-specific stereochemistry) correct FDA 54AF4JYT3F 10025840 170395 15β-Hydroxy-CPA; 15β-OH-CPA; 6-Chloro-15β,17α-dihydroxy-1α,2α-methylenepregna-4,6-diene-3,20-dione 17α-acetate; 6-Chloro-1,2α-methylene-15β,17α-dihydroxy-δ6-progesterone 17α-acetate 24 29 1 5 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)O)OC(=O)C 1S/C24H29ClO5/c1-11(26)24(30-12(2)27)10-20(29)21-14-8-18(25)17-9-19(28)13-7-16(13)23(17,4)15(14)5-6-22(21,24)3/h8-9,13-16,20-21,29H,5-7,10H2,1-4H3/t13-,14-,15+,16+,20?,21-,22+,23+,24+/m1/s1 HRANPRDGABOKNQ-XHLVMSDXSA-N 15β-Hydroxycyproterone acetate (15β-OH-CPA) is a steroidal antiandrogen and the major metabolite of cyproterone acetate (CPA). Saleh FM Pharmacological Treatment of Paraphilic Sex Offenders Saleh FM Sex Offenders: Identification, Risk Assessment, Treatment, and Legal Issues https://books.google.com/books?id=df0RDAAAQBAJ&pg=PA197 11 February 2009 Oxford University Press, USA 978-0-19-517704-6 197– Bińkowska M, Woroń J Progestogens in menopausal hormone therapy Przegla̜d Menopauzalny = Menopause Review 14 2 134–143 June 2015 26327902 4498031 10.5114/pm.2015.52154 Boarder M, Newby D, Navti P Pharmacogical Treatment of Cancer Pharmacology for Pharmacy and the Health Sciences: A Patient-centred Approach https://books.google.com/books?id=KVicAQAAQBAJ&pg=PA632 25 March 2010 OUP Oxford 978-0-19-955982-4 632– It is formed from CPA in the liver by hydroxylation via the cytochrome P450 enzyme CYP3A4. During therapy with CPA, 15β-OH-CPA circulates at concentrations that are approximately twice those of CPA. Frith RG, Phillipou G 15-Hydroxycyproterone acetate and cyproterone acetate levels in plasma and urine Journal of Chromatography 338 1 179–186 February 1985 3160716 10.1016/0378-4347(85)80082-7 15β-OH-CPA has similar or even greater antiandrogen activity compared to CPA. Neumann F Pharmacological basis for clinical use of antiandrogens James VH, Pasqualini JR Hormonal Steroids: Proceedings of the Sixth International Congress on Hormonal Steroids https://books.google.com/books?id=1VMJAwAAQBAJ&pg=PA398 22 October 2013 Elsevier 978-1-4831-9067-9 398– However, it has only about one-tenth of the activity of CPA as a progestogen. Kuhl H Pharmacology of estrogens and progestogens: influence of different routes of administration Climacteric 8 Suppl 1 3–63 August 2005 16112947 10.1080/13697130500148875 24616324 15β-OH-CPA also shows some glucocorticoid activity, similarly to CPA and unesterified cyproterone. Bhargava AS, Kapp JF, Poggel HA, Heinick J, Nieuweboer B, Günzel P Effect of cyproterone acetate and its metabolites on the adrenal function in man, rhesus monkey and rat Arzneimittel-Forschung 31 6 1005–1009 1981 6266428 Excerpta medica. Section 30. Pharmacology and toxicology https://books.google.com/books?id=5DIjAQAAIAAJ 1982 In addition, cyprosterone acetate and its main metabolite, 15β-hydroxy acetate, as well as the newly isolated free alcohol of the main metabolite were characterized for their corticosteroid-like activity in rats. Cyproterone acetate treatment of male hypersexual subjects and female rhesus monkeys did not reveal any signs of adrenal suppression. Cyproterone acetate and its metabolites gave no indication of any appreciable antiinflammatory effect in the adjuvant edema test in rats. However, there was a general increase in the level of blood glucose and liver glycogen as well as a reduction in body weight and organ weight (spleen, thymus and adrenal) in rats, in which 15β-hydroxy cyproterone was slightly more active with the exception of adrenal weight reduction, which was almost equal in all three compounds tested. It can also be concluded that adult man and rhesus monkey are much less sensitive, if at all so, to some corticosteroid-like activities of cyproterone acetate and its main metabolites than the rat. See also List of steroidal antiandrogens References Category:Acetate esters Category:Antiandrogen esters Category:Cyclopentanols Category:Organochlorides Category:Conjugated dienes Category:Cyclopropanes Category:Cyproterone acetate Category:Enones Category:Glucocorticoids Category:Human drug metabolites Category:Pregnanes Category:Progestogens Category:Steroid esters Category:Steroidal antiandrogens