15β-Hydroxycyproterone acetate

15β-Hydroxycyproterone acetate
Clinical data
Other names	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
Identifiers
	IUPAC name (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;
CAS Number	65423-26-9 ; 114884-50-3 (non-specific stereochemistry);
PubChem CID	10025840;
ChemSpider	170395;
UNII	54AF4JYT3F;
Chemical and physical data
Formula	C24H29ClO5
Molar mass	432.94 g·mol−1
3D model (JSmol)	Interactive image;
	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)O)OC(=O)C;
	InChI InChI=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; Key:HRANPRDGABOKNQ-XHLVMSDXSA-N;

15β-Hydroxycyproterone acetate (15β-OH-CPA) is a steroidal antiandrogen and the major metabolite of cyproterone acetate (CPA). 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. 15β-OH-CPA has similar or even greater antiandrogen activity compared to CPA. However, it has only about one-tenth of the activity of CPA as a progestogen. 15β-OH-CPA also shows some glucocorticoid activity, similarly to CPA and unesterified cyproterone.

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