15β-Hydroxycyproterone acetate

15β-Hydroxycyproterone acetate

Clinical data
Synonyms	15β-Hydroxy-CPA; 15β-OH-CPA
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	114884-50-3
PubChem CID	10025840
ChemSpider	170395
Chemical and physical data
Formula	C24H29ClO5
Molar mass	432.941 g/mol
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 which is formed from it in the liver by hydroxylation via the enzyme CYP3A4. It circulates at concentrations that are approximately twice those of CPA. In addition, it has similar or even greater antiandrogen activity relative to CPA but only about one-tenth of its activity as a progestogen. It also shows some glucocorticoid activity similarly to cyproterone acetate and unesterified cyproterone.