15β-Hydroxycyproterone acetate

15β-Hydroxycyproterone acetate (15β-OH-CPA) is a steroidal antiandrogen and the major metabolite of cyproterone acetate (CPA).^[1][2][3] It is formed from CPA in the liver by hydroxylation via the cytochrome P450 enzyme CYP3A4.^[1][2][3] During therapy with CPA, 15β-OH-CPA circulates at concentrations that are approximately twice those of CPA.^[4] 15β-OH-CPA has similar or even greater antiandrogen activity compared to CPA.^[5] However, it has only about one-tenth of the activity of CPA as a progestogen.^[6] 15β-OH-CPA also shows some glucocorticoid activity, similarly to CPA and unesterified cyproterone.^[7][8]

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 Y 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

See also

• List of steroidal antiandrogens