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Human drug metabolites
15β-Hydroxycyproterone acetate
Другие языки:

    15β-Hydroxycyproterone acetate

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    15β-Hydroxycyproterone acetate
    15β-Hydroxycyproterone acetate.svg
    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
    • (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
    PubChem CID
    ChemSpider
    UNII
    Chemical and physical data
    Formula C24H29ClO5
    Molar mass 432.94 g·mol−1
    3D model (JSmol)
    • 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=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.

    See also



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