Cyproterone

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This article is about a non-clinically used antiandrogen compound. For the pharmaceutical drug, see cyproterone acetate.
Cyproterone
Cyproterone.png
Systematic (IUPAC) name
6-chloro-17-hydroxy-1α,2α-methylenepregna-4,6-diene-3,20-dione
Identifiers
CAS Number 2098-66-0 YesY
ATC code G03HA01 (WHO)
PubChem CID: 5284537
DrugBank DB04839 YesY
ChemSpider 4447594 YesY
ChEMBL CHEMBL142130 YesY
Chemical data
Formula C22H27ClO3
Molecular mass 374.901 g/mol
  • O=C4\C=C3\C(\Cl)=C/[C@@H]1[C@H](CC[C@@]2([C@@](O)(C(=O)C)CC[C@@H]12)C)[C@@]3(C)[C@H]5C[C@@H]45
  • InChI=1S/C22H27ClO3/c1-11(24)22(26)7-5-14-12-9-18(23)17-10-19(25)13-8-16(13)21(17,3)15(12)4-6-20(14,22)2/h9-10,12-16,26H,4-8H2,1-3H3/t12-,13+,14-,15-,16-,20-,21-,22-/m0/s1 YesY
  • Key:DUSHUSLJJMDGTE-ZJPMUUANSA-N YesY
 NYesY (what is this?)  (verify)

Cyproterone (INN) is a steroidal antiandrogen that was never marketed.[1][2][3] An acylated derivative, cyproterone acetate, is widely used clinically as an antiandrogen and progestin.[1][2][3] While cyproterone is sometimes used as a synonym for cyproterone acetate, what is almost always being referred to is actually cyproterone acetate and not cyproterone.

Cyproterone has approximately three-fold lower potency as an antiandrogen relative to CPA,[4] and, unlike CPA, which is an extremely potent progestin, cyproterone is completely devoid of progestogenic activity.[5] In clinical studies, cyproterone was found to be far less potent and effective as an antiandrogen relative to CPA, likely due to its lack of antigonadotropic action.[6]

See also

References

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