Cyproterone

Cyproterone, also known by its developmental code name SH-80881, is a steroidal antiandrogen which was studied in the 1960s and 1970s but was never introduced for medical use. It is an precursor of cyproterone acetate (CPA), an antiandrogen, progestin, and antigonadotropin which was introduced instead of cyproterone and is widely used as a medication. Cyproterone and CPA were among the first antiandrogens to be developed.

This article is about a non-medically used antiandrogen. For the pharmaceutical medication, see Cyproterone acetate.

Cyproterone
Clinical data
Other namesSH-80881; SH-881; NSC-758636; 1α,2α-Methylene-6-chloro-17α-hydroxy-δ6-progesterone; 1α,2α-Methylene-6-chloro-17α-hydroxypregna-4,6-diene-3,20-dione
Routes of
administration		By mouth, topical
Drug classSteroidal antiandrogen
ATC code
Identifiers
  • (1S,2S,3S,5R,11R,12S,15R,16S)-15-acetyl-9-chloro-15-hydroxy-2,16-dimethylpentacyclo[9.7.0.02,8.03,5.012,16]octadeca-7,9-dien-6-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.218.313
Chemical and physical data
FormulaC22H27ClO3
Molar mass374.91 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
  • 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 Y
  • Key:DUSHUSLJJMDGTE-ZJPMUUANSA-N Y
  (verify)

It is important to clarify that the term cyproterone is often used as a synonym and shorthand for cyproterone acetate, and when the term occurs, what is almost always being referred to is, confusingly, CPA and not actually cyproterone. Cyproterone itself, unlike CPA, was never introduced for medical use and hence is not available as a medication.

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