Cyproterone

Cyproterone
Clinical data
Other names	SH-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 class	Steroidal antiandrogen
ATC code	G03HA01 (WHO) ;
Identifiers
	IUPAC name (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	2098-66-0 ;
PubChem CID	5284537;
ChemSpider	4447594 ;
UNII	E61Q31EK2F;
ChEMBL	ChEMBL142130 ;
CompTox Dashboard (EPA)	DTXSID3022873 ;
ECHA InfoCard	100.218.313
Chemical and physical data
Formula	C22H27ClO3
Molar mass	374.91 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;
	InChI 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 ; Key:DUSHUSLJJMDGTE-ZJPMUUANSA-N ;
	(verify)

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.^[1]^[2]^[3] It is a precursor of cyproterone acetate (CPA), an antiandrogen, progestin, and antigonadotropin which was introduced instead of cyproterone and is widely used as a medication.^[1]^[2] Cyproterone and CPA were among the first antiandrogens to be developed.^[4]

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.

^ ^a ^b Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 339–. ISBN 978-1-4757-2085-3.
^ ^a ^b Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 289. ISBN 978-3-88763-075-1. Retrieved 29 May 2012.
^ Orfanos CE, Happle R (1990). Hair and Hair Diseases. Springer Science & Business Media. pp. 1197–. ISBN 978-3-642-74612-3.
^ Cite error: The named reference SchröderRadlmaier2009 was invoked but never defined (see the help page).

[Elks2014-1] Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 339–. ISBN 978-1-4757-2085-3.

[IndexNominum2000-2] Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 289. ISBN 978-3-88763-075-1. Retrieved 29 May 2012.

[OrfanosHapple1990-3] Orfanos CE, Happle R (1990). Hair and Hair Diseases. Springer Science & Business Media. pp. 1197–. ISBN 978-3-642-74612-3.

[SchröderRadlmaier2009-4] Cite error: The named reference SchröderRadlmaier2009 was invoked but never defined (see the help page).

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