Structure via PubChem · Public domain (PubChem)
cyproterone
Sign in to saveAlso known as Gen-Cyproterone, CyPat, Ciproterone, SH-80881
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 a 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.
In the Vinony graph
Vinony's link graph records 750 inbound references to cyproterone, and connects out to mometasone furoate, fludrocortisone and ulipristal acetate.
It is catalogued under topics including Abandoned drugs, Chemical pages without DrugBank identifier and Conjugated dienes.
Vinony links it to 13 Wikipedia language editions.
Chemical data
- Formula
- C22H27ClO3
- Molecular weight
- 374.9 g/mol
- 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
- 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
- InChIKey
- DUSHUSLJJMDGTE-ZJPMUUANSA-N
- XLogP
- 3.1
- Polar surface area
- 54.4 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
- Indications
- polycystic ovary syndrome
via ChEMBL · EBI
Research
3,849 papers- Cyproterone. A review of its pharmacology and therapeutic efficacy in prostate cancer.Drugs & aging · 1994
- Cyproterone and hypersexuality.The New Zealand medical journal · 1977
- Cyproterone acetate.Lancet (London, England) · 1976
- Cyproterone acetate.Lancet (London, England) · 1976
- Cyproterone-induced hepatotoxicity.The Annals of pharmacotherapy · 1995
via PubMed
Wikidata facts
- Mass
- 374.165
- Has use
- medication
Show 6 more facts
- chemical formula
- C₂₂H₂₇ClO₃
- canonical SMILES
- CC(=O)C1(CCC2C1(CCC3C2C=C(C4=CC(=O)C5CC5C34C)Cl)C)O
- isomeric 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
- World Health Organisation international non-proprietary name
- cyproterone
- subject has role
- antiandrogen
- Commons category
- Cyproterone
via Wikidata · CC0
~6 min read
Encyclopedic overview
11 sectionsContents
- Pharmacology
- Pharmacodynamics
- Antiandrogenic activity
- Other activities
- Chemistry
- History
- Society and culture
- Generic names
- Research
- References
- Further reading
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 a 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.
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.
Excerpted from Wikipedia’s “cyproterone” article, available under the CC BY-SA 4.0 licence.