cyproterone acetate   

GtoPdb Ligand ID: 2865

Synonyms: Androcur® | Cyprostat® | SH-714
cyproterone acetate is an approved drug
Compound class: Synthetic organic
Comment: Cyproterone acetate is a steroidal, pure antiandrogen pharmaceutical agent.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 60.44
Molecular weight 416.18
XLogP 3.28
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CC(=O)OC1(CCC2C1(C)CCC1C2C=C(C2=CC(=O)C3C(C12C)C3)Cl)C(=O)C
Isomeric SMILES CC(=O)O[C@@]1(CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C=C(C2=CC(=O)[C@H]3[C@@H]([C@]12C)C3)Cl)C(=O)C
InChI InChI=1S/C24H29ClO4/c1-12(26)24(29-13(2)27)8-6-16-14-10-20(25)19-11-21(28)15-9-18(15)23(19,4)17(14)5-7-22(16,24)3/h10-11,14-18H,5-9H2,1-4H3/t14-,15+,16-,17-,18-,22-,23-,24-/m0/s1
InChI Key UWFYSQMTEOIJJG-FDTZYFLXSA-N
No information available.
Summary of Clinical Use
This drug is used as a form of chemical castration in patients with various androgen-dependent diseases (e.g. prostate cancer, benign prostatic hyperplasia, priapism and hypersexuality) and is used to treat acne and hirsutism in females. The progestogen activity of this compound is put to use in treatments for menopause associated hot flushes and in some combined oral contraceptive pills.
Mechanism Of Action and Pharmacodynamic Effects
This drug's primary action is as an antiandrogen but it also has additional progestogen and antigonadotropic properties.