Cyproterone acetate

Cyproterone acetate
Clinical data


Trade names	Androcur, Androcur Depot, Cyprostat, many others
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy category	X
Routes of administration	Oral, intramuscular injection
ATC code	G03HA01 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	100%
Protein binding	Albumin: 93% Free: 7%
Metabolism	Hepatic (CYP3A4)
Metabolites	• 15β-OH-CPA (major) • Cyproterone (minor) • Acetic acid (minor)
Biological half-life	Oral: 38 hours Intramusclar: 72 hours
Excretion	Feces: 70% Urine: 30%
Identifiers
IUPAC name (1S,2S,3S,5R,11R,12S,15R,16S)-15-acetyl-9-chloro-2,16-dimethyl-6-oxopentacyclo[9.7.0.0²,⁸.0³,⁵.0¹²,¹⁶]octadeca-7,9-dien-15-yl acetate
Synonyms	SH-80714; SH-714; NSC-81430; 6-Chloro-1β,2β-dihydro-17α-hydroxy-3'H-cyclopropa(1,2)pregna-1,4,6-triene-3,20-dione acetate; 6-Chloro-17α-hydroxy-1α,2α-methylenepregna-4,6-diene-3,20-dione acetate; 6-Chloro-1,2α-methylene-17α-hydroxy-δ⁶-progesterone acetate
CAS Number	427-51-0^Y
PubChem CID	9880
IUPHAR/BPS	2865
DrugBank	DB04839
ChemSpider	9496^Y
UNII	4KM2BN5JHF
KEGG	D01368
ChEBI	CHEBI:50743^Y
ChEMBL	CHEMBL139835^Y
ECHA InfoCard	100.006.409
Chemical and physical data
Formula	C₂₄H₂₉ClO₄
Molar mass	416.94 g/mol
3D model (Jmol)	Interactive image
SMILES O=C4\C=C3\C(\Cl)=C/[C@@H]1[C@H](CC[C@@]2([C@@](OC(=O)C)(C(=O)C)CC[C@@H]12)C)[C@@]3(C)[C@H]5C[C@@H]45
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 Key:UWFYSQMTEOIJJG-FDTZYFLXSA-N

Cyproterone acetate (abbreviated as CPA), sold alone under the brand name Androcur or with ethinylestradiol (EE) as Diane or Diane-35 among others, is an antiandrogen and progestogen that is used in the treatment of androgen-related conditions like acne, hirsutism (excessive hair growth), early-onset puberty, and prostate cancer, as a component of hormone therapy for transgender women, and in oral contraceptives. It is formulated and used both alone and in combination with an estrogen and is available for use both by mouth and by injection into muscle.

CPA blocks the effects of androgens like testosterone in the body, which it does by preventing them from interacting with their biological target, the androgen receptor (AR), and by reducing their production by the gonads and hence their concentrations in the body. In addition, it has progesterone-like effects by activating the progesterone receptor (PR). CPA is well-absorbed, is extensively bound to plasma proteins, and has an elimination half-life of around 40 hours.

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Wikipedia