U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C24H29ClO4
Molecular Weight 416.938
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Cyproterone Acetate

SMILES

CC(=O)O[C@@]1(CC[C@H]2[C@@H]3C=C(Cl)C4=CC(=O)[C@@H]5C[C@@H]5[C@]4(C)[C@H]3CC[C@]12C)C(C)=O

InChI

InChIKey=UWFYSQMTEOIJJG-FDTZYFLXSA-N
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

HIDE SMILES / InChI

Molecular Formula C24H29ClO4
Molecular Weight 416.938
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Cyproterone acetate is a steroid drug which was developed by Schering A.G (now Bayer). Cyproterone acetate was approved in Canada, Asia, Latin America and Europe for the treatment of sever acne under the name Diane-35 (ethinyl estradiol) and its mechanism of action in this condition is explained by competitive inhibition of androgen receptor AR. In Canada cyproterone acetate is widely used as a contraceptive, however its usage is associated with liver toxicity and clots formation. In the UK the drug is marketed for the treatment of prostate cancer (Cyproterone acetate brand name).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
4.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
DIANE-35

Approved Use

DIANE-35 (cyproterone acetate and ethinyl estradiol) is indicated for the treatment of women with severe acne, with associated symptoms of androgenization, including seborrhea and mild hirsutism.
Primary
CYPROTERONE ACETATE

Approved Use

Cyproterone Acetate tablets are used in men to treat prostate cancer
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
406 ng/mL
300 mg 1 times / week steady-state, intramuscular
dose: 300 mg
route of administration: Intramuscular
experiment type: STEADY-STATE
co-administered:
CYPROTERONE ACETATE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
70 ng × h/mL
300 mg 1 times / week steady-state, intramuscular
dose: 300 mg
route of administration: Intramuscular
experiment type: STEADY-STATE
co-administered:
CYPROTERONE ACETATE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.9 day
300 mg 1 times / week steady-state, intramuscular
dose: 300 mg
route of administration: Intramuscular
experiment type: STEADY-STATE
co-administered:
CYPROTERONE ACETATE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
200 mg 1 times / day multiple, oral
Recommended
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
unhealthy, Mean age 72.6 years
Health Status: unhealthy
Age Group: Mean age 72.6 years
Sex: M
Sources:
Other AEs: Hot flushes, Gynaecomastia...
Other AEs:
Hot flushes (30%)
Gynaecomastia (19.5%)
Headache (12.3%)
Skin and subcutaneous tissue disorders NEC (6.8%)
Sources:
100 mg 1 times / day multiple, oral
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: F
Sources:
Disc. AE: Depression, Weight increase...
Other AEs: Amenorrhea, Weight gain...
AEs leading to
discontinuation/dose reduction:
Depression
Weight increase
Headache
Libido decreased
Fatigue (6.7%)
Other AEs:
Amenorrhea (32.6%)
Weight gain
Sources:
600 mg 1 times / day multiple, oral
Highest studied dose
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
unhealthy, children
Health Status: unhealthy
Age Group: children
Sex: M+F
Sources:
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy
AEs

AEs

AESignificanceDosePopulation
Headache 12.3%
200 mg 1 times / day multiple, oral
Recommended
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
unhealthy, Mean age 72.6 years
Health Status: unhealthy
Age Group: Mean age 72.6 years
Sex: M
Sources:
Gynaecomastia 19.5%
200 mg 1 times / day multiple, oral
Recommended
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
unhealthy, Mean age 72.6 years
Health Status: unhealthy
Age Group: Mean age 72.6 years
Sex: M
Sources:
Hot flushes 30%
200 mg 1 times / day multiple, oral
Recommended
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
unhealthy, Mean age 72.6 years
Health Status: unhealthy
Age Group: Mean age 72.6 years
Sex: M
Sources:
Skin and subcutaneous tissue disorders NEC 6.8%
200 mg 1 times / day multiple, oral
Recommended
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
unhealthy, Mean age 72.6 years
Health Status: unhealthy
Age Group: Mean age 72.6 years
Sex: M
Sources:
Weight gain
100 mg 1 times / day multiple, oral
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: F
Sources:
Amenorrhea 32.6%
100 mg 1 times / day multiple, oral
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: F
Sources:
Fatigue 6.7%
Disc. AE
100 mg 1 times / day multiple, oral
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: F
Sources:
Depression Disc. AE
100 mg 1 times / day multiple, oral
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: F
Sources:
Headache Disc. AE
100 mg 1 times / day multiple, oral
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: F
Sources:
Libido decreased Disc. AE
100 mg 1 times / day multiple, oral
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: F
Sources:
Weight increase Disc. AE
100 mg 1 times / day multiple, oral
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: F
Sources:
Overview

Overview

OverviewOther

Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Genomic models of short-term exposure accurately predict long-term chemical carcinogenicity and identify putative mechanisms of action.
2014
Bisphenol A affects androgen receptor function via multiple mechanisms.
2013-05-25
Anabolic-androgenic steroids induce apoptosis and NOS2 (nitric-oxide synthase 2) in adult rat Leydig cells following in vivo exposure.
2012-12
Chemical genomics profiling of environmental chemical modulation of human nuclear receptors.
2011-08
Regulation and dysregulation of vitellogenin mRNA accumulation in daphnids (Daphnia magna).
2011-01-25
Arylpiperazines for management of benign prostatic hyperplasia: design, synthesis, quantitative structure-activity relationships, and pharmacokinetic studies.
2011-01-13
Relative progestational and androgenic activity of four progestins used for male hormonal contraception assessed in vitro in relation to their ability to suppress LH secretion in the castrate male rat.
2010-10-26
Testosterone-induced modulation of nitric oxide-cGMP signaling pathway and androgenesis in the rat Leydig cells.
2010-09
Abrupt regression of a meningioma after discontinuation of cyproterone treatment.
2010-09
Prolactinoma induced by estrogen and cyproterone acetate in a male-to-female transsexual.
2010-08
Fatal fulminant hepatitis in a chimpanzee (Pan troglodytes) receiving cyproterone acetate.
2009-12
[A case of Budd-Chiari syndrome induced by ethinylestradiol and cyproterone acetate].
2009-12
Increased thrombin-activatable fibrinolysis inhibitor antigen levels as a clue for prothrombotic state in polycystic ovary syndrome.
2008-09
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.
2008-04
Activity of androgen receptor antagonist bicalutamide in prostate cancer cells is independent of NCoR and SMRT corepressors.
2007-09-01
Venous thromboembolism and cyproterone acetate in men with prostate cancer: a study using the General Practice Research Database.
2007-06
Antiandrogenic activity of norgestimate in a human androgen-dependent stable-transfected cell line.
2007-04
Ligand-specific dynamics of the androgen receptor at its response element in living cells.
2007-03
Environmental xenobiotics and the antihormones cyproterone acetate and spironolactone use the nuclear hormone pregnenolone X receptor to activate the CYP3A23 hormone response element.
1998-12
Synthesis and biological activity of a novel series of nonsteroidal, peripherally selective androgen receptor antagonists derived from 1,2-dihydropyridono[5,6-g]quinolines.
1998-02-12
Follow-up study of children with precocious puberty treated with cyproterone acetate. Ad hoc Committee for CPA.
1997-09
Severe hepatitis and liver failure induced by cyproterone acetate.
1996-10
Lactotroph hyperplasia in an estrogen treated male-to-female transsexual patient.
1996-09
Carcinogenicity of cyproterone acetate in the mouse.
1996-07
[Fatal sub-fulminant hepatitis caused by cyproterone acetate. A new case].
1996
Cyproterone acetate in the treatment of advanced prostatic cancer: retrospective analysis of liver toxicity in the long-term follow-up of 89 patients.
1996
Hepatocellular carcinoma after treatment with cyproterone acetate combined with ethinyloestradiol.
1995-02-18
Hepatocellular carcinoma during hormonotherapy for prostatic cancer.
1994-10
[Fatal hepatitis caused by cyproterone acetate].
1994-03-01
Fatal fulminant hepatitis from cyproterone acetate.
1994-03
Double-blind placebo crossover study of cyproterone acetate in the treatment of the paraphilias.
1993-10
Cyproterone acetate generates DNA adducts in rat liver and in primary rat hepatocyte cultures.
1993-03
[Fatal subfulminant hepatitis caused by cyproterone acetate].
1991
Severe hepatitis caused by cyproterone acetate.
1990-05
Induction of dorsolateral prostate adenocarcinomas and other accessory sex gland lesions in male Wistar rats by a single administration of N-methyl-N-nitrosourea, 7,12-dimethylbenz(a)anthracene, and 3,2'-dimethyl-4-aminobiphenyl after sequential treatment with cyproterone acetate and testosterone propionate.
1990-02-01
Characterization of adenocarcinomas of the dorsolateral prostate induced in Wistar rats by N-methyl-N-nitrosourea, 7,12-dimethylbenz(a)anthracene, and 3,2'-dimethyl-4-aminobiphenyl, following sequential treatment with cyproterone acetate and testosterone propionate.
1990-02-01
[Hepatitis after treatment with cyproterone acetate. Apropos of a case].
1990
Fulminant hepatitis due to cyproterone acetate.
1989-01-28
Pulmonary embolism after short-term treatment of acne vulgaris with ovulation suppressor agents.
1986-10-06
Comparison of diethylstilbestrol, cyproterone acetate and medroxyprogesterone acetate in the treatment of advanced prostatic cancer: final analysis of a randomized phase III trial of the European Organization for Research on Treatment of Cancer Urological Group.
1986-09
Cardiovascular side effects of diethylstilbestrol, cyproterone acetate, medroxyprogesterone acetate and estramustine phosphate used for the treatment of advanced prostatic cancer: results from European Organization for Research on Treatment of Cancer trials 30761 and 30762.
1986-02
The effect of cyproterone and gonadotrophins on the adrenal gland of juvenile and adult rats. A morphological and morphometrical study.
1985-03
Follow-up of prolactin levels in long-term oestrogen-treated male-to-female transsexuals with regard to prolactinoma induction.
1985-02
Effects of cyproterone acetate on adrenal steroidogenesis in vitro.
1984
Androgen antagonists in androgen target tissues.
1984
Effect of cyproterone acetate on glucocorticoid secretion in patients treated for hirsutism.
1983-10
Teratogenic effects of cyproterone acetate and medroxyprogesterone treatment during the pre- and postimplantation period of mouse embryos. I.
1982-02
[Prevention of testosterone-vasopressin induced necrosis of the kidney cortex by cyproterone acetate].
1979-07
Cyproterone acetate-promoted prevention of renal cortical necrosis following testosterone and vasopressin administration.
1979-02
Androgen dynamics in vitro in the human prostate gland. Effect of cyproterone and cyproterone acetate.
1973-03
Patents

Sample Use Guides

Acne: 1 tablet containing 2 mg cyproterone acetate and 0.035 mg ethinyl estradiol is taken daily for 21 consecutive days beginning on day 1 of the menstrual cycle. The tablets are then discontinued for 7 days and the cycle repeats. Prostatic cancer: the usual dose range is from 1 tablet once a day (100mg) up to 1 tablet three times a day (300mg).
Route of Administration: Oral
Primary explants (approx. 1 mm3) of prostate tissue from patients with benign prostatic hyperplasia were treated with 10 nM dihydrotestosterone, 50 pM diethylstilbestrol and 100 nM cyproterone acetate to test steroids action on oxytocin secretion.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:48:40 GMT 2025
Edited
by admin
on Mon Mar 31 17:48:40 GMT 2025
Record UNII
4KM2BN5JHF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Cyproterone Acetate
EP   HSDB   JAN   MART.   MI   USAN   WHO-DD  
USAN  
Official Name English
ANDROCUR
Preferred Name English
6-Chloro-3,20-dioxo-1?,2?-dihydro-3?H-cyclopropa[1,2]pregna-1,4,6-trien-17-yl acetate
Systematic Name English
CYPROTERONE ACETATE [EP MONOGRAPH]
Common Name English
CYPROTERONE ACETATE [JAN]
Common Name English
NSC-81430
Code English
CYPROTERONE ACETATE [HSDB]
Common Name English
CYPROTERONE ACETATE [USAN]
Common Name English
SH-714
Code English
CYPROSTAT
Brand Name English
Cyproterone acetate [WHO-DD]
Common Name English
CYPROTERONE ACETATE [MI]
Common Name English
(1?,2?)-17-(Acetyloxy)-6-chloro-1,2-dihydro-3?H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione
Systematic Name English
6-Chloro-17-hydroxy-1?,2?-methylenepregna-4,6-diene-3,20-dione acetate
Systematic Name English
CYPROTERONE ACETATE [MART.]
Common Name English
SH714
Code English
3?H-Cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione, 17-(acetyloxy)-6-chloro-1,2-dihydro-, (1?,2?)-
Systematic Name English
Cyproterone 17?-acetate
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 3884
Created by admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
NCI_THESAURUS C146993
Created by admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
Code System Code Type Description
RXCUI
22054
Created by admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
PRIMARY RxNorm
ECHA (EC/EINECS)
207-048-3
Created by admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
PRIMARY
DRUG CENTRAL
766
Created by admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
PRIMARY
SMS_ID
100000090321
Created by admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
PRIMARY
NSC
81430
Created by admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
PRIMARY
EPA CompTox
DTXSID5020366
Created by admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
PRIMARY
EVMPD
SUB01539MIG
Created by admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
PRIMARY
MESH
D017373
Created by admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
PRIMARY
MERCK INDEX
m4041
Created by admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
PRIMARY Merck Index
HSDB
3592
Created by admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
PRIMARY
CHEBI
50743
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PRIMARY
PUBCHEM
9880
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PRIMARY
IUPHAR
2865
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PRIMARY
FDA UNII
4KM2BN5JHF
Created by admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
PRIMARY
NCI_THESAURUS
C1059
Created by admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
PRIMARY
WIKIPEDIA
CYPROTERONE ACETATE
Created by admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
PRIMARY
ChEMBL
CHEMBL139835
Created by admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
PRIMARY
DRUG BANK
DB04839
Created by admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
PRIMARY
CAS
427-51-0
Created by admin on Mon Mar 31 17:48:41 GMT 2025 , Edited by admin on Mon Mar 31 17:48:41 GMT 2025
PRIMARY
Related Record Type Details
TARGET -> AGONIST
BINDING
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METABOLITE ACTIVE -> PARENT
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ACTIVE MOIETY