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

Details

Stereochemistry ABSOLUTE
Molecular Formula C24H29ClO4
Molecular Weight 416.9385
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYPROTERONE ACETATE

SMILES

CC(=O)[C@]1(CC[C@@]2([H])[C@]3([H])C=C(C4=CC(=O)[C@]5([H])C[C@]5([H])[C@]4(C)[C@@]3([H])CC[C@@]21C)Cl)OC(=O)C

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 416.9385
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
Co-administed with::
LHRH analogue(monthly depot injections)
Sources:
unhealthy, Mean age 72.6 years
n = 293
Health Status: unhealthy
Condition: prostate cancer
Age Group: Mean age 72.6 years
Sex: M
Population Size: 293
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
n = 76
Health Status: unhealthy
Condition: hirsutism
Age Group: adult
Sex: F
Population Size: 76
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
Condition: precocious puberty
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
Co-administed with::
LHRH analogue(monthly depot injections)
Sources:
unhealthy, Mean age 72.6 years
n = 293
Health Status: unhealthy
Condition: prostate cancer
Age Group: Mean age 72.6 years
Sex: M
Population Size: 293
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
Co-administed with::
LHRH analogue(monthly depot injections)
Sources:
unhealthy, Mean age 72.6 years
n = 293
Health Status: unhealthy
Condition: prostate cancer
Age Group: Mean age 72.6 years
Sex: M
Population Size: 293
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
Co-administed with::
LHRH analogue(monthly depot injections)
Sources:
unhealthy, Mean age 72.6 years
n = 293
Health Status: unhealthy
Condition: prostate cancer
Age Group: Mean age 72.6 years
Sex: M
Population Size: 293
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
Co-administed with::
LHRH analogue(monthly depot injections)
Sources:
unhealthy, Mean age 72.6 years
n = 293
Health Status: unhealthy
Condition: prostate cancer
Age Group: Mean age 72.6 years
Sex: M
Population Size: 293
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
n = 76
Health Status: unhealthy
Condition: hirsutism
Age Group: adult
Sex: F
Population Size: 76
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
n = 76
Health Status: unhealthy
Condition: hirsutism
Age Group: adult
Sex: F
Population Size: 76
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
n = 76
Health Status: unhealthy
Condition: hirsutism
Age Group: adult
Sex: F
Population Size: 76
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
n = 76
Health Status: unhealthy
Condition: hirsutism
Age Group: adult
Sex: F
Population Size: 76
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
n = 76
Health Status: unhealthy
Condition: hirsutism
Age Group: adult
Sex: F
Population Size: 76
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
n = 76
Health Status: unhealthy
Condition: hirsutism
Age Group: adult
Sex: F
Population Size: 76
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
n = 76
Health Status: unhealthy
Condition: hirsutism
Age Group: adult
Sex: F
Population Size: 76
Sources:
Overview

Overview

OverviewOther

Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Androgen dynamics in vitro in the human prostate gland. Effect of cyproterone and cyproterone acetate.
1973 Mar
Teratogenic effects of cyproterone acetate and medroxyprogesterone treatment during the pre- and postimplantation period of mouse embryos. I.
1982 Feb
Effect of cyproterone acetate on glucocorticoid secretion in patients treated for hirsutism.
1983 Oct
Effects of cyproterone acetate on adrenal steroidogenesis in vitro.
1984
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 Feb
Pulmonary embolism after short-term treatment of acne vulgaris with ovulation suppressor agents.
1986 Oct 6
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 Sep
Fulminant hepatitis due to cyproterone acetate.
1989 Jan 28
[Hepatitis after treatment with cyproterone acetate. Apropos of a case].
1990
Effects of hypolipidemic drugs nafenopin and clofibrate on phenotypic expression and cell death (apoptosis) in altered foci of rat liver.
1990 Apr
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 Feb 1
Severe hepatitis caused by cyproterone acetate.
1990 May
[Fatal subfulminant hepatitis caused by cyproterone acetate].
1991
Hepatocellular carcinoma after treatment with cyproterone acetate combined with ethinyloestradiol.
1995 Feb 18
[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
Severe hepatitis and liver failure induced by cyproterone acetate.
1996 Oct
Lactotroph hyperplasia in an estrogen treated male-to-female transsexual patient.
1996 Sep
Follow-up study of children with precocious puberty treated with cyproterone acetate. Ad hoc Committee for CPA.
1997 Sep
Environmental xenobiotics and the antihormones cyproterone acetate and spironolactone use the nuclear hormone pregnenolone X receptor to activate the CYP3A23 hormone response element.
1998 Dec
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 Feb 12
Receptor-dependent regulation of the CYP3A4 gene.
2002 Dec 27
Estrogen and cyproterone acetate combination-induced autoimmune hepatitis.
2002 Jul
The nuclear pregnane X receptor: a key regulator of xenobiotic metabolism.
2002 Oct
Altered cognitive function in men treated for prostate cancer with luteinizing hormone-releasing hormone analogues and cyproterone acetate: a randomized controlled trial.
2002 Sep
Differential expression of c-fos and c-myc protooncogenes by estrogens, xenobiotics and other growth-stimulatory agents in primary rat hepatocytes.
2003 Mar
The risk of venous thromboembolism in women prescribed cyproterone acetate in combination with ethinyl estradiol: a nested cohort analysis and case-control study.
2003 Mar
Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.
2003 Oct
Metformin reduces serum C-reactive protein levels in women with polycystic ovary syndrome.
2003 Oct
Partial agonist/antagonist properties of androstenedione and 4-androsten-3beta,17beta-diol.
2004 Aug
Comparison of the Hershberger assay and androgen receptor binding assay of twelve chemicals.
2004 Feb 15
Venous thromboembolism associated with cyproterone acetate in combination with ethinyloestradiol (Dianette): observational studies using the UK General Practice Research Database.
2004 Jul
Study on anti-androgenic effects of bisphenol a diglycidyl ether (BADGE), bisphenol F diglycidyl ether (BFDGE) and their derivatives using cells stably transfected with human androgen receptor, AR-EcoScreen.
2004 Jun
Coregulator recruitment and histone modifications in transcriptional regulation by the androgen receptor.
2004 Nov
Antidiabetic activity of passive nonsteroidal glucocorticoid receptor modulators.
2005 Aug 11
CAR and PXR: xenosensors of endocrine disrupters?
2005 Aug 15
Development of androgen- and estrogen-responsive bioassays, members of a panel of human cell line-based highly selective steroid-responsive bioassays.
2005 Jan
Influence of exogenous oestrogen or (anti-) androgen administration on soluble transferrin receptor in human plasma.
2005 Jul
Transcriptomic and phylogenetic analysis of Kpna genes: a family of nuclear import factors modulated in xenobiotic-mediated liver growth.
2006 Sep
Antiandrogenic activity of norgestimate in a human androgen-dependent stable-transfected cell line.
2007 Apr
In silico prediction of pregnane X receptor activators by machine learning approaches.
2007 Jan
Venous thromboembolism and cyproterone acetate in men with prostate cancer: a study using the General Practice Research Database.
2007 Jun
Ligand-specific dynamics of the androgen receptor at its response element in living cells.
2007 Mar
Activity of androgen receptor antagonist bicalutamide in prostate cancer cells is independent of NCoR and SMRT corepressors.
2007 Sep 1
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.
2008 Apr
Increased thrombin-activatable fibrinolysis inhibitor antigen levels as a clue for prothrombotic state in polycystic ovary syndrome.
2008 Sep
[A case of Budd-Chiari syndrome induced by ethinylestradiol and cyproterone acetate].
2009 Dec
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 Oct 26
Chemical genomics profiling of environmental chemical modulation of human nuclear receptors.
2011 Aug
Regulation and dysregulation of vitellogenin mRNA accumulation in daphnids (Daphnia magna).
2011 Jan 25
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 Fri Jun 25 21:12:11 UTC 2021
Edited
by admin
on Fri Jun 25 21:12:11 UTC 2021
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
CYPROTERONE ACETATE [WHO-DD]
Common 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 [MI]
Common Name English
ANDROCUR
Brand Name English
6-CHLORO-1.BETA.,2.BETA.-DIHYDRO-17-HYDROXY-3'H-CYCLOPROPA(1,2)-PREGNA-1,4,6-TRIENE-3,20-DIONE ACETATE
Common Name English
CYPROTERONE ACETATE [MART.]
Common Name English
SH 714
Code English
3'H-CYCLOPROPA(1,2)PREGNA-1,4,6-TRIENE-3,20-DIONE, 17-(ACETYLOXY)-6-CHLORO-1,2-DIHYDRO-, (1.BETA.,2.BETA.)-
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 3884
Created by admin on Fri Jun 25 21:12:11 UTC 2021 , Edited by admin on Fri Jun 25 21:12:11 UTC 2021
NCI_THESAURUS C146993
Created by admin on Fri Jun 25 21:12:11 UTC 2021 , Edited by admin on Fri Jun 25 21:12:11 UTC 2021
Code System Code Type Description
RXCUI
22054
Created by admin on Fri Jun 25 21:12:11 UTC 2021 , Edited by admin on Fri Jun 25 21:12:11 UTC 2021
PRIMARY RxNorm
ECHA (EC/EINECS)
207-048-3
Created by admin on Fri Jun 25 21:12:11 UTC 2021 , Edited by admin on Fri Jun 25 21:12:11 UTC 2021
PRIMARY
DRUG CENTRAL
766
Created by admin on Fri Jun 25 21:12:11 UTC 2021 , Edited by admin on Fri Jun 25 21:12:11 UTC 2021
PRIMARY
EPA CompTox
427-51-0
Created by admin on Fri Jun 25 21:12:11 UTC 2021 , Edited by admin on Fri Jun 25 21:12:11 UTC 2021
PRIMARY
EVMPD
SUB01539MIG
Created by admin on Fri Jun 25 21:12:11 UTC 2021 , Edited by admin on Fri Jun 25 21:12:11 UTC 2021
PRIMARY
MESH
D017373
Created by admin on Fri Jun 25 21:12:11 UTC 2021 , Edited by admin on Fri Jun 25 21:12:11 UTC 2021
PRIMARY
MERCK INDEX
M4041
Created by admin on Fri Jun 25 21:12:11 UTC 2021 , Edited by admin on Fri Jun 25 21:12:11 UTC 2021
PRIMARY Merck Index
HSDB
3592
Created by admin on Fri Jun 25 21:12:11 UTC 2021 , Edited by admin on Fri Jun 25 21:12:11 UTC 2021
PRIMARY
PUBCHEM
9880
Created by admin on Fri Jun 25 21:12:11 UTC 2021 , Edited by admin on Fri Jun 25 21:12:11 UTC 2021
PRIMARY
IUPHAR
2865
Created by admin on Fri Jun 25 21:12:11 UTC 2021 , Edited by admin on Fri Jun 25 21:12:11 UTC 2021
PRIMARY
FDA UNII
4KM2BN5JHF
Created by admin on Fri Jun 25 21:12:11 UTC 2021 , Edited by admin on Fri Jun 25 21:12:11 UTC 2021
PRIMARY
NCI_THESAURUS
C1059
Created by admin on Fri Jun 25 21:12:11 UTC 2021 , Edited by admin on Fri Jun 25 21:12:11 UTC 2021
PRIMARY
WIKIPEDIA
CYPROTERONE ACETATE
Created by admin on Fri Jun 25 21:12:11 UTC 2021 , Edited by admin on Fri Jun 25 21:12:11 UTC 2021
PRIMARY
ChEMBL
CHEMBL139835
Created by admin on Fri Jun 25 21:12:11 UTC 2021 , Edited by admin on Fri Jun 25 21:12:11 UTC 2021
PRIMARY
DRUG BANK
DB04839
Created by admin on Fri Jun 25 21:12:11 UTC 2021 , Edited by admin on Fri Jun 25 21:12:11 UTC 2021
PRIMARY
CAS
427-51-0
Created by admin on Fri Jun 25 21:12:11 UTC 2021 , Edited by admin on Fri Jun 25 21:12:11 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> AGONIST
BINDING
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METABOLITE ACTIVE -> PARENT
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ACTIVE MOIETY