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
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
[Prevention of testosterone-vasopressin induced necrosis of the kidney cortex by cyproterone acetate].
1979 Jul
Effect of cyproterone acetate on glucocorticoid secretion in patients treated for hirsutism.
1983 Oct
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
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
Hepatocellular carcinoma after treatment with cyproterone acetate combined with ethinyloestradiol.
1995 Feb 18
Severe hepatitis and liver failure induced by cyproterone acetate.
1996 Oct
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
Rapid and sensitive reporter gene assays for detection of antiandrogenic and estrogenic effects of environmental chemicals.
1999 Mar 1
The nuclear pregnane X receptor: a key regulator of xenobiotic metabolism.
2002 Oct
Differential expression of c-fos and c-myc protooncogenes by estrogens, xenobiotics and other growth-stimulatory agents in primary rat hepatocytes.
2003 Mar
Glucocorticoid receptor antagonism by cyproterone acetate and RU486.
2003 May
Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.
2003 Oct
Partial agonist/antagonist properties of androstenedione and 4-androsten-3beta,17beta-diol.
2004 Aug
Coregulator recruitment and histone modifications in transcriptional regulation by the androgen receptor.
2004 Nov
Influence of exogenous oestrogen or (anti-) androgen administration on soluble transferrin receptor in human plasma.
2005 Jul
Receptor isoform and ligand-specific modulation of dihydrotestosterone-induced prostate specific antigen gene expression and prostate tumor cell growth by estrogens.
2005 Jul-Aug
In silico prediction of pregnane X receptor activators by machine learning approaches.
2007 Jan
Ligand-specific dynamics of the androgen receptor at its response element in living cells.
2007 Mar
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.
2008 Apr
Testosterone-induced modulation of nitric oxide-cGMP signaling pathway and androgenesis in the rat Leydig cells.
2010 Sep
Abrupt regression of a meningioma after discontinuation of cyproterone treatment.
2010 Sep
Anabolic-androgenic steroids induce apoptosis and NOS2 (nitric-oxide synthase 2) in adult rat Leydig cells following in vivo exposure.
2012 Dec
Bisphenol A affects androgen receptor function via multiple mechanisms.
2013 May 25
Genomic models of short-term exposure accurately predict long-term chemical carcinogenicity and identify putative mechanisms of action.
2014
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.
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