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 antagonists in androgen target tissues.
1984
Follow-up of prolactin levels in long-term oestrogen-treated male-to-female transsexuals with regard to prolactinoma induction.
1985 Feb
Pulmonary embolism after short-term treatment of acne vulgaris with ovulation suppressor agents.
1986 Oct 6
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
Cyproterone acetate induces DNA damage in cultured rat hepatocytes and preferentially stimulates DNA synthesis in gamma-glutamyltranspeptidase-positive cells.
1992 Mar
Cyproterone acetate generates DNA adducts in rat liver and in primary rat hepatocyte cultures.
1993 Mar
Lactotroph hyperplasia in an estrogen treated male-to-female transsexual patient.
1996 Sep
Fatal fulminant hepatic failure due to cyproterone acetate.
1999 Jul
Rapid and sensitive reporter gene assays for detection of antiandrogenic and estrogenic effects of environmental chemicals.
1999 Mar 1
Dramatic suppression of plasma and urinary prostate specific antigen and human glandular kallikrein by antiandrogens in male-to-female transsexuals.
2000 Mar
Estrogen and cyproterone acetate combination-induced autoimmune hepatitis.
2002 Jul
Twenty-one day administration of dienogest reversibly suppresses gonadotropins and testosterone in normal men.
2002 May
Acute renal artery occlusion in a 15-year-old girl taking oral contraceptives.
2002 May
Differential expression of c-fos and c-myc protooncogenes by estrogens, xenobiotics and other growth-stimulatory agents in primary rat hepatocytes.
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
Screening of some anti-androgenic endocrine disruptors using a recombinant cell-based in vitro bioassay.
2004 Feb
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
The ErbB3-binding protein Ebp1 suppresses androgen receptor-mediated gene transcription and tumorigenesis of prostate cancer cells.
2005 Jul 12
Rosiglitazone and ethinyl estradiol/cyproterone acetate as single and combined treatment of overweight women with polycystic ovary syndrome and insulin resistance.
2006 Jan
GREB1 is a novel androgen-regulated gene required for prostate cancer growth.
2006 Jun 1
[A case of Budd-Chiari syndrome induced by ethinylestradiol and cyproterone acetate].
2009 Dec
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
Related Record Type Details
METABOLITE ACTIVE -> PARENT
Related Record Type Details
ACTIVE MOIETY