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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

Description

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).

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
4.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DIANE-35
Primary
CYPROTERONE ACETATE
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
[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
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 Feb 1
Hepatitis due to cyproterone acetate.
1992
Cyproterone acetate induces DNA damage in cultured rat hepatocytes and preferentially stimulates DNA synthesis in gamma-glutamyltranspeptidase-positive cells.
1992 Mar
Double-blind placebo crossover study of cyproterone acetate in the treatment of the paraphilias.
1993 Oct
Fatal fulminant hepatitis from cyproterone acetate.
1994 Mar
Hepatocellular carcinoma during hormonotherapy for prostatic cancer.
1994 Oct
Hepatocellular carcinoma after treatment with cyproterone acetate combined with ethinyloestradiol.
1995 Feb 18
Cyproterone acetate in the treatment of advanced prostatic cancer: retrospective analysis of liver toxicity in the long-term follow-up of 89 patients.
1996
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
Fatal fulminant hepatic failure due to cyproterone acetate.
1999 Jul
Cirrhosis in a child with hypothalamic syndrome and central precocious puberty treated with cyproterone acetate.
1999 May
In vivo effects of sex steroids on lymphocyte responsiveness and immunoglobulin levels in humans.
2000 Apr
[Central retinal vein occlusion in a patient treated with antiandrogenic drug].
2000 Jan
Prostate cancer treated by anti-androgens: is sexual function preserved? EORTC Genitourinary Group. European Organization for Research and Treatment of Cancer.
2000 Jan
Dramatic suppression of plasma and urinary prostate specific antigen and human glandular kallikrein by antiandrogens in male-to-female transsexuals.
2000 Mar
Acute hepatitis induced by cyproterone acetate.
2001 Sep
Role of cadmium in the regulation of AR gene expression and activity.
2002 Jan
Estrogen and cyproterone acetate combination-induced autoimmune hepatitis.
2002 Jul
Acute renal artery occlusion in a 15-year-old girl taking oral contraceptives.
2002 May
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
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
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
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
Quality of life compared during pharmacological treatments and clinical monitoring for non-localized prostate cancer: a randomized controlled trial.
2004 May
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
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
New insights into the mechanism of imposex induction in the dogwhelk Nucella lapillus.
2005 May
Antiandrogenic therapy can cause coronary arterial disease.
2005 Oct
Activity of androgen receptor antagonist bicalutamide in prostate cancer cells is independent of NCoR and SMRT corepressors.
2007 Sep 1
Increased thrombin-activatable fibrinolysis inhibitor antigen levels as a clue for prothrombotic state in polycystic ovary syndrome.
2008 Sep
Fatal fulminant hepatitis in a chimpanzee (Pan troglodytes) receiving 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
Testosterone-induced modulation of nitric oxide-cGMP signaling pathway and androgenesis in the rat Leydig cells.
2010 Sep
Arylpiperazines for management of benign prostatic hyperplasia: design, synthesis, quantitative structure-activity relationships, and pharmacokinetic studies.
2011 Jan 13
Genomic models of short-term exposure accurately predict long-term chemical carcinogenicity and identify putative mechanisms of action.
2014
Patents

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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]
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 Tue Oct 22 00:35:45 UTC 2019 , Edited by admin on Tue Oct 22 00:35:45 UTC 2019
NCI_THESAURUS C146993
Created by admin on Tue Oct 22 00:35:45 UTC 2019 , Edited by admin on Tue Oct 22 00:35:45 UTC 2019
Code System Code Type Description
RXCUI
22054
Created by admin on Tue Oct 22 00:35:45 UTC 2019 , Edited by admin on Tue Oct 22 00:35:45 UTC 2019
PRIMARY RxNorm
ECHA (EC/EINECS)
207-048-3
Created by admin on Tue Oct 22 00:35:45 UTC 2019 , Edited by admin on Tue Oct 22 00:35:45 UTC 2019
PRIMARY
EPA CompTox
427-51-0
Created by admin on Tue Oct 22 00:35:45 UTC 2019 , Edited by admin on Tue Oct 22 00:35:45 UTC 2019
PRIMARY
EVMPD
SUB01539MIG
Created by admin on Tue Oct 22 00:35:45 UTC 2019 , Edited by admin on Tue Oct 22 00:35:45 UTC 2019
PRIMARY
MESH
D017373
Created by admin on Tue Oct 22 00:35:45 UTC 2019 , Edited by admin on Tue Oct 22 00:35:45 UTC 2019
PRIMARY
MERCK INDEX
M4041
Created by admin on Tue Oct 22 00:35:45 UTC 2019 , Edited by admin on Tue Oct 22 00:35:45 UTC 2019
PRIMARY Merck Index
HSDB
427-51-0
Created by admin on Tue Oct 22 00:35:45 UTC 2019 , Edited by admin on Tue Oct 22 00:35:45 UTC 2019
PRIMARY
PUBCHEM
9880
Created by admin on Tue Oct 22 00:35:45 UTC 2019 , Edited by admin on Tue Oct 22 00:35:45 UTC 2019
PRIMARY
IUPHAR
2865
Created by admin on Tue Oct 22 00:35:45 UTC 2019 , Edited by admin on Tue Oct 22 00:35:45 UTC 2019
PRIMARY
NCI_THESAURUS
C1059
Created by admin on Tue Oct 22 00:35:45 UTC 2019 , Edited by admin on Tue Oct 22 00:35:45 UTC 2019
PRIMARY
WIKIPEDIA
CYPROTERONE ACETATE
Created by admin on Tue Oct 22 00:35:45 UTC 2019 , Edited by admin on Tue Oct 22 00:35:45 UTC 2019
PRIMARY
ChEMBL
CHEMBL139835
Created by admin on Tue Oct 22 00:35:45 UTC 2019 , Edited by admin on Tue Oct 22 00:35:45 UTC 2019
PRIMARY
DRUG BANK
DB04839
Created by admin on Tue Oct 22 00:35:45 UTC 2019 , Edited by admin on Tue Oct 22 00:35:45 UTC 2019
PRIMARY
CAS
427-51-0
Created by admin on Tue Oct 22 00:35:45 UTC 2019 , Edited by admin on Tue Oct 22 00:35:45 UTC 2019
PRIMARY