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
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
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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
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
| Name | Type | Language | ||
|---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
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 | ||
|---|---|---|---|---|---|
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |
ACTIVE MOIETY
