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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

Unknown
99371
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2438
Prostatic Neoplasms
 4.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Androgen Receptor
Approved
7777
DIANE-35
Primary
Androgen Receptor
Approved
7777
CYPROTERONE ACETATE
PubMed

PubMed

TitleDatePubMed
Cyproterone acetate generates DNA adducts in rat liver and in primary rat hepatocyte cultures.
1993 Mar
Double-blind placebo crossover study of cyproterone acetate in the treatment of the paraphilias.
1993 Oct
[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
Carcinogenicity of cyproterone acetate in the mouse.
1996 Jul
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
The nuclear pregnane X receptor: a key regulator of xenobiotic metabolism.
2002 Oct
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
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.
2008 Apr
Patents

Patents

JP2002543159A
27
JP2007516987A
1

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
NIH
NCATS
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