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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H27ClO3
Molecular Weight 374.901
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYPROTERONE

SMILES

CC(=O)[C@@]1(O)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

InChI

InChIKey=DUSHUSLJJMDGTE-ZJPMUUANSA-N
InChI=1S/C22H27ClO3/c1-11(24)22(26)7-5-14-12-9-18(23)17-10-19(25)13-8-16(13)21(17,3)15(12)4-6-20(14,22)2/h9-10,12-16,26H,4-8H2,1-3H3/t12-,13+,14-,15-,16-,20-,21-,22-/m0/s1

HIDE SMILES / InChI
Molecular Formula C22H27ClO3
Molecular Weight 374.901
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including: https://en.wikipedia.org/wiki/Cyproterone

Cyproterone belongs to a group of medications known as steroidal antiandrogens. It suppresses testosterone and its metabolites. It has approximately three-fold lower potency as an antagonist of the androgen receptor relative to cyproterone acetate. Cyproterone acetate is used to treat advanced prostate cancer and acne.

CNS Activity

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Estradiol 17α-dehydrogenase
1
Target ID: Estradiol 17α-dehydrogenase
Inhibitor
8504
Inhibitor
8504
Androgen receptor
42
Target ID: P49699
Gene ID: NA
Gene Symbol: AR
Target Organism: Oryctolagus cuniculus (Rabbit)
Antagonist
2849
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Phase II
1147
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Ciproterone effect on compulsive masturbation in a frontotemporal dementia patient.
2010
Aurintricarboxylic acid inhibits influenza virus neuraminidase.
2009-02
Modulation of steroidogenic gene expression and hormone production of H295R cells by pharmaceuticals and other environmentally active compounds.
2007-12-01
Suspected propranolol-induced delirium.
2004-09
Impact of progestagens on activated protein C (APC) resistance among users of oral contraceptives.
2004-09
Recurrent pulmonary embolism in an elderly patient with Cushing's syndrome, adrenocortical adenoma, pheochromocytoma and prostate adenocarcinoma.
2004-07
Risk of venous thromboembolism with cyproterone or levonorgestrel contraceptives.
2001-10-27
Skin ulcers in a young woman on low-dose estrogen-combination pill.
1997-04
Glucocorticoid and sex hormones as activating or modulating factors for expression of Cyp2b-9 and Cyp2b-10 in the mouse liver and hepatocytes.
1995-05-10
Systemic sclerosis following anti-androgenic treatment for prostatic adenocarcinoma.
1993-03
Patents

Patents

JP2002525268A
31

Sample Use Guides

In Vivo Use Guide
200 mg/day
Route of Administration: Oral
In Vitro Use Guide
The 'uptake' of the anti-androgen cyproterone by human prostate slices was measured in two hyperplastic and two adenocarcinomatous glands. Samples of tissue slices of similar weight from the two hyperplastic glands were superfused with medium containing increasing amounts of cyproterone. There was no variation in the 'uptake' of cyproterone within the concentration range in the medium from 2.63 to 17.49 umol/litre.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:30:29 GMT 2025
Edited
by admin
on Mon Mar 31 18:30:29 GMT 2025
Record UNII
E61Q31EK2F
Record Status Validated (UNII)
Record Version
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Name Type Language
CIPROTERONA SERVYCAL
Preferred Name English
CYPROTERONE
INN   MI   WHO-DD  
INN  
Official Name English
cyproterone [INN]
Common Name English
CYPROTERONE [MI]
Common Name English
3?H-Cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione, 6-chloro-1,2-dihydro-17-hydroxy-, (1?,2?)-
Systematic Name English
CYPROTERONE ACETATE IMPURITY F [EP IMPURITY]
Common Name English
6-chloro-17-hydroxy-1?,2?-dihydro-3?H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione,
Systematic Name English
Cyproterone [WHO-DD]
Common Name English
(1?,2?)-6-Chloro-1,2-dihydro-17-hydroxy-3?H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione
Systematic Name English
NSC-758636
Code English
Classification Tree Code System Code
WHO-ATC G03HB01
Created by admin on Mon Mar 31 18:30:29 GMT 2025 , Edited by admin on Mon Mar 31 18:30:29 GMT 2025
WHO-VATC QG03HA01
Created by admin on Mon Mar 31 18:30:29 GMT 2025 , Edited by admin on Mon Mar 31 18:30:29 GMT 2025
NCI_THESAURUS C146993
Created by admin on Mon Mar 31 18:30:29 GMT 2025 , Edited by admin on Mon Mar 31 18:30:29 GMT 2025
WHO-VATC QG03HB01
Created by admin on Mon Mar 31 18:30:29 GMT 2025 , Edited by admin on Mon Mar 31 18:30:29 GMT 2025
WHO-ATC G03HA01
Created by admin on Mon Mar 31 18:30:29 GMT 2025 , Edited by admin on Mon Mar 31 18:30:29 GMT 2025
LIVERTOX NBK548024
Created by admin on Mon Mar 31 18:30:29 GMT 2025 , Edited by admin on Mon Mar 31 18:30:29 GMT 2025
Code System Code Type Description
INN
2050
Created by admin on Mon Mar 31 18:30:29 GMT 2025 , Edited by admin on Mon Mar 31 18:30:29 GMT 2025
PRIMARY
MERCK INDEX
m4041
Created by admin on Mon Mar 31 18:30:29 GMT 2025 , Edited by admin on Mon Mar 31 18:30:29 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C407
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PRIMARY
CHEBI
50742
Created by admin on Mon Mar 31 18:30:29 GMT 2025 , Edited by admin on Mon Mar 31 18:30:29 GMT 2025
PRIMARY
NSC
758636
Created by admin on Mon Mar 31 18:30:29 GMT 2025 , Edited by admin on Mon Mar 31 18:30:29 GMT 2025
PRIMARY
ChEMBL
CHEMBL139835
Created by admin on Mon Mar 31 18:30:29 GMT 2025 , Edited by admin on Mon Mar 31 18:30:29 GMT 2025
PRIMARY
PUBCHEM
5284537
Created by admin on Mon Mar 31 18:30:29 GMT 2025 , Edited by admin on Mon Mar 31 18:30:29 GMT 2025
PRIMARY
EVMPD
SUB06877MIG
Created by admin on Mon Mar 31 18:30:29 GMT 2025 , Edited by admin on Mon Mar 31 18:30:29 GMT 2025
PRIMARY
EPA CompTox
DTXSID3022873
Created by admin on Mon Mar 31 18:30:29 GMT 2025 , Edited by admin on Mon Mar 31 18:30:29 GMT 2025
PRIMARY
CAS
2098-66-0
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PRIMARY
FDA UNII
E61Q31EK2F
Created by admin on Mon Mar 31 18:30:29 GMT 2025 , Edited by admin on Mon Mar 31 18:30:29 GMT 2025
PRIMARY
WIKIPEDIA
CYPROTERONE
Created by admin on Mon Mar 31 18:30:29 GMT 2025 , Edited by admin on Mon Mar 31 18:30:29 GMT 2025
PRIMARY
MESH
D003534
Created by admin on Mon Mar 31 18:30:29 GMT 2025 , Edited by admin on Mon Mar 31 18:30:29 GMT 2025
PRIMARY
RXCUI
3014
Created by admin on Mon Mar 31 18:30:29 GMT 2025 , Edited by admin on Mon Mar 31 18:30:29 GMT 2025
PRIMARY RxNorm
SMS_ID
100000083989
Created by admin on Mon Mar 31 18:30:29 GMT 2025 , Edited by admin on Mon Mar 31 18:30:29 GMT 2025
PRIMARY
Related Record Type Details
ANDROGEN RECEPTOR
TARGET -> AGONIST
BINDING
Related Record Type Details
Structure of Cyproterone Acetate
PARENT -> IMPURITY
Related Record Type Details
Structure of CYPROTERONE
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
NIH
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