CYPROTERONE

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 Search

SMILES

[H][C@@]12C[C@]1([H])[C@@]3(C)C(=CC2=O)C(Cl)=C[C@@]4([H])[C@]5([H])CC[C@](O)(C(C)=O)[C@@]5(C)CC[C@]34[H]

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
Sources: http://www.medbroadcast.com/drug/getdrug/cyproterone
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

Targets

Primary Target	Pharmacology	Condition	Potency
Estradiol 17α-dehydrogenase 1 Target ID: Estradiol 17α-dehydrogenase Sources: https://www.ncbi.nlm.nih.gov/pubmed/4125095	Inhibitor 8297
Steroid 5-alpha-reductase 15 Target ID: CHEMBL2363075 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4125095	Inhibitor 8297
Androgen receptor 42 Target ID: P49699 Gene ID: NA Gene Symbol: AR Target Organism: Oryctolagus cuniculus (Rabbit) Sources: https://www.ncbi.nlm.nih.gov/pubmed/165597	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17388716	Palliative		Phase II 1132	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Systemic sclerosis following anti-androgenic treatment for prostatic adenocarcinoma.	1993 Mar	8467617
Glucocorticoid and sex hormones as activating or modulating factors for expression of Cyp2b-9 and Cyp2b-10 in the mouse liver and hepatocytes.	1995 May 10	7771797
Skin ulcers in a young woman on low-dose estrogen-combination pill.	1997 Apr	9169341
Risk of venous thromboembolism with cyproterone or levonorgestrel contraceptives.	2001 Oct 27	11705493
Recurrent pulmonary embolism in an elderly patient with Cushing's syndrome, adrenocortical adenoma, pheochromocytoma and prostate adenocarcinoma.	2004 Jul	15510934
Suspected propranolol-induced delirium.	2004 Sep	15503741
Impact of progestagens on activated protein C (APC) resistance among users of oral contraceptives.	2004 Sep	15333036
Modulation of steroidogenic gene expression and hormone production of H295R cells by pharmaceuticals and other environmentally active compounds.	2007 Dec 1	17822730
Aurintricarboxylic acid inhibits influenza virus neuraminidase.	2009 Feb	19014974
Ciproterone effect on compulsive masturbation in a frontotemporal dementia patient.	2010 Summer	20686146

Patents

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 `Fri Dec 15 16:31:33 GMT 2023` Edited by `admin` on `Fri Dec 15 16:31:33 GMT 2023`
Record UNII	E61Q31EK2F
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CYPROTERONE

Official Name

English

cyproterone [INN]

Common Name

English

CIPROTERONA SERVYCAL

Brand 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-, (1β,2β)-

Systematic Name

English

CYPROTERONE ACETATE IMPURITY F [EP IMPURITY]

Common Name

English

6-chloro-17-hydroxy-1β,2β-dihydro-3′H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione,

Systematic Name

English

Cyproterone [WHO-DD]

Common Name

English

(1β,2β)-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