EPOSTANE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H31NO3
Molecular Weight	357.4864
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC[C@@]45O[C@]4(C)C(O)=C(C[C@]35C)C#N

InChI

InChIKey=CETKWEWBSMKADK-GSXVSZIWSA-N

InChI=1S/C22H31NO3/c1-18-8-6-16-14(15(18)7-9-20(18,3)25)5-10-22-19(16,2)11-13(12-23)17(24)21(22,4)26-22/h14-16,24-25H,5-11H2,1-4H3/t14-,15-,16-,18-,19+,20-,21+,22-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C22H31NO3
Molecular Weight	357.4864
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2779238 | https://www.ncbi.nlm.nih.gov/pubmed/2713292 | https://www.ncbi.nlm.nih.gov/pubmed/3203752

Epostane (WIN-32729) a pure competitive inhibitor of 3-beta-hydroxysteroid dehydrogenase. Epostane blocks progesterone synthesis during the luteal phase and in pregnancy in women and has strong anti-steroidogenic effect in endocrine tissues. Epostane is an abortifacient agent in early human pregnancy. It inhibits ovarian follicular steroidogenesis and ovulation.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
3beta-hydroxysteroid dehydrogenase activity 1 Target ID: GO:0102727 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2779238	Inhibitor 8146		0.1 µM [Ki]

PubMed

Title	Date	PubMed
Epostane in nonpregnant females: effects on progesterone, 17 alpha-hydroxyprogesterone, and 17 beta-estradiol of two dose levels given for one month.	1988 Dec	3203752
Induction of abortion in early first trimester human pregnancy using epostane.	1989 Mar	2713292

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 16 16:08:32 UTC 2022` Edited by `admin` on `Fri Dec 16 16:08:32 UTC 2022`
Record UNII	6375T36951
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EPOSTANE

Official Name

English

EPOSTANE [MART.]

Common Name

English

EPOSTANE [MI]

Common Name

English

EPOSTANE [USAN]

Common Name

English

epostane [INN]

Common Name

English

4?,5-Epoxy-3,17?-dihydroxy-4,17-dimethyl-5?-androst-2-ene-2-carbonitrile

Common Name

English

4,5-EPOXY-3,17-DIHYDROXY-4,17-DIMETHYLANDROST-2-ENE-2-CARBONITRI

Common Name

English

WIN-32729

Code

English

ANDROST-2-ENE-2-CARBONITRILE, 4,5-EPOXY-3,17-DIHYDROXY-4,17-DIMETHYL-, (4.ALPHA.,5.APHA.,17.BETA.)-

Common Name

English

WIN 32,729

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C1891