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

C[C@]12O[C@]13CC[C@H]4[C@@H]5CC[C@](C)(O)[C@@]5(C)CC[C@@H]4[C@@]3(C)CC(C#N)=C2O

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 8504		0.1 µM [Ki]

PubMed

Title	Date	PubMed
Induction of mRNA for chemokines and chemokine receptors by prostaglandin F2α is dependent upon stage of the porcine corpus luteum and intraluteal progesterone.	2011-07	21505051
Effect of decreasing intraluteal progesterone on sensitivity of the early porcine corpus luteum to the luteolytic actions of prostaglandin F2alpha.	2011-01	20739670
Kinetic analysis of human placental, ovarian, and adrenal 3 beta-hydroxysteroid dehydrogenase inhibition by epostane in vitro.	1989-09	2779238
Induction of abortion in early first trimester human pregnancy using epostane.	1989-03	2713292
Epostane in nonpregnant females: effects on progesterone, 17 alpha-hydroxyprogesterone, and 17 beta-estradiol of two dose levels given for one month.	1988-12	3203752

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:46:01 GMT 2025` Edited by `admin` on `Mon Mar 31 17:46:01 GMT 2025`
Record UNII	6375T36951
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EPOSTANE

Official Name

English

WIN 32,729

Preferred 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

Classification Tree Code System Code

NCI_THESAURUS

C1891