AZASTENE

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Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H33NO2
Molecular Weight	355.5136
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@]1(O)CC[C@H]2[C@@H]3CC=C4C(C)(C)C5=C(C[C@]4(C)[C@H]3CC[C@]12C)C=NO5

InChI

InChIKey=AXLOCHLTNQDFFS-BESJYZOMSA-N

InChI=1S/C23H33NO2/c1-20(2)18-7-6-15-16(21(18,3)12-14-13-24-26-19(14)20)8-10-22(4)17(15)9-11-23(22,5)25/h7,13,15-17,25H,6,8-12H2,1-5H3/t15-,16+,17+,21-,22+,23+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C23H33NO2
Molecular Weight	355.5136
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/mesh/67017039 | https://www.ncbi.nlm.nih.gov/pubmed/680188 | https://www.ncbi.nlm.nih.gov/pubmed/101392

AZASTENE is an inhibitor of ovarian and adrenal steroidogenesis which can be used as an interceptive agent. Its action leads to an acute, short-term, reversible progesterone withdrawal. The reduction of progesterone levels is brought about by competitive inhibition of ovarian 3beta-hydroxysteroid dehydrogenase activity.

Approval Year

PubMed

Title	Date	PubMed
Structural and functional comparison of agents interfering with dihydroorotate, succinate and NADH oxidation of rat liver mitochondria.	1998-10-15	9776318
Inhibition of human placental progesterone synthesis and aromatase activity by synthetic steroidogenic inhibitors in vitro.	1983-06	6574022
Interceptive activity of azastene in rhesus monkeys.	1978-09	101392
Interruption of pregnancy in rats by azastene, an inhibitor of ovarian and adrenal steroidogenesis.	1978-07	680188

Sample Use Guides

In Vitro Use Guide

The 3beta-hydroxysteroid dehydrogenase and 20alpha-hydroxysteroid dehydrogenase from human placenta preparation were inhibited by azastene (IC50 1 microM and 0.6 microM, respectively).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:54:22 GMT 2025` Edited by `admin` on `Mon Mar 31 17:54:22 GMT 2025`
Record UNII	1XA84ITL1H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AZASTENE

Official Name

English

WIN 17625

Preferred Name

English

ANDROSTA-2,5-DIENO(2,3-D)ISOXAZOL-17-OL, 4,4,17-TRIMETHYL-, (17.BETA.)-

Common Name

English

azastene [INN]

Common Name

English

4,4,17-Trimethylandrosta-2,5-dieno[2,3-d]isoxazol-17?-ol

Common Name

English

4,4,17-TRIMETHYLANDROSTA-2,5-DIENO(2,3-D)ISOXAZOL-17B-OL

Common Name

English

WIN-17625

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C389