ONAPRISTONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C29H39NO3
Molecular Weight	449.6249
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC[C@](O)(CCCO)[C@]1(C)C[C@H](C3=CC=C(C=C3)N(C)C)C4=C5CCC(=O)C=C5CC[C@@]24[H]

InChI

InChIKey=IEXUMDBQLIVNHZ-YOUGDJEHSA-N

InChI=1S/C29H39NO3/c1-28-18-25(19-5-8-21(9-6-19)30(2)3)27-23-12-10-22(32)17-20(23)7-11-24(27)26(28)13-15-29(28,33)14-4-16-31/h5-6,8-9,17,24-26,31,33H,4,7,10-16,18H2,1-3H3/t24-,25+,26-,28+,29+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C29H39NO3
Molecular Weight	449.6249
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/30304013 | https://adisinsight.springer.com/drugs/800000877 | https://clinicaltrials.gov/ct2/show/NCT03909152

Onapristone is a type I progesterone receptor (PR) antagonist that prevents PR- mediated DNA transcription and was studied as an antitumor agent. This drug possessed activity in breast cancer and is participating in phase II clinical trials to test any good and bad effect for the treatment of endometrial cancer, ovarian cancer, peritoneal cancer, and prostate cancer.

Approval Year

PubMed

Title	Date	PubMed
Synthesis and biological activity of novel nonsteroidal progesterone receptor antagonists based on cyclocymopol monomethyl ether.	1996 Apr 26	8627601
Development of progesterone receptor antagonists from 1,2-dihydrochromeno[3,4-f]quinoline agonist pharmacophore.	2003 Jun 16	12781198
Characterization of a critical region in the hormone binding domain of sperm progesterone receptor.	2005 Apr	15811074
Ligand-selective targeting of the glucocorticoid receptor to nuclear subdomains is associated with decreased receptor mobility.	2005 Jun	15705660
Effects of progesterone on iNOS, COX-2, and collagen expression in the cervix.	2006 Jun	16399999
Progesterone-induced sphingosine kinase-1 expression in the rat uterus during pregnancy and signaling consequences.	2007 Apr	17164439
Regulation of homeobox A10 expression in the primate endometrium by progesterone and embryonic stimuli.	2007 Sep	17709569
Anti-apoptotic roles of prostaglandin E2 and F2alpha in bovine luteal steroidogenic cells.	2008 Aug	18463360
Luteoprotective roles of luteinizing hormone are mediated by not only progesterone production but also glucocorticoid conversion in bovine corpus luteum.	2013 Mar	23325624

Patents

Sample Use Guides

In Vivo Use Guide

onapristone tablets 10, 20, 30, 40 or 50 mg BID

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:45:07 GMT 2023` Edited by `admin` on `Fri Dec 15 18:45:07 GMT 2023`
Record UNII	H6H7G23O3N
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ONAPRISTONE

Official Name

English

onapristone [INN]

Common Name

English

11.BETA.-(P-(DIMETHYLAMINO)PHENYL)-17.ALPHA.-HYDROXY-17-(3-HYDROXYPROPYL)-13.ALPHA.-ESTRA-4,9-DIEN-3-ONE

Common Name

English

ZK98299

Common Name

English

ZK-98299

Code

English

ZK-299

Code

English

ONAPRISTONE [MI]

Common Name

English

Onapristone [WHO-DD]

Common Name

English

Code System Code Type Description

CAS

96346-61-1