U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of ONAPRISTONE

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
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

PubMed

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

Sample Use Guides

onapristone tablets 10, 20, 30, 40 or 50 mg BID
Route of Administration: Oral
Name Type Language
ONAPRISTONE
INN   MI   WHO-DD  
INN  
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
Created by admin on Fri Dec 15 18:45:07 GMT 2023 , Edited by admin on Fri Dec 15 18:45:07 GMT 2023
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ChEMBL
CHEMBL1908373
Created by admin on Fri Dec 15 18:45:07 GMT 2023 , Edited by admin on Fri Dec 15 18:45:07 GMT 2023
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EVMPD
SUB09444MIG
Created by admin on Fri Dec 15 18:45:07 GMT 2023 , Edited by admin on Fri Dec 15 18:45:07 GMT 2023
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MERCK INDEX
m8212
Created by admin on Fri Dec 15 18:45:07 GMT 2023 , Edited by admin on Fri Dec 15 18:45:07 GMT 2023
PRIMARY Merck Index
PUBCHEM
5311505
Created by admin on Fri Dec 15 18:45:07 GMT 2023 , Edited by admin on Fri Dec 15 18:45:07 GMT 2023
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WIKIPEDIA
Onapristone
Created by admin on Fri Dec 15 18:45:07 GMT 2023 , Edited by admin on Fri Dec 15 18:45:07 GMT 2023
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EPA CompTox
DTXSID90242210
Created by admin on Fri Dec 15 18:45:07 GMT 2023 , Edited by admin on Fri Dec 15 18:45:07 GMT 2023
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SMS_ID
100000083320
Created by admin on Fri Dec 15 18:45:07 GMT 2023 , Edited by admin on Fri Dec 15 18:45:07 GMT 2023
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INN
6207
Created by admin on Fri Dec 15 18:45:07 GMT 2023 , Edited by admin on Fri Dec 15 18:45:07 GMT 2023
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NCI_THESAURUS
C170255
Created by admin on Fri Dec 15 18:45:07 GMT 2023 , Edited by admin on Fri Dec 15 18:45:07 GMT 2023
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DRUG BANK
DB12637
Created by admin on Fri Dec 15 18:45:07 GMT 2023 , Edited by admin on Fri Dec 15 18:45:07 GMT 2023
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FDA UNII
H6H7G23O3N
Created by admin on Fri Dec 15 18:45:07 GMT 2023 , Edited by admin on Fri Dec 15 18:45:07 GMT 2023
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