LILOPRISTONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C29H37NO3
Molecular Weight	447.609
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=RCOWGILQXUPXEW-FUSOFXSQSA-N

InChI=1S/C29H37NO3/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/h4-6,8-9,14,17,24-26,31,33H,7,10-13,15-16,18H2,1-3H3/b14-4-/t24-,25+,26-,28-,29-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C29H37NO3
Molecular Weight	447.609
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://adisinsight.springer.com/drugs/800008704 | https://www.ncbi.nlm.nih.gov/pubmed/15774087 | https://www.ncbi.nlm.nih.gov/pubmed/2502015

Lilopristone (ZK 98.734) has a high affinity for progesterone receptors. The progesterone antagonistic effects of ZK 98.734 could be a result of the decrease in progesterone synthesis by the corpus luteum and/or placenta in addition to the interference with the progesterone binding to its cellular receptors in the target organ. ZK 98.734 has potential for fertility regulation. It is a very potent abortifacient in the common marmosets. Lilopristone could significantly suppress the proliferation of ectopic stromal cells in a time- and dose-dependent manner in vitro. The action mechanisms may be associated with the suppression of expression of NF-kappaB P65 mRNA and NF-kappaB P65.

Approval Year

PubMed

Title	Date	PubMed
Effects of progesterone antagonists RU486 and ZK98734 on embryo transport, development and implantation in laboratory mice.	1990	2095592
Suppression of bioactive luteinizing hormone and testosterone by a progesterone antagonist ZK 98.734 in adult male common marmosets, Callithrix jacchus.	1990 May-Jun	2116922

Sample Use Guides

In Vivo Use Guide

Single dose of 5 mg in 0.2 ml of the vehicle

Route of Administration: Intramuscular

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:11:41 GMT 2023` Edited by `admin` on `Fri Dec 15 16:11:41 GMT 2023`
Record UNII	3GL26H7N6T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LILOPRISTONE

Official Name

English

lilopristone [INN]

Common Name

English

11.BETA.-(P-(DIMETHYLAMINO)PHENYL)-17.BETA.-HYDROXY-17-((Z)-3-HYDROXYPROPENYL)ESTRA-4,9-DIEN-3-ONE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1891