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

CN(C)C1=CC=C(C=C1)[C@H]2C[C@@]3(C)[C@@H](CC[C@@]3(O)\C=C/CO)[C@@H]4CCC5=CC(=O)CCC5=C24

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
[Influence of mifepristone and lilopristone on proliferation and expression of nuclear factor-kappa B of ectopic stromal cells in vitro].	2005-01	15774087
Cytochrome P4503A4-mediated N-demethylation of the antiprogestins lilopristone and onapristone.	1997-10	9321513
[Determination of the progesterone antagonist lilopristone in serum by RP-HPLC].	1995	7572183
Contraceptive potential of an antiprogestin ZK 98.734: reversal of ZK 98.734--induced blockade of folliculogenesis with FSH and LH and their differential effects in bonnet monkeys.	1992-11	1293045
Effects of progesterone antagonist, lilopristone (ZK 98.734), on induction of menstruation, inhibition of nidation, and termination of pregnancy in bonnet monkeys.	1990-09	2271724
Modulatory actions of the new antiprogestins ZK 98.299 and ZK 98.734 and of RU 486 on luteinizing hormone secretion and progesterone effects in pituitary gonadotrophs.	1990-08-14	2214762
Suppression of bioactive luteinizing hormone and testosterone by a progesterone antagonist ZK 98.734 in adult male common marmosets, Callithrix jacchus.	1990-05-01	2116922
Effects of progesterone antagonists RU486 and ZK98734 on embryo transport, development and implantation in laboratory mice.	1990	2095592
Progesterone antagonist lilopristone: a potent abortifacient in the common marmoset.	1989-07	2502015

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 `Mon Mar 31 18:21:26 GMT 2025` Edited by `admin` on `Mon Mar 31 18:21:26 GMT 2025`
Record UNII	3GL26H7N6T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LILOPRISTONE

Official Name

English

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

Preferred Name

English

lilopristone [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1891