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
Progesterone antagonist lilopristone: a potent abortifacient in the common marmoset.	1989 Jul	2502015
Effects of progesterone antagonists RU486 and ZK98734 on embryo transport, development and implantation in laboratory mice.	1990	2095592
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 Aug 14	2214762
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
Effects of progesterone antagonist, lilopristone (ZK 98.734), on induction of menstruation, inhibition of nidation, and termination of pregnancy in bonnet monkeys.	1990 Sep	2271724
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 Nov	1293045
[Determination of the progesterone antagonist lilopristone in serum by RP-HPLC].	1995	7572183
Cytochrome P4503A4-mediated N-demethylation of the antiprogestins lilopristone and onapristone.	1997 Oct	9321513
[Influence of mifepristone and lilopristone on proliferation and expression of nuclear factor-kappa B of ectopic stromal cells in vitro].	2005 Jan	15774087

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 UTC 2023` Edited by `admin` on `Fri Dec 15 16:11:41 UTC 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