METENEPROST

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H38O4
Molecular Weight	378.5454
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCC(C)(C)[C@H](O)\C=C\[C@H]1[C@H](O)CC(=C)[C@@H]1C\C=C/CCCC(O)=O

InChI

InChIKey=WMLGLMGSFIXSGO-KTXJXPLISA-N

InChI=1S/C23H38O4/c1-5-6-15-23(3,4)21(25)14-13-19-18(17(2)16-20(19)24)11-9-7-8-10-12-22(26)27/h7,9,13-14,18-21,24-25H,2,5-6,8,10-12,15-16H2,1,3-4H3,(H,26,27)/b9-7-,14-13+/t18-,19+,20+,21+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C23H38O4
Molecular Weight	378.5454
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	2
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/115063 | https://www.ncbi.nlm.nih.gov/pubmed/7386275 | https://www.ncbi.nlm.nih.gov/pubmed/7449380 | https://www.ncbi.nlm.nih.gov/pubmed/10997897 | https://www.ncbi.nlm.nih.gov/pubmed/3627588 | https://www.ncbi.nlm.nih.gov/pubmed/3698595

Meteneprost (9-deoxo-16, 16-dimethyl-9-methylene PGE2) is a prostaglandin E2 analog. It exerts uterine-stimulating potency: meteneprost is able to both stimulate uterine contractions and dilate the cervical canal. It was studied as an abortifacient in early pregnancy.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prostaglandin E2 receptor EP2 subtype 5 Target ID: P43116 Gene ID: 5732.0 Gene Symbol: PTGER2 Target Organism: Homo sapiens (Human) Sources: https://www.genome.jp/dbget-bin/www_bget?D02726	Binding Agent 1064

PubMed

Title	Date	PubMed
Synthesis and biological properties of 9-deoxo-16,16-dimethyl-9-methylene-PGE2.	1979 May	115063
Synthesis and biological activity of 9-deoxo-9-methylene and related prostaglandins.	1980	7386275
Mid-trimester abortion by vaginal administration of 9-deoxo-16, 16-dimethyl-9-methylene-PGE2.	1980 Aug	7449380
Cervical dilatation with meteneprost vaginal suppositories in first trimester abortion.	1986 Feb	3698595
Cervical dilation before first-trimester elective abortion: a controlled comparison of meteneprost, laminaria, and hypan.	1987 Sep	3627588
Early abortion by mifepristone (RU 486) followed by vaginal gel (meteneprost) versus oral (misoprostol) prostaglandin.	1999	10997897

Sample Use Guides

In Vivo Use Guide

10 mg

Route of Administration: Vaginal

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:26:05 GMT 2023` Edited by `admin` on `Fri Dec 15 15:26:05 GMT 2023`
Record UNII	269EB4R1TV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METENEPROST

Official Name

English

meteneprost [INN]

Common Name

English

U 46,785

Code

English

U-46785

Code

English

METENEPROST [MART.]

Common Name

English

PROSTA-5,13-DIEN-1-OIC ACID, 11,15-DIHYDROXY-16,16-DIMETHYL-9-METHYLENE-, (5Z,11.ALPHA.,13E,15R)-

Common Name

English

U-46,785

Code

English

(Z)-7-[(1R,2R,3R)-3-Hydroxy-2-[(E)-(3R)-3-hydroxy-4,4-dimethyl-1-octenyl]-5-methylenecyclopentyl]-5-heptenoic acid

Systematic Name

English

METENEPROST [USAN]

Common Name

English

U 46785

Code

English

9-DEOXO-16,16-DIMETHYL-9-METHYLENEPROSTAGLANDIN E(SUB 2)

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C78568