GEMEPROST

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H38O5
Molecular Weight	394.5448
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(=O)[C@@H]1CCCC\C=C\C(=O)OC

InChI

InChIKey=KYBOHGVERHWSSV-VNIVIJDLSA-N

InChI=1S/C23H38O5/c1-5-6-15-23(2,3)21(26)14-13-18-17(19(24)16-20(18)25)11-9-7-8-10-12-22(27)28-4/h10,12-14,17-18,20-21,25-26H,5-9,11,15-16H2,1-4H3/b12-10+,14-13+/t17-,18-,20-,21-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C23H38O5
Molecular Weight	394.5448
Charge	0
Count

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

Description
Sources: https://gp2u.com.au/static/pdf/C/CERVAGEM-PI.pdf

Gemeprost is a PGE1 analogue indicated for softening and dilatation of the cervix uteri prior to operative procedures or therapeutic abortion. The drug is marketed under the name Cervagem.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
uterine smooth muscle contraction 3 Target ID: GO:0070471 Sources: https://www.medicines.org.uk/emc/medicine/3968	Activator 1447

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cervical dilatation 1 Sources: https://gp2u.com.au/static/pdf/C/CERVAGEM-PI.pdf	Primary		Approved 8583	CERVAGEM Approved Use For the softening and dilatation of the cervix uteri prior to transcervical, intrauterine operative procedures in the first trimester of pregnancy. Therapeutic termination of pregnancy in patients in the second trimester of gestation. Launch Date 1990

C_max

Value	Dose	Co-administered	Analyte	Population
6 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/180188_2499700H1036_1_002_2F.pdf#page=21	1 mg single, vaginal dose: 1 mg route of administration: Vaginal experiment type: SINGLE co-administered:		GEMEPROST plasma	Homo sapiens population: PREGNANT age: ADULT sex: FEMALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
1 mg 5 times / day multiple, vaginal Recommended Dose: 1 mg, 5 times / day Route: vaginal Route: multiple Dose: 1 mg, 5 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17320086/	pregnant, ADULT Health Status: pregnant Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17320086/	Disc. AE: Allergy... AEs leading to discontinuation/dose reduction: Allergy (0.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/17320086/

AEs

AE	Significance	Dose	Population
Allergy	0.5% Disc. AE	1 mg 5 times / day multiple, vaginal Recommended Dose: 1 mg, 5 times / day Route: vaginal Route: multiple Dose: 1 mg, 5 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17320086/	pregnant, ADULT Health Status: pregnant Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/17320086/

PubMed

Title	Date	PubMed
How safe is gemeprost? A case report of a middle-aged female developing acute myocardial infarction after insertion of gemeprost vaginal pessary and a review of its usage.	2007-12	18185889
A randomised study of misoprostol and gemeprost in combination with mifepristone for induction of abortion in the second trimester of pregnancy.	2002-11	12452468
Double-blind randomized trial of mifepristone in combination with vaginal gemeprost or misoprostol for induction of abortion up to 63 days gestation.	2001-10	11574498
Continuation of pregnancy after mid-trimester gemeprost administration.	2000-09	11002975
[Use of a new vaginal suppository: prostaglandin E1 analog Gemeprost for cervix maturation prior to abortion in the 1st trimester].	1985-06	3894147
Midtrimester termination of pregnancy using intravaginal gemeprost (16, 16 dimethyl-trans delta 2 PGE1 methyl ester, cervagem).	1985-04	4035402
The use of 16,16-dimethyl-trans delta 2 prostaglandin E1 methyl ester (gemeprost) vaginal pessaries for the termination of pregnancy in the early second trimester. A comparison with extra-amniotic prostaglandin E2.	1984-11	6594157
A Gemeprost vaginal suppository for cervical priming prior to termination of first trimester pregnancy.	1984-03	6539662
Abortifacient effect and uterine cervix-dilating action of 16, 16-dimethyl trans delta 2 PGE1 methyl ester (ONO 802) in the form of a vaginal suppository (a randomized, double-blind, controlled study in the second trimester of pregnancy).	1982-09	6752961
The use of prostaglandin E1 analogue pessaries in patients having first trimester induced abortions.	1980-04	7426498

Patents

Sample Use Guides

In Vivo Use Guide

One pessary to be inserted into the posterior vaginal fornix three hours before surgery.

Route of Administration: Vaginal

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:57:40 GMT 2025` Edited by `admin` on `Mon Mar 31 17:57:40 GMT 2025`
Record UNII	45KZB1FOLS
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

PREGLANDIN

Preferred Name

English

GEMEPROST

Official Name

English

Methyl (E)-7-[(1R,2R,3R)-3-hydroxy-2-[(E)-(3R)-3-hydroxy-4,4-dimethyl-1-octenyl]-5-oxocyclopentyl]-2-heptenoate

Systematic Name

English

GEMEPROST [MART.]

Common Name

English

gemeprost [INN]

Common Name

English

GEMEPROST [USAN]

Common Name

English

Gemeprost [WHO-DD]

Common Name

English

GEMEPROST [JAN]

Common Name

English

GEMEPROST [MI]

Common Name

English

PROSTA-2,13-DIEN-1-OIC ACID, 11,15-DIHYDROXY-16,16-DIMETHYL-9-OXO-, METHYL ESTER, (2E,11.ALPHA.,13E,15R)-

Common Name

English

SC-37681

Code

English

U-37026

Common Name

English

Classification Tree Code System Code

WHO-ATC

G02AD03