ENPROSTIL

Details

Stereochemistry	RACEMIC
Molecular Formula	C23H28O6
Molecular Weight	400.4648
Optical Activity	( + / - )
Defined Stereocenters	4 / 4
E/Z Centers	3
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC(=O)CCC=C=CC[C@H]1[C@H](\C=C\[C@H](O)COC2=CC=CC=C2)[C@@H](O)CC1=O

InChI

InChIKey=PTOJVMZPWPAXER-FPXSIRDUSA-N

InChI=1S/C23H28O6/c1-28-23(27)12-8-3-2-7-11-19-20(22(26)15-21(19)25)14-13-17(24)16-29-18-9-5-4-6-10-18/h3-7,9-10,13-14,17,19-20,22,24,26H,8,11-12,15-16H2,1H3/b14-13+/t2?,17-,19-,20-,22-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C23H28O6
Molecular Weight	400.4648
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	3
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3121276 | https://www.drugs.com/international/enprostil.html | https://www.ncbi.nlm.nih.gov/pubmed/7791070

Enprostil, a derivative of heptadienoic acid, is a prostaglandin E2 agonist. It is effective in the treatment of patients with duodenal or gastric ulcers.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prostanoid EP3 receptor 11 Target ID: CHEMBL3710 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10634944 \| https://www.ncbi.nlm.nih.gov/pubmed/9694973	Agonist 2752		12.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Peptic ulcer 72 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16334808 https://www.ncbi.nlm.nih.gov/pubmed/9286243 https://www.ncbi.nlm.nih.gov/pubmed/8017358	Primary		Approved 8583	Camleed Approved Use Peptic ulcer

PubMed

Title	Date	PubMed
Cloned human EP1 prostanoid receptor pharmacology characterized using radioligand binding techniques.	2002-04	11999132
Pharmacological characterization of [(3)H]-prostaglandin E(2) binding to the cloned human EP(4) prostanoid receptor.	2000-08	10952683
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs.	2000-01-17	10634944
Pharmacology of [3H]prostaglandin E1/[3H]prostaglandin E2 and [3H]prostaglandin F2alpha binding to EP3 and FP prostaglandin receptor binding sites in bovine corpus luteum: characterization and correlation with functional data.	1998-08	9694973
Molecular cloning and characterization of the four rat prostaglandin E2 prostanoid receptor subtypes.	1997-12-11	9537820

Patents

Sample Use Guides

In Vivo Use Guide

As evidenced by a few controlled trials in patients with gastric ulcers, treatment with enprostil 35 micrograms twice daily for 6 weeks provides ulcer healing in parallel with pain relief as effectively as cimetidine and ranitidine in a high percentage of patients (about 80% after 6 weeks).

Route of Administration: Oral

In Vitro Use Guide

The concentration of enprostil inducing a half maximal contraction of smooth muscle strips from the circular layer of dog colon(EC50) was 400 nM and the maximal effect was obtained at 1 uM.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:41:26 GMT 2025` Edited by `admin` on `Mon Mar 31 18:41:26 GMT 2025`
Record UNII	J4IP5Z9DAU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ENPROSTIL

Official Name

English

CAMLEED

Preferred Name

English

enprostil [INN]

Common Name

English

ENPROSTIL [USAN]

Common Name

English

ENPROSTIL [MART.]

Common Name

English

RS-84135

Code

English

ENPROSTIL [MI]

Common Name

English

METHYL 7-((1R*,2R*,3R*)-3-HYDROXY-2-((E)-(3R*)-3-HYDROXY-4-PHENOXY-1-BUTENYL)-5-OXOCYCLOPENTYL)-4,5-HEPTADIENOATE

Systematic Name

English

4,5-HEPTADIENOIC ACID, 7-(3-HYDROXY-2-(3-HYDROXY-4-PHENOXY-1-BUTENYL)-5-OXOCYCLOPENTYL)-, METHYL ESTER

Common Name

English

Enprostil [WHO-DD]

Common Name

English

ENPROSTIL [JAN]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QA02BB02