TRIMOPROSTIL

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

InChI

InChIKey=OOAHNJDZICJECC-BHWPLRMJSA-N

InChI=1S/C23H38O4/c1-5-6-15-23(3,4)21(25)14-13-18-17(2)16-20(24)19(18)11-9-7-8-10-12-22(26)27/h7,9,13-14,17-19,21,25H,5-6,8,10-12,15-16H2,1-4H3,(H,26,27)/b9-7-,14-13+/t17-,18+,19-,21-/m1/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/3140824 | https://www.ncbi.nlm.nih.gov/pubmed/2896383 | https://www.ncbi.nlm.nih.gov/pubmed/2689255 | Morton, I.K., Hall, J.M. (2012) Concise Dictionary of Pharmacological Agents, page 281, retrieved from: https://books.google.ru/books?id=tsjrCAAAQBAJ

Trimoprostil is a synthetic prostaglandin E2 derivative and prostanoid receptor agonist, with potential gastric secretion inhibitor and antiulcerogenic activity. It has been shown to reduce hydrogen ion secretion, to enhance gastric bicarbonate secretion and to reduce aspirin-induced gastric mucosal injury. In contrast to many E prostaglandins, it does not lower the tone of the lower oesophageal sphincter. Trimoprostil was well tolerated and more effective than placebo in the treatment of mild to moderate symptomatic reflux oesophagitis. It may be protective to human squamous oesophageal mucosa. Trimoprostil was not as effective as cimetidine in the treatment of duodenal ulcer.

Approval Year

PubMed

Title	Date	PubMed
Cytoprotection of gastroduodenal mucous membrane with analogues of prostaglandins.	1989-06	2672199
[Prostaglandin analogues in the treatment of peptic ulcer disease].	1989-01-09	2643240
Treatment of reflux oesophagitis with trimoprostil.	1989	2689255
The effects of prostaglandins on gastric emptying.	1989	2510256
The effect of trimoprostil (trimethyldesoxy prostaglandin E2) on the intrauterine pressure in women.	1988-08	3293873
Effect of trimoprostil on gastric secretion in man.	1988-06	3140824
Effect of a slow-release formula of trimoprostil on intragastric acidity in healthy volunteers.	1988-04	2979239
A multicentre comparison of trimoprostil and cimetidine in the treatment of duodenal ulcer. U.K. Trimoprostil Study Collaborative Group.	1988-03	2896383
[Recent developments in synergistic drugs for protective factors in peptic ulcer--clinical efficacy and problems; prostaglandins].	1988-01	3131560
Double-blind study comparing cimetidine and two doses of a slow release formulation of trimoprostil in duodenal ulcer patients with a 6-month follow-up.	1988	3234614
Effects of acute administration of a prostaglandin E2 analog, trimoprostil, on esophageal motility in man.	1987-09	3631029
Pharmacokinetics and antisecretory activity of trimoprostil in Heidenhain-pouch dogs.	1987-05	3572803
Biliary, fecal and urinary excretion of [3H]-prostaglandins in the rat.	1987-03	3554370
Effects of trimoprostil, a prostaglandin E2 analogue, on human gastric acid secretion and soluble mucin output.	1987-02	2436919
Prostaglandins in clinical treatment of gastroduodenal mucosal lesions: a review.	1987	3321405
Effects of trimoprostil on healing and recurrence of acetic acid-induced gastric ulcer in rats.	1986-12	3807049
Specificity of PGE2 analogs interaction between food intake and antisecretory effect.	1986-10	3099313
Identification of trimoprostil metabolites excreted in rat bile formed by oxidation and taurine conjugation.	1986-07-01	2873994
[Intragastric acidity under the prostaglandin E2 analog trimoprostil. Increased inhibitory effect through administration after meals].	1986-03	3518730
Current concepts in clinical therapeutics: peptic ulcer disease.	1986-02	2869852

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:56:45 GMT 2025` Edited by `admin` on `Mon Mar 31 17:56:45 GMT 2025`
Record UNII	4DVL1781YC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RO 21-6937

Preferred Name

English

TRIMOPROSTIL

Official Name

English

RO-21-6937/000

Code

English

RO-216937000

Code

English

trimoprostil [INN]

Common Name

English

TRIMOPROSTIL [MART.]

Common Name

English

RO 21-6937/000

Code

English

TRIMOPROSTIL [USAN]

Common Name

English

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

Systematic Name

English

RO-21-6937

Code

English

TRIMOPROSTIL [MI]

Common Name

English

PROSTA-5,13-DIEN-1-OIC ACID, 15-HYDROXY-11,16,16-TRIMETHYL-9-OXO-, (5Z,11.ALPHA.,13E,15R)-

Common Name

English

TRIMOPROSTIL [JAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29701