ROSAPROSTOL

Details

Stereochemistry	MIXED
Molecular Formula	C18H34O3
Molecular Weight	298.4608
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCC[C@H]1CCC(O)[C@@H]1CCCCCCC(O)=O

InChI

InChIKey=NMAOJFAMEOVURT-RTKIROINSA-N

InChI=1S/C18H34O3/c1-2-3-4-7-10-15-13-14-17(19)16(15)11-8-5-6-9-12-18(20)21/h15-17,19H,2-14H2,1H3,(H,20,21)/t15-,16+,17?/m0/s1

HIDE SMILES / InChI

Molecular Formula	C18H34O3
Molecular Weight	298.4608
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	2 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3068160 | https://www.ncbi.nlm.nih.gov/pubmed/3403108 | https://www.ncbi.nlm.nih.gov/pubmed/2885786 | https://www.ncbi.nlm.nih.gov/pubmed/27829932

Rosaprostol is an antiulcer drug. This compound acts on the mucosal barrier in the stomach, preventing a drop in pH. More specifically, rosaprostol exhibits gastric antisecretory activity and cytoprotective action. Importantly, it does not have the undesired side effects (such as diarrhea and uterine stimulation) of other prostanoids. Rosaprostol was found to antagonize gastric acid output induced by NSAID administration and to prevent and treat the digestive disorders that resulted from taking NSAIDs. Furthermore, symptoms in patients with gastritis disappeared after administration of rosaprostol, and the drug was well-tolerated. Positive effects of rosaprostol were also reported in patients with duodenal ulcer. Several stereoisomers of rosaprostol have been synthesized.

Approval Year

PubMed

Title	Date	PubMed
Amyloid precursor protein promotes endoplasmic reticulum stress-induced cell death via C/EBP homologous protein-mediated pathway.	2009-06	19476545
Gastroprotective effect of an aqueous suspension of black cumin Nigella sativa on necrotizing agents-induced gastric injury in experimental animals.	2008-07	19568521
Effects of anoxia and hypoxia on amyloid precursor protein processing in cerebral microvascular smooth muscle cells.	2006-06	16783171

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:21:36 GMT 2025` Edited by `admin` on `Mon Mar 31 18:21:36 GMT 2025`
Record UNII	W4459A2P0J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

(±)-ROSAPROSTOL

Preferred Name

English

ROSAPROSTOL

Official Name

English

ROSAPROSTOL [MI]

Common Name

English

(1RS,2SR,5RS)-2-HEXYL-5-HYDROCYCLOPENTANEHEPTANOIC ACID, MIXTURE WITH (1RS,2SR,5SR)-2-HEXYL-5-HYDROXYCYCLOPENTANEHEPTANOIC ACID

Common Name

English

rosaprostol [INN]

Common Name

English

Rosaprostol [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C78568