U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of ROSAPROSTOL

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
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

PubMed

TitleDatePubMed
Effects of anoxia and hypoxia on amyloid precursor protein processing in cerebral microvascular smooth muscle cells.
2006 Jun
Gastroprotective effect of an aqueous suspension of black cumin Nigella sativa on necrotizing agents-induced gastric injury in experimental animals.
2008 Jul
Amyloid precursor protein promotes endoplasmic reticulum stress-induced cell death via C/EBP homologous protein-mediated pathway.
2009 Jun
Patents
Name Type Language
ROSAPROSTOL
INN   MI   WHO-DD  
INN  
Official Name English
(±)-ROSAPROSTOL
Common 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
Created by admin on Fri Dec 15 16:12:02 GMT 2023 , Edited by admin on Fri Dec 15 16:12:02 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL2105331
Created by admin on Fri Dec 15 16:12:02 GMT 2023 , Edited by admin on Fri Dec 15 16:12:02 GMT 2023
PRIMARY
ECHA (EC/EINECS)
260-341-8
Created by admin on Fri Dec 15 16:12:02 GMT 2023 , Edited by admin on Fri Dec 15 16:12:02 GMT 2023
PRIMARY
FDA UNII
W4459A2P0J
Created by admin on Fri Dec 15 16:12:02 GMT 2023 , Edited by admin on Fri Dec 15 16:12:02 GMT 2023
PRIMARY
MERCK INDEX
m9661
Created by admin on Fri Dec 15 16:12:02 GMT 2023 , Edited by admin on Fri Dec 15 16:12:02 GMT 2023
PRIMARY Merck Index
EVMPD
SUB10385MIG
Created by admin on Fri Dec 15 16:12:02 GMT 2023 , Edited by admin on Fri Dec 15 16:12:02 GMT 2023
PRIMARY
MESH
C035288
Created by admin on Fri Dec 15 16:12:02 GMT 2023 , Edited by admin on Fri Dec 15 16:12:02 GMT 2023
PRIMARY
PUBCHEM
6917723
Created by admin on Fri Dec 15 16:12:02 GMT 2023 , Edited by admin on Fri Dec 15 16:12:02 GMT 2023
PRIMARY
EPA CompTox
DTXSID401021611
Created by admin on Fri Dec 15 16:12:02 GMT 2023 , Edited by admin on Fri Dec 15 16:12:02 GMT 2023
PRIMARY
INN
5243
Created by admin on Fri Dec 15 16:12:02 GMT 2023 , Edited by admin on Fri Dec 15 16:12:02 GMT 2023
PRIMARY
CAS
56695-65-9
Created by admin on Fri Dec 15 16:12:02 GMT 2023 , Edited by admin on Fri Dec 15 16:12:02 GMT 2023
PRIMARY
DRUG CENTRAL
2404
Created by admin on Fri Dec 15 16:12:02 GMT 2023 , Edited by admin on Fri Dec 15 16:12:02 GMT 2023
PRIMARY
NCI_THESAURUS
C152253
Created by admin on Fri Dec 15 16:12:02 GMT 2023 , Edited by admin on Fri Dec 15 16:12:02 GMT 2023
PRIMARY
CAS
218917-12-5
Created by admin on Fri Dec 15 16:12:02 GMT 2023 , Edited by admin on Fri Dec 15 16:12:02 GMT 2023
SUPERSEDED
SMS_ID
100000084361
Created by admin on Fri Dec 15 16:12:02 GMT 2023 , Edited by admin on Fri Dec 15 16:12:02 GMT 2023
PRIMARY