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

Details

Stereochemistry MIXED
Molecular Formula C25H36O5
Molecular Weight 416.5503
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 4
E/Z Centers 3
Charge 0

SHOW SMILES / InChI
Structure of REMIPROSTOL

SMILES

[H][C@]1(CC\C=C/CCC(=O)OC)C(=O)C[C@@H](O)[C@]1([H])\C=C\CC(C)(O)\C=C\C2=CCCC2

InChI

InChIKey=ZZVPHCPLTZTOBC-XBFCOAIZSA-N
InChI=1S/C25H36O5/c1-25(29,17-15-19-10-7-8-11-19)16-9-13-21-20(22(26)18-23(21)27)12-5-3-4-6-14-24(28)30-2/h3-4,9-10,13,15,17,20-21,23,27,29H,5-8,11-12,14,16,18H2,1-2H3/b4-3-,13-9+,17-15+/t20-,21-,23-,25?/m1/s1

HIDE SMILES / InChI

Molecular Formula C25H36O5
Molecular Weight 416.5503
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 3 / 4
E/Z Centers 3
Optical Activity UNSPECIFIED

Remiprostol (also known as SC-46275) is a potent, long-acting gastric antisecretory agent that is not readily available systemically after oral administration. This prostaglandin analog is a very potent and highly selective EP3 receptor agonist with antisecretory and cytoprotective actions. Remiprostol was suggested to be potentially useful in the therapeutic treatment of inflammatory diseases such as peptic ulcer disease (painful sores or ulcers in the stomach or small intestine), ulcerative colitis, Crohn's disease, and autoimmune inflammatory diseases of the central nervous system.

Approval Year

Substance Class Chemical
Created
by admin
on Sat Dec 16 16:25:59 UTC 2023
Edited
by admin
on Sat Dec 16 16:25:59 UTC 2023
Record UNII
YCT6Z40PQR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
REMIPROSTOL
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
REMIPROSTOL [USAN]
Common Name English
Remiprostol [WHO-DD]
Common Name English
4-HEPTENOIC ACID, 7-(2-(6-(1-CYCLOPENTEN-1-YL)-4-HYDROXY-4-METHYL-1,5-HEXADIENYL)-3-HYDROXY-5-OXOCYCLOPENTYL)-, METHYL ESTER
Common Name English
(±)-METHYL (Z)-7-((1R,2R,3R)-2-((1E,5E)-(4RS)-6-(1-CYCLOPENTEN-1-YL)-4-HYDROXY-4-METHYL-1,5-HEXADIENYL)-3-HYDROXY-5-OXOCYCLOPENTYL)-4-HEPTENOATE
Systematic Name English
SC-48834
Code English
remiprostol [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C78568
Created by admin on Sat Dec 16 16:25:59 UTC 2023 , Edited by admin on Sat Dec 16 16:25:59 UTC 2023
Code System Code Type Description
SMS_ID
100000080806
Created by admin on Sat Dec 16 16:25:59 UTC 2023 , Edited by admin on Sat Dec 16 16:25:59 UTC 2023
PRIMARY
INN
6831
Created by admin on Sat Dec 16 16:25:59 UTC 2023 , Edited by admin on Sat Dec 16 16:25:59 UTC 2023
PRIMARY
EPA CompTox
DTXSID00891410
Created by admin on Sat Dec 16 16:25:59 UTC 2023 , Edited by admin on Sat Dec 16 16:25:59 UTC 2023
PRIMARY
PUBCHEM
9844822
Created by admin on Sat Dec 16 16:25:59 UTC 2023 , Edited by admin on Sat Dec 16 16:25:59 UTC 2023
PRIMARY
USAN
CC-28
Created by admin on Sat Dec 16 16:25:59 UTC 2023 , Edited by admin on Sat Dec 16 16:25:59 UTC 2023
PRIMARY
CAS
110845-89-1
Created by admin on Sat Dec 16 16:25:59 UTC 2023 , Edited by admin on Sat Dec 16 16:25:59 UTC 2023
NON-SPECIFIC STEREOCHEMISTRY
EVMPD
SUB10274MIG
Created by admin on Sat Dec 16 16:25:59 UTC 2023 , Edited by admin on Sat Dec 16 16:25:59 UTC 2023
PRIMARY
FDA UNII
YCT6Z40PQR
Created by admin on Sat Dec 16 16:25:59 UTC 2023 , Edited by admin on Sat Dec 16 16:25:59 UTC 2023
PRIMARY
ChEMBL
CHEMBL2106965
Created by admin on Sat Dec 16 16:25:59 UTC 2023 , Edited by admin on Sat Dec 16 16:25:59 UTC 2023
PRIMARY
NCI_THESAURUS
C152188
Created by admin on Sat Dec 16 16:25:59 UTC 2023 , Edited by admin on Sat Dec 16 16:25:59 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY