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

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H32ClN3O4
Molecular Weight 425.949
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of REVEXEPRIDE

SMILES

COCCCN1CC[C@@H](CNC(=O)C2=C3OC(C)(C)CC3=C(N)C(Cl)=C2)[C@H](O)C1

InChI

InChIKey=FOUUNSGQVBGYQM-SUMWQHHRSA-N
InChI=1S/C21H32ClN3O4/c1-21(2)10-15-18(23)16(22)9-14(19(15)29-21)20(27)24-11-13-5-7-25(12-17(13)26)6-4-8-28-3/h9,13,17,26H,4-8,10-12,23H2,1-3H3,(H,24,27)/t13-,17+/m0/s1

HIDE SMILES / InChI

Molecular Formula C21H32ClN3O4
Molecular Weight 425.949
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Revexepride is a selective 5-hydroxytryptamine receptor 4 agonist and member of a class of prokinetic agents that stimulate gastric emptying. Revexepride is thought to stimulate the release of acetylcholine at the myenteric plexus, leading to increased gastrointestinal contractions. This drug has been evaluated for potential use in treatment of gastroesophageal reflux disease. Phase I studies in healthy volunteers have shown no serious adverse events after administration of revexepride. However, a phase II study reported respiratory, thoracic and mediastinal disorders and pulmonary hypertension in 1 patient (0.85%). Furthermore, a European clinical trial showed that four weeks of treatment did not improve symptoms or gastric emptying in patients with symptoms suggestive of gastroparesis compared to placebo.

Approval Year

Substance Class Chemical
Created
by admin
on Sat Dec 16 05:32:50 UTC 2023
Edited
by admin
on Sat Dec 16 05:32:50 UTC 2023
Record UNII
8C63R2Y02M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
REVEXEPRIDE
INN  
INN  
Official Name English
revexepride [INN]
Common Name English
7-BENZOFURANCARBOXAMIDE, 4-AMINO-5-CHLORO-2,3-DIHYDRO-N-(((3S,4S)-3-HYDROXY-1-(3-METHOXYPROPYL)-4-PIPERIDINYL)METHYL)-2,2-DIMETHYL-
Systematic Name English
4-AMINO-5-CHLORO-N-(((3S,4S)-3-HYDROXY-1-(3-METHOXYPROPYL)PIPERIDIN-4-YL)METHYL(-2,2-DIMETHYL-2,3-DIHYDRO-1-BENZOFURAN-7-CARBOXAMIDE
Common Name English
7-BENZOFURANCARBOXAMIDE, 4-AMINO-5-CHLORO-2,3-DIHYDRO-N-(((3R,4R)-3-HYDROXY-1-(3-METHOXYPROPYL)-4-PIPERIDINYL)METHYL)-2,2-DIMETHYL-
Systematic Name English
R149402
Code English
(-)-REVEXEPRIDE
Common Name English
SPD-557
Code English
R-149402
Code English
Classification Tree Code System Code
NCI_THESAURUS C47794
Created by admin on Sat Dec 16 05:32:50 UTC 2023 , Edited by admin on Sat Dec 16 05:32:50 UTC 2023
Code System Code Type Description
FDA UNII
8C63R2Y02M
Created by admin on Sat Dec 16 05:32:50 UTC 2023 , Edited by admin on Sat Dec 16 05:32:50 UTC 2023
PRIMARY
PUBCHEM
9823762
Created by admin on Sat Dec 16 05:32:50 UTC 2023 , Edited by admin on Sat Dec 16 05:32:50 UTC 2023
PRIMARY
CAS
219984-49-3
Created by admin on Sat Dec 16 05:32:50 UTC 2023 , Edited by admin on Sat Dec 16 05:32:50 UTC 2023
PRIMARY
SMS_ID
100000180083
Created by admin on Sat Dec 16 05:32:50 UTC 2023 , Edited by admin on Sat Dec 16 05:32:50 UTC 2023
PRIMARY
INN
9617
Created by admin on Sat Dec 16 05:32:50 UTC 2023 , Edited by admin on Sat Dec 16 05:32:50 UTC 2023
PRIMARY
ChEMBL
CHEMBL3545035
Created by admin on Sat Dec 16 05:32:50 UTC 2023 , Edited by admin on Sat Dec 16 05:32:50 UTC 2023
PRIMARY
EPA CompTox
DTXSID30176429
Created by admin on Sat Dec 16 05:32:50 UTC 2023 , Edited by admin on Sat Dec 16 05:32:50 UTC 2023
PRIMARY
NCI_THESAURUS
C152202
Created by admin on Sat Dec 16 05:32:50 UTC 2023 , Edited by admin on Sat Dec 16 05:32:50 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY