U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ABSOLUTE
Molecular Formula C34H31N5O6
Molecular Weight 605.6398
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GI-181771X

SMILES

CC(C)N(C(=O)CN1C2=CC=CC=C2N(C3=CC=CC=C3)C(=O)[C@@H](NC(=O)NC4=CC=CC(=C4)C(O)=O)C1=O)C5=CC=CC=C5

InChI

InChIKey=CABBMMXFOOZVMS-PMERELPUSA-N
InChI=1S/C34H31N5O6/c1-22(2)38(25-14-5-3-6-15-25)29(40)21-37-27-18-9-10-19-28(27)39(26-16-7-4-8-17-26)32(42)30(31(37)41)36-34(45)35-24-13-11-12-23(20-24)33(43)44/h3-20,22,30H,21H2,1-2H3,(H,43,44)(H2,35,36,45)/t30-/m0/s1

HIDE SMILES / InChI

Molecular Formula C34H31N5O6
Molecular Weight 605.6398
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

GI-181771X is part of a class of organic compounds known as benzodiazepines. It is a cholecystokinin 1 receptor agonist investigated by GlaxoSmithKline for the treatment of obesity. In one study, GI181771X did not reduce body weight and had no effect on waist circumference or other cardiometabolic risk markers. This negative result was later assigned to an inadequate trial design rather than compound activity. Gastrointestinal side effects were more common with GI181771X than with placebo treatment. Also, in rodents, morphological changes in the pancreas were observed after administration of GI-181771X, including necrotizing pancreatitis, acinar cell hypertrophy/atrophy, zymogen degranulation, focal acinar cell hyperplasia, and interstitial inflammation. In contrast however, pancreatic changes were not observed in monkeys or in human obese patients (in a clinical trial).

Approval Year

Substance Class Chemical
Record UNII
6YF0SHR37T
Record Status Validated (UNII)
Record Version