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

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H30Cl2N2O5
Molecular Weight 461.379
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEXLOXIGLUMIDE

SMILES

CCCCCN(CCCOC)C(=O)[C@@H](CCC(O)=O)NC(=O)C1=CC(Cl)=C(Cl)C=C1

InChI

InChIKey=QNQZBKQEIFTHFZ-GOSISDBHSA-N
InChI=1S/C21H30Cl2N2O5/c1-3-4-5-11-25(12-6-13-30-2)21(29)18(9-10-19(26)27)24-20(28)15-7-8-16(22)17(23)14-15/h7-8,14,18H,3-6,9-13H2,1-2H3,(H,24,28)(H,26,27)/t18-/m1/s1

HIDE SMILES / InChI
Dexloxiglumide is a selective antagonist of cholecystokinin receptor A (CCKA, CCK1). It is the dextro isomeric form of loxiglumide, Dexloxiglumide was investigated for treatment of irritable bowel syndrome. Its development in USA was discontinued.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P32238
Gene ID: 886.0
Gene Symbol: CCKAR
Target Organism: Homo sapiens (Human)
7.53 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Effect of three nonpeptide cholecystokinin antagonists on human isolated gallbladder.
2001 Dec
Development and validation of a bioanalytical method for the determination of the cholecystokinin type-1 (CCK(1)) receptor antagonist dexloxiglumide in human plasma.
2003 Jan 25
Absorption, distribution, metabolism and excretion of the cholecystokinin-1 antagonist dexloxiglumide in the rat.
2003 Jul-Sep
Effect of multiple-dose dexloxiglumide on the pharmacokinetics of oral contraceptives in healthy women.
2005 Mar
Pharmacokinetic profile of dexloxiglumide.
2006
Regulation of fat-stimulated neurotensin secretion in healthy subjects.
2008 May
Patents

Sample Use Guides

In phase 2 clinical trials for treatment of constipation predominant irritable bowel syndrome dexloxiglumide was administered at doses 200 mg tid.
Route of Administration: Oral
Binding of dexloxiglumide to cholecystokinin receptor 1 (CCK1) was studied using radioligand binding assay. CHO cells were transfected with CCK1. Cell membanes rere incubated with 60 pM 125I-BH-CCK-8S (Bolton Hunter-sulfated cholecystokinin octapeptide), and treated with varying concentration of dexloxiglumide. The bound radioactivity was separated by filtration, and radioactivity retained on the filters was measured by liquid scintillation counting.
Name Type Language
DEXLOXIGLUMIDE
INN   WHO-DD  
INN  
Official Name English
LOXIGLUMIDE (R)-FORM
MI  
Common Name English
LOXIGLUMIDE (R)-FORM [MI]
Common Name English
CR-2017
Code English
(+)-LOXIGLUMIDE
Common Name English
LOXIGLUMIDE, (R)-
Common Name English
dexloxiglumide [INN]
Common Name English
(R)-4-(3,4-DICHLOROBENZAMIDO)-N-(3-METHOXYPROPYL)-N-PENTYLGLUTARAMIC ACID
Systematic Name English
Dexloxiglumide [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29701
Created by admin on Sat Dec 16 16:27:02 GMT 2023 , Edited by admin on Sat Dec 16 16:27:02 GMT 2023
NCI_THESAURUS C28197
Created by admin on Sat Dec 16 16:27:02 GMT 2023 , Edited by admin on Sat Dec 16 16:27:02 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C96871
Created by admin on Sat Dec 16 16:27:02 GMT 2023 , Edited by admin on Sat Dec 16 16:27:02 GMT 2023
PRIMARY
MESH
C103490
Created by admin on Sat Dec 16 16:27:02 GMT 2023 , Edited by admin on Sat Dec 16 16:27:02 GMT 2023
PRIMARY
WIKIPEDIA
DEXLOXIGLUMIDE
Created by admin on Sat Dec 16 16:27:02 GMT 2023 , Edited by admin on Sat Dec 16 16:27:02 GMT 2023
PRIMARY
DRUG BANK
DB04856
Created by admin on Sat Dec 16 16:27:01 GMT 2023 , Edited by admin on Sat Dec 16 16:27:01 GMT 2023
PRIMARY
MERCK INDEX
m6916
Created by admin on Sat Dec 16 16:27:02 GMT 2023 , Edited by admin on Sat Dec 16 16:27:02 GMT 2023
PRIMARY Merck Index
CAS
119817-90-2
Created by admin on Sat Dec 16 16:27:01 GMT 2023 , Edited by admin on Sat Dec 16 16:27:01 GMT 2023
PRIMARY
EVMPD
SUB07036MIG
Created by admin on Sat Dec 16 16:27:01 GMT 2023 , Edited by admin on Sat Dec 16 16:27:01 GMT 2023
PRIMARY
ChEMBL
CHEMBL550781
Created by admin on Sat Dec 16 16:27:01 GMT 2023 , Edited by admin on Sat Dec 16 16:27:01 GMT 2023
PRIMARY
PUBCHEM
65937
Created by admin on Sat Dec 16 16:27:02 GMT 2023 , Edited by admin on Sat Dec 16 16:27:02 GMT 2023
PRIMARY
SMS_ID
100000083408
Created by admin on Sat Dec 16 16:27:02 GMT 2023 , Edited by admin on Sat Dec 16 16:27:02 GMT 2023
PRIMARY
INN
6782
Created by admin on Sat Dec 16 16:27:02 GMT 2023 , Edited by admin on Sat Dec 16 16:27:02 GMT 2023
PRIMARY
FDA UNII
69DY40RH9B
Created by admin on Sat Dec 16 16:27:02 GMT 2023 , Edited by admin on Sat Dec 16 16:27:02 GMT 2023
PRIMARY
EPA CompTox
DTXSID50152604
Created by admin on Sat Dec 16 16:27:02 GMT 2023 , Edited by admin on Sat Dec 16 16:27:02 GMT 2023
PRIMARY
DRUG CENTRAL
834
Created by admin on Sat Dec 16 16:27:02 GMT 2023 , Edited by admin on Sat Dec 16 16:27:02 GMT 2023
PRIMARY