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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
Molecular Formula C21H30Cl2N2O5
Molecular Weight 461.379
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Cholecystokinin receptor type A
2
Target ID: P32238
Gene ID: 886.0
Gene Symbol: CCKAR
Target Organism: Homo sapiens (Human)
Antagonist
2778
 7.53 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
656
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Dexloxiglumide Rotta Research Lab.
2002 Apr
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
Pharmacokinetics and metabolism of the cholecystokinin antagonist dexloxiglumide in male human subjects.
2003 Jun
Characterization of dexloxiglumide in vitro biopharmaceutical properties and active transport.
2003 Oct
CCK1 receptor antagonist, dexloxiglumide: effects on human isolated gallbladder. Potential clinical applications.
2003 Sep
Functional dyspepsia: drugs for new (and old) therapeutic targets.
2004 Aug
Absorption, distribution, metabolism and excretion of the cholecystokinin-1 antagonist dexloxiglumide in the dog.
2004 Jan-Mar
Effect of azole antifungals ketoconazole and fluconazole on the pharmacokinetics of dexloxiglumide.
2005 Nov
Basic and clinical pharmacology of new motility promoting agents.
2005 Oct
The single-dose pharmacokinetics of the novel CCK1 receptor antagonist, dexloxiglumide, are not influenced by age and gender.
2005 Sep
Signal transduction pathways mediating CCK-8S-induced gastric antral smooth muscle contraction.
2006
Use of novel prokinetic agents to facilitate return of gastrointestinal motility in adult critically ill patients.
2006 Aug
A novel, quantitative bio-assay for cholecystokinin type-1 receptor activity in the anaesthetised rat.
2006 Jul-Aug
Oral and gastrointestinal sensing of dietary fat and appetite regulation in humans: modification by diet and obesity.
2010
Association of CCK(1) Receptor Gene Polymorphisms and Irritable Bowel Syndrome in Korean.
2010 Jan
Neuropathy, retinopathy, and glucose-lowering treatments.
2010 Jun
Gastric emptying of hexose sugars: role of osmolality, molecular structure and the CCK₁ receptor.
2010 Nov
Patents

Patents

20040224983
1
20040266989
1
20050043310
1
20060014817
1
20060018933
35
20060154987
1
20060258593
1

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:27:01 GMT 2023
Edited
by admin
on Sat Dec 16 16:27:01 GMT 2023
Record UNII
69DY40RH9B
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
CHOLECYSTOKININ RECEPTOR TYPE A
TARGET -> INHIBITOR
Structure of LOXIGLUMIDE
RACEMATE -> ENANTIOMER
Related Record Type Details
Structure of DEXLOXIGLUMIDE
ACTIVE MOIETY
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