DEXLOXIGLUMIDE

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 Search

SMILES

CCCCCN(CCCOC)C(=O)[C@@H](CCC(O)=O)NC(=O)C1=CC=C(Cl)C(Cl)=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
Sources: https://www.drugbank.ca/drugs/DB04856

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

Targets

Primary Target	Pharmacology	Condition	Potency
Cholecystokinin receptor type A 2 Target ID: P32238 Gene ID: 886.0 Gene Symbol: CCKAR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17684117	Antagonist 2849		7.53 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Irritable bowel syndrome 61 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27590736	Primary		Phase III 665	Unknown Approved Use Unknown
Pancreatitis 16 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9403804	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Metabolic and toxicological considerations for the latest drugs used to treat irritable bowel syndrome.	2013-04	23330973
Gastric emptying of hexose sugars: role of osmolality, molecular structure and the CCK₁ receptor.	2010-11	20584263
Neuropathy, retinopathy, and glucose-lowering treatments.	2010-06	20508223
Current insights in to the pathophysiology of Irritable Bowel Syndrome.	2010-05-13	20465787
Defining the role of cholecystokinin in the lipid-induced human brain activation matrix.	2010-04	20080096
Role of fat hydrolysis in regulating glucagon-like Peptide-1 secretion.	2010-02	19837920
Association of CCK(1) Receptor Gene Polymorphisms and Irritable Bowel Syndrome in Korean.	2010-01	20535329
Oral and gastrointestinal sensing of dietary fat and appetite regulation in humans: modification by diet and obesity.	2010	21088697
Prokinetic drugs for feed intolerance in critical illness: current and potential therapies.	2009-06	19485878
Duodenal phytohaemagglutinin (red kidney bean lectin) stimulates gallbladder contraction in humans.	2008-07	18248661
Regulation of fat-stimulated neurotensin secretion in healthy subjects.	2008-05	18303078
Role of CCK and potential utility of CCK1 receptor antagonism in the treatment of pancreatitis induced by biliary tract obstruction.	2008-04	18297100
3-[5-(3,4-Dichloro-phenyl)-1-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-2-m-tolyl-propionate (JNJ-17156516), a novel, potent, and selective cholecystokinin 1 receptor antagonist: in vitro and in vivo pharmacological comparison with dexloxiglumide.	2007-11	17684117
Effect of CCK-1 receptor blockade on ghrelin and PYY secretion in men.	2007-04	17138722
Gateways to clinical trials.	2007-03-09	17344945
The relationship between gastric emptying, plasma cholecystokinin, and peptide YY in critically ill patients.	2007	18154642
Use of novel prokinetic agents to facilitate return of gastrointestinal motility in adult critically ill patients.	2006-08	16810038
Pharmacokinetic profile of dexloxiglumide.	2006	17112294
Signal transduction pathways mediating CCK-8S-induced gastric antral smooth muscle contraction.	2006	16954694
Effect of azole antifungals ketoconazole and fluconazole on the pharmacokinetics of dexloxiglumide.	2005-11	16236040
Basic and clinical pharmacology of new motility promoting agents.	2005-10	16185302
A novel, quantitative bio-assay for cholecystokinin type-1 receptor activity in the anaesthetised rat.	2005-09-14	16246596
The single-dose pharmacokinetics of the novel CCK1 receptor antagonist, dexloxiglumide, are not influenced by age and gender.	2005-09	16163898
Pharmacological analysis of CCK2 receptors up-regulated using engineered transcription factors.	2005-07-15	15927720
Effect of CCK-1 antagonist, dexloxiglumide, in female patients with irritable bowel syndrome: a pharmacodynamic and pharmacogenomic study.	2005-03	15743365
Effect of multiple-dose dexloxiglumide on the pharmacokinetics of oral contraceptives in healthy women.	2005-03	15703367
Functional dyspepsia: drugs for new (and old) therapeutic targets.	2004-08	15324710
Cholecystokinin pathways modulate sensations induced by gastric distension in humans.	2004-07	14764444
Absorption, distribution, metabolism and excretion of the cholecystokinin-1 antagonist dexloxiglumide in the dog.	2004-05-21	15151166
Interaction of dexloxiglumide, a cholecystokinin type-1 receptor antagonist, with human cytochromes P450.	2004-05	15108219
Stomach-brain communication by vagal afferents in response to luminal acid backdiffusion, gastrin, and gastric acid secretion.	2004-03	14592947
Absorption, distribution, metabolism and excretion of the cholecystokinin-1 antagonist dexloxiglumide in the rat.	2003-10-07	14527093
Characterization of dexloxiglumide in vitro biopharmaceutical properties and active transport.	2003-10	14502537
CCK1 receptor antagonist, dexloxiglumide: effects on human isolated gallbladder. Potential clinical applications.	2003-09	16484960
Pharmacokinetics and metabolism of the cholecystokinin antagonist dexloxiglumide in male human subjects.	2003-06	12851039
Development and validation of a bioanalytical method for the determination of the cholecystokinin type-1 (CCK(1)) receptor antagonist dexloxiglumide in human plasma.	2003-01-25	12504186
The role of fat and cholecystokinin in functional dyspepsia.	2002-07	12077066
New and emerging treatments for irritable bowel syndrome and functional dyspepsia.	2002-05	15989538
Pharmacokinetics of dexloxiglumide after administration of single and repeat oral escalating doses in healthy young males.	2002-05	12051571
Dexloxiglumide Rotta Research Lab.	2002-04	12090734
Effect of three nonpeptide cholecystokinin antagonists on human isolated gallbladder.	2001-12	11768273
Role of duodenal lipid and cholecystokinin A receptors in the pathophysiology of functional dyspepsia.	2001-03	11171824

Patents

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 `Wed Apr 02 07:52:34 GMT 2025` Edited by `admin` on `Wed Apr 02 07:52:34 GMT 2025`
Record UNII	69DY40RH9B
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LOXIGLUMIDE (R)-FORM

Preferred Name

English

DEXLOXIGLUMIDE

Official 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