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Details

Stereochemistry RACEMIC
Molecular Formula C21H30Cl2N2O5
Molecular Weight 461.379
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LOXIGLUMIDE

SMILES

CCCCCN(CCCOC)C(=O)C(CCC(O)=O)NC(=O)C1=CC(Cl)=C(Cl)C=C1

InChI

InChIKey=QNQZBKQEIFTHFZ-UHFFFAOYSA-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)

HIDE SMILES / InChI

Molecular Formula C21H30Cl2N2O5
Molecular Weight 461.379
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Loxiglumide is a potent, orally active, and selective CCK-A receptor antagonist which stimulates calorie intake and hunger feelings in humans. Loxiglumide inhibits pancreatic secretion of digestive enzymes, and also blocks CCK-induced gastric secretions and emptying. Intravenous administration of loxiglumide antagonized the CCK-induced reduction of gastric emptying in rats, acceleration of intestinal transport in mice, increase in ileal motility in rabbits, gallbladder contraction in guinea pigs and acceleration of gallbladder emptying in mice.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
195.0 nM [IC50]
Conditions
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
12.7 mg/L
400 mg 2 times / day multiple, oral
dose: 400 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
LOXIGLUMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
11.9 mg/L
400 mg 2 times / day single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LOXIGLUMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
109.8 mg × h/L
400 mg 2 times / day multiple, oral
dose: 400 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
LOXIGLUMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
60.6 mg × h/L
400 mg 2 times / day single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LOXIGLUMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
800 mg 3 times / day multiple, oral
Highest studied dose
Dose: 800 mg, 3 times / day
Route: oral
Route: multiple
Dose: 800 mg, 3 times / day
Sources: Page: p.225
unhealthy, ADULT
n = 32
Health Status: unhealthy
Condition: pancreatic cancer
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 32
Sources: Page: p.225
1200 mg 1 times / day multiple, oral
Studied dose
Dose: 1200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1200 mg, 1 times / day
Sources: Page: e3
unhealthy, ADULT
n = 50
Health Status: unhealthy
Condition: pancreatitis
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 50
Sources: Page: e3
50 mg single, intravenous
Studied dose
Dose: 50 mg
Route: intravenous
Route: single
Dose: 50 mg
Sources: Page: p.335
unhealthy, ADULT
n = 7
Health Status: unhealthy
Condition: biliary tract disease
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 7
Sources: Page: p.335
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
PubMed

PubMed

TitleDatePubMed
Pharmacological characterisation of a new potent and specific nonpolypeptidic cholecystokinin antagonist.
1987 Jun
Sensitive SPE-HPLC method to determine a novel angiotensin-AT1 antagonist in biological samples.
2004 Apr 16
Patents

Sample Use Guides

chronic pancreatitis: oral treatment with loxiglumide (300, 600, and 1,200 mg/d) for 4 weeks.
Route of Administration: Oral
In Vitro Use Guide
Loxiglumide inhibited 125I-CCK-8 binding to rat pancreatic and bovine gallbladder membranes with IC50 values of 195 and 77.1 nmol/l, respectively. Loxiglumide also inhibited 125I-CCK-8 binding to guinea pig cerebral cortex membranes and parietal cells with IC50 values of 12363 and 15455 nmol/l, respectively. In addition, loxiglumide inhibited 125I-gastrin binding to guinea pig parietal cells with IC50 values of 6134 nmol/l.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:58:37 UTC 2023
Edited
by admin
on Fri Dec 15 15:58:37 UTC 2023
Record UNII
77MPX3N42I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LOXIGLUMIDE
INN   JAN   MART.   MI  
INN  
Official Name English
loxiglumide [INN]
Common Name English
LOXIGLUMIDE [JAN]
Common Name English
(±)-4-(3,4-DICHLOROBENZAMIDO)-N-(3-METHOXYPROPYL)-N-PENTYLGLUTARAMIC ACID
Systematic Name English
LOXIGLUMIDE [MART.]
Common Name English
CR-1505
Code English
LOXIGLUMIDE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C28197
Created by admin on Fri Dec 15 15:58:37 UTC 2023 , Edited by admin on Fri Dec 15 15:58:37 UTC 2023
NCI_THESAURUS C29701
Created by admin on Fri Dec 15 15:58:37 UTC 2023 , Edited by admin on Fri Dec 15 15:58:37 UTC 2023
Code System Code Type Description
INN
6113
Created by admin on Fri Dec 15 15:58:37 UTC 2023 , Edited by admin on Fri Dec 15 15:58:37 UTC 2023
PRIMARY
MERCK INDEX
m6916
Created by admin on Fri Dec 15 15:58:37 UTC 2023 , Edited by admin on Fri Dec 15 15:58:37 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID6057615
Created by admin on Fri Dec 15 15:58:37 UTC 2023 , Edited by admin on Fri Dec 15 15:58:37 UTC 2023
PRIMARY
CAS
107097-80-3
Created by admin on Fri Dec 15 15:58:37 UTC 2023 , Edited by admin on Fri Dec 15 15:58:37 UTC 2023
PRIMARY
SMS_ID
100000082247
Created by admin on Fri Dec 15 15:58:37 UTC 2023 , Edited by admin on Fri Dec 15 15:58:37 UTC 2023
PRIMARY
FDA UNII
77MPX3N42I
Created by admin on Fri Dec 15 15:58:37 UTC 2023 , Edited by admin on Fri Dec 15 15:58:37 UTC 2023
PRIMARY
DRUG CENTRAL
1614
Created by admin on Fri Dec 15 15:58:37 UTC 2023 , Edited by admin on Fri Dec 15 15:58:37 UTC 2023
PRIMARY
MESH
C053737
Created by admin on Fri Dec 15 15:58:37 UTC 2023 , Edited by admin on Fri Dec 15 15:58:37 UTC 2023
PRIMARY
PUBCHEM
60182
Created by admin on Fri Dec 15 15:58:37 UTC 2023 , Edited by admin on Fri Dec 15 15:58:37 UTC 2023
PRIMARY
EVMPD
SUB08608MIG
Created by admin on Fri Dec 15 15:58:37 UTC 2023 , Edited by admin on Fri Dec 15 15:58:37 UTC 2023
PRIMARY
NCI_THESAURUS
C96872
Created by admin on Fri Dec 15 15:58:37 UTC 2023 , Edited by admin on Fri Dec 15 15:58:37 UTC 2023
PRIMARY
ChEMBL
CHEMBL206025
Created by admin on Fri Dec 15 15:58:37 UTC 2023 , Edited by admin on Fri Dec 15 15:58:37 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY