LORGLUMIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C22H32Cl2N2O4
Molecular Weight	459.406
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=IEKOTSCYBBDIJC-UHFFFAOYSA-N

InChI=1S/C22H32Cl2N2O4/c1-3-5-7-13-26(14-8-6-4-2)22(30)19(11-12-20(27)28)25-21(29)16-9-10-17(23)18(24)15-16/h9-10,15,19H,3-8,11-14H2,1-2H3,(H,25,29)(H,27,28)

HIDE SMILES / InChI

Molecular Formula	C22H32Cl2N2O4
Molecular Weight	459.406
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3575382 | https://www.apexbt.com/lorglumide-sodium-salt.html | https://adisinsight.springer.com/drugs/800000580 | https://www.ncbi.nlm.nih.gov/pubmed/24688146

Lorglumide (CR1409) is the first nonpeptidic, selective and potent inhibitor of the cholecystokinin-A and cholecystokinin-B receptors. Lorglumide prevented dose-dependently the emptying of the gallbladder in both experimental models; proglumide exhibited a comparable activity at much higher doses. Lorglumide was associated with significantly inhibited cell growth of human pancreatic cancer cell line Mia PaCa-2 in vitro. Lorglumide also induced G0/G1 cell cycle arrest and apoptosis. The change of invasion ability appeared to be mediated by MMP-2 expression, which was upregulated by CCK-8S and downregulated by lorglumide. Lorglumide had been in preclinical phase for the treatment of biliary dyskinesia, pancreatitis and cancer. However, this development was discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cholecystokinin A receptor 7 Target ID: CHEMBL3501 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2704023	Antagonist 2778		4.9 µM [IC50]

PubMed

Title	Date	PubMed
CR-1409: a potent inhibitor of cholecystokinin-stimulated amylase release and cholecystokinin binding in rat pancreatic acini.	1987	2437574
Development of a class of selective cholecystokinin type B receptor antagonists having potent anxiolytic activity.	1990 Sep	1975695
Pharmacological characterization of a Chinese hamster ovary cell line transfected with the human CCK-B receptor gene.	1996 Aug	8914862
Presynaptically mediated effects of cholecystokinin-8 on the excitability of area postrema neurons in rat brain slices.	2015 Aug 27	26005131
Gut vagal afferents are necessary for the eating-suppressive effect of intraperitoneally administered ginsenoside Rb1 in rats.	2015 Dec 1	26384952
Postsynaptic Depolarization Enhances GABA Drive to Dorsomedial Hypothalamic Neurons through Somatodendritic Cholecystokinin Release.	2015 Sep 23	26400945
The Role of Cholecystokinin in Peripheral Taste Signaling in Mice.	2017	29163209
Intrarenal signaling mediated by CCK plays a role in salt intake-induced natriuresis.	2017 Jul 1	28298361
Peripheral apelin-13 administration inhibits gastrointestinal motor functions in rats: The role of cholecystokinin through CCK(1) receptor-mediated pathway.	2017 Jun	28012561
CCK reduces the food intake mainly through CCK1R in Siberian sturgeon (Acipenser baerii Brandt).	2017 Sep 29	28963554
Intraperitoneal injection of nesfatin-1 primarily through the CCK-CCK1R signal pathway affects expression of appetite factors to inhibit the food intake of Siberian sturgeon (Acipenser baerii).	2018 Nov	30261207
UCN3 suppresses food intake in coordination with CCK and the CCK2R in Siberian sturgeon (Acipenser baerii).	2019 Aug	31051262

Sample Use Guides

In Vivo Use Guide

4 mg/kg was administered four times daily (at 6, 9, and 12 a.m. and 3 p.m.) for 14 days.

Route of Administration: Other

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:37:28 GMT 2023` Edited by `admin` on `Fri Dec 15 17:37:28 GMT 2023`
Record UNII	LAD1UQ73BE
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LORGLUMIDE

Official Name

English

lorglumide [INN]

Common Name

English

(±)-4-(3,4-DICHLOROBENZAMIDO)-N,N-DIPENTYLGLUTARAMIC ACID

Systematic Name

English

4-((3,4-DICHLOROBENZOYL)AMINO)-5-(DIPENTYLAMINO)-5-OXOPENTANOIC ACID

Systematic Name

English

DL-4-(3,4-DICHLOROBENZOYLAMINO)-5-(DIPENTYLAMINO)-5-OXOPENTANOIC ACID

Common Name

English

PENTANOIC ACID, 4-((3,4-DICHLOROBENZOYL)AMINO)-5-(DIPENTYLAMINO)-5-OXO-

Systematic Name

English

CR-1409

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C28197