Page last updated: 2024-09-20

lorglumide

Description

lorglumide: RN given refers to (+-)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

lorglumide : A racemate comprising equal amounts of (R)- and (S)-lorglumide. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

N(2)-(3,4-dichlorobenzoyl)-N,N-dipentyl-alpha-glutamine : A dicarboxylic acid monoamide obtained by formal condensation of the alpha-carboxy group of N-(3,4-dichlorobenzoyl)glutamic acid with the amino group of dipentylamine. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID3960
CHEMBL ID24938
CHEBI ID88307
SCHEMBL ID149509
MeSH IDM0138779

Synonyms (52)

Synonym
BRD-A29854054-236-03-5
gtpl891
cr-1409
SPECTRUM_001628
PRESTWICK3_000915
BPBIO1_000870
pentanoic acid, 4-((3,4-dichlorobenzoyl)amino)-5-(dipentylamino)-5-oxo-, (+-)-
ccris 6857
lorglumidum [latin]
lorglumida [spanish]
4-((3,4-dichlorobenzoyl)amino)-5-(dipentylamino)-5-oxopentanoic acid
d,l-4-(3,4-dichlorobenzoylamino)-5-(dipentylamino)-5-oxo-pentanoic acid
(+-)-4-(3,4-dichlorobenzamido)-n,n-dipentylglutaramic acid
lorglumide [inn]
PDSP2_000867
BSPBIO_000790
PRESTWICK2_000915
LOPAC0_000731
PDSP1_000881
lorglumide
KBIO2_004676
KBIO2_002108
KBIO2_007244
KBIOSS_002108
PRESTWICK1_000915
PRESTWICK0_000915
SPBIO_002979
HMS2090O20
CHEMBL24938 ,
chebi:88307 ,
L000350
97964-56-2
bdbm50008170
4-(3,4-dichloro-benzoylamino)-4-dipentylcarbamoyl-butyric acid
4-[(3,4-dichlorobenzoyl)amino]-5-(dipentylamino)-5-oxopentanoic acid
lad1uq73be ,
unii-lad1uq73be
lorglumida
lorglumidum
(+/-)-4-(3,4-dichlorobenzamido)-n,n-dipentylglutaramic acid
pentanoic acid, 4-((3,4-dichlorobenzoyl)amino)-5-(dipentylamino)-5-oxo-
dl-4-(3,4-dichlorobenzoylamino)-5-(dipentylamino)-5-oxopentanoic acid
SCHEMBL149509
AB01275506-01
DTXSID2046961
n(2)-(3,4-dichlorobenzoyl)-n,n-dipentyl-alpha-glutamine
SBI-0050709.P002
4-(3,4-dichlorobenzamido)-5-(dipentylamino)-5-oxopentanoic acid
Q12745785
BRD-A29854054-236-07-6
SDCCGSBI-0050709.P003
pentanoic acid,4-[(3,4-dichlorobenzoyl)amino]-5-(dipentylamino)-5-oxo-

Actions

ExcerptReference
"Lorglumide was able to inhibit the functional responses elicited by exogenous CCK administration in both pancreas, stomach and gallbladder, while deramciclane was not effective under such circumstances."( Burghardt, B; Gacsályi, I; Kordás, K; Szénási, G; Varga, G, 1999)

Treatment

ExcerptReference
"Pretreatment with lorglumide blocked the reducing effect of P."( Bombardelli, E; Cabras, C; Carai, MA; Colombo, G; Donzelli, F; Fantini, N; Gessa, GL; Lobina, C; Morazzoni, P; Riva, A, 2009)
"Pretreatment with lorglumide (1.0 mg/kg ip), a selective CCK-A receptor antagonist, reversed CCK-induced inhibition of sucrose intake."( Covasa, M; Hayes, MR; Savastano, DM, 2004)
"Pretreatment with lorglumide, a CCK(1) receptor blocker, reversed the stimulation of amylase release produced by intraduodenal application of ghrelin."( Jaworek, J; Konturek, SJ; Kot, M; Leja-Szpak, A; Macko, M; Mitis-Musioł, M; Nawrot-Porabka, K; Pawlik, WW; Szklarczyk, J, 2007)
"pretreatment with lorglumide (0.1-10 pg) but not PD135,158 (1-100 pg) dose dependently reversed CCK's inhibition of the tail-flick response induced by CWSS."( Kim, KW; Kim, YH; Kwon, SH; Min, BH; Song, DK; Suh, HW, 1996)
"Pretreatment with lorglumide caused a dose-dependent rightward shift of the dose-response curve, indicating competitive antagonism."( Almegård, B; Andersson, SE; Bill, A, 1990)

Drug Classes (4)

ClassDescription
glutamic acid derivativeAn amino acid derivative resulting from reaction of glutamic acid at the amino group or either of the carboxy groups, or from the replacement of any hydrogen by a heteroatom. The definition normally excludes peptides containing glutamic acid residues.
dicarboxylic acid monoamide
benzamides
dichlorobenzeneAny member of the class of chlorobenzenes carrying two chloro groups at unspecified positions.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (3)

lorglumide is involved in 3 pathway(s), involving a total of 75 unique proteins and 90 unique compounds

PathwayProteinsCompounds
D-Glutamine and D-Glutamate Metabolism1517
Peptidoglycan Biosynthesis I3036
Peptidoglycan Biosynthesis II3037

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cholecystokinin receptor type ARattus norvegicus (Norway rat)IC50 (µMol)0.03400.00000.43624.3000AID52912; AID53038
Cholecystokinin receptor type ARattus norvegicus (Norway rat)Ki0.12900.00010.27892.8900AID50500
Cholecystokinin receptor type ACavia porcellus (domestic guinea pig)IC50 (µMol)2.20000.00041.13803.5000AID52568
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (14)

Assay IDTitleYearJournalArticle
AID51292Ratio of IC50 against CCK-B1 and CCK-B(B2) binding1992Journal of medicinal chemistry, Jan, Volume: 35, Issue:1
Structure-antigastrin activity relationships of new (R)-4-benzamido-5-oxopentanoic acid derivatives.
AID52568Inhibition of binding of [125I]- CCK-33 to guinea pig cortex1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Novel glutamic acid derived cholecystokinin receptor ligands.
AID53038Inhibition of binding of [125I]- CCK-33 to rat pancreas1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Novel glutamic acid derived cholecystokinin receptor ligands.
AID52912Concentration required to inhibit by 50% specific binding of [125I](BH)-CCK-8 to cholecystokinin type A receptor in rat pancreatic acini1992Journal of medicinal chemistry, Jan, Volume: 35, Issue:1
Structure-antigastrin activity relationships of new (R)-4-benzamido-5-oxopentanoic acid derivatives.
AID51288Concentration required to inhibit by 50% the specific binding of [3H]pentagastrin to cholecystokinin type B receptor in rabbit gastric gland1992Journal of medicinal chemistry, Jan, Volume: 35, Issue:1
Structure-antigastrin activity relationships of new (R)-4-benzamido-5-oxopentanoic acid derivatives.
AID717844Inhibition of mouse Ido2 transfected in HEK293T cells using L-tryptophan as substrate assessed as kynurenine formation at 20 uM after 45 mins by spectrophotometric analysis relative to control2012Bioorganic & medicinal chemistry letters, Dec-15, Volume: 22, Issue:24
Identification of selective inhibitors of indoleamine 2,3-dioxygenase 2.
AID50511Ratio between IC50 CCK-A vs IC50 CCK-B(B2)1992Journal of medicinal chemistry, Jan, Volume: 35, Issue:1
Structure-antigastrin activity relationships of new (R)-4-benzamido-5-oxopentanoic acid derivatives.
AID50966Inhibition of binding of [125I]gastrin to Cholecystokinin type B receptor from guinea pig gastric glands1990Journal of medicinal chemistry, Feb, Volume: 33, Issue:2
Novel glutamic acid derived cholecystokinin receptor ligands.
AID51443Inhibition of the specific binding of [125I](BH)-CCK-8 to Cholecystokinin type B receptor in rat brain cortex1992Journal of medicinal chemistry, Jan, Volume: 35, Issue:1
Structure-antigastrin activity relationships of new (R)-4-benzamido-5-oxopentanoic acid derivatives.
AID50500Binding affinity against Cholecystokinin type A receptor using [125I](BH)-CCK-8 as radioligand in rat pancreas.1996Journal of medicinal chemistry, Feb-16, Volume: 39, Issue:4
Synthesis, biological evaluation, and quantitative receptor docking simulations of 2-[(acylamino)ethyl]-1,4-benzodiazepines as novel tifluadom-like ligands with high affinity and selectivity for kappa-opioid receptors.
AID493017Wombat Data for BeliefDocking1991Journal of medicinal chemistry, Dec, Volume: 34, Issue:12
Cholecystokinin antagonists: (R)-tryptophan-based hybrid antagonists of high affinity and selectivity for CCK-A receptors.
AID1346809Rat CCK1 receptor (Cholecystokinin receptors)1990Proceedings of the National Academy of Sciences of the United States of America, Sep, Volume: 87, Issue:17
Development of a class of selective cholecystokinin type B receptor antagonists having potent anxiolytic activity.
AID1346809Rat CCK1 receptor (Cholecystokinin receptors)1987Pancreas, , Volume: 2, Issue:1
CR-1409: a potent inhibitor of cholecystokinin-stimulated amylase release and cholecystokinin binding in rat pancreatic acini.
AID1346883Human CCK2 receptor (Cholecystokinin receptors)1996Neuropeptides, Aug, Volume: 30, Issue:4
Pharmacological characterization of a Chinese hamster ovary cell line transfected with the human CCK-B receptor gene.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (191)

TimeframeStudies, This Drug (%)All Drugs %
pre-199042 (21.99)18.7374
1990's88 (46.07)18.2507
2000's43 (22.51)29.6817
2010's18 (9.42)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (1.01%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other197 (98.99%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research Highlights

Safety/Toxicity (1)

ArticleYear
Involvement of cholecystokinin receptors in the adverse effect of glucocorticoids on diet-induced necrotizing pancreatitis.
Surgery, Volume: 106, Issue: 2
1989
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Long-term Use (7)

ArticleYear
Inhibition of gastric emptying and intestinal transit by amphetamine through a mechanism involving an increased secretion of CCK in male rats.
British journal of pharmacology, Volume: 124, Issue: 6
1998
Pancreatic growth: interaction of exogenous cholecystokinin, a protease inhibitor, and a cholecystokinin receptor antagonist in mice.
Gut, Volume: 28 Suppl
1987
Chronic administration of cholecystokinin antagonists reverses the enhancement of spinal morphine analgesia induced by acute pretreatment.
Brain research, May-21, Volume: 516, Issue: 2
1990
Effects of long-term CCK stimulation and CCK blockade on pancreatic and intestinal growth, morphology, and function.
Digestion, Volume: 46 Suppl 2
1990
Effect of lorglumide (CR-1409) on pancreatic secretory and trophic response to caerulein in newborn rats.
Acta physiologica Hungarica, Volume: 78, Issue: 1
1991
The effect of long-term administration of lorglumide (CR 1409) on rat pancreatic growth and enzyme composition.
Pancreas, Volume: 5, Issue: 5
1990
Direct effect of bombesin on pancreatic and gastric growth in suckling rats.
Regulatory peptides, Sep-22, Volume: 41, Issue: 2
1992
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Pharmacokinetics (1)

ArticleYear
Demonstration of a new resonance peak by proton NMR in rat pancreas stimulated with caerulein.
Pancreas, Volume: 5, Issue: 5
1990
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (13)

ArticleYear
Effects of lorglumide and atropine on MgSO(4)-induced gallbladder emptying in conscious dogs.
Research in veterinary science, Volume: 69, Issue: 2
2000
Supraspinal neurotensin-induced antianalgesia in mice is mediated by spinal cholecystokinin.
Japanese journal of pharmacology, Volume: 79, Issue: 2
1999
Antianalgesic action of dynorphin A mediated by spinal cholecystokinin.
Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.), Volume: 220, Issue: 3
1999
Pentobarbital antagonism of morphine analgesia mediated by spinal cholecystokinin.
The Journal of pharmacology and experimental therapeutics, Volume: 284, Issue: 3
1998
Reversal of tolerance to the antitransit effects of morphine during acute intestinal inflammation in mice.
British journal of pharmacology, Volume: 122, Issue: 6
1997
Comparative effects of CCK receptor antagonists on rat pancreatic secretion in vivo.
The American journal of physiology, Volume: 256, Issue: 1 Pt 1
1989
CR-1409: a potent inhibitor of cholecystokinin-stimulated amylase release and cholecystokinin binding in rat pancreatic acini.
Pancreas, Volume: 2, Issue: 1
1987
Effects of CCK-receptor antagonists on CCK-stimulated pepsinogen secretion and calcium increase in isolated guinea pig gastric chief cells.
Digestive diseases and sciences, Volume: 35, Issue: 7
1990
Cholecystokinin causes contraction of the pupillary sphincter in monkeys but not in cats, rabbits, rats and guinea-pigs: antagonism by lorglumide.
Acta physiologica Scandinavica, Volume: 138, Issue: 4
1990
In vivo comparison of inhibition with proglumide and CR-1409 of cholecystokinin-induced pressure in the biliary tract of the guinea pig.
Surgery, gynecology & obstetrics, Volume: 170, Issue: 3
1990
The effect of CR 1409, a potent CCK receptor antagonist, on basal and stimulated pancreatic secretion in rat.
Pancreas, Volume: 5, Issue: 1
1990
The effect of a novel CCK-antagonist (lorglumide) on human and guinea pig gallbladder strips: a tensiometric study.
Bollettino della Societa italiana di biologia sperimentale, Volume: 66, Issue: 6
1990
Cholecystokinin contracts isolated human and monkey iris sphincters; a study with CCK receptor antagonists.
European journal of pharmacology, Feb-11, Volume: 211, Issue: 2
1992
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]