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L109

Sigma-Aldrich

Lorglumide sodium salt

solid

Synonym(s):

(±)-4-[(3,4-Dichlorobenzoyl)amino]-5-(dipentylamino)-5-oxopentanoic acid sodium salt, CR 1409

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About This Item

Empirical Formula (Hill Notation):
C22H31Cl2N2NaO4
CAS Number:
1021868-76-7
Molecular Weight:
481.39
MDL number:
MFCD00083183
UNSPSC Code:
12352200
PubChem Substance ID:
24278098
NACRES:
NA.32

form

solid

color

white

solubility

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: >10 mg/mL
H2O: 10 mg/mL
methanol: 28 mg/mL

SMILES string

[Na+].CCCCCN(CCCCC)C(=O)C(CCC([O-])=O)NC(=O)c1ccc(Cl)c(Cl)c1

InChI

1S/C22H32Cl2N2O4.Na/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);/q;+1/p-1

InChI key

JCNPYMDDOUQTBK-UHFFFAOYSA-M

Gene Information

human ... CCKAR(886)

Application

Lorglumide sodium salt has been used as a cck-a (cholecystokinin A) receptor antagonist for peptide determination in rat islet cells. It has been used as a CCK1 inhibitor to check the effect of cck1 (cck-a) and cck2 (cck-b) receptors on cerulein-induced upregulation of egr-1 (early growth response 1) expression in rat pancreatic acinar cells.

Biochem/physiol Actions

Potent and selective non-peptide cholecystokinin (CCKA) receptor antagonist; orally active.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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M D'Amato et al.
British journal of pharmacology, 102(2), 391-395 (1991-02-01)
1. Three recently described non-peptide cholecystokinin (CCK) antagonists (devazepide, lorglumide, loxiglumide) have been studied for their antagonism of the contraction to cholecystokinin-octapeptide (CCK-OP) in human alimentary muscle and guinea-pig intestine. 2. Each antagonist caused a concentration-dependent inhibition of the contraction
G L Edwards et al.
Annals of the New York Academy of Sciences, 897, 192-197 (2000-02-17)
Ingestion of food and fluid stimulates release of a number of peptides from the gastrointestinal system. These peptides are recognized to act as neurotransmitters/neuromodulators and act at both peripheral and central receptors. Many studies indicate that these peptides are important
H W Suh et al.
Peptides, 16(7), 1229-1234 (1995-01-01)
Various doses of sulfated cholecystokinin octapeptide (CCK-8s) injected intracerebroventricularly (ICV) alone did not show any antinociceptive effect. CCK-8s (0.01-1 ng) pretreated ICV for 10 min dose-dependently attenuated the inhibition of the tail flick response induced by ICV-administered morphine (2 micrograms).
F Makovec et al.
Arzneimittel-Forschung, 37(11), 1265-1268 (1987-11-01)
Derivatives of 5-(dipentylamino)-5-oxo-pentanoic acid are a new class of non-peptide cholecystokinin (CCK) antagonists. The most potent compound, D,L-4-(3,4-dichlorobenzoylamino)-5-(dipentylamino)-5-oxo-pen tanoic acid (lorglumide, CR 1409), has a great affinity for the pancreatic CCK receptors and is a competitive, specific and potent CCK
Yukio Ikeda et al.
Biochemical and biophysical research communications, 333(3), 778-786 (2005-06-22)
The glucose-induced insulin secretion is fine-tuned by numerous factors. To systematically identify insulinotropic factors, we optimized a primary beta-cell-based functional assay to monitor intracellular Ca2+ flux ([Ca2+]i). By this assay system, we successfully identified several insulinotropic peptides including cholecystokinin, gastrin
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