Proglumide

HCID 178783660CAS 24485-90-3
Substructure searchFind similar structures

Basic information

Standard SMILES
CCCN(CCC)C(=O)C(CCC(=O)O)NC(=O)c1ccccc1
InChIKey
DGMKFQYCZXERLX-UHFFFAOYSA-N
Molecular formula
C18H26N2O4
Average molar mass
334.4 g/mol

Overview

Proglumide is a racemate composed of equal amounts of (R)- and (S)-proglumide. A non-selective CCK antagonist that was used primarily for treatment of stomach ulcers, but has been replaced by newer drugs. It has a role as an opioid analgesic, a cholinergic antagonist, a drug metabolite, an anti-ulcer drug, a gastrointestinal drug, a delta-opioid receptor agonist, a cholecystokinin antagonist and a xenobiotic metabolite. It contains a (R)-proglumide and a (S)-proglumide.

Names & identifiers

Preferred name
Proglumide
IUPAC
4-benzamido-5-(dipropylamino)-5-oxopentanoic acid
English name
4-(Benzoylamino)-5-(dipropylamino)-5-oxovaleric acid
Molecular weight
0

Names & synonyms

proglumide6620-60-64-benzamido-5-(dipropylamino)-5-oxopentanoic acidBinosideXylamidedl-proglumideMilidNulsaGastrotopicMidelidUlcutinProglumida
Show more names
4-(Benzoylamino)-5-(dipropylamino)-5-oxovaleric acid4-(Phenylcarbonylamino)-5-(N,N-dipropylamino)-5-oxopentanoic acid
XydeProglumidumPromidW-5219DTXSID7023516242 DLCR-242(+-)-4-Benzamido-N,N-dipropylglutaramic acid

Database identifiers

CAS
24485-90-3
ChEMBL
CHEMBL316561
ChEBI
CHEBI:32058
UNII
EPL8W5565D
EC Number
229-567-4
Nikkaji
J3.421E

Properties

Computed structural properties

XLogP
2.4
Topological polar surface area
86.7 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
4
Rotatable bonds
10
Heavy atoms
24

Experimental & physicochemical properties

Human DrugsPharmaceuticals
Collision Cross Section · 2 items

181.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

186.48 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

FDA UNII
8 W5565D · EPL8W5565D

Safety & regulation

GHS classification

GHS Classification · 3 items

This chemical does not meet GHS hazard criteria for 100% (3 of 3) of all reports.

Not Classified

Aggregated GHS information provided per 3 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory InformationStatus: Active Update: 29-03-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/23299
Other Safety InformationIMAP assessments - Pentanoic acid, 4-(benzoylamino)-5-(dipropylamino)-5-oxo-, (.+-.)-: Human health tier I assessment
Hazard Classes and CategoriesNot Classified

Chemistry & industry

Pharmacology

ATC Code · 2 items

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

MeSH Pharmacological Classification · 1 item

Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief.

Uses & manufacturing

Use ClassificationPharmaceuticals
Additional notes · 1 item

DefinitionChEBI: Proglumide is a racemate composed of equal amounts of (R)- and (S)-proglumide. A non-selective CCK antagonist that was used primarily for treatment of stomach ulcers, but has been replaced by newer drugs. It has a role as a drug metabolite, a xenobiotic metabolite, a cholinergic antagonist, an anti-ulcer drug, a cholecystokinin antagonist, a gastrointestinal drug, a delta-opioid receptor agonist and an opioid analgesic. It contains a (R)-proglumide and a (S)-proglumide.

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