Proglumide (HCID 4922)

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 A non-selective CCK antagonist that was used primarily for treatment of stomach ulcers, but has been replaced by newer drugs.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: Proglumide
Molecular formula: C18H26N2O4
Molecular weight: 334.41

Names & synonyms

proglumide6620-60-64-benzamido-5-(dipropylamino)-5-oxopentanoic acidBinosideXylamidedl-proglumideMilidNulsaGastrotopicMidelidUlcutinProglumida

Show more names

ProMkxm242dlcr242w5219milide

XydeProglumidumPromidW-5219DTXSID7023516242 DLCR-242(+-)-4-Benzamido-N,N-dipropylglutaramic acid

Database identifiers

CAS: 6620-60-6
PubChem CID: 4922
DTXSID: DTXSID7023516
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 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 4
Rotatable bonds: 10
Heavy atoms: 24
Formal charge: 0
Complexity: 413

Experimental & physicochemical properties

Human DrugsPharmaceuticals

Collision Cross Section · 2 items

181.1 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

186.48 Å² [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point: 148 · 148-150°C
Boiling point: 471.21 °C · 471.21°C (rough estimate)
Density: 1.1944 · 1.1944 (rough estimate)
refractive index: 1.57 · 1.5700 (estimate)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
solubility: DMSO (Slightly), Methanol (Slightly)
form: Solid
pka: 4.51 · 4.51±0.10(Predicted)
color: Crystals
InChI: InChI=1S/C18H26N2O4/c1-3-12-20(13-4-2)18(24)15(10-11-16(21)22)19-17(23)14-8-6-5-7-9-14/h5-9,15H,3-4,10-13H2,1-2H3,(H,19,23)(H,21,22)
InChIKey: DGMKFQYCZXERLX-UHFFFAOYSA-N
SMILES: C(O)(=O)CCC(NC(=O)C1=CC=CC=C1)C(N(CCC)CCC)=O
CAS DataBase Reference: 6620 · 6620-60-6(CAS DataBase Reference)
FDA UNII: 8 W5565D · EPL8W5565D
ATC code: 2 BX06 · A02BX06
EPA Substance Registry System: 4 · Pentanoic acid, 4-(benzoylamino)-5-(dipropylamino)-5-oxo- (6620-60-6)
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 261 · P261-P305+P351+P338
Toxicity: 50 in · LD50 in mice (mg/kg): 2211-2649 i.v.; 7350-8861 orally (Rovati)
REACH Registrations: Active

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 InformationREACH registered substance: Proglumide (EC: 229-567-4)

Other Safety InformationIMAP assessments - Pentanoic acid, 4-(benzoylamino)-5-(dipropylamino)-5-oxo-, (.+-.)-: Human health tier I assessment

Hazard Classes and CategoriesNot Classified

Safety data

Toxicity: LD50 in mice (mg/kg): 2211-2649 i.v.; 7350-8861 orally (Rovati)
Signal word: Warning
Symbol(GHS): GHS07
Hazard statements: H302-H315-H319-H335
REACH Registrations: Active
Precautionary statements: P261-P305+P351+P338

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

Applications · 2 items

DescriptionProglumide (Milid) is a drug that inhibits gastrointestinal motility and reduces gastric secretions. It acts as a cholecystokinin antagonist, which blocks both the CCKA and CCKB subtypes. It was used mainly in the treatment of stomach ulcers, although it has now been largely replaced by newer drugs for this application.Proglumide is a nonpeptide and orally active cholecystokinin (CCK)-A/B receptors antagonist. Proglumide selective blocks CCK’s effects in the central nervous system (CNS). Proglumide has ability to inhibit gastric secretion and to protect the gastroduodenal mucosa. Proglumide also has antiepileptic and antioxidant activities.

UsesAnticholinergic.

Upstream & downstream products

Upstream raw materials

Dipropylamine Benzoyl chloride

Suppliers50 total

北京华美互利生物化工010-56205725 · [email protected]

常州亚邦制药有限公司[email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

山东泰诚生物科技有限公司18769832557 18769832557 · [email protected]

武汉鹏垒生物科技有限公司15871464247 · [email protected]

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.

Related reactions

1 records

New reaction record

HRID 1191970As reactantuspto-grants-2014_03

Linked notes

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Basic information