DrugBank: Isopropamide (DB01625)

targets (2)

Identification

Name

Isopropamide

Accession Number

DB01625

Type

small molecule

Groups

approved

Description

Isopropamide iodide is a long-acting quaternary anticholinergic drug. It is used in the treatment of peptic ulcer and other gastrointestinal disorders marked by hyperacidity and hypermotility.

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

2,2-Diphenyl-4-diisopropylaminobutyramide methiodide
4-(Diisopropylamino)-2,2-diphenylbutyramide methiodide
Chloroisopropamide
Isopropamide iodide
Isoproponum iodide

Salts

Not Available

Brand names

Name	Company
Darbid
Dipramid
Dipramide
Isamid
Marygin-M
Piaccamide
Priamide
Priazimide
Sanulcin
Tyrimide

Brand mixtures

Not Available

Categories

Gastrointestinal Agents

CAS number

7492-32-2

Weight

Average: 353.5209
Monoisotopic: 353.259288688

Chemical Formula

C₂₃H₃₃N₂O

InChI Key

InChIKey=JTPUMZTWMWIVPA-UHFFFAOYSA-O

InChI

InChI=1S/C23H32N2O/c1-18(2)25(5,19(3)4)17-16-23(22(24)26,20-12-8-6-9-13-20)21-14-10-7-11-15-21/h6-15,18-19H,16-17H2,1-5H3,(H-,24,26)/p+1

Plain Text

IUPAC Name

(3-carbamoyl-3,3-diphenylpropyl)(methyl)bis(propan-2-yl)azanium

SMILES

CC(C)[N+](C)(CCC(C(N)=O)(C1=CC=CC=C1)C1=CC=CC=C1)C(C)C

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Diphenylmethanes

Substructures

Carbonyl Compounds
Amino Ketones
Benzene and Derivatives
Carbamates and Derivatives
Quaternary Ammonium Salts
Diphenylmethanes
Phenethylamines
Aromatic compounds
Carboxamides and Derivatives
Phenylpropylamines
Carboxylic Acids and Derivatives
Cations

Pharmacology

Indication

For the treatment of a wide range of gastrointestinal disorders, including such conditions as peptic ulcer, gastritis, hyperchlorhydria, functional diarrhea, irritable or spastic colon, pyloroduodenal irritability, pylorospasm, acute nonspecific gastroenteritis, biliary dyskinesia and chronic cholelithiasis, duodenitis, gastrointestinal spasm; it may also be used to treat genitourinary spasm.

Pharmacodynamics

Isopropamide is a long-acting quaternary anticholinergic drug. It is used in the treatment of peptic ulcer and other gastrointestinal disorders marked by hyperacidity and hypermotility.

Mechanism of action

Anticholinergics are a class of medications that inhibit parasympathetic nerve impulses by selectively blocking the binding of the neurotransmitter acetylcholine to its receptor in nerve cells. The nerve fibers of the parasympathetic system are responsible for the involuntary movements of smooth muscles present in the gastrointestinal tract. Inhibition here decreases acidity and motility, aiding in the treatment of gastrointestinal disorders.

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half life

Not Available

Clearance

Not Available

Toxicity

Symptoms of overdose include dryness of mouth, dysphagia, thirst, blurred vision, dilated pupils, photophobia, fever, rapid pulse and respiration, disorientation. Depression and circulatory collapse may result from severe overdosage.

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Glaxosmithkline

Packagers

Gallipot

Dosage forms

Not Available

Prices

Unit description	Cost	Unit
Isopropamide iodide powder	6.72 USD	g

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
water solubility	4.24e-05 g/l	ALOGPS
logP	2.27	ALOGPS
logP	0.14	ChemAxon
logS	-7	ALOGPS
pKa (strongest acidic)	16.31	ChemAxon
pKa (strongest basic)	-3.3	ChemAxon
physiological charge	1	ChemAxon
hydrogen acceptor count	1	ChemAxon
hydrogen donor count	1	ChemAxon
polar surface area	43.09	ChemAxon
rotatable bond count	8	ChemAxon
refractivity	120.74	ChemAxon
polarizability	41.28	ChemAxon

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
KEGG Compound	C07055
PubChem Compound	3775
PubChem Substance	46507726
ChemSpider	3643
PharmGKB	PA164781398
Wikipedia	http://en.wikipedia.org/wiki/Isopropamide_iodide

ATC Codes

A03AB09

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Drug	Interaction
Donepezil	Possible antagonism of action
Galantamine	Possible antagonism of action
Haloperidol	The anticholinergic increases the risk of psychosis and tardive dyskinesia

Food Interactions

Not Available

Targets
1. Muscarinic acetylcholine receptor M3 Pharmacological action: yes Actions: antagonist The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover Organism class: human UniProt ID: P20309 Gene: CHRM3 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Eglen RM, Whiting RL: Competitive and non-competitive antagonism exhibited by ‘selective’ antagonists at atrial and ileal muscarinic receptor subtypes. Br J Pharmacol. 1987 Apr;90(4):701-7. Pubmed Lane MA: Muscarinic cholinergic activation of mouse spleen cells cytotoxic to tumor cells in vitro. J Natl Cancer Inst. 1978 Sep;61(3):923-6. Pubmed 2. Muscarinic acetylcholine receptor M4 Pharmacological action: unknown Actions: antagonist The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is inhibition of adenylate cyclase Organism class: human UniProt ID: P08173 Gene: CHRM4 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Lane MA: Muscarinic cholinergic activation of mouse spleen cells cytotoxic to tumor cells in vitro. J Natl Cancer Inst. 1978 Sep;61(3):923-6. Pubmed Eglen RM, Whiting RL: Competitive and non-competitive antagonism exhibited by ‘selective’ antagonists at atrial and ileal muscarinic receptor subtypes. Br J Pharmacol. 1987 Apr;90(4):701-7. Pubmed

Targets

1. Muscarinic acetylcholine receptor M3

Pharmacological action: yes
Actions: antagonist

The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover

Organism class: human
UniProt ID: P20309 Link_out

Gene: CHRM3 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Eglen RM, Whiting RL: Competitive and non-competitive antagonism exhibited by ‘selective’ antagonists at atrial and ileal muscarinic receptor subtypes. Br J Pharmacol. 1987 Apr;90(4):701-7. Pubmed
Lane MA: Muscarinic cholinergic activation of mouse spleen cells cytotoxic to tumor cells in vitro. J Natl Cancer Inst. 1978 Sep;61(3):923-6. Pubmed

2. Muscarinic acetylcholine receptor M4

Pharmacological action: unknown
Actions: antagonist

Organism class: human
UniProt ID: P08173 Link_out

Gene: CHRM4 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Lane MA: Muscarinic cholinergic activation of mouse spleen cells cytotoxic to tumor cells in vitro. J Natl Cancer Inst. 1978 Sep;61(3):923-6. Pubmed
Eglen RM, Whiting RL: Competitive and non-competitive antagonism exhibited by ‘selective’ antagonists at atrial and ileal muscarinic receptor subtypes. Br J Pharmacol. 1987 Apr;90(4):701-7. Pubmed

Comments

Drug created on August 29, 2007 14:22 / Updated on February 08, 2013 16:20