You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameIsopropamide
Accession NumberDB01625
Typesmall molecule
Groupsapproved
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
Thumb
Synonyms
SynonymLanguageCode
IsopropamideNot AvailableNot Available
SID11112197Not AvailableNot Available
SID144203913Not AvailableNot Available
Salts
Name/CAS Structure Properties
Isopropamide iodide
Thumb Not applicable DBSALT001023
Brand namesNot Available
Brand mixtures
Brand NameIngredients
ValtraxIsopropamide Iodide + Diazepam
CategoriesNot Available
CAS number7492-32-2
WeightAverage: 353.5209
Monoisotopic: 353.259288688
Chemical FormulaC23H33N2O
InChI KeyJTPUMZTWMWIVPA-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
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassDiphenylmethanes
Direct parentDiphenylmethanes
Alternative parentsPhenylpropylamines; Primary Carboxylic Acid Amides; Polyamines; Enolates; Carboxylic Acids
Substituentsphenylpropylamine; primary carboxylic acid amide; carboxamide group; carboxylic acid derivative; enolate; polyamine; carboxylic acid; amine; organonitrogen compound
Classification descriptionThis compound belongs to the diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
Pharmacology
IndicationFor 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.
PharmacodynamicsIsopropamide 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 actionAnticholinergics 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySymptoms 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption - 0.8295
Blood Brain Barrier + 0.9878
Caco-2 permeable + 0.6521
P-glycoprotein substrate Substrate 0.657
P-glycoprotein inhibitor I Non-inhibitor 0.9503
P-glycoprotein inhibitor II Non-inhibitor 0.8809
Renal organic cation transporter Inhibitor 0.5178
CYP450 2C9 substrate Non-substrate 0.7878
CYP450 2D6 substrate Non-substrate 0.715
CYP450 3A4 substrate Substrate 0.69
CYP450 1A2 substrate Non-inhibitor 0.9046
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Inhibitor 0.8932
CYP450 2C19 substrate Non-inhibitor 0.9026
CYP450 3A4 substrate Non-inhibitor 0.8492
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.953
Ames test Non AMES toxic 0.8654
Carcinogenicity Non-carcinogens 0.7639
Biodegradation Not ready biodegradable 0.8598
Rat acute toxicity 2.5213 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9906
hERG inhibition (predictor II) Inhibitor 0.5525
Pharmacoeconomics
Manufacturers
  • Glaxosmithkline
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Isopropamide iodide powder6.72USDg
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point182-184U.S. Patent 2,823,233.
Predicted Properties
PropertyValueSource
water solubility4.24e-05 g/lALOGPS
logP2.27ALOGPS
logP0.14ChemAxon
logS-7ALOGPS
pKa (strongest acidic)16.31ChemAxon
pKa (strongest basic)-3.3ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count1ChemAxon
polar surface area43.09ChemAxon
rotatable bond count8ChemAxon
refractivity120.74ChemAxon
polarizability41.28ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

U.S. Patent 2,823,233.

General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC07055
PubChem Compound3775
PubChem Substance46507726
ChemSpider3643
PharmGKBPA164781398
WikipediaIsopropamide_iodide
ATC CodesA03AB09
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
DonepezilPossible antagonism of action
GalantaminePossible antagonism of action
HaloperidolThe anticholinergic increases the risk of psychosis and tardive dyskinesia
Food InteractionsNot Available

Targets

1. Muscarinic acetylcholine receptor M3

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M3 P20309 Details

References:

  1. 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
  2. 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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M4 P08173 Details

References:

  1. 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. 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
comments powered by Disqus
Drug created on August 29, 2007 14:22 / Updated on May 02, 2014 15:54