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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
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixtures
Brand NameIngredients
ValtraxIsopropamide Iodide + Diazepam
Salts
Name/CASStructureProperties
Isopropamide iodide
ThumbNot applicableDBSALT001023
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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Phenylacetamide
  • Phenylpropylamine
  • Aralkylamine
  • Fatty acyl
  • Fatty amide
  • Quaternary ammonium salt
  • Primary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organic cation
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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
PropertyValueProbability
Human Intestinal Absorption-0.8295
Blood Brain Barrier+0.9878
Caco-2 permeable+0.6521
P-glycoprotein substrateSubstrate0.657
P-glycoprotein inhibitor INon-inhibitor0.9503
P-glycoprotein inhibitor IINon-inhibitor0.8809
Renal organic cation transporterInhibitor0.5178
CYP450 2C9 substrateNon-substrate0.7878
CYP450 2D6 substrateNon-substrate0.715
CYP450 3A4 substrateSubstrate0.69
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 substrateNon-inhibitor0.9071
CYP450 2D6 substrateInhibitor0.8932
CYP450 2C19 substrateNon-inhibitor0.9026
CYP450 3A4 substrateNon-inhibitor0.8492
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.953
Ames testNon AMES toxic0.8654
CarcinogenicityNon-carcinogens0.7639
BiodegradationNot ready biodegradable0.8598
Rat acute toxicity2.5213 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9906
hERG inhibition (predictor II)Inhibitor0.5525
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Isopropamide iodide powder6.72USD g
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 mg/mLALOGPS
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 Area43.09 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity120.74 m3·mol-1ChemAxon
Polarizability41.28 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

U.S. Patent 2,823,233.

General ReferenceNot Available
External Links
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

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Drug created on August 29, 2007 14:22 / Updated on May 02, 2014 15:54