Identification
NameIsopropamide
Accession NumberDB01625
TypeSmall Molecule
GroupsApproved, Vet 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
Thumb
Synonyms
Isopropamide
External IDs Not Available
Product Ingredients
IngredientUNIICASInChI KeyDetails
Isopropamide chlorideF97R3WDS0Q 24353-18-2YDLRIMWTVADYID-UHFFFAOYSA-NDetails
Isopropamide iodideE0KNA372SZ 71-81-8BFSMWENDZZIWPW-UHFFFAOYSA-NDetails
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Stelabid ForteTabletOralGlaxosmithkline Inc1993-12-312002-07-31Canada
Stelabid No 1TabletOralGlaxosmithkline Inc1993-12-312002-01-29Canada
Stelabid No 2TabletOralGlaxosmithkline Inc1993-12-312002-01-29Canada
Categories
UNII8B9I31H724
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
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.

Structured Indications Not Available
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.

TargetKindPharmacological actionActionsOrganismUniProt ID
Muscarinic acetylcholine receptor M3Proteinyes
antagonist
HumanP20309 details
Muscarinic acetylcholine receptor M4Proteinunknown
antagonist
HumanP08173 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot 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
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis Reference

U.S. Patent 2,823,233.

General ReferencesNot Available
External Links
ATC CodesA03CA01 — Isopropamide and psycholepticsA03AB09 — Isopropamide
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
TabletOral
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 point (°C)182-184U.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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentDiphenylmethanes
Alternative ParentsAralkylamines / Tetraalkylammonium salts / Carboximidic acids / Organopnictogen compounds / Organooxygen compounds / Organic salts / Hydrocarbon derivatives / Organic cations
SubstituentsDiphenylmethane / Aralkylamine / Quaternary ammonium salt / Tetraalkylammonium salt / Carboximidic acid derivative / Carboximidic acid / Hydrocarbon derivative / Organic oxygen compound / Organic salt / Amine
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptorsdiarylmethane (CHEBI:6043 )

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Receptor activity
Specific Function:
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.
Gene Name:
CHRM3
Uniprot ID:
P20309
Uniprot Name:
Muscarinic acetylcholine receptor M3
Molecular Weight:
66127.445 Da
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:3580704 ]
  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:29133 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
General Function:
Guanyl-nucleotide exchange factor activity
Specific Function:
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.
Gene Name:
CHRM4
Uniprot ID:
P08173
Uniprot Name:
Muscarinic acetylcholine receptor M4
Molecular Weight:
53048.65 Da
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:29133 ]
  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:3580704 ]
Drug created on August 29, 2007 14:22 / Updated on August 02, 2017 16:35