Isopropamide

Identification

Summary

Isopropamide is a long-acting anticholinergic drug used to relieve symptoms of spastic and painful symptoms of gastrointestinal conditions and symptoms of flu, colds, and related conditions.

Generic Name
Isopropamide
DrugBank Accession Number
DB01625
Background

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.

Type
Small Molecule
Groups
Approved, Vet approved
Structure
Weight
Average: 353.5209
Monoisotopic: 353.259288688
Chemical Formula
C23H33N2O
Synonyms
  • Isopropamide

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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination for symptomatic treatment ofCommon coldCombination Product in combination with: Caffeine (DB00201), Acetaminophen (DB00316), Ascorbic acid (DB00126), Chlorpheniramine (DB01114)••• •••••••••• ••••••••••••
Used in combination to treatFeverCombination Product in combination with: Ascorbic acid (DB00126), Caffeine (DB00201), Chlorpheniramine (DB01114), Acetaminophen (DB00316)••• •••••••••• ••••••••••••
Used in combination for symptomatic treatment ofFlu caused by influenzaCombination Product in combination with: Chlorpheniramine (DB01114), Acetaminophen (DB00316), Caffeine (DB00201), Ascorbic acid (DB00126)••• •••••••••• ••••••••••••
Used in combination for symptomatic treatment ofNasal congestionCombination Product in combination with: Ascorbic acid (DB00126), Caffeine (DB00201), Chlorpheniramine (DB01114), Acetaminophen (DB00316)••• •••••••••• ••••••••••••
Used in combination for symptomatic treatment ofPainCombination Product in combination with: Caffeine (DB00201), Chlorpheniramine (DB01114), Acetaminophen (DB00316), Ascorbic acid (DB00126)••• •••••••••• ••••••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
AMuscarinic acetylcholine receptor M3
antagonist
Humans
UMuscarinic acetylcholine receptor M4
antagonist
Humans
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

Adverse Effects
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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.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AclidiniumThe risk or severity of adverse effects can be increased when Isopropamide is combined with Aclidinium.
AdenosineThe risk or severity of Tachycardia can be increased when Adenosine is combined with Isopropamide.
AlfentanilThe risk or severity of adverse effects can be increased when Isopropamide is combined with Alfentanil.
AlloinThe therapeutic efficacy of Alloin can be decreased when used in combination with Isopropamide.
AmantadineThe risk or severity of adverse effects can be increased when Amantadine is combined with Isopropamide.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Isopropamide chlorideF97R3WDS0Q24353-18-2YDLRIMWTVADYID-UHFFFAOYSA-N
Isopropamide iodideE0KNA372SZ71-81-8BFSMWENDZZIWPW-UHFFFAOYSA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
INFLUMEDIsopropamide iodide (0.2 mg) + Acetaminophen (500 mg) + Ascorbic acid (500 mg) + Caffeine (25 mg) + Chlorpheniramine maleate (8 mg)TabletOralIodosan S.P.A.2014-07-082023-06-16Italy flag
INFLUMEDIsopropamide iodide (0.2 mg) + Acetaminophen (500 mg) + Ascorbic acid (500 mg) + Caffeine (25 mg) + Chlorpheniramine maleate (8 mg)TabletOralIodosan S.P.A.2014-07-082023-06-16Italy flag
Stelabid ForteIsopropamide iodide (7.5 mg) + Trifluoperazine hydrochloride (2 mg)TabletOralGlaxosmithkline Inc1993-12-312002-07-31Canada flag
Stelabid No 1Isopropamide iodide (5 mg) + Trifluoperazine hydrochloride (1 mg)TabletOralGlaxosmithkline Inc1993-12-312002-01-29Canada flag
Stelabid No 2Isopropamide iodide (5 mg) + Trifluoperazine hydrochloride (2 mg)TabletOralGlaxosmithkline Inc1993-12-312002-01-29Canada flag

Categories

ATC Codes
A03CA01 — Isopropamide and psycholepticsA03AB09 — Isopropamide
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylmethanes
Direct Parent
Diphenylmethanes
Alternative Parents
Aralkylamines / Tetraalkylammonium salts / Carboximidic acids / Organopnictogen compounds / Organooxygen compounds / Organic salts / Hydrocarbon derivatives / Organic cations
Substituents
Amine / Aralkylamine / Aromatic homomonocyclic compound / Carboximidic acid / Carboximidic acid derivative / Diphenylmethane / Hydrocarbon derivative / Organic cation / Organic nitrogen compound / Organic oxygen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
diarylmethane (CHEBI:6043)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
8B9I31H724
CAS number
7492-32-2
InChI Key
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
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

References

Synthesis Reference

U.S. Patent 2,823,233.

General References
Not Available
Human Metabolome Database
HMDB0015562
KEGG Compound
C07055
PubChem Compound
3775
PubChem Substance
46507726
ChemSpider
3643
BindingDB
82074
RxNav
89784
ChEBI
6043
ChEMBL
CHEMBL1201232
ZINC
ZINC000001530668
PharmGKB
PA164781398
Wikipedia
Isopropamide

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Gallipot
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.
Patents
Not Available

Properties

State
Solid
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
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-052o-7449000000-f279105f11d6b98a55c8
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-198.9482214
predicted
DarkChem Lite v0.1.0
[M-H]-186.49382
predicted
DeepCCS 1.0 (2019)
[M+H]+199.7581214
predicted
DarkChem Lite v0.1.0
[M+H]+188.85182
predicted
DeepCCS 1.0 (2019)
[M+Na]+199.7057214
predicted
DarkChem Lite v0.1.0
[M+Na]+195.60283
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
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...
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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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...
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. [Article]
  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. [Article]

Drug created at August 29, 2007 20:22 / Updated at December 02, 2023 07:00