Diphemanil

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Diphemanil
DrugBank Accession Number
DB13720
Background

Not Available

Type
Small Molecule
Groups
Approved, Vet approved, Withdrawn
Structure
Thumb
Weight
Average: 278.418
Monoisotopic: 278.190326197
Chemical Formula
C20H24N
Synonyms
  • Diphemanil cation
  • Diphemanil ion

Pharmacology

Indication

Used in the treatment of peptic ulcer, gastric hyperacidity, and hypermotility in gastritis and pylorospasm, and in the treatment of hyperhidrosis (excessive perspiration).

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Diphemanil Methylsulfate is a quaternary ammonium anticholinergic. It binds muscarinic acetycholine receptors and thereby decreases secretory excretion of stomach acids as well as saliva and sweat.

Mechanism of action

Diphemanil Methylsulfate exerts its action by primarily binding the muscarinic M3 receptor. M3 receptors are located in the smooth muscles of the blood vessels, as well as in the lungs. This means they cause vasodilation and bronchoconstriction. They are also in the smooth muscles of the gastrointestinal tract (GIT), which help in increasing intestinal motility and dilating sphincters. The M3 receptors are also located in many glands which help to stimulate secretion in salivary glands and other glands of the body.

TargetActionsOrganism
AMuscarinic acetylcholine receptor M3
antagonist
Humans
Absorption

Poorly absorbed from the gastrointestinal tract with an absolute bioavailability of 15 to 25%.

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

Not Available

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
1,2-Benzodiazepine1,2-Benzodiazepine may increase the central nervous system depressant (CNS depressant) activities of Diphemanil.
AcetazolamideAcetazolamide may increase the central nervous system depressant (CNS depressant) activities of Diphemanil.
AcetophenazineAcetophenazine may increase the central nervous system depressant (CNS depressant) activities of Diphemanil.
AclidiniumThe risk or severity of adverse effects can be increased when Diphemanil is combined with Aclidinium.
AdenosineThe risk or severity of Tachycardia can be increased when Adenosine is combined with Diphemanil.
AgomelatineAgomelatine may increase the central nervous system depressant (CNS depressant) activities of Diphemanil.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Diphemanil.
AlimemazineAlimemazine may increase the central nervous system depressant (CNS depressant) activities of Diphemanil.
AlloinThe therapeutic efficacy of Alloin can be decreased when used in combination with Diphemanil.
AlmotriptanAlmotriptan may increase the central nervous system depressant (CNS depressant) activities of Diphemanil.
Interactions
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Diphemanil methylsulfateW2ZG23MGYI62-97-5BREMLQBSKCSNNH-UHFFFAOYSA-M
International/Other Brands
Demotil (Pharmacia) / Prantal (Schering-Plough) / Prentol (Essex)

Categories

ATC Codes
A03CA08 — Diphemanil and psycholepticsA03AB15 — Diphemanil
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
Piperidines / Tetraalkylammonium salts / Azacyclic compounds / Organopnictogen compounds / Organic salts / Hydrocarbon derivatives / Amines / Organic cations
Substituents
Amine / Aromatic heteromonocyclic compound / Azacycle / Diphenylmethane / Hydrocarbon derivative / Organic cation / Organic nitrogen compound / Organic salt / Organoheterocyclic compound / Organonitrogen compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Q26TX1UD0W
CAS number
15394-62-4
InChI Key
LCTZPQRFOZKZNK-UHFFFAOYSA-N
InChI
InChI=1S/C20H24N/c1-21(2)15-13-19(14-16-21)20(17-9-5-3-6-10-17)18-11-7-4-8-12-18/h3-12H,13-16H2,1-2H3/q+1
IUPAC Name
4-(diphenylmethylidene)-1,1-dimethylpiperidin-1-ium
SMILES
C[N+]1(C)CCC(CC1)=C(C1=CC=CC=C1)C1=CC=CC=C1

References

General References
Not Available
ChemSpider
5897
BindingDB
74260
RxNav
89782
ChEBI
93636
ChEMBL
CHEMBL1201340
ZINC
ZINC000001482039
Wikipedia
Diphemanil_metilsulfate

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000372 mg/mLALOGPS
logP-0.4ALOGPS
logP-0.15ChemAxon
logS-5.9ALOGPS
Physiological Charge1ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity111.69 m3·mol-1ChemAxon
Polarizability33.56 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available

Targets

Drugtargets
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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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Drug created on June 23, 2017 20:47 / Updated on June 12, 2020 16:53