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Identification
NameDiphemanil Methylsulfate
Accession NumberDB00729  (APRD00928)
TypeSmall Molecule
GroupsApproved, Withdrawn
Description

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.

Structure
Thumb
Synonyms
SynonymLanguageCode
4-(Diphenylmethylene)-1,1-dimethylpiperidinium methyl sulfateNot AvailableNot Available
Diphemanil methosulfateNot AvailableNot Available
Diphemanil methylsulfatGermanINN
Diphemanil metilsulfateNot AvailableNot Available
Diphemanili metilsulfas LatinINN
Métilsulfate de DiphémanilFrenchINN
Metilsulfato de difemaniloSpanishINN
N,N-Dimethyl-4-piperidylidene-1,1-diphenylmethane methylsulfateNot AvailableNot Available
P-(alpha-Phenylbenzylidene)-1,1-dimethylpiperidinium methyl sulfateNot AvailableNot Available
VagophemanilNot AvailableIS
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
DemotilPharmacia
PrantalSchering-Plough
PrentolEssex
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number62-97-5
WeightAverage: 389.508
Monoisotopic: 389.166079047
Chemical FormulaC21H27NO4S
InChI KeyBREMLQBSKCSNNH-UHFFFAOYSA-M
InChI
InChI=1S/C20H24N.CH4O4S/c1-21(2)15-13-19(14-16-21)20(17-9-5-3-6-10-17)18-11-7-4-8-12-18;1-5-6(2,3)4/h3-12H,13-16H2,1-2H3;1H3,(H,2,3,4)/q+1;/p-1
IUPAC Name
4-(diphenylmethylidene)-1,1-dimethylpiperidin-1-ium methyl sulfate
SMILES
COS([O-])(=O)=O.C[N+]1(C)CCC(CC1)=C(C1=CC=CC=C1)C1=CC=CC=C1
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
  • Phenylpropene
  • Sulfuric acid monoester
  • Sulfuric acid ester
  • Alkyl sulfate
  • Sulfate-ester
  • Piperidine
  • Quaternary ammonium salt
  • Organic sulfuric acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic zwitterion
  • Aromatic heteromonocyclic compound
  • Aliphatic acyclic compound
Molecular FrameworkNot Available
External Descriptors
Pharmacology
IndicationUsed in the treatment of peptic ulcer, gastric hyperacidity, and hypermotility in gastritis and pylorospasm, and in the treatment of hyperhidrosis (excessive perspiration).
PharmacodynamicsDiphemanil 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 actionDiphemanil 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.
AbsorptionPoorly absorbed from the gastrointestinal tract with an absolute bioavailability of 15 to 25%.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
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-0.7038
Blood Brain Barrier+0.833
Caco-2 permeable-0.5676
P-glycoprotein substrateSubstrate0.7646
P-glycoprotein inhibitor IInhibitor0.6935
P-glycoprotein inhibitor IINon-inhibitor0.9637
Renal organic cation transporterNon-inhibitor0.5581
CYP450 2C9 substrateNon-substrate0.881
CYP450 2D6 substrateNon-substrate0.791
CYP450 3A4 substrateSubstrate0.5871
CYP450 1A2 substrateNon-inhibitor0.7637
CYP450 2C9 substrateNon-inhibitor0.7642
CYP450 2D6 substrateNon-inhibitor0.8142
CYP450 2C19 substrateNon-inhibitor0.7145
CYP450 3A4 substrateNon-inhibitor0.8236
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8619
Ames testNon AMES toxic0.5415
CarcinogenicityCarcinogens 0.5205
BiodegradationReady biodegradable0.9789
Rat acute toxicity2.6718 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.883
hERG inhibition (predictor II)Non-inhibitor0.5373
Pharmacoeconomics
Manufacturers
  • Schering corp sub schering plough corp
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point196-197Sperber, N., Villani, F.J. and Papa, D.; U.S. Patent 2,739,968; March 27,1956; assigned to Schering Corporation.
logP2.57Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000204 mg/mLALOGPS
logP1.12ALOGPS
logP-0.15ChemAxon
logS-6.3ALOGPS
Physiological Charge1ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity111.69 m3·mol-1ChemAxon
Polarizability33.56 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Sperber, N., Villani, F.J. and Papa, D.; U.S. Patent 2,739,968; March 27,1956; assigned to
Schering Corporation.

General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  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. Pubmed
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on April 14, 2014 15:57