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Identification
NameMepenzolate
Accession NumberDB04843
TypeSmall Molecule
GroupsApproved
Description

Mepenzolate is a post-ganglionic parasympathetic inhibitor. It decreases gastric acid and pepsin secretion and suppresses spontaneous contractions of the colon. Mepenzolate diminishes gastric acid and pepsin secretion. Mepenzolate also suppresses spontaneous contractions of the colon. Pharmacologically, it is a post-ganglionic parasympathetic inhibitor. It has not been shown to be effective in contributing to the healing of peptic ulcer, decreasing the rate of recurrence, or preventing complications.

Structure
Thumb
Synonyms
SynonymLanguageCode
MepenzolateNot AvailableNot Available
Mepenzolic acidNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cantiltablet25 mgoralSanofi Aventis U.S. Llc1956-11-14Not AvailableUs
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Mepenzolate bromide
Thumb
  • InChI Key: JRRNZNSGDSFFIR-UHFFFAOYNA-M
  • Monoisotopic Mass: 419.10960635
  • Average Mass: 420.34
DBSALT000451
Categories
CAS number25990-43-6
WeightAverage: 340.436
Monoisotopic: 340.191268703
Chemical FormulaC21H26NO3
InChI KeyGKNPSSNBBWDAGH-UHFFFAOYSA-N
InChI
InChI=1S/C21H26NO3/c1-22(2)15-9-14-19(16-22)25-20(23)21(24,17-10-5-3-6-11-17)18-12-7-4-8-13-18/h3-8,10-13,19,24H,9,14-16H2,1-2H3/q+1
IUPAC Name
3-[(2-hydroxy-2,2-diphenylacetyl)oxy]-1,1-dimethylpiperidin-1-ium
SMILES
C[N+]1(C)CCCC(C1)OC(=O)C(O)(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
  • Phenylacetate
  • Piperidine
  • Tertiary alcohol
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor use as adjunctive therapy in the treatment of peptic ulcer. It has not been shown to be effective in contributing to the healing of peptic ulcer, decreasing the rate of recurrence, or preventing complications.
PharmacodynamicsMepenzolate diminishes gastric acid and pepsin secretion. Mepenzolate also suppresses spontaneous contractions of the colon. Pharmacologically, it is a post-ganglionic parasympathetic inhibitor.
Mechanism of actionMepenzolate is a post-ganglionic parasympathetic inhibitor. It specifically antagonizes muscarinic receptors. This leads to decreases in gastric acid and pepsin secretion and suppression of spontaneous contractions of the colon.
AbsorptionBetween 3 and 22% of an orally administered dose is excreted in the urine over a 5-day period, with the majority of the radioactivity appearing on Day 1. The remainder appears in the next 5 days in the feces and presumably has not been absorbed.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationBetween 3 and 22% of an orally administered dose is excreted in the urine over a 5-day period, with the majority of the radioactivity appearing on Day 1.
Half lifeNot Available
ClearanceNot Available
ToxicityThe signs and symptoms of overdosage are headache; nausea; vomiting; blurred vision; dilated pupils; hot, dry skin; dizziness; dryness of the mouth; difficulty in swallowing; and CNS stimulation. A curare-like action may occur (i.e., neuromuscular blockade leading to muscular weakness and possible paralysis). The oral LD50 is greater than 750 mg/kg in mice and greater than 1000 mg/kg in rats.
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-0.9306
Blood Brain Barrier+0.7923
Caco-2 permeable+0.6583
P-glycoprotein substrateSubstrate0.8542
P-glycoprotein inhibitor INon-inhibitor0.7864
P-glycoprotein inhibitor IINon-inhibitor0.9331
Renal organic cation transporterInhibitor0.6036
CYP450 2C9 substrateNon-substrate0.8141
CYP450 2D6 substrateNon-substrate0.7494
CYP450 3A4 substrateSubstrate0.6751
CYP450 1A2 substrateNon-inhibitor0.9616
CYP450 2C9 substrateNon-inhibitor0.9509
CYP450 2D6 substrateInhibitor0.8786
CYP450 2C19 substrateNon-inhibitor0.9606
CYP450 3A4 substrateNon-inhibitor0.9046
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9873
Ames testNon AMES toxic0.8752
CarcinogenicityNon-carcinogens0.9001
BiodegradationReady biodegradable0.5071
Rat acute toxicity2.3729 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9061
hERG inhibition (predictor II)Non-inhibitor0.5278
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tabletoral25 mg
Prices
Unit descriptionCostUnit
Cantil 25 mg tablet1.67USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.000627 mg/mLALOGPS
logP-1.1ALOGPS
logP-0.97ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)11.05ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity109.4 m3·mol-1ChemAxon
Polarizability37.76 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 ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesA03AB12
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (93.3 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
HaloperidolThe anticholinergic increases the risk of psychosis and tardive dyskinesia
TacrineThe therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Mepenzolate, may be reduced due to antagonism. The interaction may be beneficial when the anticholinergic action is a side effect. Monitor for decreased efficacy of both agents.
TrimethobenzamideTrimethobenzamide and Mepenzolate, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
TriprolidineTriprolidine and Mepenzolate, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
TrospiumTrospium and Mepenzolate, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Food InteractionsNot Available

Targets

1. Muscarinic acetylcholine receptor M1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M1 P11229 Details

References:

  1. Tsai CS, Guede-Guina F, Smith MO, Vangah-Manda M, Ochillo RF: Isolation of cholinergic active ingredients in aqueous extracts of Mareya micrantha using the longitudinal muscle of isolated guinea-pig ileum as a pharmacological activity marker. J Ethnopharmacol. 1995 Mar;45(3):215-22. Pubmed
  2. Tsai CS, Ochillo RF: Low temperature and muscarinic receptor activities. Cryobiology. 1989 Oct;26(5):485-95. Pubmed
  3. Ochillo RF, Pugh DA: Atropine and mepenzolate mydriasis in rabbits: a comparative pupillographic analysis of two antimuscarinic agents. Res Commun Chem Pathol Pharmacol. 1982 Jun;36(3):503-6. Pubmed

2. 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. Tsai CS, Guede-Guina F, Smith MO, Vangah-Manda M, Ochillo RF: Isolation of cholinergic active ingredients in aqueous extracts of Mareya micrantha using the longitudinal muscle of isolated guinea-pig ileum as a pharmacological activity marker. J Ethnopharmacol. 1995 Mar;45(3):215-22. Pubmed
  2. Tsai CS, Ochillo RF: Low temperature and muscarinic receptor activities. Cryobiology. 1989 Oct;26(5):485-95. Pubmed
  3. Ochillo RF, Pugh DA: Atropine and mepenzolate mydriasis in rabbits: a comparative pupillographic analysis of two antimuscarinic agents. Res Commun Chem Pathol Pharmacol. 1982 Jun;36(3):503-6. Pubmed

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Drug created on October 08, 2007 10:15 / Updated on September 16, 2013 17:26