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
Mepenzolate
Mepenzolic acid
External IDs Not Available
Product Ingredients
IngredientUNIICASInChI KeyDetails
Mepenzolate bromideAPX8D32IX1 76-90-4JRRNZNSGDSFFIR-UHFFFAOYNA-MDetails
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CantilTablet25 mg/1OralSanofi Aventis1956-11-14Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNIIONW3LB39P7
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
Pharmacology
Indication

For 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.

Structured Indications
Pharmacodynamics

Mepenzolate diminishes gastric acid and pepsin secretion. Mepenzolate also suppresses spontaneous contractions of the colon. Pharmacologically, it is a post-ganglionic parasympathetic inhibitor.

Mechanism of action

Mepenzolate 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.

TargetKindPharmacological actionActionsOrganismUniProt ID
Muscarinic acetylcholine receptor M1Proteinyes
antagonist
HumanP11229 details
Muscarinic acetylcholine receptor M3Proteinyes
antagonist
HumanP20309 details
Related Articles
Absorption

Between 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
MetabolismNot Available
Route of elimination

Between 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
Toxicity

The 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
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesA03AB12 — Mepenzolate
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (93.3 KB)
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
TabletOral25 mg/1
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 inhibitorNon-inhibitor0.9509
CYP450 2D6 inhibitorInhibitor0.8786
CYP450 2C19 inhibitorNon-inhibitor0.9606
CYP450 3A4 inhibitorNon-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
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 ParentsPiperidines / Tetraalkylammonium salts / Tertiary alcohols / Carboxylic acid esters / Monocarboxylic acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organic salts / Organic oxides / Hydrocarbon derivatives
SubstituentsDiphenylmethane / Piperidine / Quaternary ammonium salt / Tertiary alcohol / Tetraalkylammonium salt / Carboxylic acid ester / Carboxylic acid derivative / Azacycle / Organoheterocyclic compound / Monocarboxylic acid or derivatives
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Phosphatidylinositol phospholipase c 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:
CHRM1
Uniprot ID:
P11229
Uniprot Name:
Muscarinic acetylcholine receptor M1
Molecular Weight:
51420.375 Da
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:7623487 ]
  2. Tsai CS, Ochillo RF: Low temperature and muscarinic receptor activities. Cryobiology. 1989 Oct;26(5):485-95. [PubMed:2791613 ]
  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:7122991 ]
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. 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:7623487 ]
  2. Tsai CS, Ochillo RF: Low temperature and muscarinic receptor activities. Cryobiology. 1989 Oct;26(5):485-95. [PubMed:2791613 ]
  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:7122991 ]
Drug created on October 08, 2007 10:15 / Updated on June 11, 2017 16:39