Identification

Name
Mepenzolate
Accession Number
DB04843
Type
Small Molecule
Groups
Approved
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
Product Ingredients
IngredientUNIICASInChI Key
Mepenzolate bromideAPX8D32IX1 76-90-4JRRNZNSGDSFFIR-UHFFFAOYNA-M
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CantilTablet25 mg/1OralSanofi Aventis1956-11-142017-08-24Us
Categories
UNII
ONW3LB39P7
CAS number
25990-43-6
Weight
Average: 340.436
Monoisotopic: 340.191268703
Chemical Formula
C21H26NO3
InChI Key
GKNPSSNBBWDAGH-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.

TargetActionsOrganism
AMuscarinic acetylcholine receptor M1
antagonist
Human
AMuscarinic acetylcholine receptor M3
antagonist
Human
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 distribution
Not Available
Protein binding
Not Available
Metabolism
Not 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 life
Not Available
Clearance
Not 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
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference
Not Available
General References
Not Available
External Links
Human Metabolome Database
HMDB15591
KEGG Compound
C07818
PubChem Compound
4057
PubChem Substance
46508905
ChemSpider
3917
BindingDB
50377964
ChEBI
94411
ChEMBL
CHEMBL524004
Therapeutic Targets Database
DAP001115
PharmGKB
PA164746250
Drugs.com
Drugs.com Drug Page
ATC Codes
A03AB12 — Mepenzolate
AHFS Codes
Not Available
PDB Entries
Not Available
FDA label
Download (93.3 KB)
MSDS
Not Available

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not 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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not 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
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This 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.
Kingdom
Chemical entities
Super Class
Organic compounds
Class
Benzenoids
Sub Class
Benzene and substituted derivatives
Direct Parent
Diphenylmethanes
Alternative Parents
Piperidines / Tetraalkylammonium salts / Tertiary alcohols / Carboxylic acid esters / Monocarboxylic acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organic salts / Organic oxides / Hydrocarbon derivatives
show 4 more
Substituents
Diphenylmethane / Piperidine / Quaternary ammonium salt / Tertiary alcohol / Tetraalkylammonium salt / Carboxylic acid ester / Carboxylic acid derivative / Azacycle / Organoheterocyclic compound / Monocarboxylic acid or derivatives
show 14 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not 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...
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...
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 October 02, 2017 05:39