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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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
1-Methyl-3-piperidyl benzilate methyl bromide
Mepenzolate bromide
Mepenzolic acid
N-Methyl-3-piperidyl benzilate methyl bromide
N-Methyl-3-piperidyldiphenylglycolate methobromide
Salts Not Available
Brand names
Name Company
Cantil
Cantilaque
Cantilon
Cantril
Colibantil
Colopiril
Colum
Delevil
Eftoron
Gastropidil
Mepenzolon
Tralanta
Trancolon
First Prev Next Last
Brand mixtures Not Available
Categories
  • Anticholinergic Agents
  • Parasympatholytics
CAS number 25990-43-6
Weight Average: 340.436
Monoisotopic: 340.191268703
Chemical Formula C21H26NO3
InChI Key InChIKey=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
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Diphenylmethanes
Substructures
  • Carboxylic Acids and Derivatives
  • Hydroxy Compounds
  • Benzyl Alcohols and Derivatives
  • Acetates
  • Phenylacetates
  • Short-chain Hydroxy Acids
  • Ethers
  • Benzene and Derivatives
  • Quaternary Ammonium Salts
  • Alcohols and Polyols
  • Diphenylmethanes
  • Heterocyclic compounds
  • Aromatic compounds
  • Piperidines
  • Cations
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.
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.
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
Pharmacoeconomics
Manufacturers
  • Sanofi aventis us llc
Packagers
Dosage forms
Form Route Strength
Tablet Oral
Prices
Unit description Cost Unit
Cantil 25 mg tablet 1.67 USD 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
Property Value Source
water solubility 6.27e-04 g/l ALOGPS
logP -1.1 ALOGPS
logP -0.97 ChemAxon
logS -5.8 ALOGPS
pKa (strongest acidic) 11.05 ChemAxon
pKa (strongest basic) -4.5 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 46.53 ChemAxon
rotatable bond count 5 ChemAxon
refractivity 109.4 ChemAxon
polarizability 37.76 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C07818 Link_out
PubChem Compound 4057 Link_out
PubChem Substance 46508905 Link_out
ChemSpider 3917 Link_out
BindingDB 50253050 Link_out
Therapeutic Targets Database DAP001115 Link_out
PharmGKB PA164746250 Link_out
Drugs.com http://www.drugs.com/cdi/mepenzolate.html Link_out
ATC Codes
  • A03AB12
AHFS Codes Not Available
PDB Entries Not Available
FDA label show (93.3 KB)
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Haloperidol The anticholinergic increases the risk of psychosis and tardive dyskinesia
Tacrine The 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.
Trimethobenzamide Trimethobenzamide and Mepenzolate, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Triprolidine Triprolidine and Mepenzolate, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Trospium Trospium and Mepenzolate, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Food Interactions Not Available
Targets

1. Muscarinic acetylcholine receptor M1

Pharmacological action: yes
Actions: antagonist

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

Organism class: human
UniProt ID: P11229 Link_out
Gene: CHRM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Pharmacological action: yes
Actions: antagonist

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

Organism class: human
UniProt ID: P20309 Link_out
Gene: CHRM3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on October 08, 2007 10:15 / Updated on February 08, 2013 16:23