3-[(2-hydroxy-2,2-diphenylacetyl)oxy]-1,1-dimethylpiperidin-1-ium

• ChemBase ID: 4387
• Molecular Formular: C21H26NO3+
• Molecular Mass: 340.43604
• Monoisotopic Mass: 340.1912687
• SMILES: O(C1C[N+](CCC1)(C)C)C(=O)C(O)(c1ccccc1)c1ccccc1
• Canonical SMILES: O=C(C(c1ccccc1)(c1ccccc1)O)OC1CCC[N+](C1)(C)C
• 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
• InChIKey: GKNPSSNBBWDAGH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(2-hydroxy-2,2-diphenylacetyl)oxy]-1,1-dimethylpiperidin-1-ium
• IUPAC Traditional name: mepenzolate
• Brand Name: Cantil; Cantilaque; Cantilon; Cantril; Colibantil; Colopiril; Colum; Delevil; Eftoron; Gastropidil; Mepenzolon; Tralanta; Trancolon
• Synonyms: 1-Methyl-3-piperidyl benzilate methyl bromide; Mepenzolate bromide; Mepenzolic acid; N-Methyl-3-piperidyl benzilate methyl bromide; N-Methyl-3-piperidyldiphenylglycolate methobromide; Mepenzolate

Database IDs

• CAS Number: 25990-43-6
• PubChem SID: 160967819; 46508905
• PubChem CID: 4057

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.047589
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.974663
• LogD (pH = 7.4): -0.9728341
• Log P: -0.9746864
• Molar Refractivity: 109.3951 cm^3
• Polarizability: 38.60378 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.14
• LOG S: -5.78
• Solubility (Water): 6.27e-04 g/l

DETAILS

DrugBank - DB04843

• Drug 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.
• 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.
• Pharmacology: Mepenzolate diminishes gastric acid and pepsin secretion. Mepenzolate also suppresses spontaneous contractions of the colon. Pharmacologically, it is a post-ganglionic parasympathetic inhibitor.
• 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
• 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.
• 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.
• External Links: Drugs.com