MEPENZOLATE

US Previously Marketed

Details

Stereochemistry	RACEMIC
Molecular Formula	C21H26NO3
Molecular Weight	340.436
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

C[N+]1(C)CCCC(C1)OC(=O)C(O)(C2=CC=CC=C2)C3=CC=CC=C3

InChI

InChIKey=GKNPSSNBBWDAGH-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/10679slr029_cantil_lbl.pdf | https://www.drugs.com/ppa/mepenzolate.html

Mepenzolate is a postganglionic parasympathetic inhibitor. It decreases gastric acid and pepsin secretion and suppresses spontaneous contractions of the colon. It specifically antagonizes muscarinic receptors. Mepenzolate is marketed under the brand name CANTIL. CANTIL is indicated 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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Muscarinic acetylcholine receptor M3 159 Target ID: CHEMBL245 Sources: https://www.drugbank.ca/drugs/DB04843 \| https://www.ncbi.nlm.nih.gov/pubmed/24844758	Antagonist 2778	2.6 nM [Ki]
Muscarinic acetylcholine receptor M2 121 Target ID: CHEMBL211 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24844758	Antagonist 2778	0.68 nM [Ki]
Muscarinic acetylcholine receptor M1 169 Target ID: CHEMBL216 Sources: https://www.drugbank.ca/drugs/DB04843 \| http://drugcentral.org/drugcard/1689?q=anticholinergic	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Peptic ulcer 72 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/10679slr029_cantil_lbl.pdf	Primary		Approved 8429	CANTIL Approved Use CANTIL is indicated 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. Launch Date 1956

Doses

Dose	Population	Adverse events
750 mg single, oral Highest recorded dose Dose: 750 mg Route: oral Route: single Dose: 750 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/10679slr029_cantil_lbl.pdf	unhealthy, 30 years n = 1 Health Status: unhealthy Age Group: 30 years Population Size: 1 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/10679slr029_cantil_lbl.pdf	Other AEs: Adverse event... Other AEs: Adverse event (grade 5) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/10679slr029_cantil_lbl.pdf
500 mg single, oral Highest recorded dose Dose: 500 mg Route: oral Route: single Dose: 500 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/10679slr029_cantil_lbl.pdf	unhealthy, 4 years n = 1 Health Status: unhealthy Age Group: 4 years Population Size: 1 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/10679slr029_cantil_lbl.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/10679slr029_cantil_lbl.pdf

AEs

AE	Significance	Dose	Population
Adverse event	grade 5	750 mg single, oral Highest recorded dose Dose: 750 mg Route: oral Route: single Dose: 750 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/10679slr029_cantil_lbl.pdf	unhealthy, 30 years n = 1 Health Status: unhealthy Age Group: 30 years Population Size: 1 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2004/10679slr029_cantil_lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT1 512	OCT1 327

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
OCT1 543	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/18788725/	yes [IC50 64.9 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
OCT1 327	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/23984907/	yes

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P003RXM
ABI Chem	AC1L1HBG
AK Scientific	1988AC
AbovChem LLC	HY-17585
Achemo BB	AC-86672
Ambinter	Amb17616765	http://www.ambinter.com/reference/17616765
ApexBio Technology	A8467
BOC Sciences	76-90-4
BlocksMatrix Scientific	99658
Compound Cloud	4057
Compound Cloud	6461
Hairui	HR142939
Hangzhou APIChem Technology	AC-15989
Hangzhou Yuhao Chemical Technology	RT19033
MolPort	MolPort-003-666-226
Molnova	M15910
NCI Plated 2007	4358
Norris Pharm	NSZB-A127565
NovoSeek	4057
Ryan Scientific	Propitocaine_HCl
TargetMol	T0794
Tetrahedron	TS81673
Toronto Research Chemicals	M223750
Toronto Research Chemicals	T430000
ZINC	ZINC000000000449	http://zinc15.docking.org/substances/ZINC000000000449
ZINC	ZINC000003813083	http://zinc15.docking.org/substances/ZINC000003813083
eMolecules	31226781
eNovation Chemicals	D279622
mcule	MCULE-6052205967
mcule	MCULE-6453858005

PubMed

Title	Date	PubMed
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011 Jul 14	21599003

Patents

Sample Use Guides

In Vivo Use Guide

The usual adult dose is 1 or 2 tablets (25 or 50 mg) 4 times a day preferably with meals and at bedtime.

Route of Administration: Oral

In Vitro Use Guide

Mepenzolate (10(-8)-10(-5) M), a specific muscarinic receptor antagonist, antagonized contractions of the longitudinal muscle of the isolated guinea-pig ileum preparation elicited by the aqueous extracts of Mareya micrantha suggesting that the cholinergic ingredient(s) in the extract are acting at the muscarinic receptors of the preparation.

Name

Type

Language

MEPENZOLATE

Common Name

English

3-(2-HYDROXY(DIPHENYL)ACETOXY)-1,1-DIMETHYLPIPERIDINIUM

Systematic Name

English

MEPENZOLATE BROMIDE FREE BASE [MI]

Common Name

English

Mepenzolate [WHO-DD]

Common Name

English

MEPENZOLATE [VANDF]

Common Name

English

MEPENZOLATE ION

Common Name

English

PIPERIDINIUM, 3-((HYDROXYDIPHENYLACETYL)OXY)-1,1-DIMETHYL-

Systematic Name

English

MEPENZOLATE CATION

Common Name

English

Classification Tree Code System Code

WHO-ATC

A03AB12