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Details

Stereochemistry RACEMIC
Molecular Formula C21H26NO3.Br
Molecular Weight 420.34
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEPENZOLATE BROMIDE

SMILES

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

InChI

InChIKey=JRRNZNSGDSFFIR-UHFFFAOYSA-M
InChI=1S/C21H26NO3.BrH/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;1H/q+1;/p-1

HIDE SMILES / InChI

Molecular Formula BrH
Molecular Weight 80.912
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C21H25NO3
Molecular Weight 339.4281
Charge 0
Count
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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

Curator's Comment: Similar to other quaternary ammonium anticholinergics, mepenzolate has limited ability to cross lipid membranes, such as the blood-brain barrier.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

-4.14374396E11
Doses

Doses

DosePopulationAdverse events​
750 mg single, oral
Highest recorded dose
Dose: 750 mg
Route: oral
Route: single
Dose: 750 mg
Sources:
unhealthy, 30 years
n = 1
Health Status: unhealthy
Age Group: 30 years
Population Size: 1
Sources:
Other AEs: Adverse event...
500 mg single, oral
Highest recorded dose
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Sources:
unhealthy, 4 years
n = 1
Health Status: unhealthy
Age Group: 4 years
Population Size: 1
Sources:
AEs

AEs

AESignificanceDosePopulation
Adverse event grade 5
750 mg single, oral
Highest recorded dose
Dose: 750 mg
Route: oral
Route: single
Dose: 750 mg
Sources:
unhealthy, 30 years
n = 1
Health Status: unhealthy
Age Group: 30 years
Population Size: 1
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 64.9 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Patents

Patents

Sample Use Guides

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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:03:28 UTC 2023
Edited
by admin
on Fri Dec 15 16:03:28 UTC 2023
Record UNII
APX8D32IX1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MEPENZOLATE BROMIDE
INN   MART.   MI   ORANGE BOOK   VANDF   WHO-DD  
INN  
Official Name English
MEPENZOLATE BROMIDE [MART.]
Common Name English
MEPENZOLATE BROMIDE [ORANGE BOOK]
Common Name English
Mepenzolate bromide [WHO-DD]
Common Name English
CANTIL
Brand Name English
3-Hydroxy-1,1-dimethylpiperidinium bromide benzilate
Systematic Name English
FT-0671006
Code English
PIPERIDINIUM, 3-((HYDROXYDIPHENYLACETYL)OXY)-1,1-DIMETHYL-, BROMIDE
Systematic Name English
HY-17585
Code English
AN-6437
Code English
NSC-4358
Code English
MEPENZOLATE BROMIDE [JAN]
Common Name English
MEPENZOLATE BROMIDE [MI]
Common Name English
mepenzolate bromide [INN]
Common Name English
MEPENZOLATE BROMIDE [VANDF]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29704
Created by admin on Fri Dec 15 16:03:28 UTC 2023 , Edited by admin on Fri Dec 15 16:03:28 UTC 2023
NCI_THESAURUS C29698
Created by admin on Fri Dec 15 16:03:28 UTC 2023 , Edited by admin on Fri Dec 15 16:03:28 UTC 2023
Code System Code Type Description
EVMPD
SUB08745MIG
Created by admin on Fri Dec 15 16:03:28 UTC 2023 , Edited by admin on Fri Dec 15 16:03:28 UTC 2023
PRIMARY
SMS_ID
100000081495
Created by admin on Fri Dec 15 16:03:28 UTC 2023 , Edited by admin on Fri Dec 15 16:03:28 UTC 2023
PRIMARY
CAS
37717-96-7
Created by admin on Fri Dec 15 16:03:28 UTC 2023 , Edited by admin on Fri Dec 15 16:03:28 UTC 2023
ALTERNATIVE
RXCUI
52560
Created by admin on Fri Dec 15 16:03:28 UTC 2023 , Edited by admin on Fri Dec 15 16:03:28 UTC 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
200-992-7
Created by admin on Fri Dec 15 16:03:28 UTC 2023 , Edited by admin on Fri Dec 15 16:03:28 UTC 2023
PRIMARY
PUBCHEM
6461
Created by admin on Fri Dec 15 16:03:28 UTC 2023 , Edited by admin on Fri Dec 15 16:03:28 UTC 2023
PRIMARY
FDA UNII
APX8D32IX1
Created by admin on Fri Dec 15 16:03:28 UTC 2023 , Edited by admin on Fri Dec 15 16:03:28 UTC 2023
PRIMARY
NCI_THESAURUS
C61829
Created by admin on Fri Dec 15 16:03:28 UTC 2023 , Edited by admin on Fri Dec 15 16:03:28 UTC 2023
PRIMARY
CAS
76-90-4
Created by admin on Fri Dec 15 16:03:28 UTC 2023 , Edited by admin on Fri Dec 15 16:03:28 UTC 2023
PRIMARY
DRUG BANK
DBSALT000451
Created by admin on Fri Dec 15 16:03:28 UTC 2023 , Edited by admin on Fri Dec 15 16:03:28 UTC 2023
PRIMARY
MERCK INDEX
m7185
Created by admin on Fri Dec 15 16:03:28 UTC 2023 , Edited by admin on Fri Dec 15 16:03:28 UTC 2023
PRIMARY Merck Index
NSC
4358
Created by admin on Fri Dec 15 16:03:28 UTC 2023 , Edited by admin on Fri Dec 15 16:03:28 UTC 2023
PRIMARY
EPA CompTox
DTXSID4023252
Created by admin on Fri Dec 15 16:03:28 UTC 2023 , Edited by admin on Fri Dec 15 16:03:28 UTC 2023
PRIMARY
INN
889
Created by admin on Fri Dec 15 16:03:28 UTC 2023 , Edited by admin on Fri Dec 15 16:03:28 UTC 2023
PRIMARY
ChEMBL
CHEMBL524004
Created by admin on Fri Dec 15 16:03:28 UTC 2023 , Edited by admin on Fri Dec 15 16:03:28 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY