U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C28H44NO2.Cl.H2O
Molecular Weight 480.123
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BENZYLDIMETHYL(2-(2-((4-(1,1,3,3-TETRAMETHYLBUTYL)-O-TOLYL)OXY)ETHOXY)ETHYL)AMMONIUM CHLORIDE MONOHYDRATE

SMILES

O.[Cl-].CC1=CC(=CC=C1OCCOCC[N+](C)(C)CC2=CC=CC=C2)C(C)(C)CC(C)(C)C

InChI

InChIKey=VLYDPWNOCPZGEV-UHFFFAOYSA-M
InChI=1S/C28H44NO2.ClH.H2O/c1-23-20-25(28(5,6)22-27(2,3)4)14-15-26(23)31-19-18-30-17-16-29(7,8)21-24-12-10-9-11-13-24;;/h9-15,20H,16-19,21-22H2,1-8H3;1H;1H2/q+1;;/p-1

HIDE SMILES / InChI
Benzyldimethyl(2-(2-((4-(1,1,3,3-Tetramethylbutyl)-O-Tolyl)Oxy)Ethoxy)Ethyl)Ammonium colloquially known as Methylbenzethonium Chloride has been used in the study stem cell death-inducing small molecules as well as anti-leishmanial activity. It is a component of the pharmaceutical preparation 'Leshctan' antibacterial ointment in Isreal.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Leshcutan

Approved Use

Approved for use as an active ingredient in the pharmaceutical preparation of Leshcutan in Isreal.
Primary
Leshcutan

Approved Use

Approved for use as an active ingredient in the pharmaceutical preparation of Leshcutan in Isreal.
PubMed

PubMed

TitleDatePubMed
Leishmania major: in vitro and in vivo anti-leishmanial activity of paromomycin ointment (Leshcutan) combined with the immunomodulator Imiquimod.
2007 Jun
Cutaneous leishmaniasis.
2007 Mar-Apr
Magnetic "fishing" assay to screen small-molecule mixtures for modulators of protein-protein interactions.
2010 Dec 1
Gene expression signature-based screening identifies new broadly effective influenza a antivirals.
2010 Oct 4
Patents

Sample Use Guides

Methylbenzethonium Chloride is included in commercial preparations of Leshcutan ointment at a concentration of 12%. The label instructions indicate to apply ointment twice daily for about 10 days.
Route of Administration: Topical
Mouse CGR8 embryonic stem cells (ESCs), adapted to grow in the absence of feeder cells, were cultured in Glasgow Minimum Essential Medium supplemented with 10 % bovine serum, 100 units/mL leukemia inhibitory factor, 50 micro-M beta-mercaptoethanol, and 100 U/mL of penicillin/streptomycin and temperature controlled at 37 deg-C in a 5% CO2 atmosphere. Cells were distributed in a 96 well plate and screened against a library of small molecules at a final concentration of 10 micro-M per compound. Cultures were incubated with compounds for 48 hours prior to measuring cell viability by XTT colorimetric assay. Compound 199A was identified as methylbenzethonium chloride and was among those that killed or significantly attenuated the cell growth. An LD50 for methylbenzethonium chloride was determined to be 20 micro-M.
Name Type Language
BENZYLDIMETHYL(2-(2-((4-(1,1,3,3-TETRAMETHYLBUTYL)-O-TOLYL)OXY)ETHOXY)ETHYL)AMMONIUM CHLORIDE MONOHYDRATE
Common Name English
BENZENEMETHANAMINIUM, N,N-DIMETHYL-N-(2-(2-(2-METHYL-4-(1,1,3,3-TETRAMETHYLBUTYL)PHENOXY)ETHOXY)ETHYL)-, CHLORIDE, MONOHYDRATE
Systematic Name English
BENZENEMETHANAMINIUM, N,N-DIMETHYL-N-(2-(2-(2-METHYL-4-(1,1,3,3-TETRAMETHYLBUTYL)PHENOXY)ETHOXY)ETHYL)-, CHLORIDE, HYDRATE (1:1:1)
Systematic Name English
AMMONIUM, BENZYLDIMETHYL(2-(2-((4-(1,1,3,3-TETRAMETHYLBUTYL)-O-TOLYL)OXY)ETHOXY)ETHYL)-, CHLORIDE, MONOHYDRATE
Common Name English
Code System Code Type Description
FDA UNII
Z0Y4611MOJ
Created by admin on Fri Dec 15 18:22:55 GMT 2023 , Edited by admin on Fri Dec 15 18:22:55 GMT 2023
PRIMARY
CAS
6032-24-2
Created by admin on Fri Dec 15 18:22:55 GMT 2023 , Edited by admin on Fri Dec 15 18:22:55 GMT 2023
PRIMARY
PUBCHEM
23617468
Created by admin on Fri Dec 15 18:22:55 GMT 2023 , Edited by admin on Fri Dec 15 18:22:55 GMT 2023
PRIMARY