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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

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C28H44NO2
Molecular Weight 426.6545
Charge 1
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula HO
Molecular Weight 17.0073
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
A siderophore biosynthesis gene cluster from the fish pathogen Photobacterium damselae subsp. piscicida is structurally and functionally related to the Yersinia high-pathogenicity island.
2006 Nov
Treating cutaneous leishmaniasis patients in Kabul, Central Asia: cost-effectiveness of an operational program in a complex emergency setting.
2007 Jan 30
Leishmania major: in vitro and in vivo anti-leishmanial activity of paromomycin ointment (Leshcutan) combined with the immunomodulator Imiquimod.
2007 Jun
Aqueous micellar two-phase system composed of hyamine-type hydrophobically modified ethylene oxide and application for cytochrome P450 BM-3 separation.
2007 Jun 1
Optimization of topical therapy for Leishmania major localized cutaneous leishmaniasis using a reliable C57BL/6 Model.
2007 Nov 28
Magnetic "fishing" assay to screen small-molecule mixtures for modulators of protein-protein interactions.
2010 Dec 1
Cell-based and cytokine-directed chemical screen to identify potential anti-multiple myeloma agents.
2010 Jul
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:22:55 GMT 2023
Edited
by admin
on Fri Dec 15 18:22:55 GMT 2023
Record UNII
Z0Y4611MOJ
Record Status Validated (UNII)
Record Version
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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