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Details

Stereochemistry ACHIRAL
Molecular Formula C28H44NO2
Molecular Weight 426.6545
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 1

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

SMILES

CC1=CC(=CC=C1OCCOCC[N+](C)(C)CC2=CC=CC=C2)C(C)(C)CC(C)(C)C

InChI

InChIKey=UQOOPIMXBSPVJI-UHFFFAOYSA-N
InChI=1S/C28H44NO2/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/q+1

HIDE SMILES / InChI

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

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
Occupational allergic contact dermatitis from alkylammonium amidobenzoate.
2001 May-Jun
Purification and characterization of an extracellular lipase from Geotrichum marinum.
2004 Mar
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
Is paromomycin an effective and safe treatment against cutaneous leishmaniasis? A meta-analysis of 14 randomized controlled trials.
2009
Magnetic "fishing" assay to screen small-molecule mixtures for modulators of protein-protein interactions.
2010 Dec 1
Drug resistance in leishmaniasis.
2010 May
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:09:49 GMT 2023
Edited
by admin
on Fri Dec 15 18:09:49 GMT 2023
Record UNII
NJX1653L36
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
Common Name English
BENZENEMETHANAMINIUM, N,N-DIMETHYL-N-(2-(2-(2-METHYL-4-(1,1,3,3-TETRAMETHYLBUTYL)PHENOXY)ETHOXY)ETHYL)-
Systematic Name English
AMMONIUM, BENZYLDIMETHYL(2-(2-((4-(1,1,3,3-TETRAMETHYLBUTYL)-O-TOLYL)OXY)ETHOXY)ETHYL)-
Common Name English
Code System Code Type Description
PUBCHEM
4135
Created by admin on Fri Dec 15 18:09:49 GMT 2023 , Edited by admin on Fri Dec 15 18:09:49 GMT 2023
PRIMARY
FDA UNII
NJX1653L36
Created by admin on Fri Dec 15 18:09:49 GMT 2023 , Edited by admin on Fri Dec 15 18:09:49 GMT 2023
PRIMARY
CAS
72013-76-4
Created by admin on Fri Dec 15 18:09:49 GMT 2023 , Edited by admin on Fri Dec 15 18:09:49 GMT 2023
PRIMARY
EPA CompTox
DTXSID20865274
Created by admin on Fri Dec 15 18:09:49 GMT 2023 , Edited by admin on Fri Dec 15 18:09:49 GMT 2023
PRIMARY