Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C28H44NO2.Cl.H2O |
| Molecular Weight | 480.123 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
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
| 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 |
| Molecular Formula | C28H44NO2 |
| Molecular Weight | 426.6545 |
| Charge | 1 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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 |
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
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Leshcutan Approved UseApproved for use as an active ingredient in the pharmaceutical preparation of Leshcutan in Isreal. |
|||
| Primary | Leshcutan Approved UseApproved for use as an active ingredient in the pharmaceutical preparation of Leshcutan in Isreal. |
Doses
| Dose | Population | Adverse events |
|---|---|---|
12 % 2 times / day multiple, topical Recommended|Highest studied dose Dose: 12 %, 2 times / day Route: topical Route: multiple Dose: 12 %, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Other AEs: Pruritus, Burning skin... Other AEs: Pruritus (46.7%) Sources: Burning skin (30%) Pain localized (20%) Localised edema (3.3%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Pain localized | 20% | 12 % 2 times / day multiple, topical Recommended|Highest studied dose Dose: 12 %, 2 times / day Route: topical Route: multiple Dose: 12 %, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Localised edema | 3.3% | 12 % 2 times / day multiple, topical Recommended|Highest studied dose Dose: 12 %, 2 times / day Route: topical Route: multiple Dose: 12 %, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Burning skin | 30% | 12 % 2 times / day multiple, topical Recommended|Highest studied dose Dose: 12 %, 2 times / day Route: topical Route: multiple Dose: 12 %, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Pruritus | 46.7% | 12 % 2 times / day multiple, topical Recommended|Highest studied dose Dose: 12 %, 2 times / day Route: topical Route: multiple Dose: 12 %, 2 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Magnetic "fishing" assay to screen small-molecule mixtures for modulators of protein-protein interactions. | 2010-12-01 |
|
| Gene expression signature-based screening identifies new broadly effective influenza a antivirals. | 2010-10-04 |
|
| Cell-based and cytokine-directed chemical screen to identify potential anti-multiple myeloma agents. | 2010-07 |
|
| Drug resistance in leishmaniasis. | 2010-05 |
|
| Treatment strategies for mucocutaneous leishmaniasis. | 2010-05 |
|
| Interventions for American cutaneous and mucocutaneous leishmaniasis. | 2009-04-15 |
|
| WR279,396, a third generation aminoglycoside ointment for the treatment of Leishmania major cutaneous leishmaniasis: a phase 2, randomized, double blind, placebo controlled study. | 2009 |
|
| Is paromomycin an effective and safe treatment against cutaneous leishmaniasis? A meta-analysis of 14 randomized controlled trials. | 2009 |
|
| Optimization of topical therapy for Leishmania major localized cutaneous leishmaniasis using a reliable C57BL/6 Model. | 2007-11-28 |
|
| Aqueous micellar two-phase system composed of hyamine-type hydrophobically modified ethylene oxide and application for cytochrome P450 BM-3 separation. | 2007-06-01 |
|
| Leishmania major: in vitro and in vivo anti-leishmanial activity of paromomycin ointment (Leshcutan) combined with the immunomodulator Imiquimod. | 2007-06 |
|
| Cutaneous leishmaniasis. | 2007-03-14 |
|
| Treating cutaneous leishmaniasis patients in Kabul, Central Asia: cost-effectiveness of an operational program in a complex emergency setting. | 2007-01-30 |
|
| A siderophore biosynthesis gene cluster from the fish pathogen Photobacterium damselae subsp. piscicida is structurally and functionally related to the Yersinia high-pathogenicity island. | 2006-11 |
|
| Comparison of the effectiveness of two topical paromomycin treatments versus meglumine antimoniate for New World cutaneous leishmaniasis. | 2004-07 |
|
| Purification and characterization of an extracellular lipase from Geotrichum marinum. | 2004-03 |
|
| Randomized, controlled, double-blind trial of topical treatment of cutaneous leishmaniasis with paromomycin plus methylbenzethonium chloride ointment in Guatemala. | 2001-11 |
|
| Occupational allergic contact dermatitis from alkylammonium amidobenzoate. | 2001-05-19 |
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
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| Related Record | Type | Details | ||
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ANHYDROUS->SOLVATE | |||
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PARENT -> SALT/SOLVATE |
