Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C27H42NO2.Cl |
| Molecular Weight | 448.081 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Cl-].CC(C)(C)CC(C)(C)C1=CC=C(OCCOCC[N+](C)(C)CC2=CC=CC=C2)C=C1
InChI
InChIKey=UREZNYTWGJKWBI-UHFFFAOYSA-M
InChI=1S/C27H42NO2.ClH/c1-26(2,3)22-27(4,5)24-13-15-25(16-14-24)30-20-19-29-18-17-28(6,7)21-23-11-9-8-10-12-23;/h8-16H,17-22H2,1-7H3;1H/q+1;/p-1
DescriptionSources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=0a6c9eee-ddbf-5cf5-e054-00144ff8d46cCurator's Comment: description was created based on several sources, including:
http://www.news-medical.net/news/2007/12/04/33135.aspx
https://en.wikipedia.org/wiki/Benzethonium_chloride
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=0a6c9eee-ddbf-5cf5-e054-00144ff8d46c
Curator's Comment: description was created based on several sources, including:
http://www.news-medical.net/news/2007/12/04/33135.aspx
https://en.wikipedia.org/wiki/Benzethonium_chloride
Benzethonium chloride, also known as hyamine, is a synthetic quaternary ammonium salt. It has surfactant, antiseptic, and anti-infective properties and it is used as a topical antimicrobial agent in first aid antiseptics. It is also found in cosmetics and toiletries such as mouthwashes, anti-itch ointments, and antibacterial moist towelettes. Benzethonium chloride exhibits a broad spectrum of microbiocidal activity against bacteria, fungi, mold and viruses. The US Food and Drug Administration (FDA) specifies that the safe and effective concentrations for benzethonium chloride are 0.1-0.2% in first aid products. Aqueous solutions of benzethonium chloride are not absorbed through the skin. It is not approved in the US or Europe for use as a food additive. Being a quaternary ammonium salt, it is more toxic than negatively charged surfactants. However, in a two-year study on rats, there was no evidence of carcinogenic activity. Benzethonium chloride was characterized as a novel anticancer compound possessing both in vitro and in vivo efficacy justifying further investigation.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effect of concentration and biochemical assay on the accuracy of urine dipsticks in hypertensive pregnancies. | 2001 |
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| Application of an improved biuret method to the determination of total protein in urine and cerebrospinal fluid without concentration step by use of Hitachi 7170 auto-analyzer. | 2001 |
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| [Appraisal of fungistatic and fungicidal activities of quaternary compounds towards yeasts belonging to the genera Candida and Cryptococcus]. | 2001 Apr |
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| Identification of benzethonium chloride in commercial grapefruit seed extracts. | 2001 Jul |
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| Effectiveness of manual cleaning and disinfection of gastroendoscopes with 3% glutaraldehyde for decreasing risk of transmission of hepatitis C virus. | 2001 Jun |
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| Ketamine and its preservative, benzethonium chloride, both inhibit human recombinant alpha7 and alpha4beta2 neuronal nicotinic acetylcholine receptors in Xenopus oocytes. | 2001 Oct |
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| In vitro evaluation of skin sensitivity of povidone-iodine and other antiseptics using a three-dimensional human skin model. | 2002 |
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| Burns caused by dilute hydrofluoric acid in the bleach. | 2002 Apr |
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| Absence of mycoplasma contamination in the anthrax vaccine. | 2002 Jan |
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| An evaluation of protein assays for quantitative determination of drugs. | 2003 Jul 31 |
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| Evidence for concurrent effects of exposure to environmental cadmium and lead on hepatic CYP2A6 phenotype and renal function biomarkers in nonsmokers. | 2004 Nov |
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| [Relation between oxygen uptake rate and biosorption of activated sludge against chemical substance]. | 2005 Feb |
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| In vitro short-time killing activity of povidone-iodine (Isodine Gargle) in the presence of oral organic matter. | 2006 |
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| Determination of benzethonium chloride in anthrax vaccine adsorbed by HPLC. | 2006 Dec |
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| Hexadecyl-phosphorylcholine ointment for treatment of cutaneous leishmaniasis: an animal trial. | 2006 Sep |
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| Strong interference of hemoglobin concentration on CSF total protein measurement using the trichloroacetic acid precipitation method. | 2007 |
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| Simultaneous identification and quantification by liquid chromatography of benzethonium chloride, methyl paraben and triclosan in commercial products labeled as grapefruit seed extract. | 2007 Aug |
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| Evaluation of an alcohol-based surgical hand disinfectant containing a synergistic combination of farnesol and benzethonium chloride for immediate and persistent activity against resident hand flora of volunteers and with a novel in vitro pig skin model. | 2007 Feb |
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| Cationic surfactants induce apoptosis in normal and cancer cells. | 2007 Jan |
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| Presence of chemical additives and microbial inhibition capacity in grapefruit seed extracts used in apiculture. | 2007 Jan-Mar |
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| FMRFamide-like immunoreactivity in the central nervous system and alimentary tract of the non-hematophagous blow fly, Phormia regina, and the hematophagous horse fly, Tabanus nigrovittatus. | 2008 |
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| Rapid antibacterial activity of 2 novel hand soaps: evaluation of the risk of development of bacterial resistance to the antibacterial agents. | 2008 Aug |
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| Actinomycetes from sediments in the Trondheim fjord, Norway: diversity and biological activity. | 2008 Jan 23 |
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| Local anesthetics, antipsychotic phenothiazines, and cationic surfactants shut down intracellular reactions through membrane perturbation in yeast. | 2008 Nov |
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| Central sympatholytics prolong survival in experimental sepsis. | 2009 |
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| Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles. | 2009 Dec 2 |
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| Estimation of proteinuria as a predictor of complications of pre-eclampsia: a systematic review. | 2009 Mar 24 |
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| A study of the relationship between albuminuria, proteinuria and urinary reagent strips. | 2009 May |
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| Sugar alcohols, caries incidence, and remineralization of caries lesions: a literature review. | 2010 |
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| Clinical significance of EGFR, Her-2 and EGF in oral squamous cell carcinoma: a case control study. | 2010 Apr 29 |
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| Benzethonium increases the cytotoxicity of S(+)-ketamine in lymphoma, neuronal, and glial cells. | 2010 Dec |
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| Arginine metabolism in Trichomonas vaginalis infected with Mycoplasma hominis. | 2010 Dec |
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| Kinin B1 receptors mediate depression-like behavior response in stressed mice treated with systemic E. coli lipopolysaccharide. | 2010 Dec 31 |
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| Effects of high-dose major components in oral disinfectants on the cell cycle and apoptosis in primary human gingival fibroblasts in vitro. | 2010 Jan |
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| Culture-modified bone marrow cells attenuate cardiac and renal injury in a chronic kidney disease rat model via a novel antifibrotic mechanism. | 2010 Mar 4 |
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| The relative toxicity of compounds used as preservatives in vaccines and biologics. | 2010 May |
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| Caspase-1 is involved in the genesis of inflammatory hypernociception by contributing to peripheral IL-1β maturation. | 2010 Oct 4 |
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| Correlation between reduced susceptibility to disinfectants and multidrug resistance among clinical isolates of Acinetobacter species. | 2010 Sep |
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| Synthesis, self-aggregation and biological properties of alkylphosphocholine and alkylphosphohomocholine derivatives of cetyltrimethylammonium bromide, cetylpyridinium bromide, benzalkonium bromide (C16) and benzethonium chloride. | 2013 Aug |
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| A repurposing approach identifies off-patent drugs with fungicidal cryptococcal activity, a common structural chemotype, and pharmacological properties relevant to the treatment of cryptococcosis. | 2013 Feb |
Patents
Sample Use Guides
For benzethonium (48 hour incubation), the dose required to reduce cell viability by 50% was 3.8 uM in FaDu (human hypopharyngeal squamous cancer), 42.2 uM in NIH 3T3 (untransformed mouse embryonic fibroblast), 5.3 uM in C666-1 (nasopharyngeal cancer), and 17.0 uM in GM05757 (primary normal human fibroblast) cells.
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Food Contact Sustance Notif, (FCN No.) |
FCN NO. 460
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WHO-ATC |
D08AJ08
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D08AJ58
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QD08AJ58
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NCI_THESAURUS |
C28394
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EPA PESTICIDE CODE |
69122
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DBSALT001519
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204-479-9
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BENZETHONIUM CHLORIDE
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PH41D05744
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m2346
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1051500
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CHEMBL1182210
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121-54-0
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C77025
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567
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ACTIVE MOIETY
SALT/SOLVATE (SALT/SOLVATE)
SALT/SOLVATE (SALT/SOLVATE)
SUBSTANCE RECORD
