Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C27H42NO2 |
| Molecular Weight | 412.6279 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 1 |
SHOW SMILES / InChI
SMILES
CC(C)(C)CC(C)(C)C1=CC=C(OCCOCC[N+](C)(C)CC2=CC=CC=C2)C=C1
InChI
InChIKey=SIYLLGKDQZGJHK-UHFFFAOYSA-N
InChI=1S/C27H42NO2/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/q+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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| [Resistance of Staphylococcus aureus strains to quaternary ammonium compounds and chlorhexidine]. | 2002 |
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| Burns caused by dilute hydrofluoric acid in the bleach. | 2002 Apr |
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| Characteristics of hyaluronate-hydroxyethyl acrylate blend gel and release of cationic amphiphilic solutes. | 2002 Oct |
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| Steroid-induced polycystic ovaries in rats: effect of electro-acupuncture on concentrations of endothelin-1 and nerve growth factor (NGF), and expression of NGF mRNA in the ovaries, the adrenal glands, and the central nervous system. | 2003 Apr 8 |
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| An evaluation of protein assays for quantitative determination of drugs. | 2003 Jul 31 |
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| A nonpeptide provides insight into mechanisms that regulate Drosophila melanogaster heart contractions. | 2003 Oct |
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| Cetylpyridinium tetrachlorozincate as standard for tenside titration. Analytical methods with 1,3-dibromo-5,5-dimethylhydantoin (DBH) in respect to environmental and economical concern, part 19. | 2004 Aug |
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| Peptidergic innervation of the crop and the effects of an ingested nonpeptidal agonist on longevity in female Musca domestica (Diptera: Muscidae). | 2004 Jul |
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| [Study on separation of epirubicin and doxorubicin isomers by displacement chromatography]. | 2004 Mar |
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| Stimulation of TM3 Leydig cell proliferation via GABA(A) receptors: a new role for testicular GABA. | 2004 Mar 24 |
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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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| Urine protein estimation in hypertensive pregnancy: which thresholds and laboratory assay best predict clinical outcome? | 2005 |
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| [Relation between oxygen uptake rate and biosorption of activated sludge against chemical substance]. | 2005 Feb |
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| Ability of fourteen chemical agents used in dental practice to induce chromosome aberrations in Syrian hamster embryo cells. | 2005 Jan |
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| Susceptibilities to antiseptic agents and distribution of antiseptic-resistance genes qacA/B and smr of methicillin-resistant Staphylococcus aureus isolated in Asia during 1998 and 1999. | 2005 Jun |
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| Comparative efficacy of hand hygiene agents in the reduction of bacteria and viruses. | 2005 Mar |
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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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| Ormosil nanocomposite materials as modifiers for acrylic coating systems. | 2006 Feb |
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| [Properties of benzethonium chloride in micellar solutions and the effect of added sodium chloride]. | 2006 Jul |
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| Development and validation of an HPLC/UV/MS method for simultaneous determination of 18 preservatives in grapefruit seed extract. | 2006 May 31 |
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| Hexadecyl-phosphorylcholine ointment for treatment of cutaneous leishmaniasis: an animal trial. | 2006 Sep |
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| Efficacy of an alcohol-based healthcare hand rub containing synergistic combination of farnesol and benzethonium chloride. | 2006 Sep |
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| Benzethonium chloride: a novel anticancer agent identified by using a cell-based small-molecule screen. | 2006 Sep 15 |
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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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| Assessment using human dental pulp cells of clastogenicity of antiseptics used in dental practice and agents for root canal enlargement and cleaning. | 2007 Jul |
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| Adverse effects by artificial grapefruit seed extract products in patients on warfarin therapy. | 2007 Jun |
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| Displacement chromatography of proteins on hydrophobic charge induction adsorbent column. | 2007 Sep 21 |
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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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| Circulating plasma factors induce tubular and glomerular alterations in septic burns patients. | 2008 |
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| Effects of nonionic and ionic surfactants on survival, oxidative stress, and cholinesterase activity of planarian. | 2008 Feb |
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| [Case of serious renal failure induced by ingesting large volume of MAKIRON]. | 2008 Jul |
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| Reduction of disinfectant bactericidal activities in clinically isolated Acinetobacter species in the presence of organic material. | 2008 Mar |
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| Is secondary wavelength always necessary in turbidimetric urine protein measurements? | 2008 May |
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| The enhancement effect of three sugar alcohols on the fungicidal effect of benzethonium chloride toward Candida albicans. | 2008 Nov |
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| Effect of cationic surfactants on enhancement of firefly bioluminescence in the presence of liposomes. | 2008 Sep |
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| Suppression of experimental uveitis by a recombinant adeno-associated virus vector encoding interleukin-1 receptor antagonist. | 2009 Aug 8 |
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| The effect of Bacillus subtilis mouth rinsing in patients with periodontitis. | 2009 Nov |
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| Sugar alcohols, caries incidence, and remineralization of caries lesions: a literature review. | 2010 |
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| Arginine metabolism in Trichomonas vaginalis infected with Mycoplasma hominis. | 2010 Dec |
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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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| Caspase-1 is involved in the genesis of inflammatory hypernociception by contributing to peripheral IL-1β maturation. | 2010 Oct 4 |
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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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NCI_THESAURUS |
C28394
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D08AJ58
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R02AA09
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D08AJ08
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WHO-VATC |
QR02AA09
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C87255
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Benzethonium
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1VU15B70BP
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DTXSID5046984
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10172-60-8
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D001558
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1390
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DB11125
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100000084999
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2335
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3018
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SUB00719MIG
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1VU15B70BP
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
