Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C27H42NO2.Cl.H2O |
| Molecular Weight | 466.096 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.[Cl-].CC(C)(C)CC(C)(C)C1=CC=C(OCCOCC[N+](C)(C)CC2=CC=CC=C2)C=C1
InChI
InChIKey=VAPZFIMSURJAMN-UHFFFAOYSA-M
InChI=1S/C27H42NO2.ClH.H2O/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;1H2/q+1;;/p-1
| 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 | 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 | C27H42NO2 |
| Molecular Weight | 412.6279 |
| Charge | 1 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|
| Urine protein estimation in hypertensive pregnancy: which thresholds and laboratory assay best predict clinical outcome? | 2005 |
|
| 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 |
|
| In vitro short-time killing activity of povidone-iodine (Isodine Gargle) in the presence of oral organic matter. | 2006 |
|
| Determination of benzethonium chloride in anthrax vaccine adsorbed by HPLC. | 2006 Dec |
|
| Ormosil nanocomposite materials as modifiers for acrylic coating systems. | 2006 Feb |
|
| [Properties of benzethonium chloride in micellar solutions and the effect of added sodium chloride]. | 2006 Jul |
|
| Development and validation of an HPLC/UV/MS method for simultaneous determination of 18 preservatives in grapefruit seed extract. | 2006 May 31 |
|
| Hexadecyl-phosphorylcholine ointment for treatment of cutaneous leishmaniasis: an animal trial. | 2006 Sep |
|
| Efficacy of an alcohol-based healthcare hand rub containing synergistic combination of farnesol and benzethonium chloride. | 2006 Sep |
|
| Benzethonium chloride: a novel anticancer agent identified by using a cell-based small-molecule screen. | 2006 Sep 15 |
|
| Strong interference of hemoglobin concentration on CSF total protein measurement using the trichloroacetic acid precipitation method. | 2007 |
|
| Simultaneous identification and quantification by liquid chromatography of benzethonium chloride, methyl paraben and triclosan in commercial products labeled as grapefruit seed extract. | 2007 Aug |
|
| 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 |
|
| Cationic surfactants induce apoptosis in normal and cancer cells. | 2007 Jan |
|
| Presence of chemical additives and microbial inhibition capacity in grapefruit seed extracts used in apiculture. | 2007 Jan-Mar |
|
| Assessment using human dental pulp cells of clastogenicity of antiseptics used in dental practice and agents for root canal enlargement and cleaning. | 2007 Jul |
|
| Adverse effects by artificial grapefruit seed extract products in patients on warfarin therapy. | 2007 Jun |
|
| Displacement chromatography of proteins on hydrophobic charge induction adsorbent column. | 2007 Sep 21 |
|
| 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 |
|
| Circulating plasma factors induce tubular and glomerular alterations in septic burns patients. | 2008 |
|
| Rapid antibacterial activity of 2 novel hand soaps: evaluation of the risk of development of bacterial resistance to the antibacterial agents. | 2008 Aug |
|
| Validation of a quantitative NMR method for suspected counterfeit products exemplified on determination of benzethonium chloride in grapefruit seed extracts. | 2008 Aug 5 |
|
| Effects of nonionic and ionic surfactants on survival, oxidative stress, and cholinesterase activity of planarian. | 2008 Feb |
|
| Actinomycetes from sediments in the Trondheim fjord, Norway: diversity and biological activity. | 2008 Jan 23 |
|
| [Case of serious renal failure induced by ingesting large volume of MAKIRON]. | 2008 Jul |
|
| Reduction of disinfectant bactericidal activities in clinically isolated Acinetobacter species in the presence of organic material. | 2008 Mar |
|
| Is secondary wavelength always necessary in turbidimetric urine protein measurements? | 2008 May |
|
| Local anesthetics, antipsychotic phenothiazines, and cationic surfactants shut down intracellular reactions through membrane perturbation in yeast. | 2008 Nov |
|
| The enhancement effect of three sugar alcohols on the fungicidal effect of benzethonium chloride toward Candida albicans. | 2008 Nov |
|
| Effect of cationic surfactants on enhancement of firefly bioluminescence in the presence of liposomes. | 2008 Sep |
|
| Harnessing gene expression to identify the genetic basis of drug resistance. | 2009 |
|
| Central sympatholytics prolong survival in experimental sepsis. | 2009 |
|
| Suppression of experimental uveitis by a recombinant adeno-associated virus vector encoding interleukin-1 receptor antagonist. | 2009 Aug 8 |
|
| A facile synthesis of highly water-soluble, core-shell organo-silica nanoparticles with controllable size via sol-gel process. | 2009 Dec 15 |
|
| Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles. | 2009 Dec 2 |
|
| Estimation of proteinuria as a predictor of complications of pre-eclampsia: a systematic review. | 2009 Mar 24 |
|
| A study of the relationship between albuminuria, proteinuria and urinary reagent strips. | 2009 May |
|
| The effect of Bacillus subtilis mouth rinsing in patients with periodontitis. | 2009 Nov |
|
| Sugar alcohols, caries incidence, and remineralization of caries lesions: a literature review. | 2010 |
|
| Clinical significance of EGFR, Her-2 and EGF in oral squamous cell carcinoma: a case control study. | 2010 Apr 29 |
|
| Benzethonium increases the cytotoxicity of S(+)-ketamine in lymphoma, neuronal, and glial cells. | 2010 Dec |
|
| Arginine metabolism in Trichomonas vaginalis infected with Mycoplasma hominis. | 2010 Dec |
|
| Kinin B1 receptors mediate depression-like behavior response in stressed mice treated with systemic E. coli lipopolysaccharide. | 2010 Dec 31 |
|
| Effects of high-dose major components in oral disinfectants on the cell cycle and apoptosis in primary human gingival fibroblasts in vitro. | 2010 Jan |
|
| 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 |
|
| The relative toxicity of compounds used as preservatives in vaccines and biologics. | 2010 May |
|
| Caspase-1 is involved in the genesis of inflammatory hypernociception by contributing to peripheral IL-1β maturation. | 2010 Oct 4 |
|
| Correlation between reduced susceptibility to disinfectants and multidrug resistance among clinical isolates of Acinetobacter species. | 2010 Sep |
|
| Synthesis, self-aggregation and biological properties of alkylphosphocholine and alkylphosphohomocholine derivatives of cetyltrimethylammonium bromide, cetylpyridinium bromide, benzalkonium bromide (C16) and benzethonium chloride. | 2013 Aug |
|
| 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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 09:34:40 GMT 2023
by
admin
on
Sat Dec 16 09:34:40 GMT 2023
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| Record UNII |
RS89WU8V92
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| Record Status |
Validated (UNII)
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| Record Version |
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21644026
Created by
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RS89WU8V92
Created by
admin on Sat Dec 16 09:34:41 GMT 2023 , Edited by admin on Sat Dec 16 09:34:41 GMT 2023
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5929-09-9
Created by
admin on Sat Dec 16 09:34:41 GMT 2023 , Edited by admin on Sat Dec 16 09:34:41 GMT 2023
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| Related Record | Type | Details | ||
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SALT/SOLVATE -> SALT/SOLVATE |
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PARENT -> SALT/SOLVATE |
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SALT/SOLVATE -> SALT/SOLVATE |
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ANHYDROUS->SOLVATE |
