Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C27H42NO2.C10H19O3 |
| Molecular Weight | 599.8839 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCCOCC([O-])=O.CC(C)(C)CC(C)(C)C1=CC=C(OCCOCC[N+](C)(C)CC2=CC=CC=C2)C=C1
InChI
InChIKey=DLTUMMFURAWYDZ-UHFFFAOYSA-M
InChI=1S/C27H42NO2.C10H20O3/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;1-2-3-4-5-6-7-8-13-9-10(11)12/h8-16H,17-22H2,1-7H3;2-9H2,1H3,(H,11,12)/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 |
|---|---|---|
| [Appraisal of fungistatic and fungicidal activities of quaternary compounds towards yeasts belonging to the genera Candida and Cryptococcus]. | 2001 Apr |
|
| Identification of benzethonium chloride in commercial grapefruit seed extracts. | 2001 Jul |
|
| Ketamine and its preservative, benzethonium chloride, both inhibit human recombinant alpha7 and alpha4beta2 neuronal nicotinic acetylcholine receptors in Xenopus oocytes. | 2001 Oct |
|
| In vitro evaluation of skin sensitivity of povidone-iodine and other antiseptics using a three-dimensional human skin model. | 2002 |
|
| Evidence for concurrent effects of exposure to environmental cadmium and lead on hepatic CYP2A6 phenotype and renal function biomarkers in nonsmokers. | 2004 Nov |
|
| Ability of fourteen chemical agents used in dental practice to induce chromosome aberrations in Syrian hamster embryo cells. | 2005 Jan |
|
| Determination of benzethonium chloride in anthrax vaccine adsorbed by HPLC. | 2006 Dec |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Is secondary wavelength always necessary in turbidimetric urine protein measurements? | 2008 May |
|
| Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles. | 2009 Dec 2 |
|
| Benzethonium increases the cytotoxicity of S(+)-ketamine in lymphoma, neuronal, and glial cells. | 2010 Dec |
|
| 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 |
|
| Correlation between reduced susceptibility to disinfectants and multidrug resistance among clinical isolates of Acinetobacter species. | 2010 Sep |
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.
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Brand Name | English | ||
|
Systematic Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
71586914
Created by
admin on Fri Dec 15 15:43:40 GMT 2023 , Edited by admin on Fri Dec 15 15:43:40 GMT 2023
|
PRIMARY | |||
|
DTXSID60226542
Created by
admin on Fri Dec 15 15:43:40 GMT 2023 , Edited by admin on Fri Dec 15 15:43:40 GMT 2023
|
PRIMARY | |||
|
7563-43-1
Created by
admin on Fri Dec 15 15:43:40 GMT 2023 , Edited by admin on Fri Dec 15 15:43:40 GMT 2023
|
PRIMARY | |||
|
147062OTCD
Created by
admin on Fri Dec 15 15:43:40 GMT 2023 , Edited by admin on Fri Dec 15 15:43:40 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
SALT/SOLVATE (SALT/SOLVATE)
SALT/SOLVATE (SALT/SOLVATE)
SUBSTANCE RECORD
