DescriptionSources: http://www.medscape.com/viewarticle/711467_4Curator's Comment: description was created based on several sources, including:
https://en.wikipedia.org/wiki/Benzalkonium_chloride
Sources: http://www.medscape.com/viewarticle/711467_4
Curator's Comment: description was created based on several sources, including:
https://en.wikipedia.org/wiki/Benzalkonium_chloride
Benzalkonium chloride, also known as BZK, BKC, BAC, alkyldimethylbenzylammonium chloride and ADBAC, is a type of cationic surfactant. It is an organic salt called a quaternary ammonium compound. In 2011, a large clinical trial designed to evaluate the efficacy of hand sanitizers based on different active ingredients in preventing virus transmission amongst schoolchildren was re-designed to exclude sanitizers based on benzalkonium chloride due to safety concerns. Benzalkonium chloride has been in common use as a pharmaceutical preservative and antimicrobial since the 1940s. While early studies confirmed the corrosive and irritant properties of benzalkonium chloride, investigations into the adverse effects of, and disease states linked to, benzalkonium chloride have only surfaced during the past 30 years. Benzalkonium chloride is classed as a Category III antiseptic active ingredient by the United States Food and Drug Administration. Ingredients are categorised as Category III when "available data are insufficient to classify as safe and effective, and further testing is required”. Benzalkonium chloride is excluded from the current United States Food and Drug Administration review of the safety and effectiveness of consumer antiseptics and topical antimicrobial over-the-counter drug products, meaning it will remain a Category III ingredient. The mechanism of bactericidal/microbicidal action is thought to be due to disruption of intermolecular interactions. This can cause dissociation of cellular membrane lipid bilayers, which compromises cellular permeability controls and induces leakage of cellular contents. Other biomolecular complexes within the bacterial cell can also undergo dissociation. Enzymes, which finely control a wide range of respiratory and metabolic cellular activities, are particularly susceptible to deactivation. Critical intermolecular interactions and tertiary structures in such highly specific biochemical systems can be readily disrupted by cationic surfactants. Benzalkonium chloride is a human skin and severe eye irritant. It is a suspected respiratory toxicant, immunotoxicant, gastrointestinal toxicant and neurotoxicant.
Approval Year
PubMed
Title | Date | PubMed |
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Cytokine induction in human epidermal keratinocytes exposed to contact irritants and its relation to chemical-induced inflammation in mouse skin. | 1994 Jun |
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Redox imbalance induced by contact sensitizers triggers the maturation of dendritic cells. | 2005 Mar |
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CXCL8 secretion by dendritic cells predicts contact allergens from irritants. | 2006 Feb |
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Human skin in organ culture and human skin cells (keratinocytes and fibroblasts) in monolayer culture for assessment of chemically induced skin damage. | 2007 Aug |
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Suitability of macrophage inflammatory protein-1beta production by THP-1 cells in differentiating skin sensitizers from irritant chemicals. | 2008 Apr |
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Occludin gene expression as an early in vitro sign for mild eye irritation assessment. | 2010 Feb |
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Upregulation of genes orchestrating keratinocyte differentiation, including the novel marker gene ID2, by contact sensitizers in human bulge-derived keratinocytes. | 2010 Jan-Feb |
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Prediction of the contact sensitizing potential of chemicals using analysis of gene expression changes in human THP-1 monocytes. | 2010 Nov 10 |
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Refining the human iPSC-cardiomyocyte arrhythmic risk assessment model. | 2013 Dec |
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Identification of cornifelin and early growth response-1 gene as novel biomarkers for in vitro eye irritation using a 3D reconstructed human cornea model MCTT HCE™. | 2015 Sep |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/10067965
Curator's Comment: Cell exposure to 0.1% and 0.05% BAC induced cell lysis immediately after treatment. All cells (100%) treated with 0.01% BAC died in a delayed manner within 24 hours, with most of the characteristics of apoptosis (chromatin condensation and DNA fragmentation, reduction in cell volume, expression of the apoptotic marker Apo 2.7, and apoptotic changes in DNA content).
A continuous human conjunctival cell line (Wong-Kilbourne derivative of Chang conjunctiva) was exposed to benzalkonium chloride (BAC) solutions at various concentrations (0.1%-0.0001%) during a period of 10 minutes.
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Mixture
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NCI_THESAURUS |
C83486
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EPA PESTICIDE CODE |
69106
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EPA PESTICIDE CODE |
69194
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69161
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CFR |
21 CFR 310.201
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EPA PESTICIDE CODE |
69142
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69158
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EPA PESTICIDE CODE |
69105
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69141
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69199
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69157
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169135
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69137
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169106
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EPA PESTICIDE CODE |
69184
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Benzalkonium Chloride
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SUB00714MIG
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benzalkonium chloride
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68424-85-1
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ALTERNATIVE | |||
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BENZALKONIUM CHLORIDE
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PRIMARY | Description: A white or yellowish white powder, thick gel, or gelatinous pieces; odourless or a slight aromatic odour. Solubility: Very soluble in water and ethanol (~750 g/l) TS; freely soluble in acetone R; practically insoluble in ether R. Category: Antimicrobial preservative; surfactant. Storage: Benzalkonium chloride should be kept in a tightly closed container, protected from light. Additional information: Benzalkonium chloride is hygroscopic. Definition: Benzalkonium chloride is a mixture of alkylbenzyldimethylammonium chlorides, the alkyl groups having chain lengths of C8 to C18. | ||
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CHEMBL1187417
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C82282
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F5UM2KM3W7
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DTXSID6028492
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m2331
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BENZALKONIUM CHLORIDE
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All of the following components must be present:
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |
http://apps.who.int/phint/pdf/b/Jb.6.1.45.pdf
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