Quaternary Ammonium Compounds in Medicinal Chemistry, II

D’Arcy, P. F.; Taylor, E. P.

doi:10.1111/j.2042-7158.1962.tb11081.x

Cited by 19 publications

(4 citation statements)

References 178 publications

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“…Chlorhexidine gluconate (CHX) and benzalkonium chloride (BZK) are among those antiseptics that are most commonly used worldwide [1][2][3]. BZK solutions for hospital use tend to be neutral to alkaline, non-corrosive on metal surfaces, non-staining, and safe to use on all washable surfaces [1][2][3][4][5]. BZK is also added to drug products as a preservative for multiple dose containers [6].…”

Section: Introductionmentioning

confidence: 99%

Effects of Extended Storage of Chlorhexidine Gluconate and Benzalkonium Chloride Solutions on the Viability of Burkholderia cenocepacia

Ahn¹,

Kim²,

Lee³

et al. 2017

Journal of Microbiology and Biotechnology

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Chlorhexidine gluconate (CHX) and benzalkonium chloride (BZK) formulations are frequently used as antiseptics in healthcare and consumer products. Burkholderia cepacia complex (BCC) contamination of pharmaceutical products could be due to the use of contaminated water in the manufacturing process, over-diluted antiseptic solutions in the product, and the use of outdated products, which in turn reduces the antimicrobial activity of CHX and BZK. To establish a "safe use" period following opening containers of CHX and BZK, we measured the antimicrobial effects of CHX (2-10 μg/ml) and BZK (10-50 μg/ml) at sublethal concentrations on six strains of using chemical and microbiological assays. CHX (2, 4, and 10 μg/ml) and BZK (10, 20, and 50 μg/ml) stored for 42 days at 23°C showed almost the same concentration and toxicity compared with freshly prepared CHX and BZK on strains. When 5 μg/ml CHX and 20 μg/ml BZK were spiked to six strains with different inoculum sizes (10⁰ -10⁵ CFU/ml), their toxic effects were not changed for 28 days. strains in diluted CHX and BZK were detectable at concentrations up to 10² CFU/ml after incubation for 28 days at 23°C. Although abiotic and biotic changes in the toxicity of both antiseptics were not observed, our results indicate that strains could remain viable in CHX and BZK for 28 days, which in turn, indicates the importance of control measures to monitor BCC contamination in pharmaceutical products.

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Section: Introductionmentioning

confidence: 99%

Effects of Extended Storage of Chlorhexidine Gluconate and Benzalkonium Chloride Solutions on the Viability of Burkholderia cenocepacia

Ahn¹,

Kim²,

Lee³

et al. 2017

Journal of Microbiology and Biotechnology

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“…Although BAC disinfectant solutions applied in hospital settings have a pH that is neutral to alkaline, are noncorrosive, nonstaining, and considered safe to apply on all washable surfaces (10,11), at least 40 outbreaks have been attributed to infection by disinfectant-resistant pathogens contaminating antiseptic products, such as Pseudomonas aeruginosa (12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22). It has been hypothesized that the contaminating pathogens are associated with the water used in pharmaceutical processing facilities or the storage of BAC with cotton or gauze (22,23).…”

mentioning

confidence: 99%

Genomic and Transcriptomic Insights into How Bacteria Withstand High Concentrations of Benzalkonium Chloride Biocides

Kim

Hatt

Weigand

et al. 2018

Appl Environ Microbiol

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Benzalkonium chlorides (BAC) are commonly used biocides in broad-spectrum disinfectant solutions. How microorganisms cope with BAC exposure remains poorly understood, despite its importance for disinfection and disinfectant-induced antibiotic resistance. To provide insights into these issues, we exposed two isolates of an opportunistic pathogen, , to increasing concentrations of BAC. One isolate was preadapted to BAC, as it originated from a bioreactor fed with subinhibitory concentrations of BAC for 3 years, while the other originated from a bioreactor that received no BAC. Replicated populations of both isolates were able to survive high concentrations of BAC, up to 1,200 and 1,600 mg/liter for the non- and preadapted strains, respectively, exceeding typical application doses. Transcriptome sequencing (RNA-seq) analysis revealed upregulation of efflux pump genes and decreased expression of porins related to BAC transport as well as reduced growth rate. Increased expression of spermidine (a polycation) synthase genes and mutations in the (polymyxin resistance) gene, which cause a reduction in membrane negative charge, suggested that a major adaptation to exposure to the cationic surfactant BAC was to actively stabilize cell surface charge. Collectively, these results revealed that adapts to BAC exposure by a combination of mechanisms and provided genetic markers to monitor BAC-resistant organisms that may have applications in the practice of disinfection. BAC are widely used as biocides in disinfectant solutions, food-processing lines, domestic households, and health care facilities. Due to their wide use and mode of action, there has been rising concern that BAC may promote antibiotic resistance. Consistent with this idea, at least 40 outbreaks have been attributed to infection by disinfectant- and antibiotic-resistant pathogens such as However, the underlying molecular mechanisms that bacteria use to deal with BAC exposure remain poorly elucidated. Elucidating these mechanisms may be important for monitoring and limiting the spread of disinfectant-resistant pathogens. Using an integrated approach that combined genomics and transcriptomics with physiological characterization of BAC-adapted isolates, this study provided a comprehensive understanding of the BAC resistance mechanisms in Our findings also revealed potential genetic markers to detect and monitor the abundance of BAC-resistant pathogens across clinical or environmental settings. This work contributes new knowledge about high concentrations of benzalkonium chlorides disinfectants-resistance mechanisms at the whole-cell genomic and transcriptomic level.

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“…2.10. The cationic onium group may be a simple aliphatic ammonium, a pyridimum or piperidinium or other heterocyclic group (D'Arcy & Taylor, 1962b).…”

Section: Chemical Aspectsmentioning

confidence: 99%

“…Nevertheless, cells of this organism which are highly resistant to benzalkonium chloride (1 mg/mL, 0.1%) may still show ultrastructural changes when grown in its presence (Hoffman et al, 1973). The QACs have a trypanocidal activity (reviewed by D'Arcy & Taylor, 1962b) but are not mycobactericidal (Sykes, 1965;Smith, 1968), presumably because of the lipid, waxy coat of these organisms. Gram-negative bacteria, such as E. coli, P. aeruginosa and S. typhimurium, exclude QACs, but deep rough mutants are sensitive (El-Falaha et al, 1983;Russell & Furr, 1986a,b;Russell et al, 1986;Russell & Chopra, 1996).…”

Section: Antimicrobial Activitymentioning

confidence: 99%

Types of Antimicrobial Agents

Moore¹,

Payne²

Russell, Hugo &Amp; Ayliffe's Principles and Practice of Disinfection, Preservation &Amp; Sterilization

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Introduction 2 Phenols 2.1 Sources of phenols -the coal-tar industry 2.2 Properties of phenolic fractions 2.3 Formulation of coal-tar disinfectants 2.4 The modern range of solubilized and emulsified phenolic disinfectants 2.4.1 Cresol and soap solution British Pharmacopoeia (BP) 1963 (Lysol) 2.4.2 Black fluids 2.4.3 White fluids 2.5 Non-coal-tar phenols 2.5.1 4-Tertiary octylphenol 2.5.2 2-Phenylphenol (2-phenylphenoxide) 2.5.3 4-Hexylresorcinol 2.6 Halo and nitrophenols 2.6.1 2,4,6-Trichlorophenol 2.6.2 Pentachlorophenol (2-phenylphenoxide) 2.6.3 4-Chloro-3-methylphenol (chlorocresol) 2.6.4 4-Chloro-3,5-dimethylphenol (chloroxylenol; para-chloro-metaxylenol; PCMX) 2.6.5 2,4-Dichloro-3,5-dimethylphenol (dichloroxylenol; dichloro-meta-xylenol; DCMX) 2.6.6 4-Chloro-3-methylphenol (para-chlorometa-cresol; PCMC) 2.6.7 Monochloro-2-phenylphenol 2.6.8 2-Benzyl-4-chlorophenol (chlorphen; ortho-benzyl-para-chlorophenol; OBPCP) 2.6.9 Mixed chlorinated xylenols 2.6.10 Other halophenols 2.6.11 Nitrophenols 2.6.12 Formulated disinfectants containing chlorophenols 2.6.13 Phenol 2.7 Pine disinfectants 2.8Theory of solubilized systems 2.9The bisphenols 2.9.1 Derivatives of dihydroxydiphenylmethane 2.9.2 Derivatives of hydroxydiphenylether 2.9.3 Derivatives of diphenylsulphide 3 Organic and inorganic acids: esters and salts 3.1

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Quaternary Ammonium Compounds in Medicinal Chemistry, II

Cited by 19 publications

References 178 publications

Effects of Extended Storage of Chlorhexidine Gluconate and Benzalkonium Chloride Solutions on the Viability of Burkholderia cenocepacia

Effects of Extended Storage of Chlorhexidine Gluconate and Benzalkonium Chloride Solutions on the Viability of Burkholderia cenocepacia

Genomic and Transcriptomic Insights into How Bacteria Withstand High Concentrations of Benzalkonium Chloride Biocides

Types of Antimicrobial Agents

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