Benzalkonium chloride , also known as BZK , BKC , BAC , alkyldimethylbenzylammonium chloride and ADBAC , is a type of cationic surfactant. This is an organic salt classified as a quaternary ammonium compound. It has three main categories of use: as a biocide, cationic surfactant, and as a phase transfer agent. ADBACs are a mixture of alkylbenzyldimethylammonium chlorides, in which the alkyl groups have an even number of long-chain alkyl chains.
Video Benzalkonium chloride
Dissolution and physical properties
Depending on purity, benzalkonium chloride ranges from colorless to pale yellow (not pure). Benzalkonium chloride is easily soluble in ethanol and acetone. Although the dissolution in water is slow, aqueous solutions are more easily handled and preferred. Aqueous solutions should be neutral to slightly alkaline. Foam solution when shaken. The concentrated solution has a bitter taste and smells like faint almonds.
Standard concentrates are produced as 50% and 80% w/w solutions, and sold under trade names such as BC50, BC80, BAC50, BAC80, etc. The 50% solution is purely aqueous, while a more concentrated solution requires incorporation of rheology modifiers (alcohol, polyethylene glycol, etc.) to prevent increased viscosity or gel formation under low temperature conditions.
Maps Benzalkonium chloride
Cationic Surfactant
Benzalkonium chloride also has surfactant properties, dissolving the lipid phase of the tear film and increasing drug penetration, making it a useful excipient.
- Detergent and detergent treatment
- Textile softener
Transfer agent phase
Benzalkonium chloride is a phase-transfer mainstay of catalysis, an important technology in the synthesis of organic compounds, including pharmaceuticals.
Bioactive agents
Especially for their antimicrobial activity, benzalkonium chloride is an active ingredient in many consumer products:
- Pharmaceutical products such as eye drops, ears and nose or sprays, as preservatives
- Personal care products such as hand sanitizer, wet cloth, shampoo, deodorant and cosmetics
- Antiseptic on the skin, such as Bactine and Dettol.
- Throat lozenges and mouthwash, as biocide
- Spermicidal cream
- Over-the-counter single application treatments for herpes, cold-sores, and fever blisters, such as RELEEV and Viroxyn
- Burns and ulcer treatment
- Disinfectant spray for hard surface sanitation
- Cleaners for hard floors and surfaces as disinfectants, such as Lysol
- Algaecides to clean algae, moss, moss from road, tile, swimming pool, rock pairs, etc.
Benzalkonium chloride is also used in many processes and non-consumer products, including as an active ingredient in surgical disinfection. A full list of uses including industrial applications. The advantage of benzalkonium chloride, not shared by antiseptic-based ethanol or antiseptic hydrogen peroxide, is that it does not cause a burning sensation when applied to damaged skin.
Medicine
Benzalkonium chloride is a commonly used preservative in eye drops; typical concentrations ranged from 0.004% to 0.01%. A stronger concentration may cause permanent damage to the corneal endothelium.
Avoid the use of benzalkonium chloride solution while contact lenses are present at the sites discussed in the literature.
Adverse effects
Although historically benzalkonium chloride has been present everywhere as a preservative in the preparation of the eye, its ocular toxicity and irritant properties, in relation to consumer demand, have caused pharmaceutical companies to increase the production of preservative-free preparations, or to replace benzalkonium chloride with less harmful preservatives.
Many mass-marketed inhaler and nasal spray formulations contain benzalkonium chloride as a preservative, although there is substantial evidence that may affect ciliary movement, mucociliary transport, nasal mucosal histology, human neutrophil function, and leukocyte response to localized inflammation. Although some studies have found no correlation between the use of benzalkonium chloride in concentrations at or below 0.1% in nasal sprays and drug-induced rhinitis, others have recommended that benzalkonium chloride in nasal sprays be avoided. In the United States, the free steroidal preparations of benzalkonium chloride include budesonide, triamcinolone acetonide, dexamethasone, and Beconase and Vancenase aerosol inhalers.
Benzalkonium chloride irritates the middle ear tissue at a concentration normally used. Inside ear poisoning has been demonstrated.
Occupational exposure to benzalkonium chloride has been associated with the development of asthma. In 2011, major clinical trials designed to evaluate the efficacy of hand sanitizers based on different active ingredients in preventing viral transmission among schoolboys were redesigned to exclude cleansers based on benzalkonium chloride due to safety concerns.
Benzalkonium chloride has been used commonly as a pharmaceutical and antimicrobial preservative since the 1940s. While preliminary studies confirm the corrosive and irritating properties of benzalkonium chloride, investigation of the adverse effects of, and disease-related status, benzalkonium chloride has only emerged over the past 30 years.
Benzalkonium chloride is classified as an antiseptic active substance Category III by the US Food and Drug Administration. Materials are categorized as Category III when "available data are insufficient to classify as safe and effective, and further testing is required". Benzalkonium chloride is removed from the United States today. The Food and Drug Administration reviews the safety and effectiveness of consumer antiseptics and top-the-counter antimicrobial drug products, which means will remain Category 3 ingredients. There is recognition that more data on their safety, efficacy and effectiveness is needed, especially with regard to:
- The study of human pharmacokinetics, including information about its metabolites
- The study of the absorption, distribution, metabolism, and excretion of animals
- Data to help determine the effect of formulation on skin absorption
- Carcinogenicity
- The study of developmental and reproductive toxicity
- Potential of hormonal effects
- Assessment of potential development of bacterial resistance
Toxicology
RTECS lists the following acute toxicity data:
Benzalkonium chloride is a human skin and severe eye irritation. These are toxic, immunotoxic, gastrointestinal and neurotoxic toxins.
The formulation of Benzalkonium chloride for consumer use is a dilute solution. The concentrated solution is toxic to humans, causing corrosion/irritation of the skin and mucosa, and death if taken internally in sufficient volume. 0.1% is the maximum concentration of benzalkonium chloride which does not produce primary irritation on whole skin or acts as a sensitizer.
Poisoning by benzalkonium chloride is recognized in the literature. A 2014 case study detailing fatal swallow up to 8.1 oz (240 ml) of 10% benzalkonium chloride in 78-year-old men also included a summary of case reports currently published from benzalkonium chloride. While most cases are caused by confusion about container contents, one case mentions the pharmaceutical incorrect decomposition of benzalkonium chloride as the cause of the poisoning of two infants.
Domestic domestic benzalkonium chloride poisoning has been recognized as a result of direct contact with surfaces that are cleaned with disinfectant utilizing benzalkonium chloride as the active ingredient.
Biological activity
The largest biocidal activity is associated with C12 dodecyl & amp; C14 alkyl myristyl derivative. The bactericidal/microbicide action mechanism is thought to be due to intermolecular interaction interactions. This may cause dissociation of cell membrane lipid bilayers, which interfere with the control of cellular permeability and cause leakage of cellular content. Other biomolecular complexes in bacterial cells may also dissociate. Enzymes, which control subtly various respiratory and metabolic cellular activities, are particularly susceptible to deactivation. Critical intermolecular interactions and tertiary structures in very specific biochemical systems can be easily disrupted by cationic surfactants.
Benzalkonium chloride solution is a fast-acting biocidal agent with a long duration of action. They are active against bacteria and some viruses, fungi, and protozoa. Bacterial spores are considered resistant. The solution is bacteriostatic or bactericidal in accordance with its concentration. Gram-positive bacteria are generally more susceptible than gram-negative bacteria. Activity is not significantly affected by pH, but increases substantially at higher temperatures and longer exposure times.
In a 1998 study using the FDA protocol, a non-alcoholic cleanser with benzalkonium chloride as an active ingredient complied with FDA performance standards, while Purell, a popular alcohol-based cleanser, did not. The study, conducted and reported by leading US developers, manufacturers and marketers of topical antimicrobial drugs based on quaternary ammonium compounds, found that their benzalkonium chloride-based cleansers performed better than alcohol-based hand cleaners after repeated use.
Advances in the quality and efficacy of benzalkonium chloride in non-alcoholic hand cleaners have now addressed CDC concerns about gram-negative bacteria, with the same leading product if not more effective against gram-negative, especially New Delhi metallo-beta-lactamase 1 and antibiotic-resistant bacteria others.
The new formulations using benzalkonium mixed with various quaternary ammonium derivatives can be used to expand the biocidal spectrum and improve the efficacy of benzalkonium based disinfection products. Formulation techniques have been used to great effect in increasing the viral activity of quaternary ammonium-based disinfectants such as Virucide 100 for the danger of typical health infections such as hepatitis and HIV. Proper use of excipients can also greatly improve spectra, performance and detergency, and prevent deactivation under conditions of use. The formulation can also help minimize deactivation of benzalkonium solution in the presence of organic and inorganic contamination.
Degradation
Benzalkonium chloride degradation follows consecutive debenzylation, dealkylation, and demethylation steps resulting in benzyl chloride, alkyl dimethyl amine, dimethyl amine, long chain alkane, and ammonia. The intermediate, main, and minor products can then be split into CO 2 , H 2 O, NH 3 , and Cl - . The first step for BAC biodegradation is the fission or separation of the alkyl chain from quaternized nitrogen as shown in the diagram. This is done by abstracting hydrogen from the alkyl chain by using a hydroxyl radical that leads to a carbon-centered radical. It produces benzyl dimethyl amine as the first intermediate and dodecanal as the main product. From here, benzyl dimethyl amine can be oxidized to benzoic acid using the Fenton process. The trimethyl group of amines in dimethylbenzylamine can be split to form a benzyl which can be further oxidized to benzoic acid. Benzoic acid uses hydroxylation (addition of hydroxyl groups) to form p-hydroxybenzoic acid. Benzyldimethylamine can then be converted to ammonia by performing double demethylation, which removes both methyl groups, followed by debenzylation, removing benzyl groups using hydrogenation. The diagram shows the suggested pathway of BAC biodegradation for both hydrophobic and hydrophilic areas of the surfactant. Because Stearalkonium chloride is a type of BAC, the biodegradation process must occur in the same way.
Rule
In September 2016, the FDA announced a ban of nineteen ingredients in consumer antibacterial soaps for reasons of lack of evidence of safety and effectiveness. The ban of three additional ingredients, including benzalkonium chloride, is suspended to allow ongoing research to be completed.
See also
- Stearalkonium chloride
- Polyaminopropyl biguanide, alternative preservatives for contact lens solutions
- Ethylenediaminetetraacetic acid
- Triclosan
- Thiomersal
References
Further reading
- Rieger, M M (1997). "Potential Skin Irritation Quaternary" (PDF) . Soc. Cosmet. Chem . 48 : 307-317. Archived from the original (PDF) in 2014-12-07.
- Thorup I: Evaluation of health hazards with exposure to ammonium compounds Quaternary, Institute of Food Safety and Toxicology, Danish Food and Food Administration, http://www2.mst.dk/common/Udgivramme/Frame.asp?http://www2.mst.dk/udgiv/publications/2000/87-7944-210-2/html/kap04_eng.htm
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Verret, DJ; Marple, BF. (Feb 2005). "Effect of nasal topical nasal steroids on nasal mucosa and cilia function". Curr Opin Otolaryngol Head Neck Surg . 13 (1): 14-8. doi: 10.1097/00020840-200502000-00005. PMIDÃ, 15654209.
External links
- International Program on Chemical Safety, International Chemical Safety Card (ICSC) - Benzalkonium Chloride
- National Institute for Occupational Safety and Health (NIOSH), International Chemical Safety Card (ICSC) - Benzalkonium Chloride
- International Program on Chemical Security, Monographic Information Poison (PIM) - Benzalkonium Chloride
- Details Category Haz-Map - Benzalkonium Chloride
- ToxNet Human Safety Database - Benzalkonium Chloride Compound
- Recognition and Management of Pesticide Poisoning, US Environmental Protection Agency, Office of Pesticides Program, Sixth Edition, 2013
- CDC Healthcare Infection Control Management Advisory Committee (HICPAC), Guidelines for Disinfection and Sterilization at Health Care Facilities, 2008
- Santa Cruz Biotechnology, Inc. MSDS
- Spectrum Labs "Clear Bath" Algae Inhibitor MSDS
- NDS Chemicals MSDS
- TCI America MSDS
- Sciencelab.com, Inc. MSDS
- Copy Nose Sprays - Additives Possible Problem
Source of the article : Wikipedia
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