Triclosan

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Not to be confused with triclocarban.
Triclosan
Triclosan.svg
Triclosan-3D-vdW.png
Identifiers
CAS number 3380-34-5 YesY
PubChem 5564
ChemSpider 5363 YesY
UNII 4NM5039Y5X YesY
DrugBank DB08604
KEGG D06226 YesY
ChEBI CHEBI:164200 YesY
ChEMBL CHEMBL849 YesY
ATC code D08AE04,
D09AA06 (medicated dressing)
Jmol-3D images Image 1
Properties
Molecular formula C12H7Cl3O2
Molar mass 289.54 g mol−1
Appearance White solid
Density 1.49 g/cm3
Melting point 55-57 °C
Boiling point 120 °C (248 °F; 393 K)
Hazards
MSDS MSDS
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 162.2 °C (324.0 °F; 435.3 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

Triclosan, similar in its uses and mechanism of action to triclocarban, is an antibacterial and antifungal agent found in consumer products, including soaps, detergents, toys and surgical cleaning treatments. Its efficacy as an antimicrobial agent and the risk of bacterial resistance remains controversial. Additional research seeks to understand its potential effects on organisms and environmental health.

Uses[edit]

Triclosan was used as a hospital scrub in the 1970s. Since then, it has expanded commercially and is now prevalent in soaps (0.10-1.00%), shampoos, deodorants, toothpastes, mouth washes and cleaning supplies.[1] It is part of consumer products, including kitchen utensils, toys, bedding, socks and trash bags.[2][3]

In healthcare, triclosan is used in surgical scrubs and hand washes.[4] Use in surgical units is effective with a minimum contact time of approximately two minutes.[5][6] More recently, showering with 2% triclosan has become a recommended regimen in surgical units for the decolonization of patients whose skin carries methicillin-resistant Staphylococcus aureus (MRSA).[7]

Triclosan has been employed as an selective agent in molecular cloning. A bacterial host transformed by a plasmid harboring a triclosan resistant mutant FabI gene (mFabI) as a selectable marker can grow in presence of high dose of triclosan in growth media.[8]

Chemical structure and properties[edit]

This organic compound is a white powdered solid with a slight aromatic, phenolic odor. Categorized as a polychloro phenoxy phenol, triclosan is a chlorinated aromatic compound that has functional groups representative of both ethers and phenols. Phenols often demonstrate antibacterial properties. Triclosan is soluble in ethanol, methanol, diethyl ether, and strongly basic solutions such as a 1M sodium hydroxide solution, but only slightly soluble in water. Triclosan can be synthesized from 2,4-dichlorophenol.

Common impurities include 2,4-dichlorophenol, 3-chlorophenol, 4-chlorophenol, 2,3,7,8-tetrachlorodibenzo-p-dioxin, 2,3,7,8-tetrachlorodibenzo-p-furan, 2,8-dichlorobenzo-furan, 2,8-dichlorobenzo-p-dioxin, 1,3,7-trichlorodibenzo-p-dioxin, and 2,4,8-trichlorodibenzo-furan.[9]

Synthesis[edit]

Under a reflux process, 2,4,4'-trichloro-2'-methoxydiphenyl ether is treated with aluminium chloride.[10]

Triclosan can be synthesized through a three-step process starting with 1-(2-hydroxyethyl)pyrrolidin-2-one. The 1-(2-hydroxyethyl)pyrrolidin-2-one is dehydrated with either zinc or calcium oxide into 1-vinylpyrrolidin-2-one.[11] Then, 1-vinylpyrrolidin-2-one can be reacted with 5-chloro-2-(2,4-dichlorophenoxy)phenyl acrylate in n-heptane to form triclosan.[12]

Mechanism of action[edit]

At high concentrations, triclosan acts as a biocide with multiple cytoplasmic and membrane targets.[13] However, at the lower concentrations seen in commercial products, triclosan appears bacteriostatic, and it is seen to target bacteria primarily by inhibiting fatty acid synthesis.

Triclosan binds to bacterial ENR (enoyl-acyl carrier protein reductase enzyme), which is encoded by the gene FabI. This binding increases the enzyme's affinity for NAD+ (nicotinamide adenine dinucleotide). This results in the formation of a stable, ternary complex of ENR-NAD+-triclosan, which is unable to participate in fatty acid synthesis. Fatty acids are necessary for building and reproducing cell membranes. Humans do not have an ENR enzyme and thus are not affected.

Effectiveness[edit]

Some studies show that antimicrobial hand soaps containing triclosan provide a slightly greater bacterial reduction on the hands compared to plain soap, but other studies show no difference.[14] In addition, researchers at Dial found that the transfer of bacteria to objects was reduced following washing with antimicrobial hand soap containing triclosan compared to regular soap.[15] According to the FDA, antimicrobial soaps containing triclosan have not been shown to possess additional benefits over conventional soap and water.[16]

Health concerns[edit]

Triclosan is a chlorinated aromatic compound with antibacterial, antifungal and antiviral properties (sold under several trade names, including UltraFresh, Amicor, and BioFresh). Triclosan penetrates the skin on contact and enters the bloodstream.[17] According to the United States Food and Drug Administration (FDA) no evidence indicates that triclosan in personal care products provides extra benefits to health beyond its anti-gingivitis effect in toothpaste.[18] Triclosan safety is under review by the FDA[18] and Health Canada.[19] A systematic review of randomized controlled trials found that triclosan-containing toothpastes are marginally beneficial in reduction of tooth cavities and reduce dental plaque, gingival inflammation and gingival bleeding.[20]

Allergy[edit]

A 2010 study found that children who had higher exposure to triclosan had a higher incidence of hay fever.[21] Triclosan has also been associated with a higher risk of food allergy.[22] This may be because exposure to bacteria reduces allergies, as predicted by the hygiene hypothesis and not toxicology of the triclosan itself. This would also occur with chlorhexidine gluconate and PCMX, among other antibacterial agents.[21][23] Other studies have linked triclosan to allergic contact dermatitis in some individuals.[24][25]

By-products[edit]

In August 2009, the Canadian Medical Association asked the Canadian government to ban triclosan use in household products over concerns of creating bacterial resistance and producing dangerous side products (chloroform).[26]

Triclosan can react with the free chlorine in tap water to produce lesser amounts of other compounds, such as 2,4-dichlorophenol.[27] Most of these intermediates convert into dioxins upon exposure to UV radiation (from the sun or other sources). Although only small amounts of dioxins are produced, some dioxins are extremely toxic and are very potent endocrine disruptors. They are also chemically stable, so that they are eliminated from the body slowly (they can bioaccumulate to dangerous levels), and they persist in the environment.[28] The dioxins that can form from triclosan are not considered to be congeners of toxicologic concern for mammals, birds and fish.[29][30]

The United States Pharmacopeia formulary has published a monograph for triclosan that sets purity standards (>97%).[31]

The American Dental Association published a response to the concerns stemming from a Virginia Tech study stating that the study is not relevant to toothpaste.[27][32]

Environment[edit]

Triclosan is toxic to aquatic bacteria at levels found in the environment. Triclosan inhibits photosynthesis in diatom algae, which are responsible for a large part of the photosynthesis on Earth.[33]

Endocrine disruption[edit]

Triclosan has been associated with lower levels of thyroid hormone and testosterone. Specifically, triclosan decreases circulating levels of thyroxine hormone (T4) by increasing glucuronidase enzyme activity, which catabolizes T4 and other thyroid hormones.[34] This may lead to altered behavior, learning disabilities and/or infertility. Very low doses of triclosan have been shown to act as an estrogen mimic and increase proliferation rates of breast cancer tumors.[35] It may also chemically mimic thyroid hormone and bind to the hormone receptor sites, blocking them, so that normal hormones cannot be used. A study between 2003 and 2006 concluded that triclosan (as an endocrine disruptor) affects the immune system.[21] Another study in 2000 offered the result that low amounts of triclosan can be absorbed through skin and can enter the bloodstream.[36]

Triclosan has been found both in the bile of fish living downstream from wastewater processing facilities and in human milk.[37] The adverse effects of triclosan on the environment and its questionable benefits in toothpastes[38] have led the Swedish Naturskyddsföreningen (sv) to recommend avoiding triclosan in toothpaste.[39] Another 2009 study demonstrated that triclosan exposure significantly impacts thyroid hormone concentrations in male juvenile rats.[40] However, a four-year study of possible effects of triclosan (0.3%) in toothpaste on thyroid hormone function found no effect of triclosan on thyroid hormone concentration in sera of adult human subjects. [41]

Muscle contraction[edit]

Triclosan has been reported to impair excitation-contraction coupling in cardiac and skeletal muscle function in mice.[42]

Environmental concerns[edit]

Treatment and disposal[edit]

The duration of triclosan in personal product use is relatively short. Upon disposal, triclosan is sent to municipal wastewater treatment plants, where about 97-98% of triclosan is removed.[43] Studies show that substantial quantities of triclosan (170,000 – 970,000 kg/yr) can break through wastewater treatment plants and damage algae on surface waters.[43] In a study on effluent from wastewater treatment facilities, approximately 75% of triclocarban was present in sludge.[44] This poses a potential environmental and ecological hazard, particularly for aquatic systems. The volume of triclosan re-entering the environment in sewage sludge after initial successful capture from wastewater is 44,000 ± 60,000 kg/yr.[43] Triclosan can attach to other substances suspended in aquatic environments, which potentially endangers marine organisms and may lead to further bioaccumulation.[45] Ozone is considered to be an effective tool for removing triclosan during sewage treatment. As little triclosan is released through plastic and textile household consumer products, these are not considered to be major sources of triclosan contamination.[45]

During wastewater treatment, a portion of triclosan is degraded, while the remaining adsorbs to sewage sludge or exits the plant as effluent.[46][47] In the environment, triclosan may be degraded by microorganisms or react with sunlight, forming other compounds, which include between 3 and 12% of chlorophenols and dioxins (In particular, 2,8-dichlorodibenzo-p-dioxin[48] (2,8-DCDD) and 2,4-dichlorophenol (2,4-DCP) are produced. Both also are photolabile and, thus, are intermediates). As a result, triclosan was the target of a UK cancer alert, even though the study showed that the amount of chloroform generated was less than amounts often present in chlorinated drinking water.

Bioaccumulation[edit]

While studies using semi-permeable membrane devices have found that triclosan does not strongly bioaccumulate, methyl-triclosan is comparatively more stable and lipophilic and thus poses a higher risk of bioaccumulation. The ability of triclosan to bioaccumulate is affected by its ionization state in different environmental conditions. At a higher pH, triclosan is expected to bioaccumulate more significantly, while at a lower pH, methyl-triclosan is much more likely to bioaccumulate.[49] Analysis of human autopsies have shown that triclosan can bioaccumulate in the liver and adipose tissues, but not in brain tissues.[35]

Ecotoxicity[edit]

Triclosan and triclocarban (TCC) could have adverse repercussions on agriculture. Studies have indicated that TCC and TCS are absorbed through shoot systems in vegetables, at higher levels in roots than in tubers. While the levels of TCC and TCS in vegetables are largely insufficient to cause major health damage, the levels of these chemicals are higher than in the drinking water supply.[50] Crops shown to take up antimicrobials from soil include barley, meadow fescue, carrots and pinto beans. Triclosan may also affect animal wildlife behavior.[51] For example, TCS and TCC are 100-1,000 times more effective in inhibiting and killing algae, crustaceans and fish than they are in killing microbes. TCS have been observed in multiple organisms, including algae aquatic blackworms, fish and dolphins. Earth dwelling species include earth worms, and species higher up the food chain.[43]

Resistance concerns[edit]

Stuart Levy [52] warned that triclosan's overuse could cause resistant strains of bacteria to develop, in much the same way that antibiotic-resistant bacterial strains are emerging. In 2003 some UK supermarkets and other retailers were considering phasing out products containing triclosan.[53]

While Levy's laboratory method was not effective in predicting bacterial resistance for biocides like triclosan, triclosan does reduce species diversity, eradicate efficient TCS degrader species and manipulate ecological relations.[54] At least seven peer-reviewed and published studies have demonstrated that triclosan is not significantly associated with bacterial resistance over the short term, including one study coauthored by Levy.[55]

Other studies have shown that some bacterial species can develop low-level resistance to triclosan at its lower bacteriostatic concentrations because of FabI mutations, which produce a decrease of triclosan's effect on ENR-NAD+ binding, as shown in Escherichia coli and Staphylococcus aureus.[56][57] Another way for these bacteria to gain low-level resistance to triclosan is to overexpress FabI.[58] Some bacteria have innate resistance to triclosan at low, bacteriostatic levels, such as Pseudomonas aeruginosa, which possesses multi-drug efflux pumps that "pump" triclosan out of the cell.[59] Other bacteria, such as some of the Bacillus genus, have alternative FabI genes (FabK) to which triclosan does not bind and hence are less susceptible.

A larger concern pertains to the potential for cross-resistance or co-resistance to other antimicrobials. Even if short term resistance does not develop, many believe that a larger issue is that superbugs will evolve against which no bactericide can be used. Studies investigating this possibility have been limited.[60]

The European Commission Scientific Committee on Consumer Safety (SCCS) concludes that to date, no evidence that exists using triclosan leads to an increase in antibiotic resistance. However, it is difficult to say that triclosan exposure never leads to microbial resistance, as there is too much conflicting information to make a full risk analysis.[61]

Alternatives[edit]

A comprehensive analysis from the University of Michigan School of Public Health indicated that plain soaps are just as effective as consumer-grade antibacterial soaps with triclosan in preventing illness and removing bacteria from the hands.[62]

Nonorganic antibiotics and organic biocides are effective alternatives to triclosan, such as silver and copper ions and nanoparticles.[63]

Policy[edit]

The U.S. Food and Drug Administration, the Environmental Protection Agency, and the European Union[dubious ] are regulatory bodies for triclosan. In the United States, manufacturers of products containing triclosan must indicate its presence on the label. In Europe, triclosan is regulated as a cosmetic preservative and must be listed on the label.[64] The authorization of the inclusion of triclosan as an additive for plastic production for use in food packages is a legally contentious issue, as noted in the Microban International and Microban (Europe) v Commission case.[65]

In light of the health concerns, the FDA in the 1970s reviewed the safety of triclocarban and triclosan, but took no regulatory action. In 2010, the Natural Resources Defense Council forced the FDA to review triclosan after suing them for their inaction. Since the FDA prohibited hexachlorophene,a compound similar to triclosan, Halden and others argued the FDA should also ban triclosan.[43]

On May 16, 2014, Minnesota governor Mark Dayton signed a bill banning the use of triclosan in most retail consumer hygiene products sold in the state. The ban is set to take effect January 1, 2017.[66]

Current and future research[edit]

The future of TCC is unknown, but scientists are searching for more sustainable antimicrobials that maintain their antibacterial properties while also being minimally toxic to the environment, humans, and wildlife. This entails low degrees of bioaccumulation and rapid, clean biodegredation in existing wastewater treatment facilities. A lowered potential or no potential for resistance is also preferable.[67] These next generation chemicals should aim to act on a broad spectrum of microbes and pathogens while also being minimally toxic and bioaccumulating in non-target species.

Synthesis of these compounds could be improved upon by finding renewable sources for their production that lack occupational hazards.[67] Research regarding the sustainability of chemical production is currently being used to help formulate green pharmaceuticals. These same principles may be applied to the development of improved antimicrobials.[67] Development in this area would benefit both people and the environment.[67]

See also[edit]

References[edit]

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Further reading[edit]

  • Toxicological Sciences, 2009, 107 (1): 56-64, "The Effects of Triclosan on Puberty and Thyroid Hormones in Male Wistar Rats"
  • Reproductive Toxicology, Apr 2009, 27(2):177-185, "Alteration of testicular steroidogenesis and histopathology of reproductive system in male rats treated with triclosan"

External links[edit]