Triclosan

From Wikipedia, the free encyclopedia
Triclosan
IUPAC name

5-chloro-2-(2,4-dichlorophenoxy)phenol

Other names

2,4,4'-trichloro-2'-hydroxydiphenyl ether, 5-chloro-(2,4-dichlorophenoxy)phenol, trichloro-2'-hydroxydiphenyl ether, CH-3565, Lexol 300, Irgasan DP 300

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
1
2
0
Flash point 162.2 °C; 324.0 °F; 435.3 K
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Triclosan is an antibacterial and antifungal agent. It is a polychloro phenoxy phenol.

Though many consumer products contain triclosan, according to the Food and Drug Administration (FDA) at the present time, there is no evidence that triclosan in personal care products provides an extra benefit to health beyond its anti-gingivitis effect in toothpaste.[1] The FDA does not recommend changing consumer use of triclosan-containing products one way or the other due to insufficient safety evidence.[1] Studies by the Environmental Protection Agency (EPA) found triclosan to be an effective antibacterial.[2] Triclosan safety is currently under review by the FDA[1] and Health Canada.[3]A systematic review of randomized controlled trials found that Triclosan-containing toothpastes are marginally beneficial in reduction of tooth caries and reduces plaque,gingival inflammation and gingival bleeding.[4]

Chemical structure and properties

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

Some common impurities are: 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[5]

Synthesis

2,4,4'-trichloro-2'-methoxydiphenyl ether is treated with aluminium chloride in benzene under reflux.[citation needed]

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 to be dehydrated with either zinc or calcium oxide into 1-vinylpyrrolidin-2-one.[6] Then, 1-vinylpyrrolidin-2-one can be reacted with 5-chloro-2-(2,4-dichlorophenoxy)phenyl acrylate in n-heptane to form triclosan.[7]

Reactions

It can be used to produce 2-(2,4-dichloro-phenoxy)-4,5-dichloro-phenol at 20 °C with the reagent sulfuryl chloride.

Uses

Triclosan has been used since 1972, and it is present in soaps (0.10-1.00%), shampoos, deodorants, toothpastes, mouth washes, and cleaning supplies,[8] and is incorporated into an increasing number of consumer products, such as kitchen utensils, toys, bedding, socks, and trash bags.[9][10] It is also found in health care settings in surgical scrubs and personnel hand washes.[11] Triclosan has been shown to be effective in reducing and controlling bacterial contamination on the hands and on treated products. More recently, showering or bathing with 2% triclosan has become a recommended regimen in surgical units for the decolonization of patients whose skin is carrying methicillin-resistant Staphylococcus aureus (MRSA)[12] following the successful control of MRSA outbreaks in several clinical settings. Use in surgical units is effective with a minimum contact time of approximately 2 minutes.[13][14]

Antimicrobial hand soaps including those containing triclosan have been shown to provide a significantly greater bacterial reduction on the hands compared to plain soap.[15] In addition, the transfer of bacteria to objects was significantly reduced following washing with antimicrobial hand soap containing triclosan compared to plain soap.[16]

Triclosan is regulated by the U.S. Food and Drug Administration, the Environmental Protection Agency, and the European Union. During wastewater treatment, a portion of triclosan is degraded, while the remaining adsorbs to sewage sludge or exits the plant in wastewater effluent.[17][18] 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 dioxin (In particular, 2,8-dichlorodibenzo-p-dioxin[19] (2,8-DCDD) and 2,4-dichlorophenol (2,4-DCP) are produced. Both also are photolabile and, thus, are intermediates.), or it may adsorb to particles that settle out of the water column and form sediment.[17][20] Triclosan has been found in Greifensee sediment that was over 30 years old, suggesting that triclosan is degraded or removed slowly in sediment.[17]

The use of triclosan as an additive for plastic production for use in food packages has not been approved by the European Commission (EC).[21] Triclosan is used in a variety of common household products, including soaps, mouthwashes, dish detergents, toothpastes, deodorants, and hand sanitizers.[22] In the United States, manufacturers of products containing triclosan must indicate it on the label. The ingredient is regulated as a cosmetic preservative within Europe and in accordance with the European Cosmetic Regulation all cosmetic ingredients have to be listed on the label.[23]

Triclosan also has been employed as an effective selective agent in molecular cloning. Bacteria host transformed by plasmids harboring a triclosan resistant mutant FabI gene (mFabI) as a selectable marker can grow in presence of high dose of triclosan in the culture media.[24]

Mechanism of action

At in-use concentrations, triclosan acts as a biocide, with multiple cytoplasmic and membrane targets.[25] At lower concentrations, however, triclosan appears bacteriostatic and is seen to target bacteria mainly by inhibiting fatty acid synthesis. Triclosan binds to bacterial enoyl-acyl carrier protein reductase enzyme (ENR), which is encoded by the gene FabI. This binding increases the enzyme's affinity for nicotinamide adenine dinucleotide (NAD+). 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 reproducing and building cell membranes. Humans do not have an ENR enzyme, and thus are not affected. Some bacterial species can develop low-level resistance to triclosan at its lower bacteriostatic concentrations because of FabI mutations, which results in a decrease of triclosan's effect on ENR-NAD+ binding, as shown in Escherichia coli and Staphylococcus aureus.[26][27] Another way for these bacteria to gain low-level resistance to triclosan is to overexpress FabI.[28] 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.[29] 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.

Formation of dioxin in surface water

The use of triclosan in household antibacterial products introduces triclosan to surface waters where it can degrade to a non-toxic[30] type of dioxin. The dioxin-like compound that formed when triclosan degraded in sunlight and wastewater chlorine treatment were analyzed in sediment cores by University of Minnesota researchers.[31] The US EPA and World Health Organization has recognized that dioxins formed from triclosan are not considered to be those congeners of toxicologic concern for mammals, birds, and fish.[32][33]

Resistance concerns

An article coauthored by Stuart Levy in the August 6, 1998 issue of Nature[34] 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, the Scottish Sunday Herald newspaper reported that some UK supermarkets and other retailers were considering phasing out products containing triclosan.[35]

It has since been shown that while the laboratory method used by Levy was not effective in predicting bacterial resistance for biocides like triclosan, triclosan does reduce species diversity, kills off efficient TCS degrader species (see citation's Table 4), and that it should be considered that "degradation of an ecosystem may rearrange the competitive hierarchy".[36] At least seven peer-reviewed and published studies have been conducted demonstrating that triclosan is not significantly associated with bacterial resistance over the short term, including one study coauthored by Levy.[37] However, the major concern over resistant strains is not that they will alter resistance profiles over the short term. The concern is that superbugs will evolve against which no bactericide can be used. For example, as noted above, triclosan is effective against MRSA. However, overuse of triclosan could lead to MRSA that is also triclosan-resistant.[citation needed]

Some level of triclosan resistance can occur in some microorganisms, but the larger concern is with the potential for cross-resistance or co-resistance to other antimicrobials. Studies investigating this possibility have been limited.[38] The European Commission Scientific Committee on Consumer Safety (SCCS) concludes that to date, there is no evidence that using triclosan leads to an increase in antibiotic resistance. However it is too early to say that triclosan exposure never leads to microbial resistance, as there is not yet enough information to make a full risk analysis.[39]

Health concerns

Triclosan is a chlorinated aromatic compound with antibacterial, antifungal and antiviral properties (sold under several trade names, including UltraFresh, Amicor, and BioFresh). Triclosan is also a component in some pesticides, mattresses, insulation, and underlayments that install under various types of flooring, including laminate, wood, glued down, and engineered wood, and carpeting for the purpose of slowing or stopping the growth of bacteria, fungi, and mildew. For example, some high density sound-suppressing underlayments, foam floor underlayments and rebond carpet pads are treated with triclosan. Triclosan penetrates the skin on contact and enters the bloodstream.[40] The EPA concluded that total exposure to triclosan did not present risks of concern for human health, including allergy, cancer, reproductive, endocrine and neurotoxic effects.[41]

Allergy

A 2010 study found that children who had higher exposure to triclosan had a higher incidence of hay fever.[42] Triclosan has also been associated with a higher risk of food allergy.[43] 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.[42][44] Other studies have linked triclosan to allergic contact dermatitis in some individuals.[45][46] The EPA concluded in its 2008 report that triclosan does not present allergy risks.[41]

By-products

In August 2009, the Canadian Medical Association asked the Canadian government to ban triclosan use in household products under concerns of creating bacterial resistance and producing dangerous side products (chloroform).[47]

Triclosan can also react with the free chlorine in tap water to produce lesser amounts of other compounds, like 2,4-dichlorophenol.[48] Most of these intermediates convert into dioxins upon exposure to UV radiation (from the sun or other sources). Although 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 for a long time.[49] The dioxins which can be formed from triclosan are not considered to be those congeners of toxicologic concern for mammals, birds, and fish[32][33]

Triclosan is chemically somewhat similar to the dioxin class of compounds. Its production leads to small amounts of residual polychlorinated dioxins, and polychlorinated furans in the products that are produced with it.[citation needed]The United States Pharmacopeia has established a monograph for triclosan that sets purity standards (>97%).[50]

The American Dental Association published a response to the concerns stemming from the Virginia Tech study stating that the study is not relevant to toothpaste.[48][51]

Environment

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.[52]

Endocrine disruption

A 2006 study concluded that low doses of triclosan act as an endocrine disruptor in the North American bullfrog.[53] The hypothesis proposed is that triclosan blocks the metabolism of thyroid hormone because it chemically mimics thyroid hormone and binds 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 and showed a positive association with allergy or hay fever diagnosis.[54] Another study in 2000 offered the result that low amount of triclosan can be absorbed through skin and can enter the bloodstream.[55]

Triclosan has also been found in both the bile of fish living downstream from waste-water-processing plants and in human milk.[56] The negative effects of triclosan on the environment and its questionable benefits in toothpastes[57] have led to the Swedish Naturskyddsföreningen to recommend not using triclosan in toothpaste.[58] Another 2009 study demonstrated that triclosan exposure significantly impacts thyroid hormone concentrations in the male juvenile rats.[59]

Triclosan is also showing up in dolphins near South Carolina and Florida in concentrations known to disrupt hormones, growth, and development in other animals.[60]

However, a 4-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. [61]

Muscle contraction

Triclosan has been reported to impair excitation-contraction coupling in cardiac and skeletal muscle function in mice.[62]

Possible breakdown into carcinogenic metabolite

Two reports by the same authors suggest that triclosan can combine with chlorine in tap water to form chloroform,[47] which the United States Environmental Protection Agency classifies as a probable human carcinogen, meaning it likely causes cancer. These intermediates can be cleaved to form chlorophenols that can react with free chlorine to form trihalomethanes, such as chloroform.[63] 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.

Alternatives

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.[64]

Nonorganic antibiotics and organic biocides are effective alternatives to triclosan, such as silver and copper ions and nanoparticles.[65]

See also

References

  1. ↑ 1.0 1.1 1.2 "Triclosan: What Consumers Should Know". U S Food and Drug Administration. 8 April 2010. Retrieved 13 April 2010. 
  2. ↑ http://www.epa.gov/oppsrrd1/REDs/factsheets/triclosan_fs.htm[]
  3. ↑ "Toxic chemical monitoring program gets $500M". CBC. 4 October 2011. 
  4. ↑ Philip Riley and Thomas Lamont. (2013). "Triclosan/copolymer containing toothpastes for oral health.". Cochrane Database of Systematic Reviews 12. doi:10.1002/14651858.CD010514.pub2. 
  5. ↑ Triclosan and its impurities - Quantex Labs www.quantexlabs.com/Portals/159220/docs/triclosan-impurities.pdf
  6. ↑ Kahn, A.P. Production of N-Vinyl Pyrrolidone. US Patent 63970, Apr 1, 2004.
  7. ↑ Plochocka, K. Polymeric Delivery and Release Systems for Oral Care Actives. US Patent 6,315,987, Nov 13, 2001.
  8. ↑ Thompson A, Griffin P, Stuetz R, Cartmell E (2005). "The fate and removal of triclosan during wastewater treatment". Water Environ. Res. 77 (1): 63–7. doi:10.2175/106143005X41636. JSTOR 25045839. PMID 15765937. 
  9. ↑ Record in the Household Products Database of NLM
  10. ↑ Crinnion, WJ; Griffin, P.; Stuetz, R.; Cartmell, E. (2005). "The CDC Fourth National Report on Human Exposure to Environmental Chemicals: what it Tells Us about our Toxic Burden and How it Assists Environmental Medicine Physicians". Water Environ. Res. 77 (1): 63–7. doi:10.2175/106143005X41636. JSTOR 25045839. PMID 15765937. 
  11. ↑ Food and Drug Administration (17 June 1994). "Federal Register Notice: Tentative Final Monograph for OTC Healthcare Antiseptic Drug Products - June 17, 1994". 
  12. ↑ Coia JE, Duckworth GJ, Edwards DI, et al. (May 2006). "Guidelines for the control and prevention of meticillin-resistant Staphylococcus aureus (MRSA) in healthcare facilities". J. Hosp. Infect. 63 Suppl 1: S1–44. doi:10.1016/j.jhin.2006.01.001. PMID 16581155. 
  13. ↑ Brady LM, Thomson M, Palmer MA, Harkness JL (March 1990). "Successful control of endemic MRSA in a cardiothoracic surgical unit". Med. J. Aust. 152 (5): 240–5. PMID 2255283. 
  14. ↑ Zafar AB, Butler RC, Reese DJ, Gaydos LA, Mennonna PA (June 1995). "Use of 0.3% triclosan (Bacti-Stat) to eradicate an outbreak of methicillin-resistant Staphylococcus aureus in a neonatal nursery". Am J Infect Control 23 (3): 200–8. doi:10.1016/0196-6553(95)90042-X. PMID 7677266. 
  15. ↑ Montville, Rebecca; Schaffner, Donald W. (1 November 2011). "A Meta-Analysis of the Published Literature on the Effectiveness of Antimicrobial Soaps". Journal of Food Protection 74 (11): 1875–1882. doi:10.4315/0362-028X.JFP-11-122. PMID 22054188. 
  16. ↑ Fuls, Janice L.; Rodgers ND, et al. (April 2008). "Alternative Hand Contamination Technique To Compare the Activities of Antimicrobial and Nonantimicrobial Soaps under Different Test Conditions". Applied and Environmental Microbiology 74 (12): 3739–3744. doi:10.1128/AEM.02405-07. PMC 2446551. PMID 18441107. 
  17. ↑ 17.0 17.1 17.2 Singer H, Müller S, Tixier C, Pillonel L (December 2002). "Triclosan: occurrence and fate of a widely used biocide in the aquatic environment: field measurements in wastewater treatment plants, surface waters, and lake sediments". Environ. Sci. Technol. 36 (23): 4998–5004. Bibcode:2002EnST...36.4998S. doi:10.1021/es025750i. PMID 12523412. 
  18. ↑ Heidler J, Halden RU (January 2007). "Mass balance assessment of triclosan removal during conventional sewage treatment". Chemosphere 66 (2): 362–9. doi:10.1016/j.chemosphere.2006.04.066. PMID 16766013. 
  19. ↑ http://www.chemicalbook.com/ChemicalProductProperty_EN_CB5316744.htm[]
  20. ↑ Latch DE, Packer JL, Stender BL, VanOverbeke J, Arnold WA, McNeill K (March 2005). "Aqueous photochemistry of triclosan: formation of 2,4-dichlorophenol, 2,8-dichlorodibenzo-p-dioxin, and oligomerization products". Environ. Toxicol. Chem. 24 (3): 517–25. doi:10.1897/04-243R.1. PMID 15779749. 
  21. ↑ COMMISSION DECISION of 19 March 2010 concerning the non-inclusion of 2,4,4’-trichloro-2’-hydroxydiphenyl ether in the Union list of additives which may be used in the manufacture of plastic materials and articles intended to come into contact with foodstuffs under Directive 2002/72/EC 23.3.2010 Official Journal of the European Union
  22. ↑ Triclosan at Household Products Database, U.S. Department of Health and Human Services
  23. ↑ "REGULATION (EC) No 1223 /2009 OF THE EUROPEAN PARLIAMENT AND OF THE COUNCIL of 30 November 2009 on cosmetic products". Official Journal of the European Union. 2009. 
  24. ↑ Jang CW, Magnuson T (2013). "A novel selection marker for efficient DNA cloning and recombineering in E. coli". In Poteete, Anthony R. PLoS ONE 8 (2): e57075. Bibcode:2013PLoSO...857075J. doi:10.1371/journal.pone.0057075. PMC 3577784. PMID 23437314. 
  25. ↑ Russell AD (May 2004). "Whither triclosan?". J. Antimicrob. Chemother. 53 (5): 693–5. doi:10.1093/jac/dkh171. PMID 15073159. 
  26. ↑ Heath RJ, Rubin JR, Holland DR, Zhang E, Snow ME, Rock CO (April 1999). "Mechanism of triclosan inhibition of bacterial fatty acid synthesis". J. Biol. Chem. 274 (16): 11110–4. doi:10.1074/jbc.274.16.11110. PMID 10196195. 
  27. ↑ Fan F, Yan K, Wallis NG, et al. (November 2002). "Defining and combating the mechanisms of triclosan resistance in clinical isolates of Staphylococcus aureus". Antimicrob. Agents Chemother. 46 (11): 3343–7. doi:10.1128/AAC.46.11.3343-3347.2002. PMC 128739. PMID 12384334. 
  28. ↑ Slater-Radosti C, Van Aller G, Greenwood R, et al. (2001). "Biochemical and genetic characterization of the action of triclosan on Staphylococcus aureus". J. Antimicrob. Chemother. 48 (1): 1–6. doi:10.1093/jac/48.1.1. PMID 11418506. 
  29. ↑ Chuanchuen R, Karkhoff-Schweizer RR, Schweizer HP (April 2003). "High-level triclosan resistance in Pseudomonas aeruginosa is solely a result of efflux". Am J Infect Control 31 (2): 124–7. doi:10.1067/mic.2003.11. PMID 12665747. 
  30. ↑ Wisk, Joseph D.; Cooper, Keith R. (1990). "Comparison of the toxicity of several polychlorinated dibenzo-p-dioxins and 2,3,7,8-tetrachlorodibenzofuran in embryos of the Japanese medaka (Oryzias latipes)". Chemosphere 20 (3–4): 361–77. doi:10.1016/0045-6535(90)90067-4. 
  31. ↑ Buth JM, Steen PO, Sueper C, et al. (June 2010). "Dioxin photoproducts of triclosan and its chlorinated derivatives in sediment cores". Environ. Sci. Technol. 44 (12): 4545–51. Bibcode:2010EnST...44.4545B. doi:10.1021/es1001105. PMID 20476764. 
  32. ↑ 32.0 32.1 "Environmental Protection Agency". Docket. 27 March 2013. 
  33. ↑ 33.0 33.1 "Consultation on assessment of the health risk of dioxins; re-evaluation of the tolerable daily intake (TDI): Executive Summary". Food Additives and Contaminants 17 (4): 223–240. 2000. doi:10.1080/713810655. PMID 10912238. 
  34. ↑ McMurry LM, Oethinger M, Levy SB (August 1998). "Triclosan targets lipid synthesis". Nature 394 (6693): 531–2. Bibcode:1998Natur.394..531M. doi:10.1038/28970. PMID 9707111. 
  35. ↑ Supermarkets to ban toxic detergent Rob Edwards, Sunday Herald, 02 November 2003
  36. ↑ McBain AJ, Bartolo RG, Catrenich CE, et al. (September 2003). "Exposure of sink drain microcosms to triclosan: population dynamics and antimicrobial susceptibility". Appl. Environ. Microbiol. 69 (9): 5433–42. doi:10.1128/AEM.69.9.5433-5442.2003. PMC 194980. PMID 12957932. 
  37. ↑ Aiello AE, Marshall B, Levy SB, Della-Latta P, Larson E (August 2004). "Relationship between triclosan and susceptibilities of bacteria isolated from hands in the community". Antimicrob. Agents Chemother. 48 (8): 2973–9. doi:10.1128/AAC.48.8.2973-2979.2004. PMC 478530. PMID 15273108. 
  38. ↑ Yazdankhah SP, Scheie AA, Høiby EA, et al. (2006). "Triclosan and antimicrobial resistance in bacteria: an overview". Microb. Drug Resist. 12 (2): 83–90. doi:10.1089/mdr.2006.12.83. PMID 16922622. 
  39. ↑ Triclosan and Antibiotics resistance summary by GreenFacts of an opion by the European Commission Scientific Committee on Consumer Safety (March 2010)
  40. ↑ Sifferlin, Alexandra (Aug 15, 2012). "Freaky Clean: Chemical in Antibacterial Soap Weakens Muscle Function". Time. 
  41. ↑ 41.0 41.1 US Environmental Protection Agency (18 September 2008). "Reregistration Eligibility Decision for Triclosan". Reregistration Eligibility Decision (RED) Document. 
  42. ↑ 42.0 42.1 Clayton EM, Todd M, Dowd JB, Aiello AE (March 2011). "The impact of bisphenol A and triclosan on immune parameters in the U.S. population, NHANES 2003-2006". Environ. Health Perspect. 119 (3): 390–6. doi:10.1289/ehp.1002883. PMC 3060004. PMID 21062687. Lay summary – ScienceDaily (Nov. 30, 2010). 
  43. ↑ Sicherer, SH; Leung, DY (January 2013). "Advances in allergic skin disease, anaphylaxis, and hypersensitivity reactions to foods, drugs, and insects in 2012". Journal of Allergy and Clinical Immunology 131 (1): 55–66. doi:10.1016/j.jaci.2012.11.007. PMID 23199604. 
  44. ↑ "New Questions Raised On Chemicals In Soaps, Plastics : Shots - Health News Blog : NPR". npr.org. Retrieved 2010-11-30. 
  45. ↑ Bhutani T, Jacob SE (May 2009). "Triclosan: a potential allergen in suture-line allergic contact dermatitis". Dermatol Surg 35 (5): 888–9. doi:10.1111/j.1524-4725.2009.01151.x. PMID 19389086. 
  46. ↑ Campbell L, Zirwas MJ (December 2006). "Triclosan". Dermatitis 17 (4): 204–7. doi:10.2310/6620.2006.06014. PMID 17150172. 
  47. ↑ 47.0 47.1 Yang, Jeniffer (2009-08-21). "Experts concerned about dangers of antibacterial products". Globe and Mail. Retrieved 2009-08-25. 
  48. ↑ 48.0 48.1 Rule KL, Ebbett VR, Vikesland PJ (May 2005). "Formation of chloroform and chlorinated organics by free-chlorine-mediated oxidation of triclosan". Environ. Sci. Technol. 39 (9): 3176–85. doi:10.1021/es048943. PMID 15926568. 
  49. ↑ Dioxins
  50. ↑ US Pharmacopoeia National Formulary. United States Pharmacopeial. 2012. ISBN 1936424126. 
  51. ↑ "ADA.org: ADA News: Triclosan study not relevant to toothpaste". ada.org. Archived from the original on 2007-10-24. Retrieved 2010-08-16. 
  52. ↑ Ricart M, Guasch H, Alberch M, et al. (November 2010). "Triclosan persistence through wastewater treatment plants and its potential toxic effects on river biofilms". Aquat. Toxicol. 100 (4): 346–53. doi:10.1016/j.aquatox.2010.08.010. PMID 20855117. 
  53. ↑ Veldhoen N, Skirrow RC, Osachoff H, et al. (December 2006). "The bactericidal agent triclosan modulates thyroid hormone-associated gene expression and disrupts postembryonic anuran development". Aquat. Toxicol. 80 (3): 217–27. doi:10.1016/j.aquatox.2006.08.010. PMID 17011055. 
  54. ↑ Clayton EM, Todd M, Dowd JB, Aiello AE (March 2011). "The impact of bisphenol A and triclosan on immune parameters in the U.S. population, NHANES 2003-2006". Environ. Health Perspect. 119 (3): 390–6. doi:10.1289/ehp.1002883. PMC 3060004. PMID 21062687. 
  55. ↑ Moss T, Howes D, Williams FM (April 2000). "Percutaneous penetration and dermal metabolism of triclosan (2,4, 4'-trichloro-2'-hydroxydiphenyl ether)". Food Chem. Toxicol. 38 (4): 361–70. doi:10.1016/S0278-6915(99)00164-7. PMID 10722890. 
  56. ↑ Adolfsson-Erici M, Pettersson M, Parkkonen J, Sturve J (March 2002). "Triclosan, a commonly used bactericide found in human milk and in the aquatic environment in Sweden". Chemosphere 46 (9–10): 1485–9. doi:10.1016/S0045-6535(01)00255-7. PMID 12002480. 
  57. ↑ Edvardsson S, Burman LG, Adolfsson-Erici M, Bäckman N. "Risker och nytta med triklosan i tandkräm" [Risks and benefits of triclosan in toothpaste]. Tandläkartidningen (in German) 97 (10): 58–64. 
  58. ↑ Start ~ Naturskyddsföreningen
  59. ↑ Zorrilla LM, Gibson EK, Jeffay SC, et al. (January 2009). "The effects of triclosan on puberty and thyroid hormones in male Wistar rats". Toxicol. Sci. 107 (1): 56–64. doi:10.1093/toxsci/kfn225. PMID 18940961. 
  60. ↑ "Germ-killing chemical from soaps, toothpaste building up in dolphins". 2009-08-11. Retrieved 2011-04-11. 
  61. ↑ Cullinan MP, Palmer JE, Carle AD, West MJ, Seymour GJ (February 2012). "Long term use of triclosan toothpaste and thyroid function". Sci. Total Environ. 416: 75–9. doi:10.1016/j.scitotenv.2011.11.063. PMID 22197412. 
  62. ↑ Cherednichenko G, Zhang R, Bannister RA, et al. (August 2012). "Triclosan impairs excitation-contraction coupling and Ca2+ dynamics in striated muscle". Proc. Natl. Acad. Sci. U.S.A. 109 (35): 14158–63. Bibcode:2012PNAS..10914158C. doi:10.1073/pnas.1211314109. PMC 3435154. PMID 22891308. 
  63. ↑ Fiss EM, Rule KL, Vikesland PJ (April 2007). "Formation of chloroform and other chlorinated byproducts by chlorination of triclosan-containing antibacterial products". Environ. Sci. Technol. 41 (7): 2387–94. Bibcode:2007EnST...41.2387F. doi:10.1021/es062227l. PMID 17438791. 
  64. ↑ "Plain soap as effective as antibacterial but without the risk". Retrieved 2007-08-17. 
  65. ↑ Kim JS, Kuk E, Yu KN, et al. (March 2007). "Antimicrobial effects of silver nanoparticles". Nanomedicine 3 (1): 95–101. doi:10.1016/j.nano.2006.12.001. PMID 17379174. 

See also

  • 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"

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