Triclosan

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Structural formula
Triclosan's structural formula
General
Non-proprietary name Triclosan
other names
  • 5-chloro-2- (2,4-dichlorophenoxy) phenol
  • TCS
  • 2,4,4'-trichloro-2'-hydroxydiphenyl ether
  • 5-chloro (2,4-dichlorophenoxy) phenol
  • CH-3565
  • Lexol 300
  • Irgasan DP 300
  • Ster-Zac
Molecular formula C 12 H 7 Cl 3 O 2
Brief description

white, crystalline solid

External identifiers / databases
CAS number 3380-34-5
EC number 222-182-2
ECHA InfoCard 100.020.167
PubChem 5564
DrugBank DB08604
Wikidata Q408646
Drug information
ATC code

D09 AA06

Drug class

Microbicide

Mechanism of action

Destabilization of the biomembrane of bacteria , fungi and enveloped viruses

properties
Molar mass 289.53 g mol −1
Physical state

firmly

Melting point

55-60 ° C

boiling point

> 280 ° C (decomposition)

solubility
  • practically insoluble in water
  • moderately in caustic soda
  • soluble in many organic solvents
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
07 - Warning 09 - Dangerous for the environment

Caution

H and P phrases H: 315-319-410
P: 273-302 + 352-305 + 351 + 338
Toxicological data

3700 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Triclosan , which belongs to the chemical group of polychlorinated phenoxyphenols , is an antimicrobial agent that is used as a biocide and preservative in a wide range of consumer goods, cosmetic preparations and disinfectants .

use

Triclosan is mainly used in medical and dental practices as well as in hospitals to prevent the transmission of germs. Disinfectants belong to main group 1 of the biocidal products (Annex V of the former Directive 98/8 / EC or currently Regulation (EU) No. 528/2012 (Biocide Regulation) ). Triclosan is effective against bacteria, fungi and / or enveloped viruses. Triclosan is therefore used in cosmetic articles such as toothpaste, deodorants and soaps, as well as in household cleaners and detergents. However, the Federal Institute for Risk Assessment (BfR) advises against using it for disinfection in the household, e.g. B. in detergents, since the low concentration of triclosan in the detergents could lead to a build-up of resistance from bacteria, which could also spread to doxycycline or ciprofloxacin through cross-resistance (similar mechanisms of action) .

Overview of Triclosan Uses:

  • Component of disinfectants for professional use in medical practices and hospitals.
  • In concentrations of 1% to 3% as a medicinal substance for the treatment of infectious skin diseases in creams produced according to the prescription in the pharmacy (e.g. 1% in anionic hydrophilic cream, a standard formula in the DAC ). Cream bases with non-ionic emulsifiers, such as the DAC base cream , are unsuitable as the stability of the preparation can be impaired.
  • Active ingredient in cosmetic preparations and toothpastes. Triclosan has antiseptic and remanent deodorizing properties, therefore it can be used as a deodorizing additive in solid soaps and liquid soaps (use concentration: 0.2-0.5%), deodorant sprays (0.2%) and deodorants (up to 0.3%) . In antiseptic soaps and alcohol- based surgical hand disinfectants , the concentration used can be 0.2–2%.
  • Preservatives in cosmetic preparations. In Germany, the maximum permissible concentration for this application according to the Cosmetics Ordinance is 0.3%.
  • Mattress covers, sports and functional textiles, shoes, carpets, plastic cutting boards, etc. The like are sometimes treated with Triclosan and advertised as particularly "suitable for allergy sufferers" or "freshly scented". This can often be recognized by names such as Ultra-Fresh, Amicor, Microban, Monolith, or Bactonix. The use of triclosan in textiles is controversial because it attacks the natural skin flora .

Exposure

Detection of triclosan in the urine of pregnant women

Researchers have found triclosan in the urine of pregnant women and in the umbilical cord blood. The researchers point to the use of triclosan in a wide variety of products and the widespread exposure to this substance. A Canadian study published in April 2015 also reported decreased fertility (longer time until pregnancy) in women who had triclosan levels of ≥71.7 μg / l in the urine.

Enrichment in toothbrushes

In a 2017 study it was shown that Triclosan can build up in significant amounts in the plastic bristles of toothbrushes . This was preferably the case with toothbrushes with thin, soft bristles. After switching to a triclosan-free toothpaste , the stored triclosan was gradually released again from the bristles. A similar enrichment in other products was not excluded.

toxicology

Triclosan bioaccumulates in aquatic organisms including marine mammals. It is believed to be an endocrine disruptor . Triclosan is suspected of causing various disorders in humans, such as a decrease in fertility , a decrease in body mass index , a decrease in weight, height and head circumference in newborns , an increase in the risk of miscarriages , an increase in the risk of Asthma and allergies as well as an increase in blood values ​​for markers of oxidative stress and for the thyroid hormone triiodothyronine . Probably triclosan promotes human growth tumors of the liver and inflammation of the liver. The risk of developing bacterial resistance to Triclosan is low, but the health risks outweigh the benefits, as the antimicrobial effect of hand washing is only slightly better than without it. However, a meta-analysis from 2018 came to the conclusion that the current data situation does not allow a conclusive assessment of the toxicity of triclosan due to methodological deficiencies and limited comparability of the published studies.

Environmental behavior

Conversion through solar radiation

Methyltriclosan

When exposed to sunlight, polychlorinated dibenzodioxins and dibenzofurans can form from triclosan . Japanese scientists proved this in 1988 in an experiment with a sock that was exposed to the sun and triclosan, whereupon triclosan was banned in Japan for the biocidal treatment of textiles . Triclosan can be methylated in wastewater to methyltriclosan , which has a longer half-life in the environment.

Water pollution

A German-Slovak research team estimates that triclosan is the sixth most problematic substance in Europe.

regulation

The FDA classifies triclosan as a component of antibacterial hand soaps as redundant and urges manufacturers to change the composition. The headline of the information on hand soaps with Triclosan at the FDA reads: “Antibacterial Soap? You Can Skip It - Use Plain Soap and Water ". In September 2016, the FDA banned the use of triclosan in soap and liquid soap in the United States.

Triclosan was included by the EU in 2012 in accordance with Regulation (EC) No. 1907/2006 (REACH) as part of substance evaluation in the Community's ongoing action plan ( CoRAP ). The effects of the substance on human health and the environment are re-evaluated and, if necessary, follow-up measures are initiated. The reasons for the inclusion of triclosan were concerns about high (aggregated) tonnage and the dangers arising from a possible assignment to the group of PBT / vPvB substances and as a potential endocrine disruptor . The re-evaluation has been running since 2012 and is carried out by the Netherlands . In order to be able to reach a final assessment, further information was requested.

To protect the coral reefs is in the South Pacific state of Palau importation, distribution and use of Triscolan-containing since January 2020 sunscreen prohibited under penalty.

Trade names

  • Irgasan

preparations

Finished medicinal products (combination preparations)

Acne Crème Widmer / -Gel / -Lotio (CH), DuoGalen (D), InfectoCortiSept (D)

Wash lotions / cosmetics

Rutisept (D), Cliniderm (CH), Procutol (CH)

literature

Web links

Individual evidence

  1. ↑ a b Walter Böhmer, Thorsten Bernhardt, Heinz Rüdel, Martin Müller, Andrea Wenzel: Retrospective monitoring of triclosan and methyl-triclosan in bream muscle samples from the environmental specimen bank . Fraunhofer IME, 2004, on behalf of the German Environment Agency, accessed on June 9, 2013.
  2. ↑ a b c Entry on triclosan. In: Römpp Online . Georg Thieme Verlag, accessed on May 15, 2014.
  3. ↑ a b c d e f Entry for CAS no. 3380-34-5 in the GESTIS substance database of the IFA , accessed on June 26, 2016(JavaScript required) .
  4. ↑ Entry on Triclosan in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  5. ^ Entry on triclosan in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  6. ↑ Use Triclosan only in the medical field to prevent the development of resistance . (PDF; 123 kB) Federal Institute for Risk Assessment, BfR Opinion No. 030/2006 of May 8, 2006.
  7. ^ Entry on Triclosan in the Consumer Product Information Database , accessed on November 29, 2008.
  8. ↑ Appendix 6 to Section 3a of the Cosmetics Ordinance , No. 25. Code P 647, see Blue List .
  9. ^ Uta-Christina Hipler, Peter Elsner: Biofunctional Textiles and the Skin. Karger Medical and Scientific Publishers, 2006, ISBN 978-3-8055-8121-9 , p. 12.
  10. ^ Gang Sun: Antimicrobial Textiles. Woodhead Publishing, 2016, ISBN 978-0-08-100585-9 , p. 9.
  11. ↑ Pregnant women and fetuses exposed to antibacterial compounds face potential health risks . American Chemical Society, August 10, 2014, accessed December 6, 2014.
  12. ↑ Maria P. Vélez, Tye E. Arbuckle, William D. Fraser: Female exposure to phenols and phthalates and time to pregnancy: the Maternal-Infant Research on Environmental Chemicals (MIREC) Study . In: Fertility and Sterility . tape 103 , no. 4 , 2015, p. 1011-1020.e2 , doi : 10.1016 / j.fertnstert.2015.01.005 , PMID 25681860 .
  13. ↑ Triclosan accumulates in toothbrushes - experiment reveals uncontrolled accumulation and release of the disinfectant , on scinexx.de from October 26, 2017.
  14. ↑ J. Han, W. Qiu, EC Campbell, JC White, B Xing: Nylon Bristles and Elastomers Retain Centigram Levels of Triclosan and Other Chemicals from Toothpastes: Accumulation and Uncontrolled Release. In: Environ Sci Technol. October 25, 2017. PMID 29067803 , doi: 10.1021 / acs.est.7b02839 .
  15. ↑ a b c M. F. Yueh, RH Tukey: Triclosan: A Widespread Environmental Toxicant with Many Biological Effects. In: Annual review of pharmacology and toxicology. Volume 56, 2016, pp. 251-272, doi: 10.1146 / annurev-pharmtox-010715-103417 , PMID 26738475 , PMC 4774862 (free full text).
  16. ↑ a b Lisa M. Weatherly, Julie A. Gosse: Triclosan exposure, transformation, and human health effects. In: Journal of Toxicology and Environmental Health, Part B. 20, 2017, pp. 447-469, doi: 10.1080 / 10937404.2017.1399306 .
  17. ↑ CA Giuliano, MJ Rybak: Efficacy of triclosan as an antimicrobial hand soap and its potential impact on antimicrobial resistance: a focused review. In: Pharmacotherapy. Volume 35, Number 3, March 2015, pp. 328-336, doi: 10.1002 / phar.1553 , PMID 25809180 .
  18. ^ M. Goodman, DQ Naiman, JS LaKind: Systematic review of the literature on triclosan and health outcomes in humans. In: Critical reviews in toxicology. Volume 48, number 1, January 2018, pp. 1–51, doi: 10.1080 / 10408444.2017.1350138 , PMID 28741979 .
  19. ↑ T-shirts with side effects . In: NZZ .
  20. ↑ Triclosan should be monitored . UFZ , press release of October 26, 2012, accessed on May 3, 2015.
  21. ↑ Health risk: Antibacterial soaps and cleaners - The US health authority FDA (Food and Drug Administration) warns of ingredients in antibacterial soaps and household cleaners , on: heute.at of September 2, 2016. Original English: FDA issues final rule on safety and effectiveness of antibacterial soaps , FDA dated September 2, 2016.
  22. ↑ Antibacterial Soap? You Can Skip It - Use Plain Soap and Water. FDA , September 2, 2016, accessed October 6, 2016 .
  23. ↑ Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): Triclosan , accessed on March 26, 2019.Template: CoRAP status / 2012
  24. ^ The Republic of Palau Bans Sunscreen Chemicals to Protect its Coral Reefs and UNESCO World Heritage site - International Coral Reef Initiative. In: icriforum.org. November 4, 2018, accessed February 20, 2020 .
  25. ↑ Palau bans sunscreens that poison corals. In: Spiegel.de , January 1, 2020, accessed on February 24, 2020.