Zinc pyrithione explained

Zinc pyrithione (or pyrithione zinc) is a coordination complex of zinc. It has fungistatic (inhibiting the division of fungal cells) and bacteriostatic (inhibiting bacterial cell division) properties and is used in the treatment of seborrhoeic dermatitis[1] and dandruff.

Structure of the compound

The pyrithione ligands, which are formally monoanions, are chelated to Zn2+ via oxygen and sulfur centers. In the crystalline state, zinc pyrithione exists as a centrosymmetric dimer (see figure), where each zinc is bonded to two sulfur and three oxygen centers.[2] In solution, however, the dimers dissociate via scission of one Zn-O bond.

This compound was first described in the 1930s.[3]

Pyrithione is the conjugate base derived from 2-mercaptopyridine-N-oxide (CAS# 1121-31-9), a derivative of pyridine-N-oxide.

Uses

Medicine

Zinc pyrithione can be used to treat dandruff and seborrhoeic dermatitis.[4] [5] [6] It also has antibacterial properties and is effective against many pathogens from the Streptococcus and Staphylococcus genera.[7] Its other medical applications include treatments of psoriasis, eczema, ringworm, fungus, athletes foot, dry skin, atopic dermatitis, tinea versicolor,[8] and vitiligo.

Paint

Because of its low solubility in water (8 ppm at neutral pH), zinc pyrithione is suitable for use in outdoor paints and other products that protect against mildew and algae. It is an algaecide. It is chemically incompatible with paints relying on metal carboxylate curing agents. When it is used in latex paints with water containing much iron, a sequestering agent that preferentially binds the iron ions is needed. It is decomposed by ultraviolet light slowly, providing years of protection in direct sunlight.

Sponges

Zinc pyrithione is an antibacterial treatment for household sponges, as used by the 3M Corporation.[9] [10]

Clothing

A process to apply zinc pyrithione to cotton with washable results was patented in the United States in 1984.[11] Zinc pyrithione is used to prevent microbe growth in polyester.[12] Textiles with applied zinc pyrithione protect against odor-causing microorganisms. Export of antimicrobial textiles reached US$497.4 million in 2015.[13]

Mechanism of action

Antibacterial effect

Zinc pyrithione is known to exhibit antibacterial activity by disrupting cell membrane integrity and essential metabolic functions in bacteria.[14]

Antifungal effect

Its antifungal effect is thought to derive from its ability to disrupt membrane transport by blocking the proton pump that energizes the transport mechanism.[15] A study from 2011 showed that antifungal effects of Zinc pyrithione work by copper toxicity mechanism that targets critical iron–sulphur proteins.[16]

Health effects

Zinc pyrithione is approved for over-the-counter topical use in the United States as a treatment for dandruff and is the active ingredient in several anti-dandruff shampoos and body wash gels. In its industrial forms and strengths, it may be harmful by contact or ingestion. Zinc pyrithione can in the laboratory setting trigger a variety of responses, such as DNA damage in skin cells.[17]

Legal status

European Union regions

Use of zinc pyrithione is prohibited within cosmetic products in the European Union since December 2021. The substance was considered safe for use in rinse-off and leave-in products of different tested concentrations, but due to environmental toxicity standard regulation was considered against potential alternatives – and as no submission was made for its use it was automatically prohibited.

United States

Zinc pyrithione concentration of up to 2% is allowed for products when they are formulated to be applied and then washed off after brief exposure.[18]

Environmental concerns

A large Swedish study shows that it is broken down in wastewater plants and does not release into waterways.[19] A Danish study shows that it biodegrades quickly, but that a risk of continuous leaching from boat paint may cause environmental toxicity.[20]

See also

Notes and References

  1. Web site: Pyrithione Zinc . Martindale: The Complete Drug Reference . Pharmaceutical Press . 23 September 2011 . 28 March 2014 . Brayfield A . 26 March 2020 . https://web.archive.org/web/20200326121901/http://www.medicinescomplete.com/mc/martindale/current/1633-s.htm . live .
  2. Barnett BL, Kretschmar HC, Hartman FA . Structural characterization of bis(N-oxopyridine-2-thionato)zinc(II) . . 1977 . 16 . 8 . 1834–8 . 10.1021/ic50174a002 .
  3. Web site: Pyrithione zinc . 24 August 2007 . dead . https://web.archive.org/web/20070621193113/http://www.cas.astate.edu/draganjac/pyrithionezinc.html . 21 June 2007 . www.cas.astate.edu . Draganjac M . Arkansas State University.
  4. Marks R, Pearse AD, Walker AP . The effects of a shampoo containing zinc pyrithione on the control of dandruff . The British Journal of Dermatology . 112 . 4 . 415–422 . April 1985 . 3158327 . 10.1111/j.1365-2133.1985.tb02314.x . 23368244 .
  5. Piérard-Franchimont C, Goffin V, Decroix J, Piérard GE . A multicenter randomized trial of ketoconazole 2% and zinc pyrithione 1% shampoos in severe dandruff and seborrheic dermatitis . Skin Pharmacology and Applied Skin Physiology . 15 . 6 . 434–441 . November 2002 . 12476017 . 10.1159/000066452 . 23162407 . 1 July 2024 .
  6. Ive FA . An overview of experience with ketoconazole shampoo . The British Journal of Clinical Practice . 45 . 4 . 279–284 . 1991 . 1839767 .
  7. Web site: Zinc pyrithione . 14 May 2021 . Molecule of the Week Archive . American Chemical Society . en . 1 March 2021 . https://web.archive.org/web/20210301232215/https://www.acs.org/content/acs/en/molecule-of-the-week/archive/z/zinc-pyrithione.html . live .
  8. Faergemann J . Management of seborrheic dermatitis and pityriasis versicolor . American Journal of Clinical Dermatology . 1 . 2 . 75–80 . 2000 . 11702314 . 10.2165/00128071-200001020-00001 . 43516330 .
  9. Web site: Notice of Filing a Pesticide Petition to Establish . 3 December 2007 . 18 November 2017 . https://web.archive.org/web/20171118225022/http://lp.findlaw.com/ . live .
  10. Schroeder JW, Corn S, Battiste J, Stepanova N, Weiss C, Thiele J . In-situ immobilization of pyrithione in cellulose sponge for durable antimicrobial effect. . Cellulose . December 2023 . 30 . 18 . 11753-11765 . 10.1007/s10570-023-05595-w .
  11. US . US4443222A . 17 April 1984 . Morris CE, Welch CM . The United States of America as represented by the Secretary of Agriculture.
  12. Web site: Zptech, Zinc Odor Control for Textiles . microban.com . Microban International . https://web.archive.org/web/20230702013210/https://www.microban.com/odor-control/technologies/zptech . 2023-07-02 . 2023-09-23.
  13. Jain AK, Tesema AF . Development of antimicrobial textiles using zinc pyrithione. . Research Journal of Textile and Apparel. . September 2017 . 21 . 3 . 188-202 . 10.1108/RJTA-06-2017-0031 .
  14. Blanchard C, Brooks L, Ebsworth-Mojica K, Didione L, Wucher B, Dewhurst S, Krysan D, Dunman PM, Wozniak RA . Zinc Pyrithione Improves the Antibacterial Activity of Silver Sulfadiazine Ointment . mSphere . 1 . 5 . 2016-10-26 . 27642637 . 5023846 . 10.1128/mSphere.00194-16 . Fey PD .
  15. Chandler CJ, Segel IH . Mechanism of the antimicrobial action of pyrithione: effects on membrane transport, ATP levels, and protein synthesis . Antimicrobial Agents and Chemotherapy . 14 . 1 . 60–68 . July 1978 . 28693 . 352405 . 10.1128/aac.14.1.60 .
  16. Reeder NL, Xu J, Youngquist RS, Schwartz JR, Rust RC, Saunders CW . The antifungal mechanism of action of zinc pyrithione . The British Journal of Dermatology . 165 . Suppl 2 . 9–12 . October 2011 . 21919897 . 10.1111/j.1365-2133.2011.10571.x .
  17. Leading references: Lamore SD, Cabello CM, Wondrak GT . The topical antimicrobial zinc pyrithione is a heat shock response inducer that causes DNA damage and PARP-dependent energy crisis in human skin cells . Cell Stress & Chaperones . 15 . 3 . 309–322 . May 2010 . 19809895 . 2866994 . 10.1007/s12192-009-0145-6 .
  18. Web site: 21 CFR 358.710 -- Active ingredients for the control of dandruff, seborrheic dermatitis, or psoriasis. . 2024-08-18 . www.ecfr.gov . en.
  19. Web site: Results from the Swedish Screening Programme 2006 Subreport 3: Zinc pyrithione and Irgarol 1051 . September 2007 . ivl.se . . https://web.archive.org/web/20210526185320/https://www.ivl.se/download/18.343dc99d14e8bb0f58b7524/1445515665956/B1764.pdf . 26 May 2021 . 5 March 2023 .
  20. Web site: Ecotoxocicological assessment of antifouling biocides and non-biocidal antifouling paints . https://archive.today/20120525185735/http://www2.mst.dk/common/Udgivramme/Frame.asp?http://www2.mst.dk/udgiv/publications/2000/87-7944-084-3/html/kap04_eng.htm . 25 May 2012 . 5 March 2023 . Miljøstyrelsen - Miljøministeriet . Ministry of Environment (Denmark).

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