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{{short description|Chemical compound}}
{{Short description|Chemical compound}}
{{Use dmy dates|date=March 2023}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Chembox
{{Chembox
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 402542377
| verifiedrevid = 402542377
| ImageFile = Zink-Pyrithion.svg
| ImageFile = Zink-Pyrithion.svg
| ImageSize =
| ImageSize =
| ImageFile1 = Zinc-pyrithione-dimer-3D-balls.png
| ImageFile1 = Zinc-pyrithione-dimer-3D-balls.png
| ImageSize1 = 250
| ImageSize1 = 250
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| MolarMass = 317.70 g/mol
| MolarMass = 317.70 g/mol
| Appearance = colourless solid
| Appearance = colourless solid
| Density =
| Density =
| MeltingPtC = 240
| MeltingPtC = 240
| MeltingPt_notes = (decomposition)<ref name="Römpp">{{RömppOnline|ID=RD-26-00395|Name=Zink-Pyrithion|Datum=05 November 2020}}</ref>
| MeltingPt_notes = (decomposition)<ref name="Römpp">{{RömppOnline|ID=RD-26-00395|Name=Zink-Pyrithion|Datum=5 November 2020}}</ref>
| BoilingPt = decomposes
| BoilingPt = decomposes
| Solubility = 8&nbsp;ppm (pH 7)
| Solubility = 8&nbsp;ppm (pH 7)
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}}
}}
|Section7={{Chembox Hazards
|Section7={{Chembox Hazards
| MainHazards =
| MainHazards =
| FlashPt =
| FlashPt =
| AutoignitionPt =
| AutoignitionPt =
}}
}}
}}
}}
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| PubChem =26041 | C=10 | H=8 | N=2 | O=2 | S=2 | Zn=1
| PubChem =26041 | C=10 | H=8 | N=2 | O=2 | S=2 | Zn=1
| molecular_weight = 317.705
| molecular_weight = 317.705
| bioavailability =
| bioavailability =
| metabolism =
| metabolism =
| elimination_half-life=
| elimination_half-life=
| excretion =
| excretion =
| Pregnancy_category =
| Pregnancy_category =
| Legal_status = [[Over-the-counter drug|OTC]] (US)
| Legal_status = [[Over-the-counter drug|OTC]] (US)
| routes_of_administration = Topical
| routes_of_administration = Topical
}}-->
}}-->
'''Zinc pyrithione''' (or '''pyrithione zinc''') is a [[coordination compound|coordination complex]] of [[zinc]]. It has fungistatic (that is, it inhibits the division of fungal cells) and [[bacteriostatic]] (inhibits bacterial cell division) properties and is used in the treatment of [[seborrhoeic dermatitis]].<ref name = MD>{{cite web|title=Pyrithione Zinc|work=Martindale: The Complete Drug Reference|publisher=Pharmaceutical Press|date=23 September 2011|access-date=28 March 2014|editor=Brayfield, A|url=http://www.medicinescomplete.com/mc/martindale/current/1633-s.htm}}</ref>
'''Zinc pyrithione''' (or '''pyrithione zinc''') is a [[coordination compound|coordination complex]] of [[zinc]]. It has [[Fungistatics|fungistatic]] (inhibiting the division of fungal cells) and [[bacteriostatic]] (inhibiting bacterial cell division) properties and is used in the treatment of [[seborrhoeic dermatitis]]<ref name="MD">{{cite web |title=Pyrithione Zinc |work=Martindale: The Complete Drug Reference |publisher=Pharmaceutical Press |date=23 September 2011 |access-date=28 March 2014 | veditors = Brayfield A |url=http://www.medicinescomplete.com/mc/martindale/current/1633-s.htm |archive-date=26 March 2020 |archive-url=https://web.archive.org/web/20200326121901/http://www.medicinescomplete.com/mc/martindale/current/1633-s.htm |url-status=live }}</ref> and [[dandruff]].


== Structure of the compound ==
== Structure of the compound ==
The [[pyrithione]] ligands, which are formally [[Anion|monoanions]], are [[Chelation|chelated]] to Zn<sup>2+</sup> 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.<ref>{{cite journal |title= Structural characterization of bis(N-oxopyridine-2-thionato)zinc(II) |journal= [[Inorg. Chem.]] |year= 1977 |volume= 16 |issue= 8 |pages= 1834–8 |doi= 10.1021/ic50174a002 |author1=Barnett, B. L. |author2=Kretschmar, H. C. |author3=Hartman, F. A. }}</ref> In solution, however, the dimers dissociate via scission of one Zn-O bond.
The [[pyrithione]] ligands, which are formally [[Anion|monoanions]], are [[Chelation|chelated]] to Zn<sup>2+</sup> 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.<ref>{{cite journal | vauthors = Barnett BL, Kretschmar HC, Hartman FA |title=Structural characterization of bis(N-oxopyridine-2-thionato)zinc(II) |journal=[[Inorg. Chem.]] |year=1977 |volume=16 |issue=8 |pages=1834–8 |doi=10.1021/ic50174a002 }}</ref> In solution, however, the dimers dissociate via scission of one Zn-O bond.{{citation needed|date=December 2022}}


This compound was first described in the 1930s.<ref>{{cite web |url=http://www.cas.astate.edu/draganjac/pyrithionezinc.html |title=Pyrithione zinc |access-date=2007-08-24 |url-status=dead |archive-url=https://web.archive.org/web/20070621193113/http://www.cas.astate.edu/draganjac/pyrithionezinc.html |archive-date=2007-06-21}}</ref>
This compound was first described in the 1930s.<ref>{{cite web |url=http://www.cas.astate.edu/draganjac/pyrithionezinc.html |title=Pyrithione zinc |access-date=24 August 2007 |url-status=dead |archive-url=https://web.archive.org/web/20070621193113/http://www.cas.astate.edu/draganjac/pyrithionezinc.html |archive-date=21 June 2007 |website=www.cas.astate.edu | vauthors = Draganjac M |publisher=Arkansas State University}}</ref>


Pyrithione is the [[conjugate base]] derived from 2-mercaptopyridine-''N''-oxide (CAS# 1121-31-9), a derivative of [[pyridine-N-oxide|pyridine-''N''-oxide]].
Pyrithione is the [[conjugate base]] derived from 2-mercaptopyridine-''N''-oxide (CAS# 1121-31-9), a derivative of [[pyridine-N-oxide|pyridine-''N''-oxide]].{{citation needed|date=December 2022}}


== Uses ==
== Uses ==


=== Medicine ===
=== Medicine ===
Zinc pyrithione can be used to treat [[dandruff]] and [[seborrhoeic dermatitis]].<ref>{{Cite journal|last1=Marks|first1=R.|last2=Pearse|first2=A. D.|last3=Walker|first3=A. P.|date=April 1985|title=The effects of a shampoo containing zinc pyrithione on the control of dandruff|url=https://pubmed.ncbi.nlm.nih.gov/3158327/|journal=The British Journal of Dermatology|volume=112|issue=4|pages=415–422|doi=10.1111/j.1365-2133.1985.tb02314.x|issn=0007-0963|pmid=3158327|s2cid=23368244 }}</ref><ref>{{Cite journal|last1=Piérard-Franchimont|first1=Claudine|last2=Goffin|first2=Véronique|last3=Decroix|first3=Jacques|last4=Piérard|first4=Gérald E.|date=November 2002|title=A multicenter randomized trial of ketoconazole 2% and zinc pyrithione 1% shampoos in severe dandruff and seborrheic dermatitis|url=https://pubmed.ncbi.nlm.nih.gov/12476017/|journal=Skin Pharmacology and Applied Skin Physiology|volume=15|issue=6|pages=434–441|doi=10.1159/000066452|issn=1422-2868|pmid=12476017|s2cid=23162407 }}</ref><ref>{{Cite journal|last=Ive|first=F. A.|date=1991|title=An overview of experience with ketoconazole shampoo|url=https://pubmed.ncbi.nlm.nih.gov/1839767/|journal=The British Journal of Clinical Practice|volume=45|issue=4|pages=279–284|issn=0007-0947|pmid=1839767}}</ref> It also has antibacterial properties and is effective against many [[pathogen]]s from the ''[[Streptococcus]]'' and ''[[Staphylococcus]]'' genera.<ref name=":0">{{Cite web|title=Zinc pyrithione|url=https://www.acs.org/content/acs/en/molecule-of-the-week/archive/z/zinc-pyrithione.html|access-date=2021-05-14|website=American Chemical Society|language=en}}</ref> Its other medical applications include treatments of [[psoriasis]], [[eczema]], [[ringworm]], [[fungus]], [[athletes foot]], [[dry skin]], [[atopic dermatitis]], [[tinea versicolor]],<ref>{{cite journal | title = Management of Seborrheic Dermatitis and Pityriasis Versicolor | journal = American Journal of Clinical Dermatology | author = Faergemann, J. American Journal of Clinical Dermatology | date = 2000 | volume = 1 | issue = 2 | pages = 75–80 | issn = 1175-0561| doi = 10.2165/00128071-200001020-00001 | pmid = 11702314 | s2cid = 43516330 }}</ref><ref name=":0" /> and [[vitiligo]].{{medcn|date=September 2020}}
Zinc pyrithione can be used to treat [[dandruff]] and [[seborrhoeic dermatitis]].<ref>{{cite journal | vauthors = Marks R, Pearse AD, Walker AP | title = The effects of a shampoo containing zinc pyrithione on the control of dandruff | journal = The British Journal of Dermatology | volume = 112 | issue = 4 | pages = 415–422 | date = April 1985 | pmid = 3158327 | doi = 10.1111/j.1365-2133.1985.tb02314.x | s2cid = 23368244 }}</ref><ref>{{cite journal | vauthors = Piérard-Franchimont C, Goffin V, Decroix J, Piérard GE | title = A multicenter randomized trial of ketoconazole 2% and zinc pyrithione 1% shampoos in severe dandruff and seborrheic dermatitis | journal = Skin Pharmacology and Applied Skin Physiology | volume = 15 | issue = 6 | pages = 434–441 | date = November 2002 | pmid = 12476017 | doi = 10.1159/000066452 | s2cid = 23162407 }}</ref><ref>{{cite journal | vauthors = Ive FA | title = An overview of experience with ketoconazole shampoo | journal = The British Journal of Clinical Practice | volume = 45 | issue = 4 | pages = 279–284 | date = 1991 | pmid = 1839767 }}</ref> It also has antibacterial properties and is effective against many [[pathogen]]s from the ''[[Streptococcus]]'' and ''[[Staphylococcus]]'' genera.<ref name="American Chem Soc">{{Cite web |title=Zinc pyrithione |url=https://www.acs.org/content/acs/en/molecule-of-the-week/archive/z/zinc-pyrithione.html |access-date=14 May 2021 | work = Molecule of the Week Archive |publisher = American Chemical Society |language=en |archive-date=1 March 2021 |archive-url=https://web.archive.org/web/20210301232215/https://www.acs.org/content/acs/en/molecule-of-the-week/archive/z/zinc-pyrithione.html |url-status=live }}</ref> Its other medical applications include treatments of [[psoriasis]], [[eczema]], [[ringworm]], [[fungus]], [[athletes foot]], [[dry skin]], [[atopic dermatitis]], [[tinea versicolor]],<ref>{{cite journal | vauthors = Faergemann J | title = Management of seborrheic dermatitis and pityriasis versicolor | journal = American Journal of Clinical Dermatology | volume = 1 | issue = 2 | pages = 75–80 | date = 2000 | pmid = 11702314 | doi = 10.2165/00128071-200001020-00001 | s2cid = 43516330 }}</ref><ref name="American Chem Soc" /> and [[vitiligo]].{{medical citation needed|date=September 2020}}


=== Paint ===
=== Paint ===
Because of its low [[solubility]] in [[water]] (8&nbsp;ppm at neutral pH), zinc pyrithione is suitable for use in outdoor [[paint]]s 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.
Because of its low [[solubility]] in [[water]] (8&nbsp;ppm at neutral pH), zinc pyrithione is suitable for use in outdoor [[paint]]s 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.{{citation needed|date=December 2022}}


=== Sponges ===
=== Sponges ===
Zinc pyrithione is an [[antibacterial]] treatment for household [[Sponge (material)|sponge]]s, as used by the [[3M Corporation]].<ref>[http://legalminds.lp.findlaw.com/list/epa-pest/msg01049.html Notice of Filing a Pesticide Petition to Establish<!-- Bot generated title -->]</ref>
Zinc pyrithione is an [[antibacterial]] treatment for household [[Sponge (material)|sponge]]s, as used by the [[3M Corporation]].<ref>{{Cite web |url=http://legalminds.lp.findlaw.com/list/epa-pest/msg01049.html |title=Notice of Filing a Pesticide Petition to Establish<!-- Bot generated title --> |access-date=3 December 2007 |archive-date=18 November 2017 |archive-url=https://web.archive.org/web/20171118225022/http://lp.findlaw.com/ |url-status=live }}</ref><ref>{{cite journal | vauthors = Schroeder JW, Corn S, Battiste J, Stepanova N, Weiss C, Thiele J | title = In-situ immobilization of pyrithione in cellulose sponge for durable antimicrobial effect. | journal = Cellulose | date = December 2023 | volume = 30 | issue = 18 | pages = 11753–11765 | doi = 10.1007/s10570-023-05595-w
⚫
}}</ref>


=== Clothing ===
=== Clothing ===
A process to apply zinc pyrithione to cotton with washable results was patented in the United States in 1984.<ref>{{cite patent |country=US |number=US4443222A|status= |title= |pubdate= |gdate= 17 April 1984|fdate= |pridate= |inventor= Morris; Cletus E. |invent1= Morris; Cletus E. |invent2= Welch; Clark M.|assign1= The United States of America as represented by the Secretary of Agriculture}}</ref> Zinc pyrithione is used to prevent microbe growth in polyester.<ref>{{cite web |title=Zptech, Zinc Antimicrobrial Protection For Textiles |url=https://www.microban.com/odor-control/technologies/zptech |website=Microban |access-date=28 June 2020}}</ref> Textiles with applied zinc pyrithione protect against odor-causing microorganisms. Export of antimicrobial textiles reached US$497.4 million in 2015.<ref>{{cite web |last1=Jain |first1=Anil Kumar |last2=Tesema |first2=Addisu Ferede |title=Development of antimicrobial textiles using zinc pyrithione |url=https://www.researchgate.net/publication/319241462 |website=ResearchGate |access-date=28 June 2020}}</ref>
A process to apply zinc pyrithione to cotton with washable results was patented in the United States in 1984.<ref>{{cite patent |country=US |number=US4443222A |status= |title= |pubdate= |gdate= 17 April 1984 |fdate= |pridate= |inventor= Morris CE, Welch CM |assign1=The United States of America as represented by the Secretary of Agriculture}}</ref> Zinc pyrithione is used to prevent microbe growth in polyester.<ref>{{cite web |title=Zptech, Zinc Odor Control for Textiles |url=https://www.microban.com/odor-control/technologies/zptech |website=microban.com |publisher=Microban International |archive-url=https://web.archive.org/web/20230702013210/https://www.microban.com/odor-control/technologies/zptech |archive-date=2023-07-02 |access-date=2023-09-23}}</ref> Textiles with applied zinc pyrithione protect against odor-causing microorganisms. Export of antimicrobial textiles reached US$497.4 million in 2015.<ref>{{cite journal | vauthors = Jain AK, Tesema AF | title = Development of antimicrobial textiles using zinc pyrithione. | journal = Research Journal of Textile and Apparel. | date = September 2017 | volume = 21 | issue = 3 | pages= 188–202 | doi = 10.1108/RJTA-06-2017-0031 }}</ref>


== Mechanism of action ==
== Mechanism of action ==
Its antifungal effect is thought to derive from its ability to disrupt [[cell membrane|membrane]] transport by blocking the [[proton pump]] that energizes the transport mechanism.<ref>{{cite journal
|vauthors=Chandler CJ, Segel IH | title =Mechanism of the Antimicrobial Action of Pyrithione: Effects on Membrane Transport, ATP Levels, and Protein Synthesis |journal=Antimicrob. Agents Chemother.
| volume = 14
| issue = 1
| pages = 60–8
| year = 1978
| pmid = 28693
| pmc = 352405
| doi = 10.1128/aac.14.1.60
}}
⚫
</ref>


=== Antibacterial effect ===
==Health effects==
Zinc pyrithione is known to exhibit antibacterial activity by disrupting cell membrane integrity and essential metabolic functions in bacteria.<ref>{{cite journal | vauthors = Blanchard C, Brooks L, Ebsworth-Mojica K, Didione L, Wucher B, Dewhurst S, Krysan D, Dunman PM, Wozniak RA | title = Zinc Pyrithione Improves the Antibacterial Activity of Silver Sulfadiazine Ointment | journal = mSphere | volume = 1 | issue = 5 | date = 2016-10-26 | pmid = 27642637 | pmc = 5023846 | doi = 10.1128/mSphere.00194-16 | veditors = Fey PD }}</ref>
Use of zinc pyrithione is prohibited in European Union since Dec.01.2021 (ANNEX II , Lastupdate:01/12/2021 List of substances prohibited in cosmetic products).<ref>{{Cite web |title=Zinc Pyrithione in Anti-Dandruff Shampoos {{!}} TianDe Guide |url=https://tiande.guide/en/entradas_tiande/ingredientes-activos/piritionato-de-zinc-anticaspa/ |access-date=2022-04-23 |website=TianDe Guide {{!}} Cosméticos Naturales Tiande - la Guia Completa |language=en}}</ref><ref>{{Cite web |title=EU PROHIBITION OF ZINC PYRITHIONE IN COSMETIC PRODUCTS {{!}} CRITICAL CATALYST |url=https://criticalcatalyst.com/eu-prohibition-of-zinc-pyrithione-in-cosmetic-products/ |access-date=2022-07-24 |website=CRITICAL CATALYST |language=en}}</ref>


=== Antifungal effect ===
⚫
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 trigger a variety of responses, such as DNA damage in skin cells.<ref>Leading references: {{cite journal |vauthors=Lamore SD, Cabello CM, Wondrak GT |title=The topical antimicrobial zinc pyrithione is a heat shock response inducer that causes DNA damage and PARP-dependent energy crisis in cultured human skin cells. |journal=Cell Stress Chaperones |volume=15 |issue=3 |pages=309–22 |date=May 2010 |pmid=19809895 |doi=10.1007/s12192-009-0145-6 |pmc=2866994 }}</ref>
Its antifungal effect is thought to derive from its ability to disrupt [[cell membrane|membrane]] transport by blocking the [[proton pump]] that energizes the transport mechanism.<ref>{{cite journal | vauthors = Chandler CJ, Segel IH | title = Mechanism of the antimicrobial action of pyrithione: effects on membrane transport, ATP levels, and protein synthesis | journal = Antimicrobial Agents and Chemotherapy | volume = 14 | issue = 1 | pages = 60–68 | date = July 1978 | pmid = 28693 | pmc = 352405 | doi = 10.1128/aac.14.1.60 }}</ref> A study from 2011 showed that antifungal effects of Zinc pyrithione work by [[copper toxicity]] mechanism that targets critical [[Iron-sulfur protein|iron–sulphur proteins]].<ref>{{cite journal | vauthors = Reeder NL, Xu J, Youngquist RS, Schwartz JR, Rust RC, Saunders CW | title = The antifungal mechanism of action of zinc pyrithione | journal = The British Journal of Dermatology | volume = 165 | issue = Suppl 2 | pages = 9–12 | date = October 2011 | pmid = 21919897 | doi = 10.1111/j.1365-2133.2011.10571.x }}</ref>


==See also==
== Health effects ==
⚫
Zinc pyrithione is approved for [[Over-the-counter drug|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.<ref>Leading references: {{cite journal | vauthors = Lamore SD, Cabello CM, Wondrak GT | title = The topical antimicrobial zinc pyrithione is a heat shock response inducer that causes DNA damage and PARP-dependent energy crisis in human skin cells | journal = Cell Stress & Chaperones | volume = 15 | issue = 3 | pages = 309–322 | date = May 2010 | pmid = 19809895 | pmc = 2866994 | doi = 10.1007/s12192-009-0145-6 }}</ref>

== Legal status ==

=== European Union ===
Use of zinc pyrithione is prohibited within cosmetic products in the [[European Union]] since December 2021.<ref name="EU Commission Regulation-2021">{{Citation |title=Commission Regulation (EU) 2021/1902 of 29&nbsp;October 2021 amending Annexes II, III and V to Regulation (EC) No&nbsp;1223/2009 of the European Parliament and of the Council as regards the use in cosmetic products of certain substances classified as carcinogenic, mutagenic or toxic for reproduction (Text with EEA relevance) |date=3 November 2021 |url=http://data.europa.eu/eli/reg/2021/1902/oj/eng |issue=32021R1902 |language=en |access-date=9 August 2022 |archive-date=24 February 2024 |archive-url=https://web.archive.org/web/20240224043427/https://eur-lex.europa.eu/eli/reg/2021/1902/oj/eng |url-status=live }}</ref> The substance was considered safe for use in rinse-off and leave-in products of different tested concentrations, but due to potential environmental toxicity consideration of the of use of zinc pyrithione was made against potential alternative substance ingredients. Due to no industry submission to the regulators supporting the continued use of zinc pyrithione and/or an absence of indications that there were no suitable alternatives to the substance: the use of zinc pyrithione became automatically prohibited within cosmetic products as an intended ingredient. This was as a consequence of zinc pyrithione addition to the Cosmetic Product Regulation (EC) No 1223/2009 Annex II list.<ref name="EU Commission Regulation-2021" />

=== 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. Alternatively, up to 0.25 percent when formulated to be left on the skin or scalp <ref>{{Cite web |title=21 CFR 358.710 -- Active ingredients for the control of dandruff, seborrheic dermatitis, or psoriasis. |url=https://www.ecfr.gov/current/title-21/chapter-I/subchapter-D/part-358/subpart-H/section-358.710 |access-date=2024-08-18 |website=www.ecfr.gov |language=en}}</ref>

== Environmental concerns ==
A large Swedish study shows that it is broken down in [[Water treatment|wastewater plants]] and does not release into waterways.<ref>{{Cite web |title=Results from the Swedish Screening Programme 2006 Subreport 3: Zinc pyrithione and Irgarol 1051 |url=https://www.ivl.se/download/18.343dc99d14e8bb0f58b7524/1445515665956/B1764.pdf |date=September 2007 |website=ivl.se |publisher={{Interlanguage link |Swedish Environmental Research Institute |sv |IVL Svenska Miljöinstitutet}} |archive-url=https://web.archive.org/web/20210526185320/https://www.ivl.se/download/18.343dc99d14e8bb0f58b7524/1445515665956/B1764.pdf |archive-date=26 May 2021 |access-date=5 March 2023 }}</ref> A Danish study shows that it biodegrades quickly, but that a risk of continuous leaching from boat paint may cause environmental toxicity.<ref>{{Cite web |title=Ecotoxocicological assessment of antifouling biocides and non-biocidal antifouling paints |url=http://www2.mst.dk/common/Udgivramme/Frame.asp?http://www2.mst.dk/udgiv/publications/2000/87-7944-084-3/html/kap04_eng.htm |archive-url=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 |archive-date=25 May 2012 |access-date=5 March 2023 |website=Miljøstyrelsen - Miljøministeriet |publisher=[[Ministry of Environment (Denmark)]]}}</ref>

== See also ==
* [[Ketoconazole]], another antifungal agent used in shampoos
* [[Ketoconazole]], another antifungal agent used in shampoos
* [[Piroctone olamine]], another antifungal agent used in shampoos
* [[Piroctone olamine]], another antifungal agent used in shampoos
Line 118: Line 125:
== References ==
== References ==
{{reflist}}
{{reflist}}

== External links ==
* {{cite web| url = https://druginfo.nlm.nih.gov/drugportal/name/Pyrithione%20zinc | publisher = U.S. National Library of Medicine| work = Drug Information Portal| title = Pyrithione zinc }}


{{Other dermatological preparations}}
{{Other dermatological preparations}}

Latest revision as of 13:15, 27 November 2024

Zinc pyrithione

Zinc pyrithione dimer
Names
IUPAC name
bis(2-pyridylthio)zinc 1,1'-dioxide
Other names
ZnP, Pyrithione Zinc, Zinc OMADINE, ZnPT
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.033.324 Edit this at Wikidata
UNII
  • InChI=1/C5H5NOS.Zn/c7-6-4-2-1-3-5(6)8;/h1-4,7H;/q;+2
    Key: YUYSACQNSLQTMI-UHFFFAOYAS
  • monomer: c1cc[n+]2c(c1)S[Zn-2]3(O2)O[n+]4ccccc4S3
  • dimer: [O+]01[n+]2ccccc2S[Zn-3]03(O[n+]4ccccc4S3)[O+]5[n+]6ccccc6S[Zn-3]157O[n+]8ccccc8S7
Properties
C10H8N2O2S2Zn
Molar mass 317.70 g/mol
Appearance colourless solid
Melting point 240 °C (464 °F; 513 K) (decomposition)[1]
Boiling point decomposes
8 ppm (pH 7)
Pharmacology
D11AX12 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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[2] and dandruff.

Structure of the compound

[edit]

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.[3] In solution, however, the dimers dissociate via scission of one Zn-O bond.[citation needed]

This compound was first described in the 1930s.[4]

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

Uses

[edit]

Medicine

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Zinc pyrithione can be used to treat dandruff and seborrhoeic dermatitis.[5][6][7] It also has antibacterial properties and is effective against many pathogens from the Streptococcus and Staphylococcus genera.[8] Its other medical applications include treatments of psoriasis, eczema, ringworm, fungus, athletes foot, dry skin, atopic dermatitis, tinea versicolor,[9][8] and vitiligo.[medical citation needed]

Paint

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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.[citation needed]

Sponges

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Zinc pyrithione is an antibacterial treatment for household sponges, as used by the 3M Corporation.[10][11]

Clothing

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A process to apply zinc pyrithione to cotton with washable results was patented in the United States in 1984.[12] Zinc pyrithione is used to prevent microbe growth in polyester.[13] Textiles with applied zinc pyrithione protect against odor-causing microorganisms. Export of antimicrobial textiles reached US$497.4 million in 2015.[14]

Mechanism of action

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Antibacterial effect

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Zinc pyrithione is known to exhibit antibacterial activity by disrupting cell membrane integrity and essential metabolic functions in bacteria.[15]

Antifungal effect

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Its antifungal effect is thought to derive from its ability to disrupt membrane transport by blocking the proton pump that energizes the transport mechanism.[16] A study from 2011 showed that antifungal effects of Zinc pyrithione work by copper toxicity mechanism that targets critical iron–sulphur proteins.[17]

Health effects

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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.[18]

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European Union

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Use of zinc pyrithione is prohibited within cosmetic products in the European Union since December 2021.[19] The substance was considered safe for use in rinse-off and leave-in products of different tested concentrations, but due to potential environmental toxicity consideration of the of use of zinc pyrithione was made against potential alternative substance ingredients. Due to no industry submission to the regulators supporting the continued use of zinc pyrithione and/or an absence of indications that there were no suitable alternatives to the substance: the use of zinc pyrithione became automatically prohibited within cosmetic products as an intended ingredient. This was as a consequence of zinc pyrithione addition to the Cosmetic Product Regulation (EC) No 1223/2009 Annex II list.[19]

United States

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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. Alternatively, up to 0.25 percent when formulated to be left on the skin or scalp [20]

Environmental concerns

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A large Swedish study shows that it is broken down in wastewater plants and does not release into waterways.[21] A Danish study shows that it biodegrades quickly, but that a risk of continuous leaching from boat paint may cause environmental toxicity.[22]

See also

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References

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  1. ^ Entry on Zink-Pyrithion. at: Römpp Online. Georg Thieme Verlag, retrieved 5 November 2020.
  2. ^ Brayfield A, ed. (23 September 2011). "Pyrithione Zinc". Martindale: The Complete Drug Reference. Pharmaceutical Press. Archived from the original on 26 March 2020. Retrieved 28 March 2014.
  3. ^ Barnett BL, Kretschmar HC, Hartman FA (1977). "Structural characterization of bis(N-oxopyridine-2-thionato)zinc(II)". Inorg. Chem. 16 (8): 1834–8. doi:10.1021/ic50174a002.
  4. ^ Draganjac M. "Pyrithione zinc". www.cas.astate.edu. Arkansas State University. Archived from the original on 21 June 2007. Retrieved 24 August 2007.
  5. ^ Marks R, Pearse AD, Walker AP (April 1985). "The effects of a shampoo containing zinc pyrithione on the control of dandruff". The British Journal of Dermatology. 112 (4): 415–422. doi:10.1111/j.1365-2133.1985.tb02314.x. PMID 3158327. S2CID 23368244.
  6. ^ Piérard-Franchimont C, Goffin V, Decroix J, Piérard GE (November 2002). "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. doi:10.1159/000066452. PMID 12476017. S2CID 23162407.
  7. ^ Ive FA (1991). "An overview of experience with ketoconazole shampoo". The British Journal of Clinical Practice. 45 (4): 279–284. PMID 1839767.
  8. ^ a b "Zinc pyrithione". Molecule of the Week Archive. American Chemical Society. Archived from the original on 1 March 2021. Retrieved 14 May 2021.
  9. ^ Faergemann J (2000). "Management of seborrheic dermatitis and pityriasis versicolor". American Journal of Clinical Dermatology. 1 (2): 75–80. doi:10.2165/00128071-200001020-00001. PMID 11702314. S2CID 43516330.
  10. ^ "Notice of Filing a Pesticide Petition to Establish". Archived from the original on 18 November 2017. Retrieved 3 December 2007.
  11. ^ Schroeder JW, Corn S, Battiste J, Stepanova N, Weiss C, Thiele J (December 2023). "In-situ immobilization of pyrithione in cellulose sponge for durable antimicrobial effect". Cellulose. 30 (18): 11753–11765. doi:10.1007/s10570-023-05595-w.
  12. ^ US US4443222A, Morris CE, Welch CM, issued 17 April 1984, assigned to The United States of America as represented by the Secretary of Agriculture 
  13. ^ "Zptech, Zinc Odor Control for Textiles". microban.com. Microban International. Archived from the original on 2 July 2023. Retrieved 23 September 2023.
  14. ^ Jain AK, Tesema AF (September 2017). "Development of antimicrobial textiles using zinc pyrithione". Research Journal of Textile and Apparel. 21 (3): 188–202. doi:10.1108/RJTA-06-2017-0031.
  15. ^ Blanchard C, Brooks L, Ebsworth-Mojica K, Didione L, Wucher B, Dewhurst S, et al. (26 October 2016). Fey PD (ed.). "Zinc Pyrithione Improves the Antibacterial Activity of Silver Sulfadiazine Ointment". mSphere. 1 (5). doi:10.1128/mSphere.00194-16. PMC 5023846. PMID 27642637.
  16. ^ Chandler CJ, Segel IH (July 1978). "Mechanism of the antimicrobial action of pyrithione: effects on membrane transport, ATP levels, and protein synthesis". Antimicrobial Agents and Chemotherapy. 14 (1): 60–68. doi:10.1128/aac.14.1.60. PMC 352405. PMID 28693.
  17. ^ Reeder NL, Xu J, Youngquist RS, Schwartz JR, Rust RC, Saunders CW (October 2011). "The antifungal mechanism of action of zinc pyrithione". The British Journal of Dermatology. 165 (Suppl 2): 9–12. doi:10.1111/j.1365-2133.2011.10571.x. PMID 21919897.
  18. ^ Leading references: Lamore SD, Cabello CM, Wondrak GT (May 2010). "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. doi:10.1007/s12192-009-0145-6. PMC 2866994. PMID 19809895.
  19. ^ a b Commission Regulation (EU) 2021/1902 of 29 October 2021 amending Annexes II, III and V to Regulation (EC) No 1223/2009 of the European Parliament and of the Council as regards the use in cosmetic products of certain substances classified as carcinogenic, mutagenic or toxic for reproduction (Text with EEA relevance), 3 November 2021, archived from the original on 24 February 2024, retrieved 9 August 2022
  20. ^ "21 CFR 358.710 -- Active ingredients for the control of dandruff, seborrheic dermatitis, or psoriasis". www.ecfr.gov. Retrieved 18 August 2024.
  21. ^ "Results from the Swedish Screening Programme 2006 Subreport 3: Zinc pyrithione and Irgarol 1051" (PDF). ivl.se. Swedish Environmental Research Institute  [sv ]. September 2007. Archived from the original (PDF) on 26 May 2021. Retrieved 5 March 2023.
  22. ^ "Ecotoxocicological assessment of antifouling biocides and non-biocidal antifouling paints". Miljøstyrelsen - Miljøministeriet. Ministry of Environment (Denmark). Archived from the original on 25 May 2012. Retrieved 5 March 2023.
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