関: zinc pyrithione

WordNet

coat or cover with zinc
a bluish-white lustrous metallic element; brittle at ordinary temperatures but malleable when heated; used in a wide variety of alloys and in galvanizing iron; it occurs naturally as zinc sulphide in zinc blende (同)Zn, atomic number 30

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亜鉛(金属元素;化学記号は Zn)

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/01/22 17:59:55」(JST)

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Zinc pyrithione is a coordination complex of zinc. This colourless solid is used as an antifungal and antibacterial agent.

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

Medical

Zinc pyrithione is best known for its use in treating dandruff and seborrhoeic dermatitis.^[4] It also has antibacterial properties and is effective against many pathogens from the Streptococcus and Staphylococcus genera. Its other medical applications include treatments of psoriasis, eczema, ringworm, fungus, athletes foot, dry skin, atopic dermatitis, tinea, and vitiligo.

In paint

Due to its low solubility in water (8 ppm at neutral pH), zinc pyrithione is suitable for use in outdoor paints and other products that provide protection against mildew and algae. It is an effective algaecide. It is chemically incompatible with paints relying on metal carboxylate curing agents. When used in latex paints with water containing high amount of iron, a sequestering agent that will preferentially bind the iron ions is needed. Its decomposition by ultraviolet light is slow, providing years of protection even against direct sunlight.

In sponges

Zinc pyrithione is also used as an antibacterial treatment for household sponges, most notably by the 3M Corporation.^[5]

Mechanism of action

Its antifungal effect is proposed to derive from its ability to disrupt membrane transport by blocking the proton pump that energizes the transport mechanism.^[6]

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 antidandruff shampoos. However, in its industrial forms and strengths, it may be harmful by contact or ingestion. Zinc pyrithione can trigger a variety of responses.^[7]

References

^ Thieme Chemistry (Hrsg.): Römpp Online. Version 3.1. Georg Thieme Verlag, Stuttgart 2007.
^ Barnett, B. L.; Kretschmar, H. C.; Hartman, F. A. (1977). "Structural characterization of bis(N-oxopyridine-2-thionato)zinc(II)". Inorg. Chem. 16 (8): 1834–8. doi:10.1021/ic50174a002.
^ "astate.edu". Archived from the original on 2007-06-21. http://web.archive.org/web/20070621193113/http://www.cas.astate.edu/draganjac/pyrithionezinc.html. Retrieved 2007-08-24.
^ "Management of Seborrheic Dermatitis and Pityriasis Versicolor" Faergemann, J. American Journal of Clinical Dermatology 2000, Vol. 1, p75-80. ISSN 11750561
^ Notice of Filing a Pesticide Petition to Establish
^ Chandler CJ, Segel IH (1978). "Mechanism of the Antimicrobial Action of Pyrithione: Effects on Membrane Transport, ATP Levels, and Protein Synthesis". Antimicrob. Agents Chemother. 14 (1): 60–8. PMC 352405. PMID 28693. http://aac.asm.org/cgi/pmidlookup?view=long&pmid=28693.
^ 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 cultured human skin cells.". Cell Stress Chaperones 15 (3): 309–22. doi:10.1007/s12192-009-0145-6. PMC 2866994. PMID 19809895. //www.ncbi.nlm.nih.gov/pmc/articles/PMC2866994/.

External links

Some toxicity information on industrial uses
Article Omni Brain: Dandruff Shampoo to Calm Seizures, Apr. 2007
Record in the Household Products Database of NLM

UpToDate Contents

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1. 癜風 tinea versicolor pityriasis versicolor
2. 思春期および成人における脂漏性皮膚炎 seborrheic dermatitis in adolescents and adults
3. 皮膚炎の概要 overview of dermatitis
4. 乳児における新生児頭部皮膚炎および脂漏性皮膚炎 cradle cap and seborrheic dermatitis in infants
5. 瘢痕性脱毛症（CCCA） central centrifugal cicatricial alopecia

English Journal

Antineoplastic activity of ouabain and pyrithione zinc in acute myeloid leukemia.

Tailler M, Senovilla L, Lainey E, Thépot S, Métivier D, Sébert M, Baud V, Billot K, Fenaux P, Galluzzi L, Boehrer S, Kroemer G, Kepp O.SourceINSERM, U848, Villejuif, France.
Oncogene.Oncogene.2012 Jul 26;31(30):3536-46. doi: 10.1038/onc.2011.521. Epub 2011 Nov 21.
Despite recent progress in the treatment of acute myeloid leukemia (AML), the prognosis of this rather heterogeneous disease remains poor and novel chemotherapeutics that specifically target leukemic cells must be developed. To address this need at the preclinical level, we implemented a high conten
PMID 22105358

Dandruff/seborrhoeic dermatitis is characterized by an inflammatory genomic signature and possible immune dysfunction: transcriptional analysis of the condition and treatment effects of zinc pyrithione.

Mills KJ, Hu P, Henry J, Tamura M, Tiesman JP, Xu J.SourceThe Procter and Gamble Company, Miami Valley Innovation Center, 11810 East Miami River Road, Cincinnati, OH 45252, USA. mills.kj@pg.com
The British journal of dermatology.Br J Dermatol.2012 Jun;166 Suppl 2:33-40. doi: 10.1111/j.1365-2133.2012.10863.x.
BACKGROUND: Dandruff/seborrhoeic dermatitis is a common scalp condition that is characterized by flakes, pruritus and sometimes mild erythema. These symptoms reflect tissue level events that are poorly understood at the molecular level.OBJECTIVES: The purpose of this work was: (i) to compare gene ex
PMID 22670617

Japanese Journal

オオミジンコ胚への重金属イオン及び重金属ピリチオン錯体の毒性

菊地幹夫,小野寺浩樹,佐藤朱美 [他]
環境毒性学会誌 17(1), 33-40, 2014-08
NAID 40020202301

亜鉛トランスポーターZIP9によるB細胞受容体シグナルの活性化制御

谷口将済,榎本秀一,廣村信
薬学雑誌. 乙号 134(7), 809-812, 2014
… Zinc is the essential trace element and important for all living organisms. … Zinc functions not only as a nutritional factor, but also as a second messenger. … However, the effects of intracellular zinc on the B cell-receptor (BCR) signaling pathway are not poorly understood. … Here, we indicate that the ZIP9 induces increase in intracellular zinc level and plays an important role in the phosphorylation of Akt and Erk in response to BCR activation. …
NAID 130004756449

水環境における銅ピリチオン防汚剤の運命に及ぼす底質の影響

Togosmaa LUVSANTSENDT,岡村秀雄,浅岡聡
環境化学 23(2), 65-72, 2013
… Copper pyrithione (CuPT) and zinc pyrithiones used as alternatives to organotin antifoulants are toxic to aquatic organisms and are rapidly photolyzed by sunlight. …
NAID 130004513920

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リンク元	「ジンクピリチオン」「zinc pyrithione」「亜鉛ピリチオン」

「ジンクピリチオン」

Zinc pyrithione
	IUPAC name bis(2-pyridylthio)zinc 1,1'-dioxide
	Other names ZnP, pyrithione zinc, zinc OMADINE
Identifiers
CAS number	13463-41-7
PubChem	3005837
ChemSpider	21513957
UNII	R953O2RHZ5
ChEMBL	CHEMBL1200471
ATC code	D11AX12
Jmol-3D images	Image 1
	SMILES c1cc[n+]2c(c1)S[Zn-2]3(O2)O[n+]4ccccc4S3 ;
	InChI InChI=1/C5H5NOS.Zn/c7-6-4-2-1-3-5(6)8;/h1-4,7H;/q;+2; Key: YUYSACQNSLQTMI-UHFFFAOYAS ;
Properties
Molecular formula	C10H8N2O2S2Zn
Molar mass	317.70 g/mol
Appearance	colourless solid
Melting point	240 °C (decomp.)
Boiling point	decomp.
Solubility in water	8 ppm (pH 7)
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references