Zinc pyrithione

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Zinc pyrithione
Zink-Pyrithion.svg
Zinc-pyrithione-dimer-3D-balls.png
Identifiers
CAS number 13463-41-7 YesY
PubChem 3005837
ChemSpider 21513957 YesY
UNII R953O2RHZ5 YesY
ChEMBL CHEMBL1200471
ATC code D11AX12
Jmol-3D images Image 1
Properties
Molecular formula C10H8N2O2S2Zn
Molar mass 317.70 g/mol
Appearance colourless solid
Melting point 240 °C (decomposition) [1]
Boiling point decomposes
Solubility in water 8 ppm (pH 7)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Zinc pyrithione is a 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.[2]

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.

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.

Uses[edit]

Medical[edit]

Zinc pyrithione is best known for its use in treating dandruff and seborrhoeic dermatitis.[5] 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[edit]

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[edit]

Zinc pyrithione is also used as an antibacterial treatment for household sponges, most notably by the 3M Corporation.[6]

Mechanism of action[edit]

Its antifungal effect is proposed to derive from its ability to disrupt membrane transport by blocking the proton pump that energizes the transport mechanism.[7]

Health effects[edit]

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.[8]

See also[edit]

References[edit]

  1. ^ Thieme Chemistry (Hrsg.): Römpp Online. Version 3.1. Georg Thieme Verlag, Stuttgart 2007.
  2. ^ Brayfield, A, ed. (23 September 2011). "Pyrithione Zinc". Martindale: The Complete Drug Reference. Pharmaceutical Press. Retrieved 28 March 2014. 
  3. ^ 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. 
  4. ^ "astate.edu". Archived from the original on 2007-06-21. Retrieved 2007-08-24. 
  5. ^ "Management of Seborrheic Dermatitis and Pityriasis Versicolor" Faergemann, J. American Journal of Clinical Dermatology 2000, Vol. 1, p75-80. ISSN 11750561
  6. ^ Notice of Filing a Pesticide Petition to Establish
  7. ^ 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. doi:10.1128/aac.14.1.60. PMC 352405. PMID 28693. 
  8. ^ 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. 

External links[edit]