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Zinc pyrithione

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). Each zinc is bonded to two sulfur and three oxygen centers. In solution, however, the dimers dissociate via scission of one Zn-O bond.

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. It also has antibacterial properties and is effective against many pathogens from the streptococcus and staphylococcus class. Its other medical applications include treatments of psoriasis, eczema, ringworm, fungus, athletes foot, dry skin, atypical dermatitis, tinea, and vitiligo.

Zinc pyrithione is approved for over-the-counter topical use in the United States as a treatment for dandruff. It is the active ingredient in several anti-dandruff shampoos such as Head & Shoulders. However, in its industrial forms and strengths, it may be harmful by contact or ingestion. Recent research suggests that zinc pyrithione is a potent heat shock response inducer that may cause DNA damage and PARP-dependent energy crisis in cultured human keratinocytes and melanocytes.

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 and the water contains 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.

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. Experiments have suggested that fungi are capable of inactivating pyrithione in low concentrations.

References

^ Thieme Chemistry (Hrsg.): Rmpp Online. Version 3.1. Georg Thieme Verlag, Stuttgart 2007.

^ "astate.edu". http://www.cas.astate.edu/draganjac/pyrithionezinc.html. Retrieved 2007-08-24. 

^ "What is Skin Zinc?". http://www.wisegeek.com/what-is-skin-zinc.htm. Retrieved 2007-08-24. 

^ Barnett, B. L.; Kretschmar, H. C.; Hartman, F. A. (1977). "Structural characterization of bis(N-oxopyridine-2-thionato)zinc(II)". Inorg. Chem. 16 (8): 18341838. doi:10.1021/ic50174a002. 

^ The topical antimicrobial zinc pyrithione is a heat shock response inducer that causes DNA damage and PARP-dependent energy crisis in human skin cells. Lamore SD, Cabello CM, Wondrak GT. Cell Stress Chaperones. 2009 Oct 7. [Epub ahead of print

^ 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): 608. doi:10.1128/AAC.. PMID 28693. PMC 352405. http://aac.asm.org/cgi/pmidlookup?view=long&pmid=28693. 

^ 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): 1. PMID 28693. PMC 352405. http://www.pubmedcentral.nih.gov/picrender.fcgi?artid=352405&blobtype=pdf. "At ow pyrithione concentrations, transport inhibition plateaued at some finite value. This observation suggests that the fungi can detoxify low levels of the inhibitor.". 

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

v  d  e

Other dermatological preparations (D11)

Medicated shampoos

Cetrimide - Cadmium compounds - Selenium compounds - Povidone-iodine - Sulfur compounds - Xenysalate

Other dermatologicals

Seborrhoeic dermatitis/dandruff

Lithium succinate  Pyrithione zinc

Skin whitening/depigmenting

Hydroquinone  Mequinol  Monobenzone

Anti-inflammatory/Immunomodulators

Oxaceprol  Gamolenic acid  Pimecrolimus  Tacrolimus  Alitretinoin

Baldness treatments

5-alpha-reductase inhibitor (Finasteride)  potassium channel opener (Minoxidil)

Hair growth inhibitors

Eflornithine

Other

Calcium gluconate  Magnesium sulfate  Tiratricol

Categories: Antifungals | Cosmetic chemicals | Zinc compounds
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