Zinc pyrithione (or pyrithione zinc) is a

coordination complex A coordination complex consists of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of bound molecules or ions, that are in turn known as ''ligands'' or complexing agents. Many ...

zinc Zinc is a chemical element with the symbol Zn and atomic number 30. Zinc is a slightly brittle metal at room temperature and has a shiny-greyish appearance when oxidation is removed. It is the first element in group 12 (IIB) of the periodi ...

. It has

fungistatic Fungistatics are anti-fungal agents that inhibit the growth of fungus (without killing the fungus). The term ''fungistatic'' may be used as both a noun and an adjective. Fungistatics have applications in agriculture, the food industry, the paint ind ...

(inhibiting the division of fungal cells) and

bacteriostatic A bacteriostatic agent or bacteriostat, abbreviated Bstatic, is a biological or chemical agent that stops bacteria from reproducing, while not necessarily killing them otherwise. Depending on their application, bacteriostatic antibiotics, disinfect ...

(inhibiting bacterial cell division) properties and is used in the treatment of

seborrhoeic dermatitis Seborrhoeic dermatitis, sometimes inaccurately referred to as seborrhoea, is a long-term skin disorder. Symptoms include red, scaly, greasy, itchy, and inflamed skin. Areas of the skin rich in oil-producing glands are often affected including the ...

and

dandruff Dandruff is a skin condition that mainly affects the scalp. Symptoms include flaking and sometimes mild itchiness. It can result in social or self-esteem problems. A more severe form of the condition, which includes inflammation of the skin, ...

Structure of the compound

The

pyrithione Pyrithione is the common name of an organosulfur compound with molecular formula , chosen as an abbreviation of pyridinethione, and found in the Persian shallot. It exists as a pair of tautomers, the major form being the thione 1-hydroxy-2(1''H ...

ligands, which are formally monoanions, are

chelated Chelation is a type of bonding of ions and molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a polydentate (multiple bonded) ligand and a single central metal atom. These ligands are ...

to Zn²⁺ via

oxygen Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements as wel ...

and

sulfur Sulfur (or sulphur in British English) is a chemical element with the symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms form cyclic octatomic molecules with a chemical formula ...

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. In solution, however, the dimers dissociate via scission of one Zn-O bond. This compound was first described in the 1930s. Pyrithione is the

conjugate base A conjugate acid, within the Brønsted–Lowry acid–base theory, is a chemical compound formed when an acid donates a proton () to a base—in other words, it is a base with a hydrogen ion added to it, as in the reverse reaction it loses a ...

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

and

. It also has antibacterial properties and is effective against many

pathogen In biology, a pathogen ( el, πάθος, "suffering", "passion" and , "producer of") in the oldest and broadest sense, is any organism or agent that can produce disease. A pathogen may also be referred to as an infectious agent, or simply a germ ...

s from the ''

Streptococcus ''Streptococcus'' is a genus of gram-positive ' (plural ) or spherical bacteria that belongs to the family Streptococcaceae, within the order Lactobacillales (lactic acid bacteria), in the phylum Bacillota. Cell division in streptococci occurs ...

'' and ''

Staphylococcus ''Staphylococcus'' is a genus of Gram-positive bacteria in the family Staphylococcaceae from the order Bacillales. Under the microscope, they appear spherical (cocci), and form in grape-like clusters. ''Staphylococcus'' species are facultative ...

'' genera. Its other medical applications include treatments of

psoriasis Psoriasis is a long-lasting, noncontagious autoimmune disease characterized by raised areas of abnormal skin. These areas are red, pink, or purple, dry, itchy, and scaly. Psoriasis varies in severity from small, localized patches to complete ...

eczema Dermatitis is inflammation of the Human skin, skin, typically characterized by itchiness, erythema, redness and a rash. In cases of short duration, there may be small blisters, while in long-term cases the skin may become lichenification, thick ...

ringworm Dermatophytosis, also known as ringworm, is a fungal infection of the skin. Typically it results in a red, itchy, scaly, circular rash. Hair loss may occur in the area affected. Symptoms begin four to fourteen days after exposure. Multiple a ...

fungus A fungus ( : fungi or funguses) is any member of the group of eukaryotic organisms that includes microorganisms such as yeasts and molds, as well as the more familiar mushrooms. These organisms are classified as a kingdom, separately from th ...

athletes foot Athlete's foot, known medically as ''tinea pedis'', is a common skin infection of the feet caused by a fungus. Signs and symptoms often include itching, scaling, cracking and redness. In rare cases the skin may blister. Athlete's foot fungus m ...

dry skin Xeroderma, xerosis or xerosis cutis, or simply dry skin, is a skin condition characterized by excessively dry skin. The medical term ''xeroderma'', meaning "dry skin", derives from modern Latin, ''xero-'' 'dry' + Greek ''derma'' 'skin'. In most ...

atopic dermatitis Atopic dermatitis (AD), also known as atopic eczema, is a long-term type of inflammation of the skin (dermatitis). It results in puritis, itchy, red, swollen, and cracked skin. Clear fluid may come from the affected areas, which often thickens o ...

tinea versicolor Tinea versicolor (also pityriasis versicolor) is a condition characterized by a skin eruption on the trunk and proximal extremities. The majority of tinea versicolor is caused by the fungus '' Malassezia globosa'', although ''Malassezia furfur'' i ...

, and

vitiligo Vitiligo is a disorder that causes the skin to lose its color. Specific causes are unknown but studies suggest a link to immune system changes. Signs and symptoms The only sign of vitiligo is the presence of pale patchy areas of depigmen ...

Paint

Because of its low

solubility In chemistry, solubility is the ability of a substance, the solute, to form a solution with another substance, the solvent. Insolubility is the opposite property, the inability of the solute to form such a solution. The extent of the solubil ...

water Water (chemical formula ) is an inorganic, transparent, tasteless, odorless, and nearly colorless chemical substance, which is the main constituent of Earth's hydrosphere and the fluids of all known living organisms (in which it acts as a ...

(8 ppm at neutral pH), zinc pyrithione is suitable for use in outdoor

paint Paint is any pigmented liquid, liquefiable, or solid mastic composition that, after application to a substrate in a thin layer, converts to a solid film. It is most commonly used to protect, color, or provide texture. Paint can be made in many ...

s and other products that protect against

mildew Mildew is a form of fungus. It is distinguished from its closely related counterpart, mould, largely by its colour: moulds appear in shades of black, blue, red, and green, whereas mildew is white. It appears as a thin, superficial growth consi ...

and

algae Algae (; singular alga ) is an informal term for a large and diverse group of photosynthetic eukaryotic organisms. It is a polyphyletic grouping that includes species from multiple distinct clades. Included organisms range from unicellular mic ...

. It is an

algaecide Algaecide or algicide is a biocide used for killing and preventing the growth of algae, often defined in a loose sense that, beyond the biological definition, also includes cyanobacteria ("blue-green algae"). An algaecide may be used for controlle ...

. It is chemically incompatible with paints relying on metal carboxylate curing agents. When it is used in latex paints with water containing much

iron Iron () is a chemical element with symbol Fe (from la, ferrum) and atomic number 26. It is a metal that belongs to the first transition series and group 8 of the periodic table. It is, by mass, the most common element on Earth, right in f ...

, a sequestering agent that preferentially binds the iron ions is needed. It is decomposed by

ultraviolet Ultraviolet (UV) is a form of electromagnetic radiation with wavelength from 10 nanometer, nm (with a corresponding frequency around 30 Hertz, PHz) to 400 nm (750 Hertz, THz), shorter than that of visible light, but longer than ...

light slowly, providing years of protection in direct sunlight.

Sponges

Zinc pyrithione is an

antibacterial An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting bacterial infections, and antibiotic medications are widely used in the treatment and prevention of ...

treatment for household

sponge Sponges, the members of the phylum Porifera (; meaning 'pore bearer'), are a basal animal clade as a sister of the diploblasts. They are multicellular organisms that have bodies full of pores and channels allowing water to circulate through t ...

s, as used by the

3M Corporation 3M (originally the Minnesota Mining and Manufacturing Company) is an American multinational conglomerate operating in the fields of industry, worker safety, U.S. health care, and consumer goods. The company produces over 60,000 products unde ...

Clothing

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

Mechanism of action

Its antifungal effect is thought to derive from its ability to disrupt

membrane A membrane is a selective barrier; it allows some things to pass through but stops others. Such things may be molecules, ions, or other small particles. Membranes can be generally classified into synthetic membranes and biological membranes. B ...

transport by blocking the

proton pump A proton pump is an integral membrane protein pump that builds up a proton gradient across a biological membrane. Proton pumps catalyze the following reaction: : n one side of a biological membrane/sub> + energy n the other side of the membr ...

that energizes the transport mechanism.

Health effects

Zinc pyrithione is approved for over-the-counter topical use in the United States as a treatment for

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.Leading references:

Legal status

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). 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.

References

External links

* {{Portal bar , Medicine Anti-acne preparations Antifungals Antiseptics Cosmetics chemicals Pyridinium compounds Thiols Zinc compounds