Zinc pyrithione

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Zinc pyrithione
Zink-Pyrithion.svg
Zinc-pyrithione-dimer-3D-balls.png
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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
Appearancecolourless 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).
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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

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

Medicine

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

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

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

Clothing

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

Antibacterial effect

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

Antifungal effect

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

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]

European Union

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 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

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

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

Related Research Articles

<span class="mw-page-title-main">Dermatitis</span> Inflammatory disease of the skin

Dermatitis is a term used for different types of skin inflammation, typically characterized by itchiness, redness and a rash. In cases of short duration, there may be small blisters, while in long-term cases the skin may become thickened. The area of skin involved can vary from small to covering the entire body. Dermatitis is also called eczema but the same term is often used for the most common type of skin inflammation, atopic dermatitis.

<span class="mw-page-title-main">Methylisothiazolinone</span> Chemical compound

Methylisothiazolinone, MIT, or MI, is the organic compound with the formula S(CH)2C(O)NCH3. It is a white solid. Isothiazolinones, a class of heterocycles, are used as biocides in numerous personal care products and other industrial applications. MIT and related compounds have attracted much attention for their allergenic properties, e.g. contact dermatitis.

<span class="mw-page-title-main">Dandruff</span> Skin condition of the scalp

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, is known as seborrhoeic dermatitis.

<span class="mw-page-title-main">Tinea versicolor</span> Skin disease

Tinea 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 is responsible for a small number of cases. These yeasts are normally found on the human skin and become troublesome only under certain conditions, such as a warm and humid environment, although the exact conditions that cause initiation of the disease process are poorly understood.

<span class="mw-page-title-main">Seborrhoeic dermatitis</span> Skin disease

Seborrhoeic dermatitis is a long-term skin disorder. Symptoms include flaky, scaly, greasy, and occasionally itchy and inflamed skin. Areas of the skin rich in oil-producing glands are often affected including the scalp, face, and chest. It can result in social or self-esteem problems. In babies, when the scalp is primarily involved, it is called cradle cap. Mild seborrhoeic dermatitis of the scalp may be described in lay terms as dandruff due to the dry, flaky character of the skin. However, as dandruff may refer to any dryness or scaling of the scalp, not all dandruff is seborrhoeic dermatitis. Seborrhoeic dermatitis is sometimes inaccurately referred to as seborrhoea.

<span class="mw-page-title-main">Antifungal</span> Pharmaceutical fungicide or fungistatic used to treat and prevent mycosis

An antifungal medication, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis (thrush), serious systemic infections such as cryptococcal meningitis, and others. Such drugs are usually obtained by a doctor's prescription, but a few are available over the counter (OTC). The evolution of antifungal resistance is a growing threat to health globally.

<span class="mw-page-title-main">Ketoconazole</span> Antifungal chemical compound

Ketoconazole, sold under the brand name Nizoral, among others, is an antiandrogen, antifungal, and antiglucocorticoid medication used to treat a number of fungal infections. Applied to the skin it is used for fungal skin infections such as tinea, cutaneous candidiasis, pityriasis versicolor, dandruff, and seborrheic dermatitis. Taken by mouth it is a less preferred option and only recommended for severe infections when other agents cannot be used. Other uses include treatment of excessive male-patterned hair growth in women and Cushing's syndrome.

<i>Malassezia</i> Genus of fungi

Malassezia is a genus of fungi.

<span class="mw-page-title-main">Ciclopirox</span> Antifungal medication

Ciclopirox is a medication used for the treatment of moderate onychomycosis of fingernails and toenails, and for the treatment of seborrheic dermatitis.

<span class="mw-page-title-main">Cradle cap</span> Crusting or scaling of a babys scalp

Cradle cap is crusty or oily scaly patches on a baby's scalp. The condition is not painful or itchy, but it can cause thick white or yellow scales that are not easy to remove. Cradle cap most commonly begins sometime in the first three months but can occur in later years. Similar symptoms in older children are more likely to be dandruff than cradle cap. The rash is often prominent around the ear, the eyebrows or the eyelids. It may appear in other locations as well, where it is called infantile seborrhoeic dermatitis. Cradle cap is just a special—and more benign—case of this condition. The exact cause of cradle cap is not known. Cradle cap is not spread from person to person. It is also not caused by poor hygiene. It is not an allergy, and it is not dangerous. Cradle cap often lasts a few months. In some children, the condition can last until age 2 or 3.

Selenium disulfide, also known as selenium sulfide, is a chemical compound and medication used to treat seborrheic dermatitis, dandruff, and pityriasis versicolor. It is applied to the affected area as a lotion or shampoo. Symptoms frequently return if treatment is stopped.

<span class="mw-page-title-main">Sulfacetamide</span> Sulfonamide antibiotic

Sulfacetamide is a sulfonamide antibiotic commonly used in the treatment of bacterial infections, particularly those affecting the eyes and skin. It functions by inhibiting the synthesis of folic acid in bacteria, which is essential for their growth and reproduction, thereby exerting a bacteriostatic effect. Available in various forms, including eye drops, topical solutions, and creams, sulfacetamide is often prescribed for conditions such as conjunctivitis, seborrheic dermatitis, and acne vulgaris. Its efficacy, coupled with a relatively low risk of side effects, makes it a widely utilized agent in both ophthalmic and dermatologic care.

<i>Malassezia furfur</i> Species of fungus

Malassezia furfur is a species of yeast that is naturally found on the skin surfaces of humans and some other mammals. It is associated with a variety of dermatological conditions caused by fungal infections, notably seborrhoeic dermatitis and tinea versicolor. As an opportunistic pathogen, it has further been associated with dandruff, malassezia folliculitis, pityriasis versicolor (alba), and malassezia intertrigo, as well as catheter-related fungemia and pneumonia in patients receiving hematopoietic transplants.

<span class="mw-page-title-main">Isothiazolinone</span> Chemical compound

Isothiazolinone (; sometimes isothiazolone) is an organic compound with the formula (CH)2SN(H)CO. A white solid, it is structurally related to isothiazole. Isothiazolone itself is of limited interest, but several of its derivatives are widely used preservatives and antimicrobials.

<span class="mw-page-title-main">Shampoo</span> Hair care product

Shampoo is a hair care product, typically in the form of a viscous liquid, that is formulated to be used for cleaning (scalp) hair. Less commonly, it is available in solid bar format. Shampoo is used by applying it to wet hair, massaging the product in the hair, roots and scalp, and then rinsing it out. Some users may follow a shampooing with the use of hair conditioner.

<span class="mw-page-title-main">Climbazole</span> Chemical compound

Climbazole is a topical antifungal agent commonly used in the treatment of human fungal skin infections such as dandruff, seborrhoeic dermatitis and eczema. Climbazole has shown a high in vitro and in vivo efficacy against Malassezia spp. that appear to play an important role in the pathogenesis of dandruff. Its chemical structure and properties are similar to other azole fungicides such as ketoconazole, clotrimazole and miconazole.

Anti-seborrheics are drugs effective in seborrheic dermatitis. Selenium sulfide, zinc pyrithione, corticosteroids, imidazole antifungals, and salicylic acid are common anti-seborrheics.

<span class="mw-page-title-main">Pyrithione</span> Chemical compound

Pyrithione is the common name of an organosulfur compound with molecular formula C
5
H
5
NOS
, 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(1H)-pyridinethione and the minor form being the thiol 2-mercaptopyridine N-oxide; it crystallises in the thione form. It is usually prepared from either 2-bromopyridine, 2-chloropyridine, or 2-chloropyridine N-oxide, and is commercially available as both the neutral compound and its sodium salt. It is used to prepare zinc pyrithione, which is used primarily to treat dandruff and seborrhoeic dermatitis in medicated shampoos, though is also an anti-fouling agent in paints.

<span class="mw-page-title-main">Ethyl lauroyl arginate</span> Chemical compound

Ethyl lauroyl arginate (LAE) is a food preservative, antimicrobial compound, and drug more commonly known as E243. It is used to treat dermatological disorders and is often provided in the form of its hydrochloride salt. LAE is an amino acid-based surfactant with broad-spectrum antimicrobial activity, high biodegradability and low toxicity. Due to these features, LAE is a preservative used in food and cosmetic formulations.

Topical antifungaldrugs are used to treat fungal infections on the skin, scalp, nails, vagina or inside the mouth. These medications come as creams, gels, lotions, ointments, powders, shampoos, tinctures and sprays. Most antifungal drugs induce fungal cell death by destroying the cell wall of the fungus. These drugs inhibit the production of ergosterol, which is a fundamental component of the fungal cell membrane and wall.

References

  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. 1 2 "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. 1 2 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.