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Zinc omadine (ZnPT, zinc pyrithione) is a chemical compound that can be used as an antifungal agent.
Zinc omadine (ZnPT, zinc pyrithione) has been shown to have genotoxic activity in vitro and in vivo.
Zinc omadine (ZnPT, zinc pyrithione) binds to the surface of the fungal cell wall and inhibits the synthesis of ergosterol, a component of the fungal cell membrane.
CAS: 13463-41-7
MF: C10H8N2O2S2Zn
MW: 317.7
EINECS: 236-671-3
Synonyms
1-HYDROXY-2-PYRIDINE THIONE, ZN SALT;1-HYDROXYPYRIDINE-2-THIONE ZINC;Pyrithione zincique;Bis[(1-oxylatopyridinium)-2-ylthio] zinc;Bis[(1-oxylatopyridinium-2-yl)thio]zinc;Bis[[(pyridine 1-oxide)-2-yl]thio] zinc salt;Bis(2-pyridylthio) Zinc 1,1'-Dioxide 1-Hydroxypyridine-2-thione Zinc Salt 2-Pyridinethiol 1-Oxide Zinc Salt Zinc Pyrithione;zincpolyanemine
This binding prevents the formation of an ergosterol-zinc complex with cytochrome P450 enzymes, which are required for sterol biosynthesis, leading to inhibition of energy metabolism.
The model system for Zinc omadine (ZnPT, zinc pyrithione) is a mixture of 1-hydroxypyridine-2-thione (1HP) and zinc ions in water.
Some studies have shown that Zinc omadine (ZnPT, zinc pyrithione) can cause long-term toxicity, including glycol ether toxicity, when applied topically on hair or skin.
Acute toxicities may include skin irritation or contact dermatitis from shampoos containing this substance.
Zinc omadine (ZnPT, zinc pyrithione) is the pyrithione complexes of zinc bromide, in the early 1930s, was already synthesized and used as a topical antifungal or antibacterial agent.
At room temperature Zinc omadine (ZnPT, zinc pyrithione) is white to yellow crystalline powder.
Slight characteristic odor.
Insoluble in water.
Solubility: water 15mg/kg; pH = 8 Water 35mg/kg; Ethanol 100mg/kg; polyethylene glycol (PEG400) 2000mg/kg. A pH optimum range of 4.5 to 9.5; mass fraction of 10% suspension pH3.6.
Zinc omadine (ZnPT, zinc pyrithione) react with cationic and non-ionic surfactants forming insoluble precipitate, unstable in the light and oxidizer, when at higher temperatures ,Zinc omadine (ZnPT, zinc pyrithione) is not stable to acids and bases.
Zinc omadine (ZnPT, zinc pyrithione) is not compatible with EDTA, non-ionic surfactants make it partially deactivated.
When with the presence of heavy metals, chelation or anti-sequestration will occur, and these chelates are insoluble in water.
EEC and GB7916-87 provide that maximum allowable concentration of mass fraction of Zinc omadine (ZnPT, zinc pyrithione) on cosmetics is 0.5%, only for cleaning after using products.
General concentration 250~1000mg/kg (active), Zinc omadine (ZnPT, zinc pyrithione) can be used in gels, creams, lotions, talcum powder and anti-dandruff shampoo, deodorant and also for disinfecting articles.
Zinc omadine (ZnPT, zinc pyrithione) shampoos (in concentrations between 1 to 2%) and shampoos with selenium sulide have been reported to be effective in the treatment of scalp psoriasis.
However,their efficacy has not been substantiated by controlled studies.
There is also some evidence that shampoos with antifungal agents (e.g.ketoconazole)can have a beneficial effect on scalp conditions.
Zinc omadine (ZnPT, zinc pyrithione) should be noted, however, that the effectiveness of these shampoos is much smaller than these containing tars, corticosteroids or keratolytics.
Zinc omadine (ZnPT, zinc pyrithione) is the active ingredient in several shampoos used to control dandruff and seborrheic dermatitis and is also effective in the therapy of tinea versicolor.
Zinc omadine (ZnPT, zinc pyrithione) remains unclear whether the beneficial effects are caused by an antiproliferative or antimicrobial effect or both.
Zinc omadine (ZnPT, zinc pyrithione) is substantive to the hair, allowing continued therapeutic effect after washing.
Zinc omadine (ZnPT, zinc pyrithione) is widely used in antidandruff shampoos and is a classic allergen. Concomitant reactions are expected to both zinc and sodium pyrithione.
Organometallics, such as Zinc pyrithione, are reactive with many other groups.
Incompatible with acids and bases.
Organometallics are good reducing agents and therefore incompatible with oxidizing agents.
Often reactive with water to generate toxic or flammable gases.
Zinc omadine (ZnPT, zinc pyrithione) is a coordination complex of zinc.
Zinc omadine (ZnPT, zinc pyrithione) has fungistatic (inhibiting the division of fungal cells) and bacteriostatic (inhibiting bacterial cell division) properties and is used in the treatment of seborrhoeic dermatitis 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 omadine (ZnPT, 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.
Zinc omadine (ZnPT, zinc pyrithione) was first described in the 1930s.
Zinc omadine (ZnPT, zinc pyrithione) is the conjugate base derived from 2-mercaptopyridine-N-oxide, a derivative of pyridine-N-oxide.
Zinc omadine (ZnPT, zinc pyrithione) Chemical Properties
Melting point: approximate 240℃
Density: 1.782 g/cm3(Temp: 25 °C)
Vapor pressure: 0Pa at 25℃
Storage temp.: Sealed in dry,Room Temperature
Solubility: almost transparency in Pyridine
Form: Powder
Color: White to Orange to Green
Odor: Mild Characteristic
Water Solubility: Insoluble (<0.1 g/100 mL at 21 ºC)
Merck: 14,7994
InChI: InChI=1S/2C5H5NOS.Zn/c2*7-6-4-2-1-3-5(6)8;/h2*1-4,8H;/q;;+2/p-2
InChIKey: OTPSWLRZXRHDNX-UHFFFAOYSA-L
LogP: 0.9 at 25℃ and pH7.5-7.7
Surface tension: 73mN/m at 7.22mg/L and 20℃
CAS DataBase Reference: 13463-41-7(CAS DataBase Reference)
EPA Substance Registry System: Zinc omadine (ZnPT, zinc pyrithione) (13463-41-7)
Uses
Shampoo for dandruff,Zinc omadine (ZnPT, zinc pyrithione) can inhibit Gram positive and negative bacteria and mold growth,Care hair Effectively , delay hair aging ,control white hair and hair loss generation.
Zinc omadine (ZnPT, zinc pyrithione) is also used as a cosmetic preservative, oil, paint biocide.
Zinc omadine (ZnPT, zinc pyrithione) has a strong killing power on fungi and bacteria so that it can effectively kill dandruff fungus,playing a role in dandruff.
Zinc omadine (ZnPT, zinc pyrithione) is a preservative against bacteria, fungi, and yeast.
Zinc omadine (ZnPT, zinc pyrithione) is unstable in light and in the presence of oxidizing agents.
Zinc omadine (ZnPT, zinc pyrithione) is useful in gels, creams, heavy lotions, and talcum powder.
Reactions may lead to photosensitive eczema and actinic reticuloid syndrome.
Zinc omadine (ZnPT, zinc pyrithione) is used as antifungal, antibacterial and antiseborrheic agent used in many shampoos and hair creams.
Zinc omadine (ZnPT, zinc pyrithione) is directly cytotoxic and has antimicrobial effects.
Zinc omadine (ZnPT, zinc pyrithione) is found in many shampoos (DHS-Zinc, Head and Shoulders) and should be applied for 5 minutes daily for 2 weeks.
Zinc omadine (ZnPT, zinc pyrithione) is the active ingredient in several shampoos used to control dandruff and seborrheic dermatitis and is also effective in the therapy of tinea versicolor.
Zinc omadine (ZnPT, zinc pyrithione) remains unclear whether the beneficial effects are caused by an antiproliferative or antimicrobial effect or both.
Zinc omadine (ZnPT, zinc pyrithione) is substantive to the hair, allowing continued therapeutic effect after washing.
Zinc omadine (ZnPT, zinc pyrithione) is used as anti-dandruff agent and bactericide in cosmetics, and is widely used in the preparation of anti-dandruff shampoo.
Mainly used in cosmetics, shampoo, skin care, but also used in adhesives, paints, paints, etc.
Medicine
Zinc omadine (ZnPT, zinc pyrithione) can be used to treat dandruff and seborrhoeic dermatitis.
Zinc omadine (ZnPT, zinc pyrithione) also has antibacterial properties and is effective against many pathogens from the Streptococcus and Staphylococcus genera.
Zinc omadine (ZnPT, zinc pyrithione)'s other medical applications include treatments of psoriasis, eczema, ringworm, fungus, athletes foot, dry skin, atopic dermatitis, tinea versicolor,and vitiligo.
Paint
Because of its low solubility in water (8 ppm at neutral pH), Zinc omadine (ZnPT, zinc pyrithione) is suitable for use in outdoor paints and other products that protect against mildew and algae.
Zinc omadine (ZnPT, zinc pyrithione) is an algaecide.
Zinc omadine (ZnPT, zinc pyrithione) is chemically incompatible with paints relying on metal carboxylate curing agents.
When Zinc omadine (ZnPT, zinc pyrithione) is used in latex paints with water containing much iron, a sequestering agent that preferentially binds the iron ions is needed.
Zinc omadine (ZnPT, zinc pyrithione) is decomposed by ultraviolet light slowly, providing years of protection in direct sunlight.
Sponges
Zinc omadine (ZnPT, zinc pyrithione) is an antibacterial treatment for household sponges, as used by the 3M Corporation.
Clothing
A process to apply Zinc omadine (ZnPT, zinc pyrithione) to cotton with washable results was patented in the United States in 1984.
Zinc omadine (ZnPT, zinc pyrithione) is used to prevent microbe growth in polyester.
Textiles with applied Zinc omadine (ZnPT, zinc pyrithione) protect against odor-causing microorganisms.
Export of antimicrobial textiles reached US$497.4 million in 2015.
Pharmaceutical Applications
Zinc omadine (ZnPT, zinc pyrithione) is a regulator of keratinization, selenium sulfide has antimicrobial properties and ketoconazole is an antifungal agent (i.e.can provide the reduction of the lipophilic yeast Malassezia furfur).
Synthesis
1000 g of sodium pyrithione, 20% aqueous solution (1.34 mmol of sodium pyrithione) was added to a 2L reactor equipped with a mechanical agitator and warmed to 70 °C with stirring.
To the solution was added 190 g of 50 % zinc chloride (0.7 mmol of zinc chloride) over 10 minutes.
After the completion of the addition, the solution was stirred at 70 °C for one hour, dehydrated and then washed with 500 g of distilled water.
The solid thus obtained was dried with a heated-air drier at 70 °C to have a moisture content of less than 0.5 % and ground with a hammer mill to obtain a find powder of Zinc omadine (ZnPT, zinc pyrithione).
The Zinc omadine (ZnPT, zinc pyrithione) thus obtained was 212 g with a yield of 99.5 %.
