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Zinc pyrithione

 

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Zinc pyrithione



 
 
Zinc pyrithione is a coordination complex of zinc
Zinc

Zinc is a metallic chemical element with the symbol Zn and atomic number 30. It is a first-row transition metal of the group 12 element of the periodic table....
. This colourless solid is used as an antifungal and antibacterial agent. This coordination complex, which has many names, was first reported in the 1930s.

pyrithione ligands, which are formally monoanions, are chelated
Chelation

Chelation is the binding or complex of a bi- or multidentate ligand. These ligands, which are often organic compounds, are called chelants, chelators, chelating agents, or sequestration....
 to Zn2+ via oxygen
Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
 and sulfur
Sulfur

Sulfur or sulphur is the chemical element that has the atomic number 16. It is denoted with the symbol S. It is an abundant Valence non-metal....
 centers. In the crystalline state, zinc pyrithione exists as a centrosymmetric dimer (see figure).






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Zinc pyrithione is a coordination complex of zinc
Zinc

Zinc is a metallic chemical element with the symbol Zn and atomic number 30. It is a first-row transition metal of the group 12 element of the periodic table....
. This colourless solid is used as an antifungal and antibacterial agent. This coordination complex, which has many names, was first reported in the 1930s.

Structure of the compound

The pyrithione ligands, which are formally monoanions, are chelated
Chelation

Chelation is the binding or complex of a bi- or multidentate ligand. These ligands, which are often organic compounds, are called chelants, chelators, chelating agents, or sequestration....
 to Zn2+ via oxygen
Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
 and sulfur
Sulfur

Sulfur or sulphur is the chemical element that has the atomic number 16. It is denoted with the symbol S. It is an abundant Valence non-metal....
 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
Dandruff

Dandruff is due to the excessive shedding of dead skin cells from the scalp. As it is normal for skin cell s to die and flake off, a small amount of flaking is normal and in fact quite common....
 and seborrheic dermatitis. It also has antibacterial properties and is effective against many pathogen
Pathogen

A pathogen , infectious agent, or germ, is a biological agent that causes disease or illness to its Host .There are several substrates and pathways whereby pathogens can invade a host; the principal pathways have different episodic time frames, but soil contamination has the longest or most persistent potential for harboring...
s from the streptococcus
Streptococcus

Streptococcus is a genus of sphere Gram-positive bacterium belonging to the phylum Firmicutes and the lactic acid bacteria group. Cell division occurs along a single Coordinate axis in these bacteria, and thus they grow in chains or pairs, hence the name — from Greek language st?ept?? streptos, meaning easily bent or twisted,...
 and staphylococcus
Staphylococcus

Staphylococcus is a genus of Gram-positive Bacterium. Under the microscope they appear round , and form in grape-like clusters.The Staphylococcus genus include just thirty-three species....
 class. Its other medical applications include treatments of psoriasis
Psoriasis

Psoriasis is a chronic, non-contagious autoimmune disease which affects the skin and joints. It commonly causes red scaly patches to appear on the skin....
, eczema
Eczema

Eczema is a form of dermatitis, or inflammation of the epidermis. The term eczema is broadly applied to a range of persistent skin conditions....
, ringworm
Ringworm

Ringworm is a fungal infection of the skin in humans and domestic animals such as sheep and cattle. Fungi are organisms that survive by eating plant or animal material....
, fungus
Fungus

A fungus is a Eukaryote organism that is a member of the Kingdom Fungi . The fungi are a monophyletic group, also called the Eumycota , that is phylogeny distinct from the morphologically similar slime molds and water molds ....
, athletes foot, dry skin, atypical dermatitis, tinea
Tinea

Tinea is a general term used to describe skin mycoses. The term "ringworm" is even less precise, but is usually considered a synonym.It is sometimes equated with dermatophytosis, and it is true that most conditions identified as "tinea" are members of the imperfect fungi that make up the dermatophytes....
, and vitiligo
Vitiligo

Vitiligo or leukoderma is a Chronic skin disorder that causes loss of Biological pigment, resulting in irregular pale patches of skin. It occurs when the melanocytes, cells responsible for skin pigmentation, die or are unable to function....
.

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

Dandruff is due to the excessive shedding of dead skin cells from the scalp. As it is normal for skin cell s to die and flake off, a small amount of flaking is normal and in fact quite common....
. It is the active ingredient in several anti-dandruff shampoos such as Head & Shoulders
Head & Shoulders

Head & Shoulders is a brand of anti-dandruff shampoo produced by Procter & Gamble. Head & Shoulders Classic Clean Shampoo is the top selling shampoo in the United States by Dollar Sales....
. However, in its industrial forms and strengths, it may be harmful by contact or ingestion.

In paint

Due to its low solubility
Solubility

Solubility is often seen as a property of a substance; for instance the solubility of a solid substance usually refers to the concentration of the substance in a liquid that has reached equilibrium with the substance in solid phase ....
 in water
Water

Water is a common chemical substance that is essential for the survival of all known forms of life. In typical usage, water refers only to its liquid form or States of matter, but the substance also has a solid state, ice, and a gaseous state, water vapor or steam....
 (8 ppm at neutral pH), zinc pyrithione is suitable for use in outdoor paint
Paint

Paint is any liquid, liquifiable, or mastic composition which after application to a Substrate in a thin layer is converted to an opaque solid film....
s and other products that provide protection against mildew
Mildew

Mildew refers to certain kinds of mold or fungus. In Old English, it meant honeydew , and later came to mean mildew in the modern senses.*The term mildew is often used generically to refer to mold growth, usually with a flat growth habit....
 and algae
Algae

Algae are a large and diverse group of simple, typically autotrophic organisms, ranging from unicellular to multicellular forms. The largest and most complex marine forms are called seaweeds....
. It is an effective algaecide
Algaecide

An algaecide or algicide is a substance used for killing and preventing the growth of algae....
. 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
Iron

Iron is a chemical element with the symbol Fe and atomic number 26. Iron is a Group 8 element and period 4 element. Iron is lustrous and silvery in color....
, a sequestering agent that will preferentially bind the iron ions is needed. Its decomposition by ultraviolet
Ultraviolet

Ultraviolet light is electromagnetic radiation with a wavelength shorter than that of visible light, but longer than x-rays, in the range 400 nanometer to 10 nm, and energies from 3 Electron volt to 124 eV....
 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
Cell membrane

The cell membrane is the interface between the cellular machinery inside the cell and the fluid outside.It is a semipermeable lipid bilayer found in all cell ....
 transport by blocking the proton pump that energizes the transport mechanism. Fungi are capable of inactivating pyrithione in low concentrations.

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