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Pyrithione information


Pyrithione

Interconversion of pyrithione tautomers
thione form on the left, thiol form on the right
Names
Preferred IUPAC name
1-Hydroxy-2(1H)-pyridinethione (thione)
2-Pyridinethiol 1-oxide (thiol)
Other names
Omadine
thione: 1-Hydroxypyridine-2-thione
      N-Hydroxypyridine-2-thione
thiol: 2-Mercaptopyridine monoxide
        2-Mercaptopyridine N-oxide
        2-Mercaptopyridine 1-oxide
Identifiers
CAS Number
  • thione: 1121-30-8
  • thiol: 1121-31-9
  • 3811-73-2 thiolate salt: sodium 2-pyridinethiolate 1-oxide
  • 15922-78-8 thione salt: sodium 2-thioxo-1(2H)-pyridinolate
3D model (JSmol)
  • thione: Interactive image
  • thiol: Interactive image
  • thiolate salt: Interactive image
  • thione salt: Interactive image
Beilstein Reference
109936
ChEBI
  • thione: CHEBI:36578
  • thiol: CHEBI:36584
ChEMBL
  • thione: ChEMBL1650619
  • thiol: ChEMBL1356238
ChemSpider
  • thione: 1514
  • thiol: 10446934
  • 1513 thiolate salt
  • 18517 thione salt
DrugBank
  • DB06815
ECHA InfoCard 100.013.027 Edit this at Wikidata
EC Number
  • 214-328-9
  • thione: 214-329-4
Gmelin Reference
913415
PubChem CID
  • thione: 1570
  • 23685289 sodium pyrithione salt
UNII
  • 6GK82EC25D checkY
CompTox Dashboard (EPA)
  • DTXSID00149908 Edit this at Wikidata
InChI
  • thione: InChI=1S/C5H5NOS/c7-6-4-2-1-3-5(6)8/h1-4,7H
    Key: YBBJKCMMCRQZMA-UHFFFAOYSA-N
  • thiol: InChI=1S/C5H5NOS/c7-6-4-2-1-3-5(6)8/h1-4,8H
    Key: FGVVTMRZYROCTH-UHFFFAOYSA-N
  • thiolate salt: InChI=1S/C5H5NOS.Na/c7-6-4-2-1-3-5(6)8;/h1-4,8H;/q;+1/p-1
    Key: WNGMMIYXPIAYOB-UHFFFAOYSA-M
  • thione salt: InChI=1S/C5H4NOS.Na/c7-6-4-2-1-3-5(6)8;/h1-4H;/q-1;+1
    Key: XNRNJIIJLOFJEK-UHFFFAOYSA-N
SMILES
  • thione: c1ccn(c(=S)c1)O
  • thiol: C1=CC=[N+](C(=C1)S)[O-]
  • thiolate salt: c1cc[n+](c(c1)[S-])[O-].[Na+]
  • thione salt: c1ccn(c(=S)c1)[O-].[Na+]
Properties
Chemical formula
C5H5NOS
Molar mass 127.16 g·mol−1
Appearance Beige crystalline powder
Melting point 70 to 73 °C (158 to 163 °F; 343 to 346 K)
Solubility in water
2.5 g L−1 at 20 °C
Solubility Soluble: benzene, chloroform, dichloromethane, dimethylformamide, dimethylsulfoxide, ethyl acetate[1]
Slightly soluble: diethyl ether, ethanol, methyl tert-butyl ether, tetrahydrofuran[1]
Acidity (pKa) −1.95 (proton addition), 4.6[2][3]
Hazards
GHS labelling:
Pictograms
GHS06: Toxic
Signal word
Danger
Hazard statements
H301, H315, H319, H335
Precautionary statements
P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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.[4] 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.[5] It is usually prepared from either 2-bromopyridine,[1] 2-chloropyridine,[6][7] or 2-chloropyridine N-oxide,[8] and is commercially available as both the neutral compound and its sodium salt.[1] It is used to prepare zinc pyrithione,[9][10] which is used primarily to treat dandruff and seborrhoeic dermatitis in medicated shampoos,[11][12] though is also an anti-fouling agent in paints.[13]

  1. ^ a b c d Cite error: The named reference eEROS-Pyrithione was invoked but never defined (see the help page).
  2. ^ Cite error: The named reference pKa was invoked but never defined (see the help page).
  3. ^ Cite error: The named reference pKa2 was invoked but never defined (see the help page).
  4. ^ Cite error: The named reference PersianShallot was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference SolidThione was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference 2-mercaptopyridine was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference UroniumChloropyridine was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference Rompp was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference ZnP2patent1 was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference ZnP2patent2 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference ZnDermatology was invoked but never defined (see the help page).
  12. ^ Cite error: The named reference SebDerm was invoked but never defined (see the help page).
  13. ^ Cite error: The named reference ACS was invoked but never defined (see the help page).

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Pyrithione

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Keratolytic

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acid, and trichloroacetic acid. While cytostatic agents such as zinc pyrithione are first line, keratolytics (salicylic acid and sulfur) can also be used...

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Seborrhoeic dermatitis

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scalp is often treated with shampoo preparations of ketoconazole or zinc pyrithione. The condition is common in infants within the first three months of age...

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Gram-negative bacteria. Pyrithione-containing plant extracts are used in herbal medicine for treatment of malaria. Zinc pyrithione is used in commercial...

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Tinea versicolor

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antifungal agents such as clotrimazole, miconazole, terbinafine, or zinc pyrithione can lessen symptoms in some patients. Additionally, hydrogen peroxide...

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Dandruff

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treatments including piroctone olamine, ketoconazole (Sebizole), zinc pyrithione, and selenium disulfide (Selsun Blue) have been found to be effective...

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Hyaluronic acid

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Zinc

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gluconate (as dietary supplements), zinc chloride (in deodorants), zinc pyrithione (anti-dandruff shampoos), zinc sulfide (in luminescent paints), and dimethylzinc...

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Antifungal

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antiviral, and inhibits Candida morphogenesis[citation needed] Zinc pyrithione Incidents of liver injury or failure among modern antifungal medicines...

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Herpes simplex virus

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demonstrated the effectiveness of natural products as promising anti-HSV drugs. Pyrithione, a zinc ionophore, has shown antiviral activity against herpes simplex...

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ATC code D11

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Tiratricol D11AX09 Oxaceprol D11AX10 Finasteride D11AX11 Hydroquinone D11AX12 Pyrithione zinc D11AX13 Monobenzone D11AX16 Eflornithine D11AX18 Diclofenac D11AX21...

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Climbazole

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conditioners. It may be accompanied by other active ingredients such as zinc pyrithione or triclosan.[citation needed] May cause localized irritation of the skin...

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Ionophore

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used in the management of rheumatoid arthritis and lupus erythematosus. Pyrithione is used as an anti-dandruff agent in medicated shampoos for seborrheic...

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Unique selling proposition

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needed] Head & Shoulders: "Clinically proven to reduce dandruff." 1961 Pyrithione Zinc was found, after 10 years of research, to be an ingredient that was...

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Malassezia furfur

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medications such as ketoconazole, ciclopirox olamine, piroctone-olamine, zinc pyrithione, or sulfur compounds are commonly prescribed to treat diseases caused...

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Management of hair loss

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Spironolactone

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Piroctone olamine Selenium disulfide (selenium sulfide) Xenysalate Zinc pyrithione (pyrithione zinc) Antihistamines Calcineurin inhibitors Cyclosporin Pimecrolimus...

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Cradle cap

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recommend keratolytic (dandruff) shampoos (e.g. with sulfur, selenium, zinc pyrithione, or salicylic acid) while others warn against the use of medicated shampoos...

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Lokivetmab

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Ivermectin

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Cromoglicic acid

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Medical uses of magnesium sulfate

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Mequinol

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Chloropyridine

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of 2-chloropyridine is the production of production of the fungicide pyrithione. Reaction of 4-chloropyridine with thioglycolic acid gives pyridylmercaptoacetic...

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