Piroctone olamine

Piroctone olamine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.065.957 Edit this at Wikidata
MeSH Piroctone+olamine
UNII
  • InChI=1S/C14H23NO2.C2H7NO/c1-10-6-12(15(17)13(16)8-10)7-11(2)9-14(3,4)5;3-1-2-4/h6,8,11,17H,7,9H2,1-5H3;4H,1-3H2 ☒N
    Key: BTSZTGGZJQFALU-UHFFFAOYSA-N ☒N
  • InChI=1/C14H23NO2.C2H7NO/c1-10-6-12(15(17)13(16)8-10)7-11(2)9-14(3,4)5;3-1-2-4/h6,8,11,17H,7,9H2,1-5H3;4H,1-3H2
    Key: BTSZTGGZJQFALU-UHFFFAOYAP
  • CC1=CC(=O)N(C(=C1)CC(C)CC(C)(C)C)O.C(CO)N
Properties
C16H30N2O3
Molar mass 298.421
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Piroctone olamine (INN; also known as piroctone ethanolamine) is a compound sometimes used in the treatment of fungal infections.[1] Piroctone olamine is the ethanolamine salt of the hydroxamic acid derivative piroctone was first synthesized in 1979 by Schwarzkopf-Henkel (Germany).

It is often used in anti-dandruff shampoo as a replacement for the commonly used compound zinc pyrithione which was banned in the EU in 2021 because of concerns for environmental toxicity.

It is structurally similar to ciclopirox and pyrithione, containing a substituted pyridine (pyridinone) group which inhibits ergosterol synthesis.[citation needed]

References

  1. ^ Dubini F, Bellotti MG, Frangi A, Monti D, Saccomani L (2005). "In vitro antimycotic activity and nail permeation models of a piroctone olamine containing transungual water soluble technology". Arzneimittel-Forschung. 55 (8): 478–83. doi:10.1055/s-0031-1296892. PMID 16149717. S2CID 11337188.
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