Piroctone olamine

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).

Piroctone olamine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.065.957
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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Infobox references

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 due to potentially DNA-damaging effects. In addition to reducing the prevalence of dandruff through actively decreasing sebum production, Piroctone Olamine has been found to improve hair shaft diameter and reduce hair fall, while providing hair conditioning advantages.

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

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.
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