Piroctone olamine

Piroctone olamine (INN; also known as piroctone ethanolamine; brand name Octopirox) is a compound sometimes used in the treatment of fungal infections.[1] Piroctone olamine is the ethanolamine salt of the hydroxamic acid derivative piroctone.

Piroctone olamine

Identifiers
CAS Number	68890-66-4
3D model (JSmol)	Interactive image
ChemSpider	45574
ECHA InfoCard	100.065.957
MeSH	Piroctone+olamine
PubChem CID	50258
UNII	A4V5C6R9FB
CompTox Dashboard (EPA)	DTXSID4046735
InChI 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 Key: BTSZTGGZJQFALU-UHFFFAOYSA-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
SMILES CC1=CC(=O)N(C(=C1)CC(C)CC(C)(C)C)O.C(CO)N
Properties
Chemical formula	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. 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 (octopirox) containing transungual water soluble technology". Arzneimittel-Forschung. 55 (8): 478–83. doi:10.1055/s-0031-1296892. PMID 16149717.