Piroctone olamine

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Structural formula
Structure of piroctone olamine
Structural formula without stereochemistry
General
Non-proprietary name Piroctone olamine
other names
  • 1-Hydroxy-4-methyl-6- (2,4,4-trimethylpentyl) -2 (1 H ) -pyridone monoethanolamine salt
  • 1-Hydroxy-4-methyl-6- (2,4,4-trimethylpentyl) pyridin-2 (1 H ) -one, compound with 2-aminoethanol (1: 1)
  • PIROCTONE OLAMINE ( INCI )
Molecular formula C 16 H 29 N 2 O 2
Brief description

yellow solid

External identifiers / databases
CAS number 68890-66-4
EC number 272-574-2
ECHA InfoCard 100.065.957
PubChem 50258
Wikidata Q412572
properties
Molar mass 298.43 g mol −1
Physical state

firmly

Melting point

130-135 ° C

solubility

practically insoluble in water

safety instructions
GHS labeling of hazardous substances
05 - Corrosive

danger

H and P phrases H: 315-318-412
P: 264-273-280-305 + 351 + 338 + 310-332 + 313-501
Toxicological data

5000 mg kg −1 ( LD 50 ,  mouse ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Piroctone Olamine ( INN ) is the ethanolamine salt of a derivative of 2-pyridone . It is a fungicidal and antibacterial substance from the pyridone class .

use

Fungicidal effect

Piroctone olamine is an additive in many anti-dandruff shampoos due to its fungicidal effect . It has fungicidal activity against all medically relevant dermatophytes , yeasts and molds . The active ingredient can penetrate the cell wall of yeasts such as Malassezia furfur and complexes iron (III) ions. This results in an inhibition of the energy metabolism in the mitochondria of the mushrooms.

Another important advantage for the cosmetics industry is that the active ingredient also dissolves in surfactants - a typical ingredient in shampoos.

Piroctone olamine was first manufactured on an industrial scale by Hoechst AG . Under the brand name Octopirox ® , it was first used in July 1979 in the Seborin ® hair tonic produced by Schwarzkopf & Henkel Düsseldorf (until 1995: Hoechst) . The compound is now contained in many cosmetic products for the treatment of dandruff ( pityriasis simplex capillitii ), including shampoos for dogs and cats.

Bactericidal effect

In addition to being fungicidal, piroctone olamine also has a bactericidal effect against gram-positive and gram-negative bacteria.

literature

  • Marcus Blömer: A four-armed, double-blind, randomized, placebo-controlled study regarding the effectiveness of a zinc-octopirox shampoo formulation vs. a formulation containing oxiconazole or zinc pyrithione for pityriasis simplex capillitii (dandruff) , inaugural dissertation from 2005. DNB 978038053
  • Information from the FDA. Online (PDF file; 1.79 MB)

Individual evidence

  1. ↑ a b Entry on piroctone olamine in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  2. ↑ Entry on PIROCTONE OLAMINE in the CosIng database of the EU Commission, accessed on 2020-08-12.
  3. ↑ a b c d e Entry on 1-hydroxy-4-methyl-6- (2,4,4-trimethylpentyl) pyridin-2 (1H) -one, compound with 2-aminoethanol (1: 1) in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
  4. ↑ codecheck.info - Products that contain piroctone olamine.