Piroctone olamine

Piroctone olamine
Names
IUPAC name
1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-1,2-dihydropyridin-2-one; 2-aminoethan-1-ol
Other names
Piroctone ethanolamine; Octopirox
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

Piroctone olamine (INN; also known as piroctone ethanolamine) is an organic compound used as an antimicrobial active in anti-dandruff and anti-seborrhoeic dermatitis scalp products. It is the ethanolamine salt of piroctone, a hydroxamic acid derivative. It is described as a white to slightly yellowish-white crystalline powder with a mild characteristic odour, very slightly soluble in water and freely soluble in ethanol, chloroform, and ether.[1] It has been marketed by Clariant under the trade name Octopirox.[2]

According to later published sources, piroctone olamine was first synthesized in 1979 by Schwarzkopf-Henkel in Germany.[3]

Uses

Piroctone olamine is widely used in anti-dandruff shampoos and other scalp-care products.[4][5] It has also been used in topical preparations for fungal infections and has been studied in formulations for seborrhoeic dermatitis.[6][7] In KEGG it is classified as an antiseborrheic drug.[8]

Mechanism of action

Piroctone olamine is generally described as an antifungal active associated with suppression of scalp microorganisms, especially species of Malassezia linked to dandruff and seborrhoeic dermatitis.[4][9] Proposed mechanisms in the literature include inhibition of ergosterol synthesis and, alternatively, penetration of the fungal cell membrane followed by chelation of iron ions, with interference in mitochondrial energy metabolism. The exact mechanism of action has not been fully established.[10][7]

Regulation

In the European Union, piroctone olamine is listed in Annex V of Regulation (EC) No 1223/2009 as an allowed preservative in cosmetic products, with a maximum concentration of 1.0% in rinse-off products and 0.5% in other products.[11] The former Scientific Committee on Cosmetic Products and Non-Food Products Intended for Consumers (SCCNFP) also reviewed the safety of piroctone olamine and its monoethanolamine salt for non-preservative uses in leave-on facial products.[12]

References

  1. ^ Antypenko, Lyudmyla M.; Solodovnyk, Vitaliy A. (2017). "Determination of Piroctone Olamine (Octopirox) in Bulk by UV Spectrophotometric Method". Dhaka University Journal of Pharmaceutical Sciences. 16 (1): 37–42. doi:10.3329/dujps.v16i1.33380.
  2. ^ "Octopirox™ Anti-Dandruff Agent". Clariant. Retrieved 2026-04-18.
  3. ^ do Couto, F. M. M.; Pedroso e Silva Azevedo, C.; de Souza Nunes, E.; Colla Ruver Beck, R.; von Poser, G.; Seixas Nunes, R. J.; Kaufmann, D.; Macedo, A. J. (2016). "Antifungal activity of the piroctone olamine in experimental intra-abdominal candidiasis". SpringerPlus. 5 468. doi:10.1186/s40064-016-2120-x. PMC 4833761. PMID 27119006.
  4. ^ a b Mayser, Peter (2024). "Scalp Microbiome and Dandruff—Exploring Novel Treatment Approaches and Their Effects Compared to Established Active Agents". Cosmetics. 11 (5): 174. doi:10.3390/cosmetics11050174.
  5. ^ "Octopirox™ Anti-Dandruff Agent". Clariant. Retrieved 2026-04-18.
  6. ^ 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): 478–483. doi:10.1055/s-0031-1296892. PMID 16149717. S2CID 11337188.
  7. ^ a b Youn, Hye Jung; Kim, Ji Young; Park, Mi Seon; Kim, In-Sik; Choi, Yoon Seok (2016). "Efficacy and Safety of Cream Containing Climbazole/Piroctone Olamine for Facial Seborrheic Dermatitis: A Single-Center, Open-Label Split-Face Clinical Study". Annals of Dermatology. 28 (6): 733–739. doi:10.5021/ad.2016.28.6.733. PMC 5125955. PMID 27904272.
  8. ^ "KEGG DRUG: Piroctone olamine". KEGG. Retrieved 2026-04-18.
  9. ^ Borda, Luis J.; Perper, Martin; Keri, Jonette E. (2015). "Seborrheic Dermatitis and Dandruff: A Comprehensive Review". The Journal of Clinical and Investigative Dermatology. 3 (2): 10. PMC 4852869. PMID 27148560.
  10. ^ Piquero-Casals, J.; Hexsel, D.; Mir-Bonafé, J. F.; Rozas-Muñoz, E. (2019). "Topical Non-Pharmacological Treatment for Facial Seborrheic Dermatitis". Dermatology and Therapy. 9 (3): 469–477. doi:10.1007/s13555-019-00319-0. PMC 6704200. PMID 31165409.
  11. ^ "Annex V - List of preservatives allowed in cosmetic products". CosIng. European Commission. Retrieved 2026-04-18.
  12. ^ "Opinion of the SCCNFP on piroctone olamine and its monoethanolamine salt" (PDF). European Commission. Retrieved 2026-04-18.
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