Chemistry:Piroctone olamine
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| IUPAC name
1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-1,2-dihydropyridin-2-one; 2-aminoethan-1-ol
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| Other names
Piroctone ethanolamine; Octopirox
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| MeSH | Piroctone+olamine |
PubChem CID
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| 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). | |
 (what is   ?)
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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
- ↑ 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. https://www.dujps.com/index.php/online-first?download=5:determination-of-iroctone-olamine-octopirox-in-bulk-by-uv-spectrophotometric-method.
- ↑ "Octopirox™ Anti-Dandruff Agent". https://www.clariant.com/en/Business-Units/Care-Chemicals/Personal-Care/Functional-Claims/Octopirox.
- ↑ 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. doi:10.1186/s40064-016-2120-x. PMID 27119006.
- ↑ 4.0 4.1 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.
- ↑ "Octopirox™ Anti-Dandruff Agent". https://www.clariant.com/en/Business-Units/Care-Chemicals/Personal-Care/Functional-Claims/Octopirox.
- ↑ "In vitro antimycotic activity and nail permeation models of a piroctone olamine containing transungual water soluble technology". Arzneimittel-Forschung 55 (8): 478–483. 2005. doi:10.1055/s-0031-1296892. PMID 16149717.
- ↑ 7.0 7.1 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. PMID 27904272.
- ↑ "KEGG DRUG: Piroctone olamine". https://www.kegg.jp/entry/D05505.
- ↑ 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. PMID 27148560.
- ↑ 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. PMID 31165409.
- ↑ "Annex V - List of preservatives allowed in cosmetic products". European Commission. https://ec.europa.eu/growth/tools-databases/cosing/reference/annexes/list/V.
- ↑ "Opinion of the SCCNFP on piroctone olamine and its monoethanolamine salt". https://ec.europa.eu/health/ph_risk/committees/sccp/documents/out162_en.pdf.
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