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Piroctone ethanolamine (INN; also known as piroctone ethanolamine; brand name Octopirox) is a compound sometimes used in the treatment of fungal infections.
Piroctone ethanolamine is the ethanolamine salt of the hydroxamic acid derivative piroctone.
Piroctone olamine (Standard) is the analytical standard of Piroctone olamine.
CAS: 68890-66-4
MF: C16H30N2O3
MW: 298.43
EINECS: 272-574-2
Mol File: 68890-66-4.mol
Synonyms: 2(1H)-Pyridinone,1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-,compd.with2-aminoethanol(1:1),4,4-trimethylpentyl)-1-hydroxy-4-methyl-6-(compd.with2-2(1h)-pyridinon,octopiroxolamine,1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1h)-pyridinoncompd.with2-aminoethanol(1:1),Hydroxyl pyrazole ketones,1-Hydroxy-4-methyl-6(2,4,4-trimethylpentyl)2-pyridon monoethanolamine,1-Hydroxy-4-methyl-6-(2,4,4-trimethylpentyl),-one compound with 2-aminoethanol (1:1)
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.
Piroctone ethanolamine is the ethanolamine salt of piroctone, a hydroxamic acid derivative.
Piroctone ethanolamine 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.
Piroctone ethanolamine has been marketed by Clariant under the trade name Octopirox.
Piroctone olamine is a pyridine derivate.
Piroctone ethanolamine is known to have a fungicidal effect.
Piroctone ethanolamine, the ethanolamine salt of the hydroxamic acid derivative Piroctone, is a hydroxypyridone anti-mycotic agent.
Piroctone ethanolamine penetrates the cell membrane and forms complexes with iron ions, inhibiting energy metabolism in mitochondria.
Piroctone olamine (PO) is an ethanolamine salt of the hydroxamic acid derivative Piroctone.
All Candida strains show low minimum inhibitory concentrations (MICs) for Piroctone olamine (0.125-0.5 μg/mL) and Amphotericin B (AMB) (0.03-1 μg/mL).
Piroctone ethanolamine is a synthetic antifungal agent commonly used in personal care products, particularly as an active ingredient in anti-dandruff shampoos and conditioners.
Chemically, it is the ethanolamine salt of 1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)pyridin-2(1H)-one, with the molecular formula C₁₆H₃₀N₂O₃ and a molar mass of 298.42 g/mol.
Known by trade names such as Octopirox, Piroctone olamine appears as a white to off-white crystalline powder that is sparingly soluble in water but soluble in ethanol and aqueous systems with surfactants or co-solvents, enabling its formulation in aqueous-based cosmetics.
Piroctone ethanolamine exerts its antifungal effects primarily by penetrating the cell membranes of fungi, where Piroctone ethanolamine chelates iron ions (Fe²⁺ and Fe³⁺) essential for metabolic processes, thereby inhibiting energy production and fungal growth.
This mechanism is particularly effective against Malassezia species, such as Malassezia furfur (formerly Pityrosporum ovale), which are implicated in dandruff, seborrheic dermatitis, and scalp irritation.
In cosmetics, Piroctone olamine is incorporated at concentrations typically ranging from 0.1% to 1% to provide both antimicrobial preservation and targeted treatment for fungal-related scalp conditions, often outperforming alternatives like zinc pyrithione in terms of mildness and efficacy against resistant strains.
While piroctone olamine is well-tolerated in diluted cosmetic formulations and considered non-toxic for topical use even on sensitive skin, undiluted forms can cause skin irritation, serious eye damage, and respiratory irritation upon inhalation.
Regulatory bodies, including the European Cosmetics Regulation, approve its use in rinse-off products up to 1% and leave-on products up to 0.5%, with no significant sensitization potential reported in clinical studies.
Piroctone olamine is also noted for being safe on colored hair without causing fading and for its low environmental impact at recommended levels, though Piroctone olamine is harmful to aquatic life if released undiluted.
Physical and chemical characteristics
Piroctone ethanolamineis a white to off-white or slightly yellow crystalline powder, suitable for incorporation into solid and liquid formulations.
Piroctone ethanolamine exhibits a melting point of approximately 132–136 °C, which supports its thermal stability during manufacturing processes involving moderate heating.
Solubility characteristics include slight solubility in water, with experimental values ranging from 0.03 g/L at 20 °C to 7.2 mg/mL (0.72 g/100 mL) at 32 °C, and similar limited solubility in oils; it is more readily soluble in ethanol (up to 59 mg/mL) and chloroform.
These properties facilitate its use in alcoholic or surfactant-containing vehicles but require careful selection of co-solvents for aqueous systems.
In aqueous solutions, piroctone olamine yields a pH of 8.5–10 for 1% suspensions or saturated solutions at ambient temperatures, a range that influences its ionization and compatibility in formulations.
Piroctone ethanolamine demonstrates good stability under normal storage conditions, including temperatures up to 80 °C and pH values from 3 to 9, but is sensitive to extreme pH outside this range and direct ultraviolet light, which can lead to decomposition.
As the ethanolamine salt of a synthetic hydroxypyridone derivative, Piroctone ethanolamine originates from petrochemical-based synthesis processes.
Chemically, piroctone olamine acts as a hydroxypyridone with chelating capabilities, forming complexes with metal ions such as iron (Fe²⁺), which contributes to its reactivity in formulations containing trace metals.
This property necessitates the inclusion of antioxidants or chelating agents in some product matrices to prevent potential discoloration or instability.
Piroctone ethanolamine is used in combination with other substances as a part of shampoo effectively reduced the amount of dandruff and, at the same time, provided hair conditioning advantages.
Recently was shown, that piroctone olamine could induce apoptosis and possessed a significant in vivo effect against myeloma.
Appearance
White or slightly yellow crystalline powder.
Solubility
Freely soluble in 10% ethanol in water; soluble in solution containing surfactants in water or in 1%-10% ethanol; slightly soluble in water and in oil.
The solubility in water varies by pH value, and is a litter larger in neutral or weak basic solution than in acid solution.
Toxicity
Acute toxicity : Acute oral LD50 –rat 8100mg/kg, practically nontoxic.
Subchronic toxicity : NOEL: 100mg//kg/d (rat, orally, 3 months).
Chronic toxicity and carcinogencity : Negative.
Mutagenicity : Negative.
Irritation to skin and eye : Very low.
Uses
Piroctone ethanolamine is an anti-dandruff agent used in shampoo formulations.
Piroctone ethanolamine is used in combination with other substances as a part of shampoo effectively reduced the amount of dandruff and, at the same time, provided hair conditioning advantages.
Recently was shown, that piroctone olamine could induce apoptosis and possessed a significant in vivo effect against myeloma.
Piroctone olamine is widely used in anti-dandruff shampoos and other scalp-care products.
Piroctone olamine has also been used in topical preparations for fungal infections and has been studied in formulations for seborrhoeic dermatitis.
In KEGG Piroctone olamine is classified as an antiseborrheic drug.
Piroctone Olamine is an ethanolamine salt of the hydroxamic acid derivative Piroctone.
Piroctone ethanolamine is widely used in personal care and pharmaceutical products due to its antifungal and antibacterial properties.
Piroctone ethanolamine is a white to off-white crystalline powder, soluble in water and alcohols, and typically used in formulations for dandruff treatment and fungal skin infections.
Pictrone olamine manufactured as Water-Soluble Antifungal Complex; Anti-Dandruff Agent.
Clinical Use
Piroctone olamine has both antifungal and antioxidant properties.
Piroctone olamine has been reported to be as effective as other antidandruff products at concentrations of 0.5–1% and is considered less toxic than zinc pyrithione when accidentally swallowed. Piroctone olamine products can be used by all patients and at any age.
Like zinc pyrithione, they should be used daily.
Because of their reduced toxicity, they may be preferred if used around small children.
Other uses
Piroctone olamine serves as a preservative and antimicrobial agent in various cosmetic formulations, including conditioners, lotions, and pet shampoos, typically incorporated at concentrations of 0.1–0.5% to inhibit bacterial and fungal growth and prevent product contamination.
In hair conditioners and creams, Piroctone olamine is used at 0.1–0.3% to maintain microbial stability while supporting scalp health.
For pet shampoos, such as those formulated for sensitive skin, Piroctone olamine helps control overgrowth of microorganisms like Malassezia at similar low levels.
Beyond preservation, piroctone olamine contributes to hair care by indirectly reducing hair loss through improved scalp health, as its antioxidant properties mitigate oxidative stress on the scalp.
A randomized, double-blind, placebo-controlled clinical study demonstrated that topical application of piroctone olamine in shampoo and leave-on formulations significantly increased hair density and reduced shedding over 8 weeks by enhancing scalp condition and lowering biomarkers of oxidative damage.
This effect is particularly noted in antioxidant-based hair retention products, where Piroctone olamine promotes a healthier scalp environment conducive to hair growth.
In veterinary medicine, piroctone olamine is incorporated into medicated shampoos for dogs and cats to manage allergic dermatitis and fungal infections, such as those caused by Malassezia overgrowth.
Products like Allermyl shampoo utilize Piroctone olamine to restore microbial balance, soothe itchy and inflamed skin, and support the epidermal barrier in animals with environmental or food-related allergies.
Its broad-spectrum antifungal and antibacterial activity makes Piroctone olamine effective for topical treatment of seborrheic and keratoseborrheic conditions in pets.
Piroctone olamine has been investigated for potential use in acne products due to its topical antibacterial effects against skin bacteria, including Propionibacterium acnes and Staphylococcus species, though Piroctone olamine is not a primary acne therapeutic.
In a randomized exploratory study on mild acne vulgaris, a dermocosmetic formulation containing piroctone olamine modulated the skin microbiome by increasing beneficial Cutibacterium abundance and decreasing Staphylococcus, without significantly reducing overall bacterial diversity, unlike traditional acne treatments.
At concentrations up to 0.2% in leave-on anti-acne gels or cleansers, Piroctone olamine helps reduce sebum production and inflammation associated with acne lesions.
Applications of piroctone olamine are confined to topical personal care products and have not been approved for systemic medical treatments, emphasizing its role in external formulations like shampoos, lotions, and deodorants.
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.
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.
Application
The compound is the grade of analytical standard, which is the reference standard supplied assay.
Piroctone olamine is commonly used in qualitative, quantitative and methodological research experiments in HPLC, GC and MS.
Definition
ChEBI: An organoammonium salt that is the ethanolamine salt of piroctone.
benefits
Piroctone Olamine is a popular ingredient in hair care products that treat dandruff and other scalp conditions.
Controls dandruff: Piroctone Olamine is effective at controlling the growth of Malassezia, a yeast that can contribute to dandruff and other scalp issues.
By controlling the growth of this yeast, Piroctone Olamine can help to reduce or eliminate dandruff.
Soothes the scalp: Piroctone Olamine has moisturizing properties that can help to soothe and hydrate the scalp.
This can help prevent dryness, flakiness, and itching, common symptoms of dandruff and other scalp conditions.
Safe for coloured hair: Piroctone Olamine is safe for use on coloured hair and will not cause fading or strip colour.
Prevents fungal growth: Piroctone Olamine not only controls the growth of Malassezia, but Piroctone ethanolamine also prevents the growth of other fungi that can cause scalp problems.
Long-lasting effect: Piroctone Olamine has been shown to have a longer-lasting effect than some other dandruff-fighting ingredients, meaning you may be able to go longer between washes.
Gentle on the scalp: Piroctone Olamine is gentle on the scalp, making Piroctone ethanolamine suitable for sensitive skin.
Side effects
Piroctone Olamine should be kept in mind that shampoos with Piroctone Olamine should not be used more than twice a week, unlike other daily-use shampoos that don't have this ingredient.
One of the biggest side effects of Piroctone Olamine is that Piroctone Olamine can cause irritation and itchiness on the head.
Mechanism of action
Piroctone olamine, also known as Octopirox, is an antifungal and antibacterial agent commonly used in cosmetic and personal care products, such as shampoos, conditioners, and lotions.
Piroctone ethanolamine works by inhibiting the growth of various microorganisms, including yeasts and fungi, by disrupting their cell membranes and interfering with their metabolism.
Specifically, piroctone olamine targets the enzymes responsible for synthesizing the cell membrane of microorganisms, inhibiting their growth and causing their eventual death.
Piroctone ethanolamine also has anti-inflammatory properties that help to reduce redness and itching on the scalp and skin.
Melting point: 134.0 to 138.0 °C
Boiling point: 135-235℃[at 101 325 Pa]
density : 1.1[at 20℃]
vapor pressure: 0-0Pa at 20-25℃
storage temp.: Inert atmosphere,2-8°C
solubility: Chloroform (Slightly, Sonicated), Methanol (Slightly)
pka: 5.9-7.4[at 20 ℃]
form : Solid
color: White to Off-White
Water Solubility: 400-50000mg/L at 20-25℃
Merck: 14,7502
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
InChIKey: BTSZTGGZJQFALU-UHFFFAOYSA-N
