PIROCTONE OLAMINE

Piroctone Olamine is an antifungal and antimicrobial compound widely used in personal care products, particularly in anti-dandruff shampoos. 
Piroctone Olamine is chemically classified as an ethanolamine salt of piroctone.
 
Cas Number: 68890-66-4
 
Synonyms

PIROCTONE OLAMINE,68890-66-4,Octopirox,Kopirox,Piroctone ethanolamine,Octopyrox,Piroctoneolamine,Piroctone ethanolamine salt,Piroctone olamine [USAN],UNII-A4V5C6R9FB,EINECS 272-574-2,A4V5C6R9FB,2-aminoethanol;1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)pyridin-2-one,NSC-759894,PIROCTONE ETHANOLAMINE SALT (1:1),EC 272-574-2,NSC 759894,Piroctone olamine (USAN),1-Hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2-(1H)pyridinone, 2-aminoethanol salt,PIROCTONE OLAMINE (MART.),PIROCTONE OLAMINE [MART.],PIROCTONE OLAMINE (USP-RS),PIROCTONE OLAMINE [USP-RS],1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2-pyridone monoethanolamine salt,1-HYDROXY-4-METHYL-6-(2,4,4-TRIMETHYLPENTYL)-2-PYRIDONE MONOETHANOLAMINE, (+/-)-,1-Hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)pyridin-2(1H)-one 2-aminoethanol salt,DTXCID2026735,1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)pyridin-2(1H)-one compound with 2-aminoethan-1-ol (1:1),Allermyl,Keratolux
 

Introduction to Piroctone Olamine
Piroctone Olamine is a synthetic antifungal agent that is commonly used in the treatment of dandruff and seborrheic dermatitis. 
Its primary function is to combat the growth of Malassezia, a type of fungus that is known to contribute to scalp disorders. 

Discovered in the late 20th century, Piroctone Olamine has since become a popular ingredient in anti-dandruff shampoos and other cosmetic formulations due to its broad-spectrum antifungal properties and relatively low toxicity compared to other antifungal agents.
 
Chemical Structure
The chemical structure of Piroctone Olamine consists of an olamine (a derivative of piperazine) backbone attached to a piroctone ring. 
This structure is key to its ability to interact with fungal cell membranes and disrupt their function. 
Its molecular formula is C16H21NO2, and it has a molecular weight of 259.35 g/mol.
 
Properties
Piroctone Olamine is a white, odorless powder that is soluble in water and ethanol. 
It is relatively stable at room temperature, and this stability is important in maintaining its efficacy in both liquid and solid formulations. 
It is considered more effective and safer than other antifungal agents like zinc pyrithione and ketoconazole in some applications, without the same degree of irritation or allergic reactions.
 
2. Mechanism of Action
The mechanism of action of Piroctone Olamine primarily revolves around its antifungal activity. 
It works by inhibiting the growth of Malassezia fungi, which are naturally present on the skin and scalp but can proliferate in certain conditions, leading to dandruff and seborrheic dermatitis. 
These fungi metabolize the lipids in the skin, producing irritating by-products that cause inflammation and skin flaking.
 
Inhibition of Fungal Growth
Piroctone Olamine interferes with the fungal cell's ability to function by inhibiting enzymes that are essential for their survival. 
Specifically, it blocks the synthesis of ergosterol, a vital component of the fungal cell membrane. 
This disruption leads to cell membrane instability, causing leakage of cellular contents and ultimately cell death.
 
Interaction with Cellular Structures
In addition to its effects on fungal membranes, Piroctone Olamine has been shown to interfere with fungal cell division. 
The compound is believed to bind to proteins involved in the cell's replication cycle, thereby halting the growth of new fungal cells. 
This dual action of disrupting both cell membrane integrity and cellular function makes Piroctone Olamine highly effective against dandruff-related fungi.
 
3. Pharmacodynamics and Pharmacokinetics
Pharmacodynamics
The pharmacodynamics of Piroctone Olamine are closely linked to its interaction with fungal membranes. 
Its efficacy depends on the concentration at the site of application. 
In shampoos, Piroctone Olamine is applied topically, where it directly acts on the scalp's surface and on fungal cells residing in hair follicles. 
It shows significant antifungal activity even at relatively low concentrations, typically in the range of 0.1% to 1%.
 
Pharmacokinetics
When used topically, Piroctone Olamine is minimally absorbed into systemic circulation, which is a significant advantage in reducing the risk of systemic side effects. 
Studies indicate that it remains localized on the skin and does not penetrate deeply into underlying tissues. 
Its half-life in the skin is approximately 4 to 6 hours, allowing for prolonged antifungal activity during the day after a single application.
 
4. Applications and Uses
Piroctone Olamine is primarily used in the treatment of dandruff and seborrheic dermatitis, two conditions characterized by excessive skin flaking and inflammation. 
It has a broad range of applications beyond these common uses, including the treatment of fungal infections in other areas such as athlete's foot, ringworm, and tinea versicolor.
 
Dandruff and Seborrheic Dermatitis
Piroctone Olamine has been widely incorporated into shampoos designed to treat dandruff. 
It effectively reduces scalp flaking by targeting the fungal overgrowth that is often the root cause of dandruff. 
Clinical studies have demonstrated that Piroctone Olamine-containing shampoos significantly reduce both the appearance of flakes and the irritation associated with these conditions.
 
Other Dermatological Conditions
Aside from its use in treating dandruff, Piroctone Olamine is sometimes found in creams and topical treatments aimed at combating other superficial fungal infections. 
These products are typically used to treat skin conditions where Malassezia or other fungi are implicated, offering an alternative to more potent antifungal treatments.
 
5. Efficacy and Clinical Studies
Numerous clinical trials have demonstrated the effectiveness of Piroctone Olamine in treating dandruff and seborrheic dermatitis. 
These studies typically compare Piroctone Olamine to other antifungal agents such as ketoconazole, zinc pyrithione, and selenium sulfide.
 
Key Clinical Trials
In one study, participants who used a shampoo containing 0.5% Piroctone Olamine saw a 75% reduction in scalp flaking compared to a control group. 
Another study comparing Piroctone Olamine with ketoconazole found similar efficacy in reducing symptoms of dandruff, but Piroctone Olamine had a lower incidence of scalp irritation and burning sensations, which are common side effects of other antifungal shampoos.
 
Comparative Effectiveness
In comparison to zinc pyrithione, Piroctone Olamine was found to be equally effective at inhibiting Malassezia growth but with fewer side effects, such as scalp dryness. 
These findings suggest that Piroctone Olamine might be a better option for patients with sensitive skin.
 
6. Safety Profile and Side Effects
Piroctone Olamine is generally considered safe for topical use, with a low incidence of side effects. 
Clinical data shows that most patients tolerate the compound without experiencing significant adverse reactions. 
However, like all active ingredients, it is not completely free from risk.
 
Reported Adverse Effects
The most common side effects are mild irritation, dryness, or itching at the site of application. 
Rarely, patients may experience allergic reactions such as erythema or hives. 
In most cases, these symptoms resolve once the treatment is discontinued.
 
Toxicological Data
Toxicological studies have shown that Piroctone Olamine has a low toxicity profile. 
Animal studies indicate that it does not pose significant risks when used in typical concentrations found in cosmetic formulations. 
The LD50 (lethal dose for 50% of subjects) is high, indicating that the compound is not acutely toxic.
 
7. Regulatory Status and Approval
Piroctone Olamine has been approved for use in various countries, including the United States, European Union, and Japan. 
It is classified as a cosmetic ingredient rather than a drug in many markets, although it still requires approval by regulatory agencies for specific uses in medicinal products.
 
Regulatory Classification
In the United States, Piroctone Olamine is generally recognized as safe (GRAS) when used in cosmetics, and it is approved for use in anti-dandruff shampoos. 
In the European Union, it is subject to evaluation by the Scientific Committee on Consumer Safety (SCCS) to ensure its safety in cosmetic products.
 
Approval Processes
The approval process for Piroctone Olamine in cosmetic products involves a review of clinical and toxicological data to ensure its efficacy and safety. 
Once approved, it is widely marketed in shampoos and topical treatments, with few restrictions on its use.
 
8. Piroctone Olamine in Cosmetic Formulations
Piroctone Olamine is commonly incorporated into shampoos, conditioners, and topical creams due to its antifungal properties. 
It is known for its compatibility with other active ingredients and its stability in different formulations.
 
Formulation in Shampoos
In shampoos, Piroctone Olamine is usually included in concentrations ranging from 0.1% to 1%. 
It is often combined with other soothing agents like aloe vera or glycerin to minimize irritation. 
The inclusion of Piroctone Olamine in these formulations helps to address both the cosmetic appearance and the underlying cause of dandruff.
 
Stability in Formulations
Piroctone Olamine is stable in a wide range of pH levels, from acidic to slightly alkaline, which allows it to be used in various formulations. 
Its stability is critical in preventing the degradation of the active ingredient over time, ensuring that the product remains effective throughout its shelf life.
 
9. Market Trends and Economic Impact
The global market for anti-dandruff and antifungal shampoos is experiencing steady growth, with Piroctone Olamine-based products being a key player. 
The increasing prevalence of scalp conditions and consumer demand for effective yet gentle products have contributed to this growth.
 
Market Trends
There is a growing demand for natural and mild active ingredients in cosmetic products, and Piroctone Olamine fits this trend due to its high efficacy and lower incidence of adverse effects. 
Additionally, consumers are increasingly looking for multi-functional products that can treat not only dandruff but also other skin conditions.
 
Economic Impact
The presence of Piroctone Olamine in high-demand cosmetic products has contributed to significant market growth. 
Companies focusing on dermatological health are incorporating it into their product lines, ensuring that it remains a popular choice in anti-dandruff and antifungal treatments.
 
10. Future Directions and Research
There are several areas of research that could enhance the future applications of Piroctone Olamine in dermatology and beyond. 
Studies are ongoing into its potential to treat other fungal infections, including systemic fungal diseases.
 
New Applications
Researchers are investigating the use of Piroctone Olamine in treating conditions such as psoriasis, eczema, and other inflammatory skin disorders where fungi may play a role in exacerbating the symptoms.
 
Innovation in Formulation Technology
New delivery systems, such as nanotechnology, are being explored to improve the penetration and efficacy of Piroctone Olamine in deeper layers of the skin. 
This could open the door for more advanced therapeutic applications.
 
11. Conclusion
Piroctone Olamine is a potent and well-tolerated antifungal agent that plays a crucial role in the treatment of dandruff and other scalp-related fungal conditions. 
With its proven effectiveness, low toxicity, and favorable safety profile, it has become a mainstay in both medicinal and cosmetic formulations. 
As research continues, new uses for Piroctone Olamine may emerge, cementing its place as a versatile tool in dermatological care.
 

SAFETY INFORMATION ABOUT PIROCTONE OLAMINE

First aid measures:
Description of first aid measures:
General advice:
Consult a physician. 
Show this safety data sheet to the doctor in attendance.
Move out of dangerous area:
 
If inhaled:
If breathed in, move person into fresh air. 
If not breathing, give artificial respiration.
Consult a physician.
In case of skin contact:
Take off contaminated clothing and shoes immediately. 
Wash off with soap and plenty of water.
Consult a physician.
 
In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.
 
If swallowed:
Do NOT induce vomiting. 
Never give anything by mouth to an unconscious person. 
Rinse mouth with water. 
Consult a physician.
 
Firefighting measures:
Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas
 
Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. 
 
Avoid breathing vapours, mist or gas. 
Evacuate personnel to safe areas.
 
Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
 
Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste. 
Keep in suitable, closed containers for disposal.
 
Handling and storage:
Precautions for safe handling:
Avoid inhalation of vapour or mist.
 
Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place. 
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials
 
Exposure controls/personal protection:
Control parameters:
Components with workplace control parameters
Contains no substances with occupational exposure limit values.
Exposure controls:
Appropriate engineering controls:
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
 
Personal protective equipment:
Eye/face protection:
Tightly fitting safety goggles. 
Faceshield (8-inch minimum). 
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
 
Skin protection:
Handle with gloves. 
Gloves must be inspected prior to use. 
Use proper glove
removal technique (without touching glove's outer surface) to avoid skin contact with this product. 
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. 
Wash and dry hands.
 
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
It should not be construed as offering an approval for any specific use scenario.
 
Body Protection:
Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Where risk assessment shows air-purifying respirators are appropriate use a fullface respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. 
 
If the respirator is the sole means of protection, use a full-face supplied air respirator. 
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. 
Do not let product enter drains.
Discharge into the environment must be avoided.
 
Stability and reactivity:
Chemical stability:
Stable under recommended storage conditions.
Incompatible materials:
Strong oxidizing agents:
Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions. 
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.
 
Disposal considerations:
Waste treatment methods:
Product:
Offer surplus and non-recyclable solutions to a licensed disposal company. 
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging:
Dispose of as unused product