OCTOPIROX

Octopirox or Piroctone olamine is one of the most efficient anti-dandruff actives available on the market today. Designed specifically to treat seborrheic dermatitis and dry scalp, piroctone olamine offers additional benefits: it is environmentally friendly, multifunctional (doubles as preserving agent), and can be used in various cosmetic formats. We present a key active ingredient from Clariant’s product range for the personal care industry: Octopirox – your best alternative

Octopirox (INCI: Piroctone Olamine) is a nontoxic antidandruff active ingredient which is particularly suitable for the manufacture of hair care products such as shampoos and hair care products such as hair tonics and cream rinses with an antidandruff action. It is extremely easy to formulate, enabling stable formulations with no effort. Octopirox controls the growth of microorganisms effectively and is directly targeting the cause of dandruff.

Octopirox is an antidandruff agent used in antidandruff shampoos and hair care products such as hair tonics and cream rinses with an antidandruff action.

EC / List no.: 272-574-2
CAS no.: 68890-66-4
Mol. formula: C16H30N2O3

Piroctone Olamine has a petrochemical origin. It is an ethanolamine salt extracted from hydroxamic acid derivative piroctone.
Typically, piroctone olamine is an alternative to the commonly used compound zinc pyrithione.

Almost everyone faces hair related issues like dandruff, hair loss, slow hair growth, and split ends.
Shampoos containing piroctone olamine are effective in treating various kinds of hair problems.

Microorganisms such as Malassezia Furfur produce enzymes which decompose fats into the respective fatty acids.
These and further decomposition products like lipo-peroxides irritate the scalp.
As a result, increased production of keratinocytes and increased mitosis occur which leads to desquamation and occurrence of parakeratosis.

Octopirox controls the growth of microorganisms effectively and is directly targeting the cause of dandruff.
Use concentration can be chosen between 0.1 and 1.0%, depending on the finished product.
For leave-on products, the concentration can be lowered to 0.05 and 0.1%.

According to Clariant product specifications, Octopirox is white to slightly yellowish-white crystalline powder with mild characteristic odor, very slightly soluble in water, and freely soluble in ethanol, chloroform and ether.
Its pKa is 7.4.
The solubility of Octopirox is greatly dependent on the pH: it is greater in the neutral and weakly alkaline ranges than in the acidic one, due to formation of free acid form

PIROCTONE OLAMINE (Octopirox) has anti-bacterial, anti-mycotic, anti-dandruff and anti-oxidant properties

ANTI-DANDRUFF, FLAKE & ITCH-FREE, AND ANTI-MICROBIAL
Octopirox has been successfully used for over 30 years for its good compatibility, its antimicrobial functionality and its long shelf life.
It is generally considered safe, non-irritating and non-allergenic.
Due to the good solubility in aqueous surfactant systems as well as alcohol/water mixtures, Octopirox is especially suitable for the formulation of clear products.

Piroctone olamine (INN; also known as piroctone ethanolamine; brand name Octopirox) is a compound sometimes used in the treatment of fungal infections.
Piroctone olamine is the ethanolamine salt of the hydroxamic acid derivative piroctone.
CAS Number: 68890-66-4

It is often used in anti-dandruff shampoo as a replacement for the commonly used compound zinc pyrithione.
It is structurally similar to ciclopirox and pyrithione, containing a substituted pyridine (pyridinone) group which inhibits ergosterol synthesis.

Piroctone Olamine.
Octopirox by Clariant is a highly effective antidandruff agent and an anti-acne active agent.
Octopirox is antimicrobial, soluble in surfactant systems.
Octopirox is used shampoos, shower products, liquid soaps, hair conditioners, hair styling products, antiperspirant & deodorants.

Recommended Uses
Antidandruff Shampoo
Cream rinse
Hair treatment
Setting lotion
Hair tonic
Hair gel
Hair cream
Hair oil
Deodorants
Anti acne products

Piroctone Oleamine
Synonyms piroctone olamine
1-hydroxy-4-methyl-6(2,4,4-trimethylpentyl)2-pyridon monoethanolamine salt
1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)pyridin-2(1H)-one-2-aminoethanol (1:1)
1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1h)-pyridinoncompd.with2-aminoethanol(1:1)
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-pyridon monoethanolamine salt
Octopirox
Pyridine-amino ethanol

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 olamine 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.

Generally, the solubility of Octopirox is highly depending on the pH value of the solution.
As a rule of thumb, it is better dissolved in neutral and slightly alkaline aqueous solutions than in acidic solutions.
It is possible to dissolve between pH=5 to pH=8 in surfactant

solutions and alcohol/water mixtures
readily soluble in alcohol (10 %)
soluble in aqueous surfactant solutions
and water/alcohol mixtures (1–10 %)
slightly soluble in water (ca. 0.05 %) and
oils (0.05 – 0.1 %)

Due to the good solubility in aqueous surfactant systems as well as alcohol/water mixtures, Octopirox is especially suitable for the formulation of clear products.
Aqueous or alcoholic solutions of Octopirox have a pH of 9-10 which can be adjusted using organic acids like citric acid or lactic acid.

The piroctone olamine (CAS # 68890-66-4) is 1-hydroxy-4-methyl-6-(2,4,4-trimethyl)-pentyl-2(1H)-pyridone 2-aminoethanol salt

Scalp Care Benefits

Dandruff and flake-free
Scalp itch-free
Mild to scalp
Scalp Care Features

Transparent formulation
Easy to formulate
pH & temperature stability
Additional Benefits

Low aquatic toxicity
Broad spectrum preservation

Octopirox is an effective, practically nontoxic antidandruff active ingredient. It is particularly suitable for the manufacture of antidandruff shampoos and hair care products such as hair tonics and cream rinses with an antidandruff action.

Under the brand name Octopirox, it was used for the first time in July 1979 in the Seborin produced by Schwarzkopf & Henkel Düsseldorf (subsidiary of Hoechst).
Now-a-days, the compound is present in many cosmetic products for the treatment of dandruff (Pityriasis simplex capillitii), like shampoos, even for dogs and cats.
It has fungicidal activity against all medically relevant dermatophytes, yeasts and mold fungi, due to penetration into the cell wall of yeast, fungi such as Malassezia furfur and complexation with iron (III) ions, which results in an inhibition of the energy metabolism in the mitochondria of the fungi.
The concentrations should be between 0.1 and 1.0%, depending on the type of final product, or should be further reduced for preparations that remain on the hair or the scalp.
Minimum inhibition concentration for the most important species of fungi lies between 0.5 and 4.0 µg/ml.
In addition to the fungicidal activity, piroctone olamine also exhibits a bactericidal activity against gram-positive and gram- negative bacteria in 0.1-3.0% concentration in personal care compositions.
Moreover, in vitro model of experimental onychomycosis caused by T. rubrum pointed out a possible role of 0.5% octopirox nail lacquer as a preventive tool for subjects at risk or as a curative tool in the first stage of onychomycosis

Goods and Services: Raw materials, namely, piroctone olamine for manufacturing products in the nature of antimicrobial, antiseborrheic products and deodorants for use in beauty care, body care and sanitary purposes

Benefits
Scalp Care Benefits
•   Dandruff-and flake-free
•   Itch-free
•   Gentle on scalp

Additional Benefits
•   Low aquatic toxicity (no labeling required)
•   Broad-spectrum preservation

Taking anti-dandruff shampoos to the next level – Octopirox

Piroctone olamine is one of the most efficient anti-dandruff actives available on the market today.
Designed specifically to treat seborrheic dermatitis and dry scalp, piroctone olamine offers additional benefits: it is environmentally friendly, multifunctional (doubles as preserving agent), and can be used in various cosmetic formats.
We present a key active ingredient from Clariant’s product range for the personal care industry: Octopirox – your best alternative

Scalp Care Benefits
• Dandruff- and flake-free
• Itch-free
• Gentle on scalp
Taking anti-dandruff shampoos to the next level – Octopirox
Scalp Care
DANDRUFF- & FLAKE-FREE

Octopirox is an effective, nontoxic anti-dandruff active ingredient. It is particularly suitable for the manufacture of anti-dandruff shampoos and hair care products such as hair tonics and cream rinses.
Microorganisms such as Malassezia furfur produce enzymes which decompose fats into their respective fatty acids.
These and other products of decomposition, such as lipo-peroxides, irritate the scalp.
As a result, mitosis and production of keratinocytes increases, leading to desquamation and parakeratosis.

Octopirox controls the growth of microorganisms effectively and directly targets the cause of dandruff.
Use concentration can be between 0.1 and 1.0%, depending on the finished product.
For leave-on products,the concentration can be lowered to between 0.05 and 0.1%.

STUDY: ANTI-DANDRUFF ACTION IN SHAMPOOS
In a study over the course of 1.5 months, a formulation with Octopirox at a concentration of 0.75% showed clear decrease of dandruff compared to a placebo shampoo.

Formulation Features
• Transparent formulation
• Easy to formulate
• pH- and temperature stable

Additional Benefits
• Low aquatic toxicity (no labeling required)
• Broad-spectrum preservation

EASE OF FORMULATION
Piroctone olamine is extremely easy to formulate, giving a stable formulation with no effort.
It is well soluble in surfactant systems and can increase the system‘s viscosity.
Zinc pyrithione requires a stabilizer and suspending agent to be dispersed (insoluble in water).

INFLUENCE OF THE PH VALUE AND THERMAL STABILITY
With a pKa value of ca. 7.4, Octopirox is present as free acid in neutral solutions and is chemically stable over a wide pH range.
It can be formulated in a pH range of 3-9. When used in a normal manner during production, temperatures of up to 80 °C do not cause decomposition of the product or loss of efficacy.
Nevertheless, prolonged heating should be avoided.

The cosmetic industry’s growing concern about the effect of its supply chain on the environment increases the need to ensure that the final product has a low environmental impact.
Favorable ecotoxicity parameters of raw materials can allow more sustainable products to be developed, prioritizing substances with low environmental impact.

Contrary to ZnPTO, Octopirox has no environmental toxicity labeling.

Preservatives are added to most personal care products today in order to inhibit growth of bacteria and fungi.
Piroctone olamine and blends thereof have been successfully used as preservatives for over 30 years because of their formulation compatibility, antimicrobial functionality and long shelf life.

TYPICAL CONCENTRATIONS FOR PERSONAL CARE PRODUCTS ARE:
• Hair shampoos 0.3 – 1.0%
• Hair tonics 0.05 – 0.1%
• Hair conditioners 0.1 – 0.3%
• Setting lotions / hair gels 0.05 – 0.2%
• Hair creams 0.1 – 0.3%
• Deodorants 0.1 – 0.3%
• Anti-acne leave-on: up to 0.2%

COMPATIBILITY WITH COSMETIC RAW MATERIALS
Octopirox is compatible with most surfactants, additives and active ingredients used in cosmetics. Compatibility with perfume oils with aldehyde and ketone functionality may be limited in some cases. Despite the anionic character of the active ingredient molecule, Octopirox can be used together with most cationic surfactants (quaternary ammonium compounds) and cationic active ingredients. In some cases, the solubility of Octopirox in water will be increased.
Nevertheless, it is advisable to carry out compatibility and stability tests when using these substances.
Attention must be drawn to the product’s propensity to form complexes with metal ions, especially iron and copper ions.
For example, with mere traces of iron (1 ppm Fe) a clearly visible yellow iron complex is formed. Adding the usual complexing agents does not prevent this complex from forming (see section on processing information).

INFLUENCE ON VISCOSITY IN SURFACTANT SYSTEMS
In some surfactant systems, Octopirox may cause an increase in viscosity which can be leveraged to economize on consistency modifiers during formulation development

SOLUBILITY
Generally, the solubility of Octopirox is highly dependent on the pH value of the solution. As a rule of thumb, it is better dissolved in neutral and slightly alkaline aqueous solutions than in acidic solutions. It can be dissolved at levels of pH=5 to pH=8 in surfactant solutions and alcohol/water mixtures.
• readily soluble in alcohol (10%),
• soluble in aqueous surfactant solutions
• soluble in water/alcohol mixtures (1 – 10%),
• slightly soluble in water (ca. 0.05%) and oils (0.05 – 0.1%)

A Comparison of Clinical Efficacy between a Basic Shampoo with Herbal Extracts Containing Climbazole and Its Similar Sample Containing Piroctone Olamine in the Treatment of Dandruff and Seborrheic Dermatitis

Abstract Background: Dandruff especially with itching and inflammation is a common complaint among patients in the clinic and its treatment is much challenging.
Chemical anti fungal substances used in antidandruff shampoos are common treatments.
The aim of this study was to compare the clinical efficacy of two of these anti dandruff substances, climbazole and piroctone olamine in the treatment of dandruff and seborrheic dermatitis in shampoos with herbal extracts.

Methods: One hundred and twenty men with scalp dandruff of the same severity, between 20-30 years old and in the same occupational condition in terms of sun exposure or environmental pollution were selected and divided randomly into two 60-subject groups.
After each shampoo was applied 3 times a week for 5 weeks one in group 1 and the other in group 2, patients were assessed for existence of itching and redness of scalp and reduction in dandruff and results were compared between two groups.

Results: Itching and redness were completely cured in both groups after treatment.
Dandruff was completely cured in 80% of patients and reduced in 20% of patients in climbazole group (p < 0.001), though completely cured in 55% of patients and reduced in 45% of patients in piroctone olamine group (p < 0.001).
Climbazole was over piroctone olamine in reduction of dandruff with significant difference (p < 0.01).
Conclusion: Both shampoos containing climbazole or piroctone olamine beside herbal extracts are effective in the reduction of dandruff and relief of other seborrheic dermatitis symptoms but climbazole seems to be more effective than piroctone olamine in the treatment of dandruff.

Keywords: dandruff, seborrheic dermatitis, climbazole, piroctone olamine, comparison

Dandruff and seborrheic dermatitis are features of fungal involvement of the scalp and occur in nearly half of population in every gender and race.
Dandruff is a non-inflammatory condition of scalp scaling and seborrheic dermatitis is an inflammatory condition of scalp with redness, itching and scaling.
They both have three main etiologic factors ever known including malassezia fungi, sebaceous lipids and individual sensitivity.
Topical treatments for these two conditions are provided by the use of substances such as zinc pyrithione, selenium sulphide, ketoconazole, piroctone olamine and climbazole.
Piroctone olamine and climbazole are widely used in the formulation of antidandruff shampoos, imported or produced inside country and no sideeffects have been reported yet.
There are no studies in publication that have compared the efficacy of these two substances in controlled conditions among human beings.
Herbal extracts because of some special properties such as hair fortifying and anti hair loss effects in addition to their less side effects, lower costs and being more available are also now increasingly used in shampoos.
There are few studies that have evaluated herbal extracts besides chemicals and there is no document dealing with cross reactions between them and their effects on clinical efficacy.
In this study, we aimed to compare clinical efficacy of climbazole with piroctone olamine in the treatment of dandruff and seborrheic dermatitis in shampoos with herbal extracts.

LIGHT STABILITY
Octopirox is sensitive to UV light and may decompose depending on the degree of exposure. Therefore formulations should be protected from direct strong sunlight.

STORAGE
Octopirox should be stored in its original container at ambient temperature protected from moisture. If stored correctly in its original sealed container, Octopirox can be kept for at least five years. A safety data sheet is available on request. MSDS available on Clariant.com/octopirox

PROCESS INFORMATION FOR OCTOPIROX
Due to the good solubility in aqueous surfactant systems as well as alcohol/water mixtures, Octopirox is especially suitable for formulating of clear products. Aqueous or alcoholic solutions of Octopirox have a pH of 9-10, which can be adjusted using organic acids like citric acid or lactic acid. During the formulation process, Octopirox can be heated up to 80 °C if necessary, but should not exceed this temperature for a longer time period.

APPLICATIONS
Anti-dandruff /anti-itch: Shampoo, conditioner, scalp tonic, cream rinse
Deodorants: Roll-on, spray, foot deodorant cream, stick
Anti-acne products: Gel, lotion, cleanser

The safety and efficacy of dandruff control ingredient piroctone olamine in .05%-.5% and .1%-1% concentrations in leave-on and rinse-off products, respectively, is established by animal and human data, warranting the ingredient’s inclusion in the OTC anti-dandruff monograph, according to Clariant

Technical Data
Appearance: White to faintly yellowish-white crystalline powder
Active Substance (ca.): min 99%
INCI-Name: Piroctone olamine
Applications
Anti-dandruff/anti-itch: Shampoo, conditioner, scalp tonic, cream rinse

Deodorants: Roll-on, spray, foot deodorant cream, stick

Anti-acne products: Gel, lotion, cleanser

Formulation Features
Transparent formulation
Easy to formulate
pH- and temperature stable

FORMULATIONS CONTAINING OCTOPIROX

Transparent Anti-Dandruff Shampoo BI/ 6254
Basic formulation suitable for the mass market.
Genagen SC 35 is an effective and easy-touse thickener, which is activated in the presence of salt.
It does not contain DEA, which makes the product safe from nitrosamines.
Octopirox is not only an effective anti-dandruff agent, but also an efficient preservative for cosmetic products.

A Water q.s.
Genapol LRO paste (Clariant)
Sodium Laureth Sulfate
Anionic surfactant 9.00%
Genagen SC 35 (Clariant)
Sodium Laureth Sulfate, Cocamide MEA, Aqua
Surfactant 2.00%
Genagen CAB 818 (Clariant)
Cocamidopropyl Betaine
Amphoteric surfactant 12.00%

B Octopirox
(Clariant)
Piroctone Olamine
Active ingredient 0.50%
Water 5.00%

C Sodium Chloride Consistency factor 1.30%
Water 15.00%

D Citric Acid pH regulator q.s.

Procedure
I Prepare phase A by adding the listed ingredients
II Prepare phase B by dispersing Octopirox and add to I.
III Adjust viscosity with phase C and pH with phase D (around 5.0-6.0)

Results
pH 5.00 Appearance: transparent liquid
Viscosity (Brookfield, 20°C 20 rpm): 18000 mPa s Stability: 3 months at 4°C, RT, 37°C, 45°C
Preservation: challenge test according to
European Pharmacopoeia, pass A

Instant Anti-Dandruff Vitamin Hair Repair Leave-On BII/ 3001
A Propylene Glycol Solvent 0.70%

B Octopirox
(Clariant)
Piroctone Olamine
Active ingredient 0.05%

C Carbopol 980
Carbomer
Polymer (thickening/
suspending)
0.60%

D Genamin KDMP (Clariant)
Behentrimonium Chloride
Cationic surfactant 0.20%
Genamin CTAC (Clariant)
Cetrimonium Chloride
Cationic surfactant 0.50%
Starch (Wheat) Consistency factor 0.50
Dimethicone Copolyol Acetate Silicone 0.80%
Dimethicone Copolyol Silicone 0.50%

E Water Ad 100%
Panthenol Active ingredient 0.20%
Polyquaternium-4 Conditioning agent 0.10%
Benzophenone-4 Sun filter 0.05%
Nicotinamide Active ingredient 0.30%
Tocopheryl Acetate Ingredient protectant 0.10%
Caustic soda (50% in water) pH regulator 0.80%

F Guar Hydroxypropyltrimonium Chloride Polymer (conditioning/
additive)
0.20%

G Fragrance Fragrance q.s.
Procedure
I Dissolve B in A
II Melt D at about 80°C
III Stir F in E with high shear dispenser tool
IV Add I to III
V Heat IV to about 80°C
VI Add C to II and add V directly
VII Stir until cool
VIII Add the components of G at about 35°C

Hair Conditioner/ Treatment BII/ 2024 With Octopirox
A Octopirox
(Clariant)
Piroctone Olamine
Active ingredient 0.20%.

B Propylene Glycol Solvent 5.00%

C Genapol HS 200 (Clariant)
Steareth-20
O/W emulsifier 3.00%
SilCare Silicone 41M15 (Clariant)
Caprylyl Methicone
Silicone 0.50%
Cetearyl Alcohol Consistency factor 5.00%
Mineral Oil Emollient 1.00%
Genamin KDMP (Clariant)
Behentrimonium Chloride
Cationic surfactant 1.00%

D Water Ad 100%
Genamin CTAC (Clariant)
Cetrimonium Chloride
Cationic surfactant 6.60%
Biobranil water soluble
Water (Aqua), Propylene Glycol, Wheat (Triticum
Vulgare) Bran Extract, Ethoxydiglycol, PEG- 40
Hydrogenated Castor Oil, Trideceth-9, Tocopherol Polymer (conditioning/ additive)
0.50%
Preservative Preservative q.s.

E Fragrance Fragrance/ parfum 0.30%
Dyestuff solution q.s.

F Citric Acid pH regulator q.s.

Procedure
I Dissolve A in B, add the components of C and heat to approx. 70°C.
II Heat D to approx. 70°C.
III Add II to I while stirring, and stir until cool.
IV At about 30°C add the comonents of E to III.
V Finally, adjust pH with F to 4.00-5.00

ONE OF THE MOST EFFICIENT ANTI-DANDRUFF ACTIVES AVAILABLE ON THE MARKET TODAY
Octopirox is designed specifically to treat seborrheic dermatitis and dry scalp, Piroctone Olamine offers additional benefits: it is environmentally friendly, multifunctional (doubles as preserving agent), and flexible for various cosmetic formats. Octopirox is compatible with most surfactants, additives and active ingredients used in cosmetic formulations.

Octopirox is an effective, practically nontoxic antidandruff active ingredient.

Octopirox is particularly suitable for the manufacture of antidandruff shampoos and hair care products such as hair tonics and cream rinses with an antidandruff action.
Octopirox is highly effective antidandruff agent, soluble in surfactant systems, ideal for clear formulations Decorative Cosmetic.

PIROCTONE OLAMINE

68890-66-4

Octopirox

Kopirox

Piroctone ethanolamine

Piroctone olamine [USAN]

C14H23NO2.C2H7NO

EINECS 272-574-2

2-aminoethanol;1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)pyridin-2-one

Piroctone olamine (USAN)

1-Hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1H)-pyridone compound with 2-aminoethanol (1:1)

1-Hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)pyridin-2(1H)-one compound with 2-aminoethanol (1:1)

1-Hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)pyridin-2(1H)-one, compound with 2-aminoethanol (1:1)

2(1H)-Pyridinone, 1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-, compd. with 2-aminoethanol (1:1)

2(1H)-Pyridinone, 1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-, compound with 2-aminoethanol (1:1)

Piroctoneolamine

1-Hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2-(1H)pyridinone, 2-aminoethanol salt

2(1H)-Pyridinone, 1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-, compd.with 2-aminoethanol (1:1)OTHER CA INDEX NAMES:Ethanol, 2-amino-, compd. with1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1H)-pyridinone (1:1)

Octopirox (TN)

Hydroxyl pyrazole ketones

EC 272-574-2

SCHEMBL2843

CHEMBL2107154

Octopirox/ Piroctone ethanolamine

BCP29912

HY-B1345

MFCD01690792

s5213

Piroctone olamine, analytical standard

AKOS025149526

CCG-267454

CS-7659

KS-0000113P

AS-15254

O639

LS-133057

FT-0653357

P2178

D05505

M-1284

Piroctone ethanolamine salt; Octopirox; Kopirox

890P664

Q412572

W-104652

1-Hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1H)-pyridone Ethanolamine

Piroctone olamine, United States Pharmacopeia (USP) Reference Standard

1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-1,2-dihydropyridin-2-one; 2-aminoethan-1-ol

The use of octopirox (i.e. 1-hydroxy-4-methyl-6-(2,4,4-trimethyl pentyl)-2-(1H)-pyridinone) (I) in cosmetic and dermatological compositions for application to human skin is new.

The present invention relates to the use of octopirox as a depigmenting or whitening agent in a cosmetic and / or dermatological composition, as well as to a depigmenting composition containing octopirox.
EP0801947A1
European Patent Office

It is certainly known to use octopirox as an antimycotic agent (see document FR-A-2022146), as a fall prevention agent (see document FR-A-2618068) and as an anti-acne agent (see document EP-A-218410) . However, to date no one had considered using it as a depigmenting agent.
The present invention therefore relates to the use of octopirox in and / or for the manufacture of a cosmetic and / or dermatological composition for depigmenting and / or bleaching human skin and / or removing pigmentary spots from the skin.

The present invention also relates to the use of octopirox in and / or for the manufacture of a cosmetic and / or dermatological composition, as an inhibitor of tyrosinase and / or of the synthesis of melanin.

Another subject of the present invention is the use of octopirox in a depigmenting and / or whitening cosmetic composition for human skin.
Another subject of the present invention is the use of octopirox for the manufacture of a dermatological composition for bleaching and / or depigmentation of human skin.
The present invention also relates to a cosmetic and / or dermatological process for depigmentation and / or bleaching of human skin, consisting in applying to the pigmented skin a composition comprising octopirox.
The composition according to the invention is suitable for topical use and therefore contains a cosmetically or dermatologically acceptable medium, that is to say compatible with the skin.
The present invention also relates to a depigmenting composition, characterized in that it contains in a cosmetically and / or dermatologically acceptable medium, octopirox.
The octopirox can in particular be present in an amount ranging from 0.01 to 10% and preferably from 0.3 to 3% of the total weight of the composition.

The invention will now be illustrated by means of the following examples.
The concentrations are given as a percentage by weight.

Example 1: Treating cream
Cetyl alcohol 1.05%
PEG-20 stearate (Myrj 49 sold by the company ICI) 1.65%
0.3% glyceryl stearate
Cyclomethicone 6%
Octopirox 0.5%
Propylene glycol 6%
Carbomer 0.6%
Glycerin 3%
Triethanolamine 1%
Preservatives 0.5%
Demineralized water qs 100%
The cream obtained used in daily application, makes it possible to obtain a whitening of the skin.

Example 2: Treating gel
Propylene glycol 10%
Ethyl alcohol 40%
Glycerin 3%
Octopirox 0.5%
Preservatives 0.15%
Perfume 0.15%
Demineralized water qs 100%
The gel obtained can be used daily and is able to depigment the skin.

Example 3: Treatment Stick
Carnauba wax 5%
Ozokerite 7%
Cetyl alcohol 1.4%
Lanolin 6%
Iron oxides (pigments) 4%
Titanium dioxide (pigments) 20%
Rice starch (load) 7%
Salicylic acid 1%
EDTA 0.1%
Octopirox 2%
Perhydrosqualene qs 100%

The stick obtained, used on pigmentation spots, makes it possible to attenuate them even to make them disappear.

Dandruff (also called scurf and historically termed Pityriasis capitis) is due to the excessive shedding of dead skin cells from the scalp.
As it is normal for skin cells to die and flake off, a small amount of flaking is normal and in fact quite common. Some people, however, either chronically or as a result of certain triggers, experience an unusually large amount of flaking, which can also be accompanied by redness and irritation. Most cases of dandruff can be easily treated with specialized shampoos. Dandruff is not an organism like lice; it is just dead skin that accumulates in the scalp. Dandruff is unlikely to be the cause of hair loss.

Excessive flaking can also be a symptom of seborrhoeic dermatitis, psoriasis, fungal infection or excoriation associated with infestation of head lice.

Dandruff is a global phenomenon and many people find that dandruff can cause social or self-esteem problems.
Treatment may be important purely for psychological reasons.

Causes
As the epidermal layer continually replaces itself, cells are pushed outward where they eventually die and flake off.
In most people, these flakes of skin are too small to be visible. However, certain conditions cause cell turnover to be unusually rapid, especially in the scalp. For people with dandruff, skin cells may mature and be shed in 2 – 7 days, as opposed to around a month in people without dandruff. The result is that dead skin cells are shed in large, oily clumps, which appear as white or grayish patches on the scalp skin and clothes.

Dandruff has been shown to be the result of three required factors:[1]

Skin oil commonly referred to as sebum or sebaceous secretions[2]
The metabolic by-products of skin micro-organisms (most specifically Malassezia yeasts)
Individual susceptibility
Common older literature cites the fungus Malassezia furfur (previously known as Pityrosporum ovale) as the cause of dandruff.
While this fungus is found naturally on the skin surface of both healthy people and those with dandruff, it has recently been shown that a scalp specific fungus, Malassezia globosa, is the responsible agent. This fungus metabolizes triglycerides present in sebum by the expression of lipase, resulting in a lipid byproduct oleic acid (OA). Penetration by OA of the top layer of the epidermis, the stratum corneum, results in an inflammatory response in susceptible persons which disturbs homeostasis and results in erratic cleavage of stratum corneum cells.[5]

Rarely, dandruff can be a manifestation of an allergic reaction to chemicals in hair gels/sprays, hair oils, or sometimes even dandruff medications like ketoconazole.

There is no convincing evidence that food (such as sugar or yeast), excessive perspiration, or climate have any role in the pathogenesis of dandruff.

Seborrheic dermatitis
Flaking is a symptom of seborrheic dermatitis.

Seasonal changes, stress, and immuno-suppression seem to affect seborrheic dermatitis.

Treatment
There have been many strategies for the control of dandruff.
Simply increasing shampooing will remove flakes.
However, elimination of the fungus results in dramatic improvement.
Regular shampooing with an anti-fungal product can reduce recurrence.

Active ingredient   Example of product
Zinc pyrithione       Head & Shoulders, Clinic All Clear, Pantene Pro V
Ketoconazole       Nizoral
Selenium sulphide   Selsun Blue, Vichy Dercos Anti-Dandruff shampoo
Tea tree oil       Himalaya Anti-dandruff shampoo
Tar           Neutrogena T/Gel
Piroctone olamine (INCI) Octopirox

Anti-fungal/anti-dandruff shampoos containing ketoconazole have been shown to be more effective than zinc pyrithione.
Ketoconazole is the most effective antifungal agent concluded by multiple studies.

Herbal vs. Chemical Actives as Antidandruff Ingredients -Which Are More Effective in the Management of Dandruff?– An Overview

Issued November 01, 2009
Abstract
Dandruff, a clinical condition caused by Malassezia (Pityrosporum) species is of great cosmetic concern all over the world.
Dandruff is known to be controlled by fungistatic ingredients in Anti-dandruff shampoos.
A comparative study on the efficacy of chemical and herbal anti-dandruff ingredients on ‘as is’ basis and their performance in market shampoos was done in vitro against Pityrosporum ovale (MTCC 1374). Zinc pyrithione (ZnPTO), ketoconazole and other azole compounds recorded good anti-Pityrosporum activity among the chemical ingredients.
Herbal ingredients like tea tree oil, rosemary oil, coleus oil, clove oil,pepper extract, neem extract, and basil extract also recorded anti-pityrosporum activity, but their MIC values are much higher than the synthetic ingredients.
Shampoos containing ZnPTO and ketoconazole recorded higher in vitro activities than the shampoos containing herbal AD ingredients.

Key Words : Malassezia, Pityrosporum, Dandruff, Anti-dandruff activity, Shampoos.

Introduction
Dandruff is a common scalp disorder affecting almost half of the post pubertal population of any ethnicity and both genders.
The exact nature and etiology of dandruff has always been controversial since the time of the Greeks, through Sabouraud’s era in late nineteenth century till to-date (Saint-Leger, 1990).

Dandruff represents 25% of all scalp disorders (Herrera-Arellano et al 2004). It is present in an estimated 15-20% of the total population (Selden, 2005) and more than 50% of adult population (Ro and Dawson, 2005).

The pathogenesis of dandruff involves hyper proliferation, resulting in deregulation of keratinization.
The corneocytes clump together, manifesting as large flakes of skin. Essentially keratolytic agents, such as salicylic acid and sulfur, loosen the attachments between the corneocytes and allow them to be washed away with shampooing.
Keratolytics soften, dissolve and release the adherent scale seen in dandruff, although the mechanism is not fully understood (Angela San Philippo, 2006).

The causative agents of dandruff belong to the group of scalp commensal lipophilic yeasts of the genus, Malassezia.
Eradicating or controlling the abundance of yeasts appears to be the cleverest strategy for treating dandruff.
Using various methods, different clinical and experimental protocols and distinct active ingredients, all indicate that applying antifungal based antidandruff shampoos lead to a stereotyped sequence of events. (Pierard-Franchimont et al, 2006)

Several fungi static compounds have been shown to improve dandruff condition.
The main active ingredients include imidazole derivatives such as ketoconazole and other compounds such as selenium sulphide, zinc pyrithione (ZnPTO), piroctone olamine, cipropirox olamine, etc.
The ultimate goals of antidandruff products are to remove scales, reduce Malassezia (Pityrosporum) spp adherence to corneocytes and inhibit the yeast growth.
Besides the chemical actives, there is a wide range of herbal ingredients like pepper extract, basil extract, neem extract, rosemary oil, basil oil, clove oil, coleus oil, tea tree oil which have been documented to have good anti pityrosporum or antidandruff (AD) activity.

There are several independent studies on these chemical or herbal actives and their efficacy in AD shampoos.
However, there is no comprehensive comparative in vitro study on the AD efficacy of the chemical and herbal actives on ‘as is’ basis or as a functional ingredient in the formulation (AD shampoo).
Hence the present study was undertaken.

Materials and Methods
All natural and synthetic ingredients were procured from the local market. P. ovale MTCC 1374 culture was received from IMTECH, Chandigarh. The shampoos used in the study were popular brands in the Chennai market (names not disclosed to avoid any commercial implication). The base shampoo was
prepared without any anti-dandruff ingredients

Minimum Inhibitory Concentration (MIC) (Krishnamoorthy et al (2006) and Takashi Sugita et al (2005):.
1. 24 hrs broth culture of the test organism was used for the study.
2. Doubling dilution of ingredients were done (5, 2.5, 1.25, 0.6 µg/ml) in the appropriate solvents.
3. The culture (104 cfu/ml) in the SDA broth with olive oil was used for inoculation of the tubes with the test ingredients and incubated at 300 C for 24 hrs.
4. After 24 hrs from the broth a loop full of culture was streaked on a SDA agar plate overlaid with olive oil to know the presence or absence of growth of Malassezia.
5. Agar dilution method was adapted for evaluation of shampoos. Different concentrations viz 2.5, 5,7.5, 10, 25, 50, 75, 100, 125, 150 mg/ml of shampoos (containing active ingredients) were weighed separately in the petriplates and the molten SDA was poured and mixed thoroughly.
6. 20 µl of culture was spread over the agar.
7. The plates were incubated at 300 C for 3-5 days.
8. Experiments were done in triplicates with suitable controls. Zone of Inhibition (ZOI) (Kumar GS et al, 2007)

1. 24 hrs broth culture was swabbed over the surface of Dixon agar
2. All the active ingredients and the shampoos were dissolved in their respective solvents at 10 mg/ml concentration.
3. A well of 7 mm diameter was cut at the centre of the agar and 100 µl of the above prepared samples were loaded on the well.
4. Plates were incubated at 30 0 C for 3-5 days.
5. After incubation the zone was measured using zone measuring scale and recorded.
Results and Discussion:
The recorded results are presented in Tables 1 & 2, Fig 1 & 2.
1. Ketoconazole, Metronidazole and Fluconazole showed MIC of 2.5 µg/ml and ZOI of 25 mm.
2. ZnPTO and Octopirox showed MIC of 5 µg/ml and ZOI of 25 and 13 mm respectively.
3. Climbazole showed MIC of 20 µg/ml and ZOI of 30 mm.
4. Clove oil recorded good activity with a least MIC of 1000 µg/ml.
5. Coleus oil showed MIC at 25 mg/ml and ZOI of 8 mm, Basil oil recorded MIC at 10 mg/ml and ZOI of 5 mm, tea tree oil at 100 mg/ml and ZOI was nil and Rosemary oil at 200 mg/ml and ZOI was nil.
6. Propylene glycol extract of pepper showed MIC of 80 mg/ml, neem and Basil extracts showed inhibition at 100 mg/ml. No zones were observed.
7. Base shampoo (Control) showed MIC of 150 mg/ml and ZOI of 10 mm.
8. Shampoos A,B,C with 1% ZnPTO showed MIC at 5 mg/ml and ZOI of 27 mm dia., 1% ketoconazole showed MIC of 5 mg/ml and ZOI of 30 mm, 0.5 % climbazole showed MIC of 10 mg/ml and ZOI of 27 mm.
9. Herbal shampoo with 0.23% of Climbazole and tea tree oil, henna and lemon extract showed MIC at 25 mg/ml and ZOI of 23 mm.
10. Herbal shampoo with rosemary oil and tea tree oil showed MIC of 100 mg/ml and ZOI of 10 mm.
The lack of ZOI for the oils may be attributed to their inability to diffuse through the agar medium.

Among the shampoos, those containing ZnPTO and Ketoconazole recorded higher activity levels.
According to our survey in Chennai, India, most of the consumers with dandruff prefer to use shampoos with ZnPTO than any other actives.

In the survey conducted in Chennai population (consisting of both sexes) of 324 consumers only 138 were using AD shampoos of which 114 were users of shampoos with ZnPTO (82.6%), 8 were users of shampoo with ketoconazole, 8 were users of herbal shampoos and another 8 were using shampoos with climbazole.
A large population (n= 186) were using shampoos with no specific antidandruff ingredients despite having dandruff problem.
This could be due to the lack of awareness regarding use of anti-dandruff shampoos or that their dandruff condition may be in the range of mild to moderate which would have been managed by regular hair washing with an ordinary shampoo.
The preference to ZnPTO based shampoos by the consumers is mainly because of the better management of dandruff by these shampoos.

The results of the present in vitro studies also justify this stand. ZnPTO besides controlling the proliferation of the causative agent may also heal the scalp by normalizing epithelial keratinization, sebum production, or both.
Some of the earlier studies have also shown a significant reduction in the numbers of yeast organisms after the application of zinc pyrithione.
Ketoconazole is a broad spectrum antimycotic agent that is active against P. ovale (Angela San Philippo, 2006).
Ketoconazole, an imidazole derivative, is effective against many fungi both in vivo and in vitro (Heel et al, 1982).
It is effective in many dermatomycoses, including pityriasis versicolor (Faergamann et al, 1982).
However the lower preference to the ketoconazole based shampoos by the consumers may be attributed to the relatively higher costs.
However, the people (n=8) who have turned to ketoconazole based shampoos in the present study had extensive dandruff and they have been prescribed to use the shampoos by their dermatologists.
Further, even though Metronidazole, Fluconazole have also recorded significant anti-Pityrosporum activity in vitro (MIC and ZOI), their usage (oral/ topical drugs) may be limited to severe manifestations of Malassezia as in conditions like seborrheic dermatitis and pityriasis versicolor.

Among the herbal ingredients tea tree oil recorded significant anti-fungal activity.
Tea tree oil is the essential oil of the leaves of the Australian Melaleuca alternifolia tree.
It is a mixture of hydrocarbons and terpenes, consisting of almost 100 substances.
The antimicrobial property is attributed primarily to the major component, terpinen-4-ol.
Tea tree oil represents a sound alternative for patients with dandruff who prefer a natural product and who are willing to shampoo their hair daily (Angela San Philippo, 2006).
In our current study, basil oil and coleus oil recorded the highest activity among the herbal ingredients.

Table 1: MIC and ZOI for all synthetic and Herbal ingredients
S.No Sample MIC ZOI (dia in mm)
Synthetic Ingredients
1. Ketoconazole 2.5 µg/ml 25
2. Metronidazole 2.5 µg/ml 25
3. Fluconazole 2.5 µg/ml 25
4. ZnPTO 5 µg/ml 25
5. Octopirox 5 µg/ml 13
6. Climbazole 20 µg/ml 30
Herbal Ingredients
1. Clove oil 1000 µg/ml 20
2. Coleus oil 25 mg/ml 8
3. Basil oil 10 mg/ml 5
4. Tea tree oil 100 mg/ml Nil
5. Rosemary oil 200 mg/ml Nil
6. Pepper Extract 80 mg/ml Nil
7. Neem extract 100 mg/ml Nil
8. Basil extract 100 mg/ml Nil
Table 2 : Anti dandruff activity of Shampoos with synthetic and herbal active ingredients
S.No Shampoo with Actives MIC ZOI(dia in mm)
1 Base shampoo 150 mg/ml 10
2 1% ketoconazole 5 mg/ml 30
3 Shampoo A with 1 %
ZnPTO
5 mg/ml 27
4 Shmapoo B with 1 %
ZnPTO
5 mg/ml 27
5 Shampoo C wih 1 %
ZnPTO
5 mg/ml 27
0.5 % Climbazole 10 mg/ml 25
6 0.23 % Climbazole 25 mg/ml 23
7 0.15 % Tea tree oil,
Rosemary oil
100 mg/ml 10
Figure 1: ZOI of different active ingredients against P.ovale 1374.

Figure 2: ZOI for Shampoos with different active ingredients against P.ovale 1374.

Ketoconazole and ZnPTO based shampoos (OTC products) are used more by the consumers for common dandruff problems.
The shampoos with ZnPTO are preferred by majority of the consumers not only as the shampoo brands with ZnPTO (AD ingredient) are cheaper but also provide the desired functional benefit.
However, in very severe cases of dandruff , ketoconazole based shampoos are preferred despite their relatively higher costs.

Herbal ingredients like tea tree oil, rosemary oil, coleus oil, clove oil, pepper extract, neem extract, and basil extract also recorded anti-pityrosporum activity, but their MIC are much higher than the synthetic ingredients.
These ingredients can be exploited for its AD activity individually or in combination in AD shampoos.
The commercial shampoos with tea tree oil, rosemary oil, henna, lemon also recorded good anti- pityrosporum activity in vitro but not better than shampoos with synthetic ingredients in both MIC and ZOI assays.
But for regular usage even shampoos with herbal AD ingredients may suffice the purpose.

Piroctone Vs Ketoconazole Vs Zinc Pyrithione
A study by NCBI compared the three ingredients typically found in anti-dandruff shampoos to treat hair shedding and thinning.

The study was conducted among 150 people who had dandruff related androgenic alopecia. These people were divided into three groups, each using different ingredients two to three times every week for six months. The results are as follows:

Piroctone Olamine

Ketoconazole

Zinc Pyrithione

16.5% of hair fall was reduced among people after using Piroctone Olamine.

Ketoconazole reduced hair fall by 17.3%

Zinc pyrithione managed to lessen the hair loss by 10.1%.

People who used piroctone olamine saw improvement in their hair shaft diameter by 7.9%.

Hair shaft diameter increased by 4.9% among people who used Ketoconazole.

Zinc pyrithione enhanced hair diameter by 6.8%.

Piroctone olamine decreases sebum production in the scalp.

Sebum oil volume reduces after the usage of Ketoconazole.

There is no such effect of zinc pyrithione on sebum output in the scalp.

Environmental Working Group has classified piroctone olamine as a non-toxic ingredient.
However, anything is harmful when it is overused, and the same goes for piroctone olamine.
This is why shampoos with piroctone olamine use a tiny proportion of it to keep any side effects at bay.

Piroctone Olamine is generally safe even for pregnant women, but we suggest taking a gynecologist’s advice before using it.

Wrapping Up

Dandruff can be a real trouble maker and can cost you your precious locks.
But piroctone olamine can be a solution for dandruff and other major hair problems.
Now that you know the benefits of piroctone olamine, you can opt for hair care products that include it.
Dry Scalp And Anti-Dandruff Shampoo contains piroctone olamine as an active ingredient to fight dandruff and provide intense moisturization.

The effect of Ketoconazole and Piroctone olamine on hair growth
Dandruff and seborrheic dermatitis can cause hair loss and thinning hair. It is assumed that dandruff and seborrheic dermatitis (dandruff is a form of seborrheic dermatitis) are caused by a yeast (single cell fungus) on the skin, the Malassezia globose. This is a fungus that occurs only on the scalp.

Often times, the problem will not go away on its own and requires continues treatment. A well-known agent for this is shampoo with Ketoconazole in high concentration. Multiple studies about the effectiveness of this substance have shown that it stimulates hair growth and helps against hereditary hair loss.

Ketoconazole is most well-known, but it is not the only proven anti-dandruff ingredient in shampoos which stimulates hair growth. Piroctone olamine has a similar effect as Ketoconazole. Piroctone olamine is also listed under the brand name ‘Octopirox’.

Ketoconazole vs. Piroctone olamine
In a study with 150 men who suffer from hereditary hair loss and dandruff, Ketoconazole and Piroctone olamine were compared*. Excessive secretion of sebum, dandruff and seborrheic dermatitis are often linked with hair loss and hereditary hair loss. The 150 men received a shampoo with 1% Ketoconazole or 1% Piroctone olamine. They had to use this shampoo 2 to 3 times per week for a duration of six months.

All treatments showed a reduction in itching and dandruff after 2 to 6 weeks. If we take a look at the effect of the treatments on various hair growth parameters, we see the following figures (in percentages):

The severity of hair loss decreases (Ketoconazole: -17.3%, Piroctone olamine: -16.5%)
The percentage of hairs in the growth phase increases (Ketoconazole 4.9%, Piroctone olamine: 7.9%)
The effect on the hair diameter is increased by 5.4% with Ketoconazole and by 7.7% with Piroctone olamine.
Thus, the study shows that Piroctone olamine scores better in a number of areas in comparison to Ketoconazole**:

Compared to Ketoconazole, Piroctone olamine ensures an increase in the number of hairs in the growth phase (anagen phase) by more than 10% in 33% of people.
Piroctone olamine gives 88% of the people thicker hair, despite hereditary hair loss, whereby this is 78% with Ketoconazole.
If we take a look at how many people experience a significant increase (more than 10%) of the hair diameter, this is 28% with Ketoconazole and as much as 34% with Piroctone olamine (10% larger diameter means that the hair became 20% heavier).
Shampoos against dandruff for stimulating hair growth
The above results show that both Ketoconazole and Piroctone olamine have a positive effect on multiple aspects of hair growth. They have a similar effect on itch and dandruff. Piroctone olamine generally scores better when it comes to hair growth.

Thus, the study shows that there is a preference for the use of 1% Piroctone olamine in order to achieve the greatest possible effect on hair growth. 1% Piroctone olamine can be found in the shampoo of Neofollics Hair Technology. In addition to Piroctone olamine, this shampoo contains many more proven effective ingredients, such as Ecklonia cava and Raspberry ketone.

* In this study, Zinc Pyrithione was included, which we will leave out of the picture seeing the minimal results that came forward.
** With the number of subjects that was used, it is not possible to significantly determine the differences between Ketoconazole and Piroctone olamine statistically.

•   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)
•   Ethanolamine salt (1:1)
•   Piroctone olamine Solution, 100ppm
•   PIROCTONE OLAMINE 98.0+%
•   1-hydroxy-4-methyl-6(2,4,4-trimethylpentyl)2-pyridon monoethanolamine salt
•   OCTOPIROX
•   PIROCTONE OLAMINE
•   Piroctone olamine (OCTO)
•   PIROCTONE OLEAMINE
•   1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)pyridin-2(1H)-one, compound with 2-aminoethanol (1:1)
•   Piorctone Olamine
•   1-HYDROXY-4-METHYL-6-(2,4,4-TRIMETHYLPENTYL)2(1H)-PYRIDONE.
•   1-Hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)pyridin-2(1H)-on, Verbindung mit 2-Aminoethanol (1:1)
•   1-hydroxy-4-Methyl-6-(2,4,4-triMethylpentyl)pyridin-2(1H)-one-2-aMinoethanol (1:1)
•   Pyridine-aMino ethanol
•   1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)pyridin-2-one
•   1-Hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1H)-pyridone·2-aminoethanol
•   2-Aminoethanol/1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1H)-pyridone,(1:1)
•   Piroctone Olamine (200 mg)
•   1-Hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1H)-pyridone ethanolammonium salt
•   PiroCLone olaMine
•   LGB-PO
•   OCTO
•   1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)pyridin-2(1H)-one
•   4-methyl-1-oxido-6-(2,4,4-trimethylpentyl)-2-pyridinone
•   Piroctone olamine/octopirox
•   Piroctone Olamine >
•   Piroctone ethanolamine
•   Piroctone ethanolamine fandachem
•   2(1H)-Pyridinone, 1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-, compd.with 2-aminoethanol (1:1)OTHER CA INDEX NAMES:Ethanol, 2-amino-, compd. with1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1H)-pyridinone (1:1)
•   68890-66-4
•   68890-64-4
•   C14H23NO2C2H7NOC16H30N2O3
•   C14H23NO2C2H7NO
•   C14H23NO2C2H7NOC16H30
•   bacteriostatic and fungistatic
•   ARAMINE
•   OLED materials,pharm chemical,electronic

1-Hydroxy-4-methyl-6-(2,4,4-trimethylpentyl) 2-pyridon, monoethanolamine salt
Cosmetic Products Regulation, Annex V – Allowed Preservatives
1-Hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2-(1H)pyridinone, 2-aminoethanol salt

1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)pyridin-2(1H)-one, compound with 2-aminoethanol (1:1)

EC Inventory
1-Hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)pyridin-2(1H)-one, compound with 2-aminoethanol (1:1)
1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)pyridin-2(1H)-one, compound with 2-aminoethanol (1:1)
2(1H)-Pyridinone, 1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-, compd. with 2-aminoethanol (1:1)

Kopirox
Octopirox
Piroctone ethanolamine salt
Piroctone olamine
CAS names
2(1H)-Pyridinone, 1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-, compd. with 2-aminoethanol (1:1)

IUPAC names
(RS)-1-HYDROXY-4-METHYL-6-(2,4,4-TRIMETHYLPENTYL)-2(1H)-PYRIDINONE ETHANOLAMINE (1:1)
1-Hydroxy-4-methyl-6(2,4,4-trimethylpentyl)2-pyridon monoethanolamine salt
1-hydroxy-4-methyl-6-(2,4,4-trimethylpently)pyridin-2-(1H)-one compound with 2-aminoethanol (1:1)
1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-1,2-dihydropyridin-2-one; 2-aminoethan-1-ol
1-Hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2-(1H)pyridinone, 2-aminoethanol salt
1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)pyridin-2(1H)-one – 2-aminoethanol (1:1)
1-Hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)pyridin-2(1H)-one, compound with 2-aminoethanol (1:1)
1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)pyridin-2(1H)-one, compound with 2-aminoethanol (1:1)
1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)pyridin-2(1H)-one, compound with 2-aminoethanol (1:1)
1-Hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)pyridin-2(1H)-one,compound with 2-aminoethanol (1:1)
1-hydroxy-4methyl-6-(2,4,4-trimethylphenyl)pyridine-2(1H)-one, compound with 2-aminoethanol(1:1)
2-aminoethanol; 1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)pyridin-2-one
2-aminoethanol;1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)pyridin-2-one

2-amminoetanolo; 1-idrossi-4-metil-6-(2,4,4-trimethylpentyl) pyridin-2-one

Octopirox
Piroctone Olamine

Piroctone Olamine
Piroctone olamine

Trade names
Picroctone Olamine
Piroctone olamine

Synonyms : piroctone olamine;1-hydroxy-4-methyl-6(2,4,4-trimethylpentyl)2-pyridon monoethanolamine salt;1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)pyridin-2(1H)-one-2-aminoethanol (1:1);1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1h)-pyridinoncompd.with2-aminoethanol(1:1);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-pyridon monoethanolamine salt;Octopirox;Pyridine-amino ethanol;

OCTOPIROX

OCTOPIROX

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