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Identifiers | |
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3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.065.957 |
MeSH | Piroctone+olamine |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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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). |
Piroctone olamine (INN; also known as piroctone ethanolamine) is a compound sometimes used in the treatment of fungal infections. [1] Piroctone olamine is the ethanolamine salt of the hydroxamic acid derivative piroctone was first synthesized in 1979 by Schwarzkopf-Henkel (Germany).
It is often used in anti-dandruff shampoo as a replacement for the commonly used compound zinc pyrithione which was banned in the EU in 2021 because of concerns for environmental toxicity.
It is structurally similar to ciclopirox and pyrithione, containing a substituted pyridine (pyridinone) group which inhibits ergosterol synthesis.[ citation needed ]
Dandruff is a skin condition that mainly affects the scalp. Symptoms include flaking and sometimes mild itchiness. It can result in social or self-esteem problems. A more severe form of the condition, which includes inflammation of the skin, is known as seborrhoeic dermatitis.
Seborrhoeic dermatitis, sometimes inaccurately referred to as seborrhoea, is a long-term skin disorder. Symptoms include flaky, scaly, greasy, and occasionally itchy and inflamed skin. Areas of the skin rich in oil-producing glands are often affected including the scalp, face, and chest. It can result in social or self-esteem problems. In babies, when the scalp is primarily involved, it is called cradle cap. Seborrhoeic dermatitis of the scalp may be described in lay terms as dandruff due to the dry, flaky character of the skin. However, as dandruff may refer to any dryness or scaling of the scalp, not all dandruff is seborrhoeic dermatitis.
Zinc pyrithione is a coordination complex of zinc. It has fungistatic and bacteriostatic properties and is used in the treatment of seborrhoeic dermatitis and dandruff.
Ketoconazole, sold under the brand name Nizoral among others, is an antiandrogen, antifungal, and antiglucocorticoid medication used to treat a number of fungal infections. Applied to the skin it is used for fungal skin infections such as tinea, cutaneous candidiasis, pityriasis versicolor, dandruff, and seborrheic dermatitis. Taken by mouth it is a less preferred option and only recommended for severe infections when other agents cannot be used. Other uses include treatment of excessive male-patterned hair growth in women and Cushing's syndrome.
Hair conditioner is a hair care cosmetic product used to improve the feel, texture, appearance and manageability of hair. Its main purpose is to reduce friction between strands of hair to allow smoother brushing or combing, which might otherwise cause damage to the scalp. Various other benefits are often advertised, such as hair repair, strengthening, or a reduction in split ends.
Keratolytic therapy is a type of medical treatment to remove warts, calluses and other lesions in which the epidermis produces excess skin. In this therapy, acidic topical medicines, such as Whitfield's ointment or Jessner's solution, are applied to the lesion in order to thin the skin on and around it. This therapy causes the outer layer of the skin to loosen and shed.
Ethanolamine is a naturally occurring organic chemical compound with the formula HOCH
2CH
2NH
2 or C
2H
7NO. The molecule is bifunctional, containing both a primary amine and a primary alcohol. Ethanolamine is a colorless, viscous liquid with an odor reminiscent of ammonia.
Head & Shoulders (H&S) is an American brand of anti-dandruff and non-dandruff shampoo produced by parent company Procter & Gamble. It was introduced in the United States on 1 January 1961 based in Manhattan and used the slogan THE AMERICA AND WORLD's NO. 1 SHAMPOO. The active anti-fungal ingredient in Head & Shoulders is piroctone olamine, with some "clinical strength" varieties also containing selenium disulfide.
Cradle cap causes crusty or oily scaly patches on a baby's scalp. The condition is not painful or itchy, but it can cause thick white or yellow scales that are not easy to remove. Cradle cap most commonly begins sometime in the first three months but can occur in later years. Similar symptoms in older children are more likely to be dandruff than cradle cap. The rash is often prominent around the ear, the eyebrows or the eyelids. It may appear in other locations as well, where it is called infantile seborrhoeic dermatitis. Cradle cap is just a special—and more benign—case of this condition. The exact cause of cradle cap is not known. Cradle cap is not spread from person to person (contagious). It is also not caused by poor hygiene. It is not an allergy, and it is not dangerous. Cradle cap often lasts a few months. In some children, the condition can last until age 2 or 3.
Dander is material shed from the body of humans and other animals that have fur, hair, or feathers. The term is similar to dandruff, when an excess of flakes becomes visible. Skin flakes that come off the main body of an animal are dander, while the flakes of skin called dandruff come from the scalp and are composed of epithelial skin cells. The surface layer of mammalian skin is called the stratum corneum, which is shed as part of normal skin replacement.
Selenium disulfide, also known as selenium sulfide, is a chemical compound and medication used to treat seborrheic dermatitis, dandruff, and pityriasis versicolor. It is applied to the affected area as a lotion or shampoo. Symptoms frequently return if treatment is stopped.
Selsun Blue is an over-the-counter brand of dandruff shampoo now owned by Sanofi. First made by Abbott Laboratories, the brand was bought by Chattem in 2002. Chattem was acquired by Sanofi in 2010, although in some markets, it is sold by Rohto Pharmaceutical instead. Selsun Blue has been marketed as a more effective alternative to brand leader Head & Shoulders due to its superior performance in randomized trials.
Diethanolamine, often abbreviated as DEA or DEOA, is an organic compound with the formula HN(CH2CH2OH)2. Pure diethanolamine is a white solid at room temperature, but its tendencies to absorb water and to supercool meaning that it is often encountered as a colorless, viscous liquid. Diethanolamine is polyfunctional, being a secondary amine and a diol. Like other organic amines, diethanolamine acts as a weak base. Reflecting the hydrophilic character of the secondary amine and hydroxyl groups, DEA is soluble in water. Amides prepared from DEA are often also hydrophilic. In 2013, the chemical was classified by the International Agency for Research on Cancer as "possibly carcinogenic to humans" (Group 2B).
Hair straightening is a hair styling technique used since the 1890s involving the flattening and straightening of hair in order to give it a smooth, streamlined, and sleek appearance. It became very popular during the 1950s among black males and females of all races. It is accomplished using a hair iron or hot comb, chemical relaxers, Japanese hair straightening, Brazilian hair straightening, or roller set/blowdryer styling. In addition, some shampoos, conditioners, and hair gels can help to make hair temporarily straight.
Shampoo is a hair care product, typically in the form of a viscous liquid, that is used for cleaning hair. Less commonly, shampoo is available in solid bar format. Shampoo is used by applying it to wet hair, massaging the product into the scalp, and then rinsing it out. Some users may follow a shampooing with the use of hair conditioner.
Climbazole is a topical antifungal agent commonly used in the treatment of human fungal skin infections such as dandruff, seborrhoeic dermatitis and eczema. Climbazole has shown a high in vitro and in vivo efficacy against Malassezia spp. that appear to play an important role in the pathogenesis of dandruff. Its chemical structure and properties are similar to other fungicides such as ketoconazole and miconazole.
Allium stipitatum, Persian shallot, is an Asian species of onion native to central and southwestern Asia.
Anti-seborrheics are drugs effective in seborrheic dermatitis. Selenium sulfide, zinc pyrithione, corticosteroids, imidazole antifungals, and salicylic acid are common anti-seborrheics.
Pyrithione is the common name of an organosulfur compound with molecular formula C
5H
5NOS, chosen as an abbreviation of pyridinethione, and found in the Persian shallot. It exists as a pair of tautomers, the major form being the thione 1-hydroxy-2(1H)-pyridinethione and the minor form being the thiol 2-mercaptopyridine N-oxide; it crystallises in the thione form. It is usually prepared from either 2-bromopyridine, 2-chloropyridine, or 2-chloropyridine N-oxide, and is commercially available as both the neutral compound and its sodium salt. It is used to prepare zinc pyrithione, which is used primarily to treat dandruff and seborrhoeic dermatitis in medicated shampoos, though is also an anti-fouling agent in paints.
Ethyl lauroyl arginate (LAE) is a food preservative, antimicrobial compound, and drug more commonly known as E243. It is used to treat dermatological disorders and is often provided in the form of its hydrochloride salt. LAE is an amino acid-based surfactant with broad-spectrum antimicrobial activity, high biodegradability and low toxicity. Due to these features, LAE is a preservative used in food and cosmetic formulations.