Climbazole

Last updated
Climbazole
Climbazole.svg
Clinical data
Routes of
administration
topical
ATC code
  • none
Identifiers
  • (RS)-1-(4-Chlorophenoxy)-1-imidazol-1-yl-3,3-dimethylbutan-2-one [1]
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.048.870 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C15H17ClN2O2
Molar mass 292.76 g·mol−1
3D model (JSmol)
Chirality Racemic mixture
  • CC(C)(C)C(=O)C(n1ccnc1)Oc2ccc(cc2)Cl
  • InChI=1S/C15H17ClN2O2/c1-15(2,3)13(19)14(18-9-8-17-10-18)20-12-6-4-11(16)5-7-12/h4-10,14H,1-3H3 X mark.svgN
  • Key:OWEGWHBOCFMBLP-UHFFFAOYSA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Climbazole is a topical antifungal agent commonly used in the treatment of human fungal skin infections such as dandruff, seborrhoeic dermatitis and eczema. [2] 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. [2] Its chemical structure and properties are similar to other azole fungicides such as ketoconazole, clotrimazole and miconazole.

Contents

Indications and formulations

It is most commonly found as an active ingredient in OTC anti-dandruff and anti-fungal products, including shampoos, lotions and conditioners. It may be accompanied by other active ingredients such as zinc pyrithione or triclosan.[ citation needed ]

Side effects

It may cause localized irritation of the skin with symptoms including redness, rashes and itching.[ citation needed ]

Related Research Articles

<span class="mw-page-title-main">Dermatitis</span> Inflammatory disease of the skin

Dermatitis is a term used for different types of skin inflammation, typically characterized by itchiness, redness and a rash. In cases of short duration, there may be small blisters, while in long-term cases the skin may become thickened. The area of skin involved can vary from small to covering the entire body. Dermatitis is also called eczema but the same term is often used for the most common type of skin inflammation, atopic dermatitis.

<span class="mw-page-title-main">Dandruff</span> Skin condition of the scalp

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.

<span class="mw-page-title-main">Seborrhoeic dermatitis</span> Skin disease

Seborrhoeic dermatitis 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. Seborrhoeic dermatitis is sometimes inaccurately referred to as seborrhoea.

<span class="mw-page-title-main">Zinc pyrithione</span> Chemical compound

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.

<span class="mw-page-title-main">Benzyl alcohol</span> Aromatic alcohol

Benzyl alcohol (also known as α-cresol) is an aromatic alcohol with the formula C6H5CH2OH. The benzyl group is often abbreviated "Bn" (not to be confused with "Bz" which is used for benzoyl), thus benzyl alcohol is denoted as BnOH. Benzyl alcohol is a colorless liquid with a mild pleasant aromatic odor. It is useful as a solvent for its polarity, low toxicity, and low vapor pressure. Benzyl alcohol has moderate solubility in water (4 g/100 mL) and is miscible in alcohols and diethyl ether. The anion produced by deprotonation of the alcohol group is known as benzylate or benzyloxide.

<span class="mw-page-title-main">Head & Shoulders</span> Shampoo brand by Procter & Gamble

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.

<span class="mw-page-title-main">Cradle cap</span> Crusting or scaling of a babys scalp

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.

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.

<span class="mw-page-title-main">Hair care</span> Hygiene and cosmetology involving human hair

Hair care or haircare is an overall term for hygiene and cosmetology involving the hair which grows from the human scalp, and to a lesser extent facial, pubic and other body hair. Hair care routines differ according to an individual's culture and the physical characteristics of one's hair. Hair may be colored, trimmed, shaved, plucked or otherwise removed with treatments such as waxing, sugaring and threading. Hair care services are offered in salons, barbershops and day spas, and products are available commercially for home use. Laser hair removal and electrolysis are also available, though these are provided by licensed professionals in medical offices or speciality spas.

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.

<span class="mw-page-title-main">Lotion</span> Skin treatment preparation

Lotion is a low-viscosity topical preparation intended for application to the skin. By contrast, creams and gels have higher viscosity, typically due to lower water content. Lotions are applied to external skin with bare hands, a brush, a clean cloth, or cotton wool.

<span class="mw-page-title-main">Baby shampoo</span> Personal care product

Baby shampoo is a hair care product that is used for the removal of oils, dirt, skin particles, dandruff, environmental pollutants and other contaminant particles that gradually build up in hair; specially formulated for use on infants and young children by means of substituting chemicals which are purportedly less irritating to the eyes than those commonly found in regular shampoo.

<span class="mw-page-title-main">Piroctone olamine</span> Chemical compound

Piroctone olamine is a compound sometimes used in the treatment of fungal infections. Piroctone olamine is the ethanolamine salt of the hydroxamic acid derivative piroctone was first synthesized in 1979 by Schwarzkopf-Henkel (Germany).

<span class="mw-page-title-main">Ecotoxicity</span>

Ecotoxicity, the subject of study in the field of ecotoxicology, refers to the biological, chemical or physical stressors that affect ecosystems. Such stressors could occur in the natural environment at densities, concentrations, or levels high enough to disrupt natural biochemical and physiological behavior and interactions. This ultimately affects all living organisms that comprise an ecosystem.

<span class="mw-page-title-main">Shampoo</span> Hair care product

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.

<span class="mw-page-title-main">Dry shampoo</span> Hair product

Dry shampoo otherwise known as hybrid shampoo is a type of shampoo which reduces hair greasiness without the need for water. It is in powder form and is typically administered from an aerosol can. Dry shampoo is often based on corn starch or rice starch. In addition to cleansing hair, it can also be used as a tool for hair-styling as it can create volume, help tease hair, keep bobby pins in place, and be used in place of mousse in wet hair. Dry shampoo proponents attest that daily wash-and-rinse with detergent shampoo can strip away natural oils from hair. However, others attest that spraying dry shampoo every day will lead to a build-up of product that can dull hair color and irritate the scalp, arguing that the scalp needs regular cleansing and exfoliating to get rid of bacteria, remove dead skin cells, and stay healthy.

Vosene is a brand of medicated shampoo, intended to provide relief from dandruff. It is widely available in the United Kingdom in 250 ml bottles.

Malassezia sympodialis is a species in the genus Malassezia. It is characterized by a pronounced lipophily, unilateral, percurrent or sympodial budding and an irregular, corrugated cell wall ultrastructure. It is one of the most common species found on the skin of healthy and diseased individuals. It is considered to be part of the skin's normal human microbiota and begins to colonize the skin of humans shortly after birth. Malassezia sympodialis, often has a symbiotic or commensal relationship with its host, but it can act as a pathogen causing a number of different skin diseases, such as atopic dermatitis.

<span class="mw-page-title-main">Ethyl lauroyl arginate</span> Chemical compound

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.

Topical antifungaldrugs are used to treat fungal infections on the skin, scalp, nails, vagina or inside the mouth. These medications come as creams, gels, lotions, ointments, powders, shampoos, tinctures and sprays. Most antifungal drugs induce fungal cell death by destroying the cell wall of the fungus. These drugs inhibit the production of ergosterol, which is a fundamental component of the fungal cell membrane and wall.

References

  1. Chemical Properties of Climbazole Archived 2007-11-13 at the Wayback Machine
  2. 1 2 Wigger-Alberti W, Kluge K, Elsner P (August 2001). "[Clinical effectiveness and tolerance of climbazole containing dandruff shampoo in patients with seborrheic scalp eczema]". Praxis. 90 (33): 1346–9. PMID   11534318.