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Trade names | Mentax, Lotrimin Ultra |
AHFS/Drugs.com | Monograph |
Routes of administration | Topical (cream) |
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Pharmacokinetic data | |
Metabolism | Hepatic |
Elimination half-life | 35–100 hours |
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Chemical and physical data | |
Formula | C23H27N |
Molar mass | 317.476 g·mol−1 |
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Butenafine, sold under the brand names Lotrimin Ultra, Mentax, and Butop (In India only), is a synthetic benzylamine derived antifungal drug.
It is structurally related to the allylamine antifungals terbinafine & naftifine.
Butenafine is indicated for the topical treatment of tinea (pityriasis) versicolor due to Malassezia furfur , as well as athlete's foot (Tinea pedis), ringworm (Tinea corporis) and jock itch (Tinea cruris) due to Epidermophyton floccosum , Trichophyton mentagrophytes , Trichophyton rubrum , and Trichophyton tonsurans .
It also displays superior activity against Candida albicans than terbinafine and naftifine. Butenafine demonstrates low minimum inhibitory concentrations against Cryptococcus and Aspergillus .
There is some evidence that it is effective against dermatophyte infections of the toenails, but needs to be applied daily for prolonged periods (at least one year). [1]
Butenafine is typically available as a 1% topical cream.
Like the allylamine antifungals (e.g terbinafine), butenafine works by inhibiting the synthesis of ergosterol by binding to and inhibiting squalene epoxidase, an enzyme in the pathway used for creation of the sterols needed in fungal cell membranes. Lacking ergosterol, the cell membranes increase in permeability, allowing their contents to leak out. Furthermore, inhibition of squalene epoxidase leads to a toxic buildup of squalene. This double action of butenafine (increased membrane permeability and toxic buildup of squalene) makes butenafine fungicidal rather than merely fungistatic.
In addition to being an antifungal, butenafine is an anti inflammatory. Because fungal skin infections are often accompanied by significant inflammation, this is a desirable property. The fact that butenafine has intrinsic anti inflammatory properties is also desirable since it is not necessary to add topical glucocorticoids, which often come with undesired side effects.
Butenafine hydrochloride is an odorless white crystalline powder that is freely soluble in methanol, ethanol, and chloroform, yet is only slightly soluble in water.
Reductive amination of 1-naphthaldehyde (1) with methylamine (2) gives the intermediate secondary amine (3). Alkylation of this with p-tert-butyl benzyl bromide (4) yields the tertiary amine butenafine. [2] [3] [4]
Tinea cruris, also known as jock itch, is a common type of contagious, superficial fungal infection of the groin and buttocks region, which occurs predominantly but not exclusively in men and in hot-humid climates.
An antifungal medication, also known as an antimycotic medication, is a pharmaceutical fungicide or fungistatic used to treat and prevent mycosis such as athlete's foot, ringworm, candidiasis (thrush), serious systemic infections such as cryptococcal meningitis, and others. Such drugs are usually obtained by a doctor's prescription, but a few are available over the counter (OTC). The evolution of antifungal resistance is a growing threat to health globally.
Athlete's foot, known medically as tinea pedis, is a common skin infection of the feet caused by a fungus. Signs and symptoms often include itching, scaling, cracking and redness. In rare cases the skin may blister. Athlete's foot fungus may infect any part of the foot, but most often grows between the toes. The next most common area is the bottom of the foot. The same fungus may also affect the nails or the hands. It is a member of the group of diseases known as tinea.
Tolnaftate (INN) is a synthetic thiocarbamate used as an anti-fungal agent that may be sold without medical prescription in most jurisdictions. It is supplied as a cream, powder, spray, liquid, and liquid aerosol. Tolnaftate is used to treat fungal conditions such as jock itch, athlete's foot and ringworm.
Terbinafine is an antifungal medication used to treat pityriasis versicolor, fungal nail infections, and ringworm including jock itch and athlete's foot. It is either taken by mouth or applied to the skin as a cream or ointment. The cream and ointment should not be used for fungal nail infections.
Dermatophyte is a common label for a group of fungus of Arthrodermataceae that commonly causes skin disease in animals and humans. Traditionally, these anamorphic mold genera are: Microsporum, Epidermophyton and Trichophyton. There are about 40 species in these three genera. Species capable of reproducing sexually belong in the teleomorphic genus Arthroderma, of the Ascomycota. As of 2019 a total of nine genera are identified and new phylogenetic taxonomy has been proposed.
Tinea corporis is a fungal infection of the body, similar to other forms of tinea. Specifically, it is a type of dermatophytosis that appears on the arms and legs, especially on glabrous skin; however, it may occur on any superficial part of the body.
Tinea capitis is a cutaneous fungal infection (dermatophytosis) of the scalp. The disease is primarily caused by dermatophytes in the genera Trichophyton and Microsporum that invade the hair shaft. The clinical presentation is typically single or multiple patches of hair loss, sometimes with a 'black dot' pattern, that may be accompanied by inflammation, scaling, pustules, and itching. Uncommon in adults, tinea capitis is predominantly seen in pre-pubertal children, more often boys than girls.
Dermatophytosis, also known as tinea and ringworm, is a fungal infection of the skin, that may affect skin, hair, and nails. Typically it results in a red, itchy, scaly, circular rash. Hair loss may occur in the area affected. Symptoms begin four to fourteen days after exposure. The types of dermatophytosis are typically named for area of the body that they affect. Multiple areas can be affected at a given time.
Onychomycosis, also known as tinea unguium, is a fungal infection of the nail. Symptoms may include white or yellow nail discoloration, thickening of the nail, and separation of the nail from the nail bed. Fingernails may be affected, but it is more common for toenails. Complications may include cellulitis of the lower leg. A number of different types of fungus can cause onychomycosis, including dermatophytes and Fusarium. Risk factors include athlete's foot, other nail diseases, exposure to someone with the condition, peripheral vascular disease, and poor immune function. The diagnosis is generally suspected based on the appearance and confirmed by laboratory testing.
Sertaconazole, sold under the brand name Ertaczo among others, is an antifungal medication of the Benzothiophene class. It is available as a cream to treat skin infections such as athlete's foot.
Tinea manuum is a fungal infection of the hand, mostly a type of dermatophytosis, often part of two feet-one hand syndrome. There is diffuse scaling on the palms or back of usually one hand and the palmer creases appear more prominent. When both hands are affected, the rash looks different on each hand, with palmer creases appearing whitish if the infection has been present for a long time. It can be itchy and look slightly raised. Nails may also be affected.
Undecylenic acid is an organic compound with the formula CH2=CH(CH2)8CO2H. It is an unsaturated fatty acid. It is a colorless oil. Undecylenic acid is mainly used for the production of Nylon-11 and in the treatment of fungal infections of the skin, but it is also a precursor in the manufacture of many pharmaceuticals, personal hygiene products, cosmetics, and perfumes. Salts and esters of undecylenic acid are known as undecylenates.
Trichophyton rubrum is a dermatophytic fungus in the phylum Ascomycota. It is an exclusively clonal, anthropophilic saprotroph that colonizes the upper layers of dead skin, and is the most common cause of athlete's foot, fungal infection of nail, jock itch, and ringworm worldwide. Trichophyton rubrum was first described by Malmsten in 1845 and is currently considered to be a complex of species that comprises multiple, geographically patterned morphotypes, several of which have been formally described as distinct taxa, including T. raubitschekii, T. gourvilii, T. megninii and T. soudanense.
Squalene monooxygenase is a eukaryotic enzyme that uses NADPH and diatomic oxygen to oxidize squalene to 2,3-oxidosqualene. Squalene epoxidase catalyzes the first oxygenation step in sterol biosynthesis and is thought to be one of the rate-limiting enzymes in this pathway. In humans, squalene epoxidase is encoded by the SQLE gene. Several eukaryote genomes lack a squalene monooxygenase encoding gene, but instead encode an alternative squalene epoxidase that performs the same task.
Naftifine hydrochloride is an allylamine antifungal drug for the topical treatment of tinea pedis, tinea cruris, and tinea corporis.
Clotrimazole, sold under the brand name Lotrimin, among others, is an antifungal medication. It is used to treat vaginal yeast infections, oral thrush, diaper rash, tinea versicolor, and types of ringworm including athlete's foot and jock itch. It can be taken by mouth or applied as a cream to the skin or in the vagina.
Microsporum audouinii is an anthropophilic fungus in the genus Microsporum. It is a type of dermatophyte that colonizes keratinized tissues causing infection. The fungus is characterized by its spindle-shaped macroconidia, clavate microconidia as well as its pitted or spiny external walls.
Liranaftate is a topical antifungal drug. It is used as a 2% cream used to treat tinea pedis, tinea corporis (ringworm), and tinea cruris. It was approved for use in Japan in August 2000.
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.