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Tolnaftate is a thiocarbamate antifungal agent. It is active against clinical isolates of the dermatophytes
T. rubrum,
T. mentagraphytes,
T. verrucosum,
E. floccosum, and
M. canis (MIC
50s = 50, 100, 6, 50, and 50 ng/ml, respectively), as well as 18 additional yeast and filamentous fungi species (MIC = 0.003-0.8 μg/ml)., Tolnaftate also reduces aflatoxin production in
A. parasiticus in a concentration-dependent manner. It inhibits squalene epoxidase with an IC
50 value of 12.5 μg/ml in a cell-free assay.
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White Solid
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antifungal for cutaneous infections.
Tolnaftate (Aftate, Tinactin, etc.) is an odorless and nonstaining synthetic antifungal agent whose exact mechanism of action is unknown. It is effective against dermatophytes and P. orbiculare and Pityrosporum ovale. It is ineffective against C. albicans and bacteria.
Indications
Tolnaftate (Aftate, Tinactin, etc.) is an odorless and nonstaining synthetic
antifungal agent whose exact mechanism of action is unknown. It is effective
against dermatophytes and P. orbiculare and Pityrosporum ovale. It is
ineffective against C. albicans and bacteria.
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ChEBI: A monothiocarbamic ester that is the methyl(3-tolyl)carbamothioate ester of 2-naphthol. A synthetic anti-fungal agent used to treat jock itch, athlete's foot and ringworm.
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Crystals or white powder.
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Thio and dithiocarbamates slowly decompose in aqueous solution to form carbon disulfide and methylamine or other amines. Such decompositions are accelerated by acids. Insoluble in water.
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Tolnaftate is a thiocarbamate. Flammable gases are generated by the combination of thiocarbamates and dithiocarbamates with aldehydes, nitrides, and hydrides. Thiocarbamates and dithiocarbamates are incompatible with acids, peroxides, and acid halides.
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SYMPTOMS: In susceptible persons, Tolnaftate may cause sensitization or irritation.
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Flash point data on Tolnaftate are not available, Tolnaftate is probably combustible.
Clinical Use
O,2-Naphthyl m,N-dimethylthiocarbanilate (Tinactin,Aftate, NP-27) is a white crystalline solid that is insoluble inwater, sparingly soluble in alcohol, and soluble in most organicsolvents. The compound, a thioester of β-naphthol, isfungicidal against dermatophytes, such as Trichophyton,Microsporum, and Epidermophyton spp., that cause superficialtinea infections. Tolnaftate is available in a concentrationof 1% in creams, powders, aerosols, gels, and solutionsfor the treatment of ringworm, jock itch, and athlete’s foot.Tolnaftate has been shown to act as an inhibitor of squaleneepoxidase in susceptible fungi, so it is classified with theallylamine antimycotics. Tolnaftate is formulated into preparationsintended to be used with artificial fingernails to counteractthe increased chance of ringworm of the nail beds.
Safety Profile
Mtldly toxic by
ingestion. An experimental teratogen. When
heated to decomposition it emits toxic
fumes of SOx and NOx. A fungicide used to
control athlete's foot. See also ESTERS and
CARBAMATES.
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