|Trade names||Tinactin, Absorbine, others|
|Other names||2-Naphthyl N-methyl-N-(3-tolyl)thionocarbamate|
|Main uses||Jock itch, athlete's foot, ringworm, pityriasis versicolor|
|Side effects||Skin irritation|
|Chemical and physical data|
|Molar mass||307.41 g·mol−1|
|3D model (JSmol)|
|Melting point||110 to 111.5 °C (230.0 to 232.7 °F)|
|(what is this?)|
Tolnaftate, sold under various brand names, is a medication used to treat fungal infections including jock itch, athlete's foot, ringworm, and pityriasis versicolor. It is applied to the skin. It comes in cream, powder, spray and solution forms.
Tolnaftate was developed around 1962. It is available as a generic medication and over the counter. In the United States a 28 gram tube of medication costs about 6 USD as of 2021. It is also available in the United Kingdom without a prescription.
Since the availability of more potent antifungals such as terbinafine and naftifine, its use has declined. Tolnaftate as a powder can be used on the feet to prevent athlete's foot in those susceptible. It is useful when dealing with ringworm, especially when passed from pets to humans. It has also been used to treat otitis externa due to Aspergillus app., but its poor penetration into nail has not allowed it to be of use in fungal infections of the nail.
Although the exact mechanism of action is not entirely known, it is believed to inhibit squalene epoxidase, an important enzyme in the biosynthetic pathway of ergosterol (a key component of the fungal cell membrane) in a similar way to terbinafine.
- Liranaftate, a similar thiocarbamate antifungal
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- Ghannoum, Mahmoud; Isham, Nancy (2017). "Tolnaftate". Kucers’ The Use of Antibiotics (7 ed.). CRC Press. ISBN 978-1-315-15211-0.
- James, William D.; Elston, Dirk; Treat, James R.; Rosenbach, Misha A.; Neuhaus, Isaac (2020). "15. Diseases resulting from fungi and yeasts". Andrews' Diseases of the Skin: Clinical Dermatology (13th ed.). Elsevier. pp. 297–299. ISBN 978-0-323-54753-6.
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- Ryder NS, Frank I, Dupont MC (May 1986). "Ergosterol biosynthesis inhibition by the thiocarbamate antifungal agents tolnaftate and tolciclate". Antimicrob. Agents Chemother. 29 (5): 858–60. doi:10.1128/aac.29.5.858. PMC 284167. PMID 3524433.
- "antifung". Archived from the original on 2008-06-17. Retrieved 2008-07-09.