Tolnaftate
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| Clinical data | |
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| Trade names | Tinactin |
| Other names | 2-Naphthyl N-methyl-N-(3-tolyl)thionocarbamate[1] |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a682617 |
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| CAS Number | |
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| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.017.516 |
| Chemical and physical data | |
| Formula | C19H17NOS |
| Molar mass | 307.41 g/mol g·mol−1 |
| 3D model (JSmol) | |
| Melting point | 110 to 111.5 °C (230.0 to 232.7 °F) |
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Tolnaftate (INN)[1] 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, and liquid aerosol. Tolnaftate is used to treat fungal conditions such as jock itch, athlete's foot and ringworm.
Mechanism
Although the exact mechanism of action is not entirely known, it is believed to inhibit squalene epoxidase,[2] an important enzyme in the biosynthetic pathway of ergosterol (a key component of the fungal membrane) in a similar way to allylamines.[3]
Uses
Tolnaftate has been found to be generally slightly less effective than azoles when used to treat tinea pedis (athlete's foot). It is, however, useful when dealing with ringworm, especially when passed from pets to humans.[4]
References
- ^ a b "International Non-Proprietary Names for Pharmaceutical Preparations. Recommended International Non-Proprietary names (Rec. I.N.N.): List 6" (PDF). World Health Organization. Retrieved 12 November 2016.
- ^ 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". Retrieved 2008-07-09.
- ^ Crawford F, Hart R, Bell-Syer S, Torgerson D, Young P, Russell I. Topical treatments for fungal infections of the skin and nails of the foot (Cochrane Review). In: The Cochrane Library, Issue 1, 2003. Oxford: Update Software.