A topical antifungal agent.
Tolnaftate
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| Systematic (IUPAC) name | |
|---|---|
| O-2-naphthyl methyl(3-methylphenyl)thiocarbamate | |
| Identifiers | |
| CAS number | 2398-96-1 |
| ATC code | D01AE18 |
| PubChem | 5510 |
| Chemical data | |
| Formula | C19H17NOS |
| Mol. mass | 307.41 g/mol |
| SMILES | eMolecules & PubChem |
| Physical data | |
| Melt. point | 110–111.5 °C (230–233 °F) |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
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| Legal status |
OTC |
| Routes | ? |
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Tolnaftate is a synthetic over-the-counter anti-fungal agent. It may come as a cream, powder, spray, or liquid aerosol, and is used to treat jock itch, athlete's foot and ringworm. It is sold under several brand names, most notably Tinactin (Schering-Plough Corporation) and Odor Eaters (Combe Incorporated). Other brands are Absorbine, Aftate, Genaspor, Lamasil AF, NP 27, Scholl and Ting.
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Synthesis
The synthesis of tolnaftate is a three step process first involving 2-napthol with a base, to deprotonate the acidic phenol hydrogen. NaH,NaNH2, or really any base of choice will work just fine. Treatment of N-methyl-m-toluidine with CS2 and CH3Br results in a thiocarbamate intermediate that reacts with the negatively charged oxygen on the deprotonated 2-napthol, displacing the -SCH3 group and forming the final product.
Mechanism
Although the exact mechanism of action is not entirely known, it is believed to inhibit the squalene epoxidase,[1] an important enzyme in the biosynthetic pathway of ergosterol (a key component of the fungal membrane) in a similar way to allylamines.[2]
Uses
Tolnaftate has been found to be generally slightly less effective than azoles when used to treat tinea pedis. It is, however, useful when dealing with ringworm, especially when passed from pets to humans.[3]
References
- ^ 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. PMID 3524433. PMC 284167. http://aac.asm.org/cgi/pmidlookup?view=long&pmid=3524433.
- ^ "antifung". http://faculty.swosu.edu/scott.long/phcl/antifung.htm. 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.
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 | Veterinary Dictionary. Saunders Comprehensive Veterinary Dictionary 3rd Edition. Copyright © 2007 by D.C. Blood, V.P. Studdert and C.C. Gay, Elsevier. All rights reserved. Read more |
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| Wikipedia. This article is licensed under the Creative Commons Attribution/Share-Alike License. It uses material from the Wikipedia article "Tolnaftate". Read more |
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