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Tolnaftate
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)
Therapeutic considerations
Pregnancy cat.  ?
Legal status OTC
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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.

Contents

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

  1. ^ 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. 
  2. ^ "antifung". http://faculty.swosu.edu/scott.long/phcl/antifung.htm. Retrieved 2008-07-09. 
  3. ^ 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.

External links

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