The synthesis of tolnaftate is a three-step process first involving 2-napthol with a base, to deprotonate the acidic phenol hydrogen. NaH, NaNH2 are commonly used. Other common bases may also be used with the same effect. 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.
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. Tolnaftate is ineffective against Candida albicans, and thus ineffective against candidal intertrigo, which may sometimes masquerade as fungal infections by dermatophytic fungi that are typically the cause of tinea.
^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.