Tolnaftate (TN)

Tolnaftate 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. 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. Although the exact mechanism of action is not entirely known, it is believed to inhibit the squalene epoxidase, an important enzyme in the biosynthetic pathway of ergosterol in a similar way to allylamines.