Tolnaftate is an anti-fungal drug used under different pharmaceutical forms (cream, ointment, gel, liquid, spray, powder) to treat fungal infections, such as athlete’s foot (also called tinea pedis), Pityriasis Versicolor (skin eruption on the trunk and proximal extremities generally caused by the fungus Malassezia globosa) and other mycosic skin infections, such as dermatophytosis (ringworm). It is still used today to treat various fungal infections of the skin and nails of the feet (onychomycosis), but other more potent anti-mycosic agents (such as terbinafine) are often preferred. It can be used also in animals to treat superficial fungal infections.

Tolnaftate is a simple thiocarbamate derivative, made from naphthol, thiophosgene and N-methyl-toluidine. The drug inhibits sterol biosynthesis, blocking the epoxidation of squalene in the yeast Candida albicans. Thus, the drug must first penetrate the microorganism to exert its activity. This is the reason why the drug formulations often contain permeability enhancers, to facilitate the skin and cell penetration. The drug was initially synthesized by a group of researchers in Japan (1962) and the first in vitro data demonstrating the antifungal activity of the drug were published in 1964. Clinical investigations in Human begun in the mid-1960s leading to the approval of the drug a few years later in different countries. Still present in pharmacies in 2020.

Spinario (Boy with Thorn, also called Fedelino or Il Fedele, “The faithful boy”) is a Greco-Roman Hellenistic bronze sculpture of a boy withdrawing a thorn from the sole of his foot, exposed at the Palazzo dei Conservatori (Rome, Italy). Dated from around 1200. Here the illustration refers to the Roman marble version of this subject from the Medici collections (Uffizi Gallery, Florence). An (invented) anecdote claims that the faithful messenger, a young shepherd, had delivered his message to the Roman Senate first, only then stopping to remove a painful thorn from his foot. A very well-thought-out allegory of the application of the drug to treat tinea pedis.

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