tolciclate

Originator

Tolmicen,Carlo Erba,Italy,1979

Definition

ChEBI: Tolciclate is a monothiocarbamic ester. It has a role as an antifungal drug.

Indications

The indications for tolciclate are defined by its narrow spectrum and limited to the treatment of dermatophytoses. Because of inadequate penetration into the nail keratin, it is unlikely to be effective for the treatment of onychomycoses. On average, the efficacy of tolciclate in topical therapy of dermatomycoses is lower than that of most other antimycotics for topical treatment.

Manufacturing Process

Thiophosgene (1.15 g, 0.01 mol) in chloroform (40 ml) was slowly treated at room temperature with sodium 1,4-methano-1,2,3,4-tetrahydro-6- naphthoxide (1.82 g, 0.01 mol). After 30 minutes, N-methyl-m-toluidine (2.42 g, 0.02 mol) in chloroform (40 ml) was added dropwise to the solution so obtained at room temperature. The reaction mixture was stirred for 48 hours at room temperature and then refluxed for 2 hours. The solvent was evaporated, and the residue redissolved in water and extracted repeatedly with diethyl ether. The organic phase was dried (Na2SO4) and evaporated to dryness to give, after crystallization from isopropanol, O-(1,4-methano- 1,2,3,4-tetrahydro-6-naphthyl)-N-methyl-N-(m-tolyl)-thiocarbamate (1.3 g) melting point 92°C to 94°C.

Therapeutic Function

Topical antimycotic

Antimicrobial activity

In vitro, tolciclate has a narrow activity spectrum with good efficacy only towards dermatophytes. Isolates of susceptible species showing primary resistance or developing secondary resistance are rarely observed.