Tolnaftate

Tolnaftate (Aftate, Tinactin, and others) is available in a 1% concentration as a cream, gel, powder, aerosol powder, and topical solution, or as a topical aerosol liquid. 

Tolnaftate is a weak sensitizer, with few reported cases of contact allergy (Gellin et al. 1972). 

The organic fractions are combined and washed successively with N,N-dimethyl-1,3-propane-diamine, dilute hydrochloric acid, saturated sodium bicarbonate solution and saturated sodium chloride solution. The organic fraction is dried over anhydrous magnesium sulfate. The solvent is then evaporated off. Upon trituration of the residue with methanol, a solid crystallizes, 5-(p-toluovl)-1 -methvlpvrrole-2-acetonitrile, which is removed by filtration and purified by recrystallization from benzene. 

Additional product is isolated from the mother liquors which are combined, concentrated in vacuo and the resulting oily residue column chromatographed on neutral alumina using hexane, benzene and ether as successive solvents. The product is isolated by concentrating in vacuo the first few major compound-bearing fractions (10% ether in benzene). The solids are combined and recrystallized from methanol and then from benzene-hexane, melting point 102°C to 105°C. 

5-(p-Toluovl)-1 methylpyrrole-2-aceticacid — A solution of 3.67 g (0.01 5 mol) of 5-(p-tolu-oyD-l -methvlpvrrole-2-acetonitrile, 24 ml of 1 N sodium hydroxide and 50 ml of 95% ethanol Is stirred and refluxed for 24 hours. 

The resulting solution is poured into ice acidified with dilute hydrochloric acid. A white solid precipitates which Is extracted into ether. The ether phase is washed with a saturated solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent is evaporated and a white solid, 5-(p-toluoyl)-1 -methylpvrrole-2-acetic acid is obtained which is recrystal-lized twice from isopropanol, melting point 155°C to 157°C. 

Chemical Name Methyl (3-methylphenyl)carbamothioic acid 0-2-naphthaienyl ester Common Name Naphthiomate T Structural Formula  

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There is no fiiU-scale U.S. commercial production of thiophosgene, but it is available in glass ampuls from laboratory reagent suppHers. Thiophosgene may be produced in Israel as an intermediate for tolnaftate (2-naphthyl A/-methyl-A/-y -tolylthiocarbamate) [2398-96-17, an antifimgal dmg. 

Tolnaftate [2398-96-17, C H NOS, which is active against dermatophytes, is the active component ia another antifimgal powder it also contains cetylpyridinium chloride and talcum venetum. 

In addition to tolnaftate and cetylpytidinium chlotide, the ointment also contains poly(ethylene glycol). This piepaiation is not active against C. albicans. 

C11H7CIOS 10506-37-3) see Tolnaftate carbonocyanidimidic acid methyl ester (C3H4N2O 13369-03-4) see Sulfametrole A, Af -[carbonylbis(iminosulfonyl-4,l-phenylene)Jhis[acet-amlde]... 

CCI2S 463-71-8) see Tizanidine Tolnaftate thiophosphoryl chloride (Cl,PS 3982-91-0) see Thiotepa thiosalicylic acid... 

The synthetic thiocarbamates, of which tolnaftate (Fig. 5.20J) is an example, also inhibit squalene epoxidase. Tolnaftate inhibits this enzyme from C. albicans, but is inactive against whole cells, presumably because of its inability to penetrate the cell wall. Tolnaftate is used topically in the treatment or prophylaxis of tinea. 

Fig. 5.20 Imidazoles (A-F) A, metronidazole B, clotrimazole C, miconazole D, econazole E, ketoconazole F, fluconazole G, flucytosine H, 5-fluorouracil I, terbinafme J, tolnaftate.

An analogue of tolindate (2) which has had greater success as an antifungal drug is tolnaftate (20). 

Antifungals Biphenamine Ciclopirox Econazole Ethonam Antihelmintics Miconazole To1indate Tolnaftate... 

Pharmaceutical powder is a mixture of finely divided drugs and/or chemicals in dry form. They are dispensed as bulk powders or divided powders. When the prescription is received for powders, first determine whether it is based upon one unit or upon a bulk formula to be subdivided into individual units. Bulk powders are provided as multiple doses in a container and the patient measures the dose as instructed at the time of administration. Some examples of bulk powders include Tolnaftate Powder USP and Nystatin Topical Powder USP as antifungals, and Desitin Powder for diaper rash. Divided powders are meant to be provided as single dose units in individually wrapped powder papers. Such single dose packets are stacked in a powder box, and the label... 

Tollen s aldehyde test analychem A test that uses an ammonlacal solution of silver oxides to test for aldehydes and ketones. tal anz al da.hTd. test) tolnaftate org chem C19H17NOS An agricultural fungicide It Is also used medically as an antifungal agent. tol naf.tat ... 

Q94 To use tolnaftate powder as a dusting powder for shoes and socks... 

Athlete s foot, tinea pedis, is a condition caused by a fungus. Management of athlete s foot lies with the use of antifungal preparations such as clotrimazole (an imidazole antifungal) and tolnaftate. Salicylic acid is a keratolytic agent indicated for use in treatment of corns, calluses and warts. 

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