Description
Tioconazole is an antifungal agent, closely related to
miconazole. Tioconazole is effective in the topical
treatment of superficial fungal infections and appears to be more potent than
miconazole against Candida and Trichophyton species.
Chemical Properties
White powder EINECS: 265-973-8
Originator
Pfizer (United Kiugdom)
Uses
Potent inhibitor of cytochrome-P450
Uses
Tioconazole is an antifungal that is more active than Fluconazole (F421000) or Voriconazole (V760000) against Candida glabrata mutant strains. Antifungal (topical).
Definition
ChEBI: A member of the class of imidazoles that comprises 2-(2,4-dichlorophenyl)ethylimidazole carrying an additional (2-chloro-3-thienyl)methoxy substituent at position 2.
Manufacturing Process
A solution of 1-(2,4-dichlorophenyl)-2-(1-imidazolyl)ethanol (1.5 g, 5.8 mmol)
dissolved in dry tetrahydrofuran (10 ml) was added to a stirred suspension of
sodium hydride (0.39 g, as 80% dispersion in oil, 16 mmol) in dry
tetrahydrofuran (10 ml) and warmed to 70°C for 90 minutes.
The mixture was cooled in ice and a solution of 2-chloro-3-
chloromethylthiophene (8.8 mmol) in dry tetrahydrofuran was added. The
mixture was heated at 70°C for 3 hours and allowed to stir at room
temperature overnight. The solvent was removed under vacuum and the
residue stirred with dry ether (200 ml). The ether solution was filtered
through Celite and saturated with hydrogen chloride gas to precipitate an oil
which was solidified by trituration with ether and ethyl acetate. The solid
product was collected and recrystallized from a mixture of acetone and
diisopropyl ether to give the product, melting point 168°C to 170°C.
Therapeutic Function
Antifungal
Clinical Use
1-[2-[(2-chloro-3-thienyl)methoxy]2-(2,4-dichlorophenyl)-ethyl]-1H-imidazole (Vagistat) is used for the treatment ofvulvovaginal candidiasis. A vaginal ointment containing6.5% of the free base is available. Tioconazole is more effectiveagainst Torulopsis glabrata than are other azoles.
