Tioconazole

Tioconazole
Systematic (IUPAC) name
(RS)-1-[2-[(2-Chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole
Clinical data
Trade names Vagistat-1
AHFS/Drugs.com monograph
Legal status
Routes of
administration		 Topical
Identifiers
CAS Number 65899-73-2 YesY
ATC code D01AC07 G01AF08
PubChem CID 5482
DrugBank DB01007 N
ChemSpider 5282 N
UNII S57Y5X1117 N
KEGG D00890 YesY
ChEBI CHEBI:9604 N
ChEMBL CHEMBL1200438 N
Synonyms Thioconazole
Chemical data
Formula C16H13Cl3N2OS
Molar mass 387.711 g/mol
Chirality 1 : 1 mixture (racemate)
 NYesY (what is this?)  (verify)

Tioconazole is an antifungal medication of the imidazole class used to treat infections caused by a fungus or yeast. It is marketed under the brand names Trosyd and Gyno-Trosyd (Pfizer). Tioconazole ointments serve to treat women's vaginal yeast infections.[1] They are available in one day doses, as opposed to the 7-day treatments more common in use in the past.

Tioconazole topical (skin) preparations are also available for ringworm, jock itch, athlete's foot, and tinea versicolor or "sun fungus".

Side effects

Side effects (for the women's formulas) may include temporary burning/irritation of the vaginal area, moderate drowsiness, headache similar to a sinus headache, hives, and upper respiratory infection. These side effects may be only temporary, and do not normally interfere with the patient's comfort enough to outweigh the end result.

Synthesis

Antimycotic imidazole derivative.

Tiaconazole synthesis:[2]

A displacement reaction between 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol and 2-chloro-3-(chloromethyl)thiophene is performed.

See also

Orconazole:[3]

References

  1. ↑ Tioconazole, Mayo Clinic
  2. ↑ G. E. Gymer, BE 841309; idem, U.S. Patent 4,062,966 (1976, 1977 both to Pfizer).
  3. ↑ Godefroi, E. F.; Heeres, J.; Van Cutsem, J.; Janssen, P. A. J. (1969). "Preparation and antimycotic properties of derivatives of 1-phenethylimidazole". Journal of Medicinal Chemistry 12 (5): 784. doi:10.1021/jm00305a014.
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