Tioconazole

Chemical compound From Wikipedia, the free encyclopedia

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, later Johnson & Johnson and now Kenvue). 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 commonly used in the past.

Trade namesVagistat-1, 1-Day
Other namesThioconazole
Quick facts Clinical data, Trade names ...
Tioconazole
Clinical data
Trade namesVagistat-1, 1-Day
Other namesThioconazole
AHFS/Drugs.comMonograph
Routes of
administration
Topical
ATC code
Legal status
Legal status
Identifiers
  • (RS)-1-[2-[(2-Chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.059.958 Edit this at Wikidata
Chemical and physical data
FormulaC16H13Cl3N2OS
Molar mass387.70 g·mol−1
ChiralityRacemic mixture
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Tioconazole topical (skin) preparations are also available for ringworm, jock itch, athlete's foot, and tinea versicolor or "sun fungus".

Tioconazole is known to bind to tubulin and inhibit its polymerization.[2]

It was patented in 1975 and approved for medical use in 1982.[3]

Side effects

Side effects of vaginal tioconazole may include temporary burning itching, or irritation of the vagina. Vaginal swelling or redness, difficulty or burning during urination, headache, abdominal pain, and upper respiratory tract infection have been reported by people using tioconazole.[4] These side effects may be only temporary, and do not normally interfere with the patient's comfort enough to outweigh the result.[citation needed]

Synthesis

Tiaconazole synthesis

Tioconazole can be synthesized by a displacement reaction between 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol and 2-chloro-3-(chloromethyl)thiophene.[5][6]

References

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