Tioconazole

Tioconazole
Clinical data
Trade names	Vagistat-1
Other names	Thioconazole
AHFS/Drugs.com	Monograph
Routes of; administration	Topical
ATC code	D01AC07 (WHO) G01AF08 (WHO);
Legal status
Legal status	US: OTC ;
Identifiers
	IUPAC name (RS)-1-[2-[(2-Chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole;
CAS Number	65899-73-2 ;
PubChem CID	5482;
DrugBank	DB01007 ;
ChemSpider	5282 ;
UNII	S57Y5X1117;
KEGG	D00890 ;
ChEBI	CHEBI:9604 ;
ChEMBL	ChEMBL1200438 ;
CompTox Dashboard (EPA)	DTXSID3046619 ;
ECHA InfoCard	100.059.958
Chemical and physical data
Formula	C16H13Cl3N2OS
Molar mass	387.70 g·mol−1
Chirality	Racemic mixture
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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, now Johnson & Johnson). 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".

It was patented in 1975 and approved for medical use in 1982.[2]

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:[3]

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

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gollark: You're in group one then.

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References

Tioconazole, Mayo Clinic
Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 503. ISBN 9783527607495.
G. E. Gymer, BE 841309; idem, U.S. Patent 4,062,966 (1976, 1977 both to Pfizer).

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[1] Tioconazole, Mayo Clinic

[Fis2006-2] Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 503. ISBN 9783527607495.

[3] G. E. Gymer, BE 841309; idem, U.S. Patent 4,062,966 (1976, 1977 both to Pfizer).