Tioconazole

Tioconazole
Clinical data
Trade names	Vagistat-1, 1-Day
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
	(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, 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.

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 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.^[3] 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

Antimycotic imidazole derivative.

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

References

^ Tioconazole, Mayo Clinic
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 503. ISBN 9783527607495.
^ "VAGISTAT-1 Print Label" (PDF). Food and Drug Administration. 6 February 1997. Retrieved 25 January 2021.
^ BE 841309, Gymer GE, issued 1976, assigned to Pfizer
^ US 4062966, Gymer GE, issued 1977, assigned to Pfizer