Tioconazole

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 415485693

| IUPAC_name = (RS)-1-[2-[(2-Chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl]-1H-imidazole

| image = Tioconazole.svg

| chirality = Racemic mixture

| tradename = Vagistat-1, 1-Day

| Drugs.com = {{drugs.com|monograph|tioconazole}}

| pregnancy_category =

| legal_US= OTC

| routes_of_administration = Topical

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 65899-73-2

| ATC_prefix = D01

| ATC_suffix = AC07

| ATC_supplemental = {{ATC|G01|AF08}}

| PubChem = 5482

| DrugBank_Ref = {{drugbankcite|changed|drugbank}}

| DrugBank = DB01007

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 5282

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = S57Y5X1117

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D00890

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 9604

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1200438

| C=16 | H=13 | Cl=3 | N=2 | O=1 | S=1

| synonyms = Thioconazole

}}

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.[http://www.mayoclinic.com/health/drug-information/DR601345 Tioconazole], Mayo Clinic 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.{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=503 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA503 |language=en}}

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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.{{cite web |title=VAGISTAT-1 Print Label |url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/97/20-676_VAGISTAT-1_PRNTLBL.PDF |publisher=Food and Drug Administration |access-date=25 January 2021 |date=6 February 1997}} These side effects may be only temporary, and do not normally interfere with the patient's comfort enough to outweigh the result.{{cn|date=December 2022}}

Synthesis

Antimycotic imidazole derivative.

File:Tiaconazole synthesis.svg

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

References