Tolnaftate

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 470611568

| IUPAC_name = O-2-Naphthyl methyl(3-methylphenyl)thiocarbamate

| image = Tolnaftate.svg

| tradename = Tinactin

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

| MedlinePlus = a682617

| pregnancy_category =

| legal_status = OTC

| routes_of_administration =

| bioavailability =

| metabolism =

| excretion =

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

| CAS_number = 2398-96-1

| ATC_prefix = D01

| ATC_suffix = AE18

| PubChem = 5510

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB00525

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 5309

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 06KB629TKV

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

| KEGG = D00381

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

| ChEBI = 9620

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 83668

| synonyms = 2-Naphthyl N-methyl-N-(3-tolyl)thionocarbamate{{cite web|title=International Non-Proprietary Names for Pharmaceutical Preparations. Recommended International Non-Proprietary names (Rec. I.N.N.): List 6|url=https://www.who.int/medicines/publications/druginformation/innlists/RL06.pdf|publisher=World Health Organization|access-date=12 November 2016}}

| C=19 | H=17 | N=1 | O=1 | S=1

| smiles = S=C(Oc2ccc1c(cccc1)c2)N(c3cc(ccc3)C)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C19H17NOS/c1-14-6-5-9-17(12-14)20(2)19(22)21-18-11-10-15-7-3-4-8-16(15)13-18/h3-13H,1-2H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = FUSNMLFNXJSCDI-UHFFFAOYSA-N

| melting_point = 110

| melting_high = 111.5

}}

Tolnaftate (INN), sold under the brand name TAGRID, among others, is a synthetic thiocarbamate used as an anti-fungal agent that may be sold without medical prescription in most jurisdictions. It is supplied as a cream, powder, spray, liquid, and liquid aerosol. Tolnaftate is used to treat fungal conditions such as jock itch, athlete's foot and ringworm.{{Cite web|title=Tolnaftate|url=https://medlineplus.gov/druginfo/meds/a682617.html|website=MedlinePlus,gov}}

Mechanism

Although the exact mechanism of action is not entirely known, it is believed to inhibit squalene epoxidase,{{cite journal |vauthors=Ryder NS, Frank I, Dupont MC |title=Ergosterol biosynthesis inhibition by the thiocarbamate antifungal agents tolnaftate and tolciclate |journal=Antimicrob. Agents Chemother. |volume=29 |issue=5 |pages=858–60 |date=May 1986 |pmid=3524433 |pmc=284167 |doi= 10.1128/aac.29.5.858}} an important enzyme in the biosynthetic pathway of ergosterol (a key component of the fungal cell membrane) in a similar way to terbinafine.{{cite web |url=http://faculty.swosu.edu/scott.long/phcl/antifung.htm |title=antifung |access-date=2008-07-09 |url-status=dead |archive-url=https://web.archive.org/web/20080617102546/http://faculty.swosu.edu/scott.long/phcl/antifung.htm |archive-date=2008-06-17 }}

Uses

Tolnaftate has been found to be generally slightly less effective than azoles when used to treat tinea pedis (athlete's foot). It is, however, useful when dealing with ringworm, especially when passed from pets to humans.Crawford F, Hart R, Bell-Syer S, Torgerson D, Young P, Russell I. Topical treatments for fungal infections of the skin and nails of the foot (Cochrane Review). In: The Cochrane Library, Issue 1, 2003. Oxford: Update Software.

Side effects

Side effects that may occur include:{{Cite web|title=Tolnaftate skin cream, gel, solution, or spray|url=https://my.clevelandclinic.org/health/drugs/19260-tolnaftate-skin-cream-gel-solution-or-spray|website=Cleveland Clinic}}

Less severe side effects include:

  • dry skin
  • mild skin irritation, burning, or itching at the affected area

See also

References

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