{{Short description|Chemical compound}} {{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 470611568 | IUPAC_name = ''O''-2-Naphthyl methyl(3-methylphenyl)thiocarbamate | image = Tolnaftate.svg | image_class = skin-invert-image
<!--Clinical data--> | tradename = Tinactin | Drugs.com = {{drugs.com|monograph|tolnaftate}} | MedlinePlus = a682617 | pregnancy_category = | legal_status = OTC | routes_of_administration =
<!--Pharmacokinetic data--> | bioavailability = | metabolism = | excretion =
<!--Identifiers--> | 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 = <small>2-Naphthyl ''N''-methyl-''N''-(3-tolyl)thionocarbamate</small><ref name="INN">{{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}}</ref>
<!--Chemical data--> | 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),<ref name="INN" /> sold under the brand names '''TAGRID''', and Tinactin, 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.<ref name=":1" /> Tolnaftate is used to treat fungal conditions such as jock itch, athlete's foot and ringworm.<ref name=":1">{{Cite web|title=Tolnaftate|url=https://medlineplus.gov/druginfo/meds/a682617.html|website=MedlinePlus,gov}}</ref> Tolnaftate was discovered by Teruhisa Noguchi in 1962 while he was working for the Nippon Soda Company.<ref>{{Cite journal |last=Hashimoto |first=Y |date=May 1966 |title=Toxicologic and pharmacologic properties of tolnaftate, an antitrichophyton agent |url=https://linkinghub.elsevier.com/retrieve/pii/0041008X66900482 |journal=Toxicology and Applied Pharmacology |language=en |volume=8 |issue=3 |pages=380–385 |doi=10.1016/0041-008X(66)90048-2|url-access=subscription }}</ref>
==Mechanism== Although the exact mechanism of action is not entirely known, it is believed to inhibit squalene epoxidase,<ref name="pmid3524433">{{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}}</ref> an important enzyme in the biosynthetic pathway of ergosterol (a key component of the fungal cell membrane) in a similar way to terbinafine.<ref name="urlantifung">{{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 }}</ref>
==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.<ref>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.</ref>
== Side effects == Side effects that may occur include:<ref name=":0">{{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}}</ref> * allergic reactions like: ** skin rash ** itching or hives ** swelling of the face, lips, or tongue * inflammation, redness, or pain at the affected area Less severe side effects include:<ref name=":0" /> * dry skin * mild skin irritation, burning, or itching at the affected area
==See also== * Liranaftate, a similar thiocarbamate antifungal
==References== {{reflist}}
==External links== * [https://www.medlineplus.gov/druginfo/meds/a682617.html Medline's entry for tolnaftate] * {{usurped|1=[https://web.archive.org/web/20240225173131/https://www.smellyfeetpowder.com/blog/is-it-ok-to-use-foot-powder-every-day/ Is It OK to Use Foot Powder Every Day?]}}
{{Antifungals}} {{Xenobiotic-sensing receptor modulators}}
Category:Antifungals Category:Naphthol esters Category:Thiocarbamates Category:Drugs developed by Merck & Co. Category:Drugs developed by Bayer Category:3-Tolyl compounds Category:2-Naphthyl compounds Category:Over-the-counter drugs in the United States