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			{{Short description|Chemical compound}}
⚫	{{Drugbox| verifiedrevid = 408964517
			{{Drugbox
	|
			| Verifiedfields = changed
⚫	|IUPAC_name = ''O''-2-naphthyl methyl(3-methylphenyl)thiocarbamate
			| Watchedfields = changed
⚫	| image=Tolnaftate.svg
		⚫	| verifiedrevid = 470611568
⚫	| CASNo_Ref = {{cascite|correct|CAS}}
		⚫	| IUPAC_name = ''O''-2-Naphthyl methyl(3-methylphenyl)thiocarbamate
		⚫	| image = Tolnaftate.svg
			<!--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_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 5309		| ChemSpiderID = 5309
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = 06KB629TKV		| UNII = 06KB629TKV
		⚫	| KEGG_Ref = {{keggcite|correct|kegg}}
	| InChI = 1/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
		⚫	| KEGG = D00381
	| InChIKey = FUSNMLFNXJSCDI-UHFFFAOYAF
			| ChEBI_Ref = {{ebicite|changed|EBI}}
			| ChEBI = 9620
	| ChEMBL_Ref = {{ebicite|correct|EBI}}		| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 83668		| 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_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		| 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_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = FUSNMLFNXJSCDI-UHFFFAOYSA-N		| StdInChIKey = FUSNMLFNXJSCDI-UHFFFAOYSA-N
		⚫	| melting_point = 110
⚫	| CAS_number= 2398-96-1
		⚫	| melting_high = 111.5
⚫	| ATC_prefix=D01
⚫	| ATC_suffix=AE18
	| ATC_supplemental=
⚫	| PubChem=5510
⚫	| DrugBank=
⚫	| KEGG_Ref = {{keggcite|correct|kegg}}
⚫	| KEGG = D00381
⚫	| smiles = S=C(Oc2ccc1c(cccc1)c2)N(c3cc(ccc3)C)C
⚫	| C = 19 | H = 17 | N = 1 | O = 1 | S = 1
	| molecular_weight = 307.41 g/mol
⚫	| melting_point = 110
⚫	| melting_high = 111.5
⚫	| bioavailability=
⚫	| metabolism =
	| elimination_half-life=
⚫	| excretion =
⚫	| pregnancy_category =
⚫	| legal_status = OTC
⚫	| routes_of_administration=
	}}		}}
	'''Tolnaftate''' is a synthetic ] ] agent. It may come as a cream, powder, spray, or ], and is used to treat ], ] and ]. It is sold under several brand names, most notably '''Tinactin''' (]) and ''']''' (]). Other brands are Absorbine, Aftate, Genaspor, Lamisil AF, NP 27, Scholl and Ting. Tolnaftate is a ].		'''Tolnaftate''' (])<ref name="INN" /> sold under the brand name '''TAGRID''' among, others is a synthetic ] used as an ] agent that may be sold ] in most jurisdictions. It is supplied as a cream, powder, spray, liquid, and ].<ref name=":1" /> Tolnaftate is used to treat fungal conditions such as ], ] and ].<ref name=":1">{{Cite web|title=Tolnaftate|url=https://medlineplus.gov/druginfo/meds/a682617.html|website=MedlinePlus,gov}}</ref>
	==Synthesis==
	The synthesis of tolnaftate is a three step process first involving 2-napthol with a base, to deprotonate the acidic phenol hydrogen. NaH, NaNH<sub>2</sub> are commonly used. Other common bases may also be used with the same effect. Treatment of N-methyl-m-toluidine with CS<sub>2</sub> and CH<sub>3</sub>Br results in a thiocarbamate intermediate that reacts with the negatively charged oxygen on the deprotonated 2-napthol, displacing the -SCH<sub>3</sub> group and forming the final product.<ref>Noguchi, T.; Hashimoto, Y.; Miyazaki, K.; Kaji, A.; J. Pharm. Soc. Japan 1968, 88, 335</ref>
	==Mechanism==		==Mechanism==
	Although the exact mechanism of action is not entirely known, it is believed to inhibit the ],<ref name="pmid3524433">{{cite journal |author=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 |year=1986 |month=May |pmid=3524433 |pmc=284167 |doi= |url=http://aac.asm.org/cgi/pmidlookup?view=long&pmid=3524433}}</ref> an important enzyme in the biosynthetic pathway of ] (a key component of the ]) in a similar way to ].<ref name="urlantifung">{{cite web |url=http://faculty.swosu.edu/scott.long/phcl/antifung.htm |title=antifung |format= |work= |accessdate=2008-07-09}}</ref>		Although the exact mechanism of action is not entirely known, it is believed to inhibit ],<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 ] (a key component of the fungal cell membrane) in a similar way to ].<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==		==Uses==
	Tolnaftate has been found to be generally slightly less effective than ]s when used to treat ]. It is, however, useful when dealing with ], 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>		Tolnaftate has been found to be generally slightly less effective than ]s when used to treat ] (athlete's foot). It is, however, useful when dealing with ], 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:
			** ]
			** ]ing or ]
			** swelling of the face, lips, or tongue
			* ], redness, or ] at the affected area
			Less severe side effects include:<ref name=":0" />
			* ]
			* mild skin irritation, burning, or itching at the affected area
			==See also==
			* ], a similar ] antifungal
	==References==		==References==
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	==External links==		==External links==
	*		*
			*
	*
	{{Antifungals}}		{{Antifungals}}
			{{Xenobiotic-sensing receptor modulators}}
	]		]
	]		]
	]		]
			]
			]
			]
	{{antiinfective-drug-stub}}
			]
	{{dermatologic-drug-stub}}
	]
	]
	]