| Revision as of 13:43, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 456542196 of page Tolnaftate for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 22:58, 19 December 2024 edit Hebrooo (talk | contribs)8 editsmNo edit summary |
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{{Short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 408965720 |
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| verifiedrevid = 470611568 |
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| IUPAC_name = ''O''-2-naphthyl methyl(3-methylphenyl)thiocarbamate |
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| IUPAC_name = ''O''-2-Naphthyl methyl(3-methylphenyl)thiocarbamate |
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| image = Tolnaftate.svg |
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| image = Tolnaftate.svg |
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| Drugs.com = {{drugs.com|monograph|tolnaftate}} |
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| Drugs.com = {{drugs.com|monograph|tolnaftate}} |
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| MedlinePlus = a682617 |
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| MedlinePlus = a682617 |
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| pregnancy_category = |
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| pregnancy_category = |
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| legal_status = OTC |
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| legal_status = OTC |
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| routes_of_administration = |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| bioavailability = |
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| metabolism = |
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| metabolism = |
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| excretion = |
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| excretion = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 2398-96-1 |
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| CAS_number = 2398-96-1 |
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| ATC_suffix = AE18 |
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| ATC_suffix = AE18 |
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| PubChem = 5510 |
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| PubChem = 5510 |
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| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB00525 |
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| DrugBank = DB00525 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D00381 |
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| KEGG = D00381 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 9620 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 83668 |
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| ChEMBL = 83668 |
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| 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> |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=19 | H=17 | N=1 | O=1 | S=1 |
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| C=19 | H=17 | N=1 | O=1 | S=1 |
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| molecular_weight = 307.41 g/mol |
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| smiles = S=C(Oc2ccc1c(cccc1)c2)N(c3cc(ccc3)C)C |
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| smiles = S=C(Oc2ccc1c(cccc1)c2)N(c3cc(ccc3)C)C |
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| 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 |
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| InChIKey = FUSNMLFNXJSCDI-UHFFFAOYAF |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| 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 |
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| 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 |
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| melting_high = 111.5 |
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| melting_high = 111.5 |
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}} |
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}} |
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'''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> |
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==Mechanism== |
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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> |
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==Uses== |
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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> |
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== Side effects == |
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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> |
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* allergic reactions like: |
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** ] |
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** ]ing or ] |
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** swelling of the face, lips, or tongue |
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* ], redness, or ] at the affected area |
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Less severe side effects include:<ref name=":0" /> |
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* ] |
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* mild skin irritation, burning, or itching at the affected area |
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==See also== |
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* ], a similar ] antifungal |
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==References== |
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{{reflist}} |
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==External links== |
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* |
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* |
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{{Antifungals}} |
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{{Xenobiotic-sensing receptor modulators}} |
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] |
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] |
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] |
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] |
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] |
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] |