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{{short description|Chemical compound}} |
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{{Unreferenced stub|auto=yes|date=December 2009}} |
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{{cs1 config|mode=cs1|name-list-style=vanc|display-authors=6}} |
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{{Drugbox |
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{{Drugbox |
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| verifiedrevid = 443491765 |
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| verifiedrevid = 459987694 |
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| IUPAC_name = (methyl)(naphthalen-1-ylmethyl)amine |
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| IUPAC_name = (methyl)(naphthalen-1-ylmethyl)amine |
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| image = Butenafine structure.svg |
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| image = Butenafine.svg |
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| width = |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = Mentax |
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| tradename = Mentax, Lotrimin Ultra |
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| Drugs.com = {{drugs.com|monograph|butenafine-hydrochloride}} |
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| Drugs.com = {{drugs.com|monograph|butenafine-hydrochloride}} |
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| pregnancy_category = |
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| pregnancy_US = C |
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| pregnancy_US_comment = <ref>{{cite web|title=Mentax (butenafine hydrochloride) Cream. Human Prescription Drug Label|url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=167ecefd-4553-41b8-8160-81a48dbca076|website=dailymed.nlm.nih.gov| author =Mylan Pharmaceuticals Inc. | publisher = National Institutes of Health, U.S. National Library of Medicine, Health & Human Services |access-date=24 August 2016}}</ref> |
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| legal_status = |
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| legal_status = OTC (Lotrimin Ultra), Rx-only (Mentax) |
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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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| protein_bound = |
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| protein_bound = |
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| metabolism = ] |
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| metabolism = ] |
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| elimination_half-life = 35-100 hours |
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| elimination_half-life = 35–100 hours |
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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 = 101828-21-1 |
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| CAS_number = 101828-21-1 |
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| ATC_prefix = D01 |
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| ATC_prefix = D01 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 990 |
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| ChEMBL = 990 |
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| synonyms = |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=23 | H=27 | N=1 |
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| C=23 | H=27 | N=1 |
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| SMILES = N(C)(Cc1ccc(cc1)C(C)(C)C)Cc3c2ccccc2ccc3 |
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| molecular_weight = 317.47 g/mol |
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| smiles = N(C)(Cc1ccc(cc1)C(C)(C)C)Cc3c2ccccc2ccc3 |
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| InChI = 1/C23H27N/c1-23(2,3)21-14-12-18(13-15-21)16-24(4)17-20-10-7-9-19-8-5-6-11-22(19)20/h5-15H,16-17H2,1-4H3 |
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| InChIKey = ABJKWBDEJIDSJZ-UHFFFAOYAT |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C23H27N/c1-23(2,3)21-14-12-18(13-15-21)16-24(4)17-20-10-7-9-19-8-5-6-11-22(19)20/h5-15H,16-17H2,1-4H3 |
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| StdInChI = 1S/C23H27N/c1-23(2,3)21-14-12-18(13-15-21)16-24(4)17-20-10-7-9-19-8-5-6-11-22(19)20/h5-15H,16-17H2,1-4H3 |
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| StdInChIKey = ABJKWBDEJIDSJZ-UHFFFAOYSA-N |
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| StdInChIKey = ABJKWBDEJIDSJZ-UHFFFAOYSA-N |
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}} |
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'''Butenafine hydrochloride''' is a synthetic ] ], marketed under the trade names '''Mentax''', '''Butop''' (India) and is the active ingredient in Schering-Plough's '''Lotrimin Ultra.''' It is structurally related to synthetic ] antifungals such as ]. |
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'''Butenafine''', sold under the brand names '''Lotrimin Ultra''', '''Mentax''', and '''Butop''' (In ] only), is a ] ] derived ]. |
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==Pharmacology== |
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Butenafine ] is an odorless white crystalline powder that is freely soluble in ], ], and ], and slightly soluble in water. |
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It is structurally related to the ] antifungals ] & ]. |
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Like the allylamine antifungals, butenafine works by inhibiting the synthesis of ] by inhibiting ], an enzyme responsible for the creation of sterols needed in fungal cell membranes. Lacking ergosterol, the cell membranes increase in permeability, allowing their contents to leak out. |
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==Indications== |
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==Medical uses== |
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Butenafine is indicated for the topical treatment of tinea (pityriasis) versicolor due to M. furfur, as well as ] (''Tinea pedis''), ] (''Tinea corporis'') and ] (''Tinea cruris'') due to E. floccosum, T. mentagrophytes, T. rubrum, and T. tonsurans. It has superior fungicidal activity against this group of fungi when compared to that of ], ], ], and ]. |
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Butenafine is indicated for the topical treatment of tinea (pityriasis) versicolor due to '']'', as well as ] (''Tinea pedis''), ] (''Tinea corporis'') and ] (''Tinea cruris'') due to '']'', '']'', '']'', and '']''. |
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It also displays superior activity against Candida albicans when compared against terbinafine and naftifine. Butenafine demonstrates low minimum inhibitory concentrations against ] and ]. |
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It also displays superior activity against '']'' than terbinafine and ]. Butenafine demonstrates low minimum inhibitory concentrations against '']'' and '']''. |
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There is some evidence that it is effective against dermatophyte infections of the toenails, but needs to be applied daily for prolonged periods (at least one year).<ref>{{cite journal | vauthors = Crawford F, Hollis S | title = Topical treatments for fungal infections of the skin and nails of the foot | journal = The Cochrane Database of Systematic Reviews | volume = 2007 | issue = 3 | pages = CD001434 | date = July 2007 | pmid = 17636672 | pmc = 7073424 | doi = 10.1002/14651858.CD001434.pub2 }}</ref> |
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===Available forms=== |
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Butenafine is typically available as a 1% topical cream. |
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Butenafine is typically available as a 1% topical cream. |
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==Typical usage== |
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==Pharmacology== |
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For 1% cream |
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*for adults and children 12 years and older |
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*wash the affected skin with soap and water and dry completely before applying |
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*apply once a day to affected skin for 2 weeks or as directed by a doctor |
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*wash hands after each use |
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*children under 12 years: ask a doctor |
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Like the allylamine antifungals (e.g ]), butenafine works by inhibiting the synthesis of ] by binding to and inhibiting ], an enzyme in the pathway used for creation of the sterols needed in fungal cell membranes. Lacking ergosterol, the cell membranes increase in permeability, allowing their contents to leak out. Furthermore, inhibition of squalene epoxidase leads to a toxic buildup of squalene. This double action of butenafine (increased membrane permeability and toxic buildup of squalene) makes butenafine fungicidal rather than merely fungistatic. |
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{{Antifungals}} |
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In addition to being an antifungal, butenafine is an anti inflammatory. Because fungal skin infections are often accompanied by significant inflammation, this is a desirable property. The fact that butenafine has intrinsic anti inflammatory properties is also desirable since it is not necessary to add topical ]s, which often come with undesired side effects. |
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==Chemistry== |
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Butenafine ] is an odorless white crystalline powder that is freely soluble in ], ], and ], yet is only slightly soluble in water. |
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==Synthesis== |
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{{antiinfective-drug-stub}} |
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:] |
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{{dermatologic-drug-stub}} |
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] of ] (1) with ] (2) gives the intermediate secondary ] (3). ] of this with p-] ] (4) yields the tertiary amine butenafine.<ref>{{cite patent |country=US |number=5021458 |inventor=Maeda T, Yamamoto T, Takase M, Sasaki K, Arika T, Yokoo M, Hashimoto R, Amemiya K, Koshikawa S |title=Amine derivatives and fungicides containing the same |status=patent |gdate=1991-06-04 |fdate=1988-12-07 |assign1=Kaken Pharmaceutical Co Ltd}}</ref><ref>{{cite journal | vauthors = Maeda T, Takase M, Ishibashi A, Yamamoto T, Sasaki K, Arika T, Yokoo M, Amemiya K | title = | language = JA | journal = Yakugaku Zasshi | volume = 111 | issue = 2 | pages = 126–137 | date = February 1991 | pmid = 2056447 | doi = 10.1248/yakushi1947.111.2_126 | doi-access = free }}</ref><ref>{{cite web |url=https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-02-0157 |title=Butenafine | work = Pharmaceutical Substances |publisher=Thieme |access-date=2024-07-04}}</ref> |
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== References == |
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] |
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{{Reflist}} |
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] |
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{{Antifungals}} |
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] |
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] |
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