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| {{short description|Chemical compound}} | |||
| {{Unreferenced stub|auto=yes|date=December 2009}} | |||
| {{cs1 config|mode=cs1|name-list-style=vanc|display-authors=6}} | |||
| {{Drugbox | {{Drugbox | ||
| | verifiedrevid = |
| verifiedrevid = 459987694 | ||
| | IUPAC_name = (methyl)(naphthalen-1-ylmethyl)amine | | IUPAC_name = (methyl)(naphthalen-1-ylmethyl)amine | ||
| | image = Butenafine |
| image = Butenafine.svg | ||
| | width = | |||
| <!--Clinical data--> | <!--Clinical data--> | ||
| | tradename = Mentax | | tradename = Mentax, Lotrimin Ultra | ||
| | Drugs.com = {{drugs.com|monograph|butenafine-hydrochloride}} | | Drugs.com = {{drugs.com|monograph|butenafine-hydrochloride}} | ||
| | |
| pregnancy_US = C | ||
| | 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> | |||
| | legal_status = | |||
| | legal_status = OTC (Lotrimin Ultra), Rx-only (Mentax) | |||
| | routes_of_administration = ] | |||
| | routes_of_administration = ] (]) | |||
| <!--Pharmacokinetic data--> | <!--Pharmacokinetic data--> | ||
| | bioavailability = |
| bioavailability = | ||
| | protein_bound = |
| protein_bound = | ||
| | metabolism = ] | | metabolism = ] | ||
| | elimination_half-life = |
| elimination_half-life = 35–100 hours | ||
| | excretion = | |||
| <!--Identifiers--> | <!--Identifiers--> | ||
| | |
| CAS_number_Ref = {{cascite|correct|??}} | ||
| | CAS_number = 101828-21-1 | | CAS_number = 101828-21-1 | ||
| | ATC_prefix = D01 | | ATC_prefix = D01 | ||
| Line 36: | Line 40: | ||
| | ChEMBL_Ref = {{ebicite|correct|EBI}} | | ChEMBL_Ref = {{ebicite|correct|EBI}} | ||
| | ChEMBL = 990 | | ChEMBL = 990 | ||
| | synonyms = | |||
| <!--Chemical data--> | <!--Chemical data--> | ||
| | C=23 | H=27 | N=1 |
| C=23 | H=27 | N=1 | ||
| ⚫ | | SMILES = N(C)(Cc1ccc(cc1)C(C)(C)C)Cc3c2ccccc2ccc3 | ||
| | molecular_weight = 317.47 g/mol | |||
| ⚫ | | |
||
| | 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 | |||
| | InChIKey = ABJKWBDEJIDSJZ-UHFFFAOYAT | |||
| | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | ||
| | 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 | | 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 | ||
| Line 48: | Line 50: | ||
| | StdInChIKey = ABJKWBDEJIDSJZ-UHFFFAOYSA-N | | StdInChIKey = ABJKWBDEJIDSJZ-UHFFFAOYSA-N | ||
| }} | }} | ||
| '''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 ]. | |||
| '''Butenafine''', sold under the brand names '''Lotrimin Ultra''', '''Mentax''', and '''Butop''' (In ] only), is a ] ] derived ]. | |||
| ==Pharmacology== | |||
| ⚫ | Butenafine ] is an odorless white crystalline powder that is freely soluble in ], ], and ], |
||
| It is structurally related to the ] antifungals ] & ]. | |||
| ⚫ | Like the allylamine antifungals, butenafine works by inhibiting the synthesis of ] by inhibiting ], an enzyme |
||
| == |
==Medical uses== | ||
| Butenafine is indicated for the topical treatment of tinea (pityriasis) versicolor due to |
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 '']''. | ||
| It also displays superior activity against Candida albicans |
It also displays superior activity against '']'' than terbinafine and ]. Butenafine demonstrates low minimum inhibitory concentrations against '']'' and '']''. | ||
| 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> | |||
| ===Available forms=== | |||
| Butenafine is typically available as a 1% topical cream. | Butenafine is typically available as a 1% topical cream. | ||
| == |
==Pharmacology== | ||
| For 1% cream | |||
| *for adults and children 12 years and older | |||
| *wash the affected skin with soap and water and dry completely before applying | |||
| *apply once a day to affected skin for 2 weeks or as directed by a doctor | |||
| *wash hands after each use | |||
| *children under 12 years: ask a doctor | |||
| ⚫ | 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. | ||
| ⚫ | {{Antifungals}} | ||
| 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. | |||
| ⚫ | ] | ||
| ⚫ | ] | ||
| ] | |||
| ==Chemistry== | |||
| ⚫ | Butenafine ] is an odorless white crystalline powder that is freely soluble in ], ], and ], yet is only slightly soluble in water. | ||
| ==Synthesis== | |||
| {{antiinfective-drug-stub}} | |||
| :] | |||
| {{dermatologic-drug-stub}} | |||
| ] 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> | |||
| == References == | |||
| ] | |||
| {{Reflist}} | |||
| ] | |||
| ⚫ | {{Antifungals}} | ||
| ⚫ | ] | ||
| ⚫ | ] | ||
| ] | |||
| ] | |||
Latest revision as of 16:52, 15 July 2024
Chemical compoundPharmaceutical compound
 | |
| Clinical data | |
|---|---|
| Trade names | Mentax, Lotrimin Ultra |
| AHFS/Drugs.com | Monograph |
| Routes of administration | Topical (cream) |
| ATC code | |
| Legal status | |
| Legal status |
|
| Pharmacokinetic data | |
| Metabolism | Hepatic |
| Elimination half-life | 35–100 hours |
| Identifiers | |
IUPAC name
| |
| CAS Number | |
| PubChem CID | |
| DrugBank | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEBI | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| Chemical and physical data | |
| Formula | C23H27N |
| Molar mass | 317.476 g·mol |
| 3D model (JSmol) | |
SMILES
| |
InChI
| |
| (verify) | |
Butenafine, sold under the brand names Lotrimin Ultra, Mentax, and Butop (In India only), is a synthetic benzylamine derived antifungal drug.
It is structurally related to the allylamine antifungals terbinafine & naftifine.
Medical uses
Butenafine is indicated for the topical treatment of tinea (pityriasis) versicolor due to Malassezia furfur, as well as athlete's foot (Tinea pedis), ringworm (Tinea corporis) and jock itch (Tinea cruris) due to Epidermophyton floccosum, Trichophyton mentagrophytes, Trichophyton rubrum, and Trichophyton tonsurans.
It also displays superior activity against Candida albicans than terbinafine and naftifine. Butenafine demonstrates low minimum inhibitory concentrations against Cryptococcus and Aspergillus.
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).
Available forms
Butenafine is typically available as a 1% topical cream.
Pharmacology
Like the allylamine antifungals (e.g terbinafine), butenafine works by inhibiting the synthesis of ergosterol by binding to and inhibiting squalene epoxidase, 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.
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 glucocorticoids, which often come with undesired side effects.
Chemistry
Butenafine hydrochloride is an odorless white crystalline powder that is freely soluble in methanol, ethanol, and chloroform, yet is only slightly soluble in water.
Synthesis
Reductive amination of 1-naphthaldehyde (1) with methylamine (2) gives the intermediate secondary amine (3). Alkylation of this with p-tert-butyl benzyl bromide (4) yields the tertiary amine butenafine.
References
- Mylan Pharmaceuticals Inc. "Mentax (butenafine hydrochloride) Cream. Human Prescription Drug Label". dailymed.nlm.nih.gov. National Institutes of Health, U.S. National Library of Medicine, Health & Human Services. Retrieved 24 August 2016.
- Crawford F, Hollis S (July 2007). "Topical treatments for fungal infections of the skin and nails of the foot". The Cochrane Database of Systematic Reviews. 2007 (3): CD001434. doi:10.1002/14651858.CD001434.pub2. PMC 7073424. PMID 17636672.
- US patent 5021458, Maeda T, Yamamoto T, Takase M, Sasaki K, Arika T, Yokoo M, Hashimoto R, Amemiya K, Koshikawa S, "Amine derivatives and fungicides containing the same", issued 1991-06-04, assigned to Kaken Pharmaceutical Co Ltd
- Maeda T, Takase M, Ishibashi A, Yamamoto T, Sasaki K, Arika T, et al. (February 1991). "[Synthesis and antifungal activity of butenafine hydrochloride (KP-363), a new benzylamine antifungal agent]". Yakugaku Zasshi (in Japanese). 111 (2): 126–137. doi:10.1248/yakushi1947.111.2_126. PMID 2056447.
- "Butenafine". Pharmaceutical Substances. Thieme. Retrieved 2024-07-04.