 | |
| 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 |
| Eliminationhalf-life | 35–100 hours |
| Identifiers | |
| |
| CAS Number | |
| PubChemCID | |
| DrugBank |
|
| ChemSpider |
|
| UNII | |
| KEGG |
|
| ChEBI | |
| ChEMBL | |
| CompTox Dashboard(EPA) | |
| Chemical and physical data | |
| Formula | C23H27N |
| Molar mass | 317.476 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
| (verify) | |
Butenafine, sold under the brand namesLotrimin Ultra,Mentax, andButop (InIndia only), is asyntheticbenzylamine derivedantifungal drug.
It is structurally related to theallylamine antifungalsterbinafine &naftifine.
Butenafine is indicated for the topical treatment of tinea (pityriasis) versicolor due toMalassezia furfur, as well asathlete's foot (Tinea pedis),ringworm (Tinea corporis) andjock itch (Tinea cruris) due toEpidermophyton floccosum,Trichophyton mentagrophytes,Trichophyton rubrum, andTrichophyton tonsurans.
It also displays superior activity againstCandida albicans than terbinafine andnaftifine. Butenafine demonstrates low minimum inhibitory concentrations againstCryptococcus andAspergillus.
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).[2]
Butenafine is typically available as a 1% topical cream.
Like the allylamine antifungals (e.gterbinafine), butenafine works by inhibiting the synthesis ofergosterol by binding to and inhibitingsqualene 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 topicalglucocorticoids, which often come with undesired side effects.
Butenafinehydrochloride is an odorless white crystalline powder that is freely soluble inmethanol,ethanol, andchloroform, yet is only slightly soluble in water.
Reductive amination of1-naphthaldehyde (1) withmethylamine (2) gives the intermediate secondaryamine (3).Alkylation of this with p-tert-butylbenzyl bromide (4) yields the tertiary amine butenafine.[3][4][5]
