Butenafine

Butenafine, sold under the brand names Lotrimin Ultra, Mentax, and Butop (India), is a synthetic benzylamine antifungal. It is structurally related to synthetic allylamine antifungals such as terbinafine.

Butenafine
Clinical data
Trade namesMentax, Lotrimin Ultra
AHFS/Drugs.comMonograph
Pregnancy
category
  • US: C (Risk not ruled out) [1]
    Routes of
    administration    		Topical (cream)
    ATC code
    Legal status
    Legal status
    • OTC (Lotrimin Ultra), ℞-only (Mentax)
    Pharmacokinetic data
    MetabolismHepatic
    Elimination half-life35–100 hours
    Identifiers
    CAS Number
    PubChem CID
    DrugBank
    ChemSpider
    UNII
    KEGG
    ChEBI
    ChEMBL
    CompTox Dashboard (EPA)
    Chemical and physical data
    FormulaC23H27N
    Molar mass317.47 g·mol−1
    3D model (JSmol)
      (verify)

    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).[2]

    Typical usage

    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

    Available forms

    Butenafine is typically available as a 1% topical cream.

    Pharmacology

    Like the allylamine antifungals, butenafine works by inhibiting the synthesis of ergosterol by inhibiting squalene epoxidase, 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. 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 cortical steroids (which decrease the ability to fight infection) to reduce inflammation.

    Chemistry

    Butenafine hydrochloride is an odorless white crystalline powder that is freely soluble in methanol, ethanol, and chloroform, and slightly soluble in water.

    References
    1. "Mentax (butenafine hydrochloride) Cream. Human Prescription Drug Label". dailymed.nlm.nih.gov. Mylan Pharmaceuticals Inc. Retrieved 24 August 2016.
    2. Crawford, Fay (1996). "Topical treatments for fungal infections of the skin and nails of the foot". Reviews (3): CD001434. doi:10.1002/14651858.CD001434.pub2. PMID 17636672.


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