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
Routes of
administration		Topical (cream)
ATC code
Legal status
Legal status
  • OTC (Lotrimin Ultra), Rx-only (Mentax)
Pharmacokinetic data
MetabolismHepatic
Elimination half-life35–100 hours
Identifiers
IUPAC name
  • [(4-tert-butylphenyl)methyl](methyl)(naphthalen-1-ylmethyl)amine
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)
SMILES
  • N(C)(Cc1ccc(cc1)C(C)(C)C)Cc3c2ccccc2ccc3
InChI
  • InChI=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 Y
  • Key:ABJKWBDEJIDSJZ-UHFFFAOYSA-N Y
  (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).[1]

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. 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 (3): CD001434. doi:10.1002/14651858.CD001434.pub2. PMC 7073424. PMID 17636672.
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