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Butenafine

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Pharmaceutical compound
Butenafine
Clinical data
Trade namesMentax
AHFS/Drugs.comMonograph
Routes of
administration
topical
ATC code
Pharmacokinetic data
MetabolismHepatic
Elimination half-life35-100 hours
Identifiers
IUPAC name
  • (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 g·mol
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
  • Key:ABJKWBDEJIDSJZ-UHFFFAOYSA-N
  (verify)

Butenafine hydrochloride is a synthetic benzylamine antifungal, 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 allylamine antifungals such as terbinafine.

Pharmacology

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

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.

Indications

Butenafine is indicated for the topical treatment of tinea (pityriasis) versicolor due to M. furfur, as well as athlete’s foot (Tinea pedis), ringworm (Tinea corporis) and jock itch (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 terbinafine, naftifine, clotrimazole, and tolnaftate.

It also displays superior activity against Candida albicans when compared against terbinafine and naftifine. Butenafine demonstrates low minimum inhibitory concentrations against cryptococcus and aspergillus.

Butenafine is typically available as a 1% topical cream.

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
Antifungals (D01 and J02)
Wall/
membrane
Ergosterol
inhibitors
Azoles (lanosterol 14α-
demethylase
inhibitors)
Imidazoles
  • Systemic: ketoconazole
Triazoles
Thiazoles
Polyene antimycotics
(ergosterol binding)
Squalene monooxygenase
inhibitors
Allylamines
Benzylamines
Others
β-glucan synthase
inhibitors
Intracellular
Pyrimidine analogues/
thymidylate synthase inhibitors
Mitotic inhibitors
Aminoacyl tRNA synthetase inhibitors
Others


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