Butenafine - Wikipedia, the free encyclopedia

Butenafine

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Butenafine
Systematic (IUPAC) name
[(4-tert-butylphenyl)methyl](methyl)(naphthalen-1-ylmethyl)amine
Clinical data
Trade names Mentax
AHFS/Drugs.com monograph
Pregnancy cat.  ?
Legal status  ?
Routes topical
Pharmacokinetic data
Metabolism Hepatic
Half-life 35-100 hours
Identifiers
CAS number 101828-21-1 YesY
ATC code D01AE23
PubChem CID 2484
DrugBank APRD00833
ChemSpider 2390 YesY
UNII 91Y494NL0X YesY
KEGG D07596 YesY
ChEBI CHEBI:3238 YesY
ChEMBL CHEMBL990 YesY
Chemical data
Formula C23H27N 
Mol. mass 317.47 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (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
  • v
  • d
  • e
Antifungals (D01 and J02)
Wall/
membrane
Ergosterol
inhibitors
Azoles
(lanosterol 14
alpha-demethylase inhibitors)
Imidazoles
topical: Bifonazole, Butoconazole, Clomidazole, Clotrimazole#, Croconazole, Econazole, Fenticonazole, Ketoconazole, Isoconazole, Miconazole#, Neticonazole, Omoconazole, Oxiconazole, Sertaconazole, Sulconazole, Tioconazole
Triazoles

topical: (Fluconazole#, Fosfluconazole, Terconazole)

systemic: (Fluconazole, Hexaconazole, Isavuconazole†, Itraconazole, Posaconazole, Voriconazole)

unknown: (Albaconazole)
Thiazoles
topical: (Abafungin)
Polyene antimycotics
(ergosterol binding)
topical: (Hamycin, Natamycin, Nystatin#)
systemic: (Amphotericin B#, Hamycin)
Allylamines
(squalene monooxygenase
inhibitors)
topical: (Amorolfine, Butenafine, Naftifine, Terbinafine)
systemic: (Terbinafine)
β-glucan synthase
inhibitors
echinocandins (Anidulafungin, Caspofungin, Micafungin)
Intracellular
Pyrimidine analogues/
Thymidylate synthase inhibitors
Flucytosine#
Mitotic inhibitors
Griseofulvin#
Others

Bromochlorosalicylanilide • Methylrosaniline • Tribromometacresol • Undecylenic acid • Polynoxylin • Chlorophetanol • Chlorphenesin • Ticlatone • Sulbentine • Ethyl hydroxybenzoate • Haloprogin • Salicylic acid • Selenium sulfide# • Ciclopirox • Amorolfine • Dimazole • Tolnaftate • Tolciclate • Sodium thiosulfate# • Whitfield's ointment# • Potassium iodide# • Taurolidine

Tea tree oil • citronella oil • lemon grass • orange oil • patchouli • lemon myrtle

PCP: Pentamidine • Dapsone • Atovaquone
  • #WHO-EM
  • ‡Withdrawn from market
  • Clinical trials:
    • †Phase III
    • §Never to phase III

M: MYC

fung, clas

fung

drug (fung)


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