Butenafine

Butenafine
Systematic (IUPAC) name

[(4-tert-butylphenyl)methyl](methyl)(naphthalen-1-ylmethyl)amine
Clinical data
Trade names	Mentax
AHFS/Drugs.com	monograph
Routes of administration	topical
Pharmacokinetic data
Metabolism	Hepatic
Biological half-life	35-100 hours
Identifiers
CAS Number	101828-21-1^Y
ATC code	D01AE23 (WHO)
PubChem	CID 2484
DrugBank	DB01091^Y
ChemSpider	2390^Y
UNII	91Y494NL0X^Y
KEGG	D07596^Y
ChEBI	CHEBI:3238^Y
ChEMBL	CHEMBL990^Y
Chemical data
Formula	C₂₃H₂₇N
Molar mass	317.47 g/mol
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)

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.

Medical uses

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 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]

Butenafine is typically available as a 1% topical cream.

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.

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

References

↑ The Cochrane Library: Topical treatments for fungal infections of the skin and nails of the foot, 2009.

Antifungals (D01 and J02)

Wall/
membrane

Ergosterol
inhibitors

Azoles
(lanosterol 14
alpha-demethylase inhibitors)

Imidazoles	Topical: bifonazole^‡ chlormidazole^‡ croconazole^‡ fenticonazole^‡ isoconazole^‡ luliconazole neticonazole^‡ omoconazole^‡ butoconazole clotrimazole^# econazole ketoconazole miconazole^# oxiconazole sertaconazole sulconazole tioconazole Systemic: ketoconazole

Triazoles	Topical: fluconazole^#, fosfluconazole efinaconazole terconazole Systemic: hexaconazole^‡ isavuconazole fluconazole^# 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

Intracellular

Pyrimidine analogues/ thymidylate synthase inhibitors	flucytosine^#

Mitotic inhibitors	griseofulvin^#

Aminoacyl tRNA synthetase inhibitors	tavaborole

Others

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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