Chemistry:Butenafine

Short description: Chemical compound

Butenafine

Clinical data
Trade names	Mentax, Lotrimin Ultra
AHFS/Drugs.com	Monograph
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	Topical (cream)
ATC code	D01AE23 (WHO)
Legal status
Legal status	OTC (Lotrimin Ultra), Rx-only (Mentax)
Pharmacokinetic data
Metabolism	Hepatic
Elimination half-life	35–100 hours
Identifiers
IUPAC name [(4-tert-butylphenyl)methyl](methyl)(naphthalen-1-ylmethyl)amine
CAS Number	101828-21-1 Y
PubChem CID	2484
DrugBank	DB01091 Y
ChemSpider	2390 Y
UNII	91Y494NL0X
KEGG	D07596 Y
ChEBI	CHEBI:3238 Y
ChEMBL	ChEMBL990 Y
Chemical and physical data
Formula	C23H27N
Molar mass	317.47 g·mol−1
3D model (JSmol)	Interactive image
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
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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.

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).

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.