Butenafine

Summary

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
  • [(4-tert-butylphenyl)methyl](methyl)(naphthalen-1-ylmethyl)amine
CAS Number
  • 101828-21-1 checkY
PubChem CID
  • 2484
DrugBank
  • DB01091 checkY
ChemSpider
  • 2390 checkY
UNII
  • 91Y494NL0X
KEGG
  • D07596 checkY
ChEBI
  • CHEBI:3238 checkY
ChEMBL
  • ChEMBL990 checkY
CompTox Dashboard (EPA)
  • DTXSID7040657 Edit this at Wikidata
Chemical and physical data
FormulaC23H27N
Molar mass317.476 g·mol−1
3D model (JSmol)
  • Interactive image
  • N(C)(Cc1ccc(cc1)C(C)(C)C)Cc3c2ccccc2ccc3
  • 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 checkY
  • Key:ABJKWBDEJIDSJZ-UHFFFAOYSA-N checkY
  (verify)

Medical uses edit

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).[2]

Available forms edit

Butenafine is typically available as a 1% topical cream.

Pharmacology edit

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 edit

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

References edit

  1. ^ Mylan Pharmaceuticals Inc. "Mentax (butenafine hydrochloride) Cream. Human Prescription Drug Label". dailymed.nlm.nih.gov. National Institutes of Health, U.S. National Library of Medicine, Health & Human Services. Retrieved 24 August 2016.
  2. ^ 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. 2016 (3): CD001434. doi:10.1002/14651858.CD001434.pub2. PMC 7073424. PMID 17636672.