Butenafine

Butenafine
Names
Trade namesMentax, Lotrimin Ultra, others
Other namesButenafine hydrochloride
IUPAC name
  • [(4-tert-butylphenyl)methyl](methyl)(naphthalen-1-ylmethyl)amine
Clinical data
Drug classAntifungal[1]
Main usesRingworm, pityriasis versicolor[1]
Side effectsItchiness, stinging[1]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Pregnancy
category
  • US: C (Risk not ruled out)[2]
    Routes of
    use    		Topical (cream)
    External links
    AHFS/Drugs.comMonograph
    Legal
    Legal status
    • OTC (Lotrimin Ultra), ℞-only (Mentax)
    Pharmacokinetics
    MetabolismLiver
    Elimination half-life35–100 hours
    Chemical and physical data
    FormulaC23H27N
    Molar mass317.47 g·mol−1
    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 checkY
    • Key:ABJKWBDEJIDSJZ-UHFFFAOYSA-N checkY

    Butenafine, sold under the brand names Mentax among others, is an antifungal used to treat ringworm and pityriasis versicolor.[1] It is applied to the skin.[1]

    Common side effects include itchiness, and stinging.[1] Other side effects may include allergic reactions.[1] There is no evidence of harm in pregnancy; however, such use has not been well studied.[3] It is a benzylamine, which is similar to allylamines, such as terbinafine.[1] It is believed to work by affecting the cell membrane.[1]

    Butenafine was approved for medical use in the United States in 1996.[1] It is available over the counter.[4] In the United States a 30 gram tube costs about 20 USD as of 2022.[4]

    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).[5]

    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.

    References

    1. 1 2 3 4 5 6 7 8 9 10 "Butenafine Monograph for Professionals". Drugs.com. Archived from the original on 24 January 2021. Retrieved 12 January 2022.
    2. ↑ 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. Archived from the original on 28 August 2016. Retrieved 24 August 2016.
    3. ↑ "Butenafine topical Use During Pregnancy". Drugs.com. Archived from the original on 26 November 2020. Retrieved 12 January 2022.
    4. 1 2 "Butenafine topical Prices, Coupons & Patient Assistance Programs". Drugs.com. Retrieved 12 January 2022.
    5. ↑ 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 (3): CD001434. doi:10.1002/14651858.CD001434.pub2. PMC 7073424. PMID 17636672.
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