Butenafine and analogues: An expeditious synthesis and cytotoxicity and antifungal activities

Garzón-Porras, Ana M.; Terra, Bruna Silva; Braga, Taniris Cafiero; Magalhães, Thaís Furtado Ferreira; Martins, Cleide Viviane Buzanello; Silva, Danielle Letícia da; Baltazar, Ludmila Matos; Gouveia, Ludmila Ferreira; Freitas, Gustavo José Cota de; Santos, Danielle Anjos dos; Stoianoff, Maria Aparecida de Resende; Fuchs, Beth Burgwyn; Mylonakis, Eleftherios; Freitas, Rossimiriam Pereira de; Fátima, Ângelo de

doi:10.1016/j.jare.2018.06.004

Cited by 10 publications

(4 citation statements)

References 64 publications

(61 reference statements)

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“…The compounds investigated were synthesised following general procedures reported in the patent literature, 16,17 and then converted into the respective hydrochlorides by treatment with anhydrous hydrogen chloride in ethanol. For purification, the crude hydrochlorides were recrystallised from ethanol-diethyl ether mixtures to yield crystalline solids, facilitating the handling of the otherwise relatively unstable free amines.…”

Section: Methodsmentioning

confidence: 99%

Fragment-based approach to study fungicide-biomimetic membrane interactions

Jaikishan,

Lavainne,

Ravald

et al. 2024

Soft Matter

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Section: Methodsmentioning

confidence: 99%

Fragment-based approach to study fungicide-biomimetic membrane interactions

Jaikishan,

Lavainne,

Ravald

et al. 2024

Soft Matter

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“…Naftifine was the first SQLE inhibitor, developed as an antifungal agent. After naftifine, other compounds were discovered, such as terbinafine, butenafine, and SDZ-SBA-586 [88]. In Candida albicans, the inhibition of SQLE induces the toxic accumulation of squalene and the direct damage of cell membranes, resulting in fungal death [89].…”

Section: Sqlementioning

confidence: 99%

Sterol synthesis pathway inhibition as a target for cancer treatment

et al. 2020

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“…Chemically it is a benzylamine and naphthalene having the molecular formula C 23 H 27 N·HCl and molecular weight of 353.93 gm/mol [ 1 ]. It comes under a broad-spectrum antifungal agent and acts by inhibiting fungal squalene epoxidase synthesis of ergosterol, an important intermediate of fungal cell membrane synthesis [ 2 , 3 ]. BF has shown better therapeutic efficacy than terbinafine [ 4 ].…”

Section: Introductionmentioning

confidence: 99%

Formulation and Optimization of Butenafine-Loaded Topical Nano Lipid Carrier-Based Gel: Characterization, Irritation Study, and Anti-Fungal Activity

et al. 2021

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The present study aims to prepare and optimize butenafine hydrochloride NLCs formulation using solid and liquid lipid. The optimized selected BF-NLCopt was further converted into Carbopol-based gel for topical application for the treatment of fungal infection. Box Behnken design was employed to optimize the nanostructure lipids carriers (NLCs) using the lipid content (A), Tween 80 (B), and homogenization cycle (C) as formulation factors at three levels. Their effects were observed on the particle size (Y1) and entrapment efficiency (Y2). The selected formulation was converted into gel and further assessed for gel characterization, drug release, anti-fungal study, irritation study, and stability study. The solid lipid (Compritol 888 ATO), liquid lipid (Labrasol), and surfactant (tween 80) were selected based on maximum solubility. The optimization result showed a particle size of 111 nm with high entrapment efficiency of 86.35% for BF-NLCopt. The optimized BF-NLCopt converted to gel (1% w/v, Carbopol 934) and showed ideal gel evaluation results (drug content 99.45 ± 2.11, pH 6.5 ± 0.2, viscosity 519 ± 1.43 CPs). The drug release study result depicted a prolonged drug release (65.09 ± 4.37%) with high drug permeation 641.37 ± 46.59 µg (32.07 ± 2.32%) than BF conventional gel. The low value of irritation score (0.17) exhibited negligible irritation on the skin after application. The anti-fungal result showed greater efficacy than the BF gel at both time points. The overall conclusion of the results revealed NLCs-based gel of BF as an ideal delivery system to treat the fungal infection.

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Butenafine and analogues: An expeditious synthesis and cytotoxicity and antifungal activities

Abstract: Graphical abstract

Cited by 10 publications

References 64 publications

Fragment-based approach to study fungicide-biomimetic membrane interactions

Fragment-based approach to study fungicide-biomimetic membrane interactions

Sterol synthesis pathway inhibition as a target for cancer treatment

Formulation and Optimization of Butenafine-Loaded Topical Nano Lipid Carrier-Based Gel: Characterization, Irritation Study, and Anti-Fungal Activity

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