Bifonazole

Manufactured by Merck Group

Sourced in United States

Bifonazole is a broad-spectrum antifungal agent used in the treatment of various fungal infections. It is a synthetic imidazole derivative that acts by inhibiting the synthesis of ergosterol, an essential component of the fungal cell membrane. Bifonazole demonstrates activity against a wide range of dermatophytes, yeasts, and other fungal pathogens.

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Lab products found in correlation

15 protocols using bifonazole

Validation Experiments with Pharmacological Compounds

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Bifonazole (B3563, Sigma-Aldrich), cisapride (21657, Cayman Chemicals), 17a-ethynylestradiol (E4876, Sigma-Aldrich), nicardipine HCl (N7510, Sigma-Aldrich), ketoconazole (K1003, Sigma-Aldrich), and econazole nitrate salt (E4632, Sigma-Aldrich) were purchased and reconstituted to 50 or 100 mM in DMSO and used as indicated for validation experiments.

Taha Z., Arulanandam R., Maznyi G., Godbout E., Carter-Timofte M.E., Kurmasheva N., Reinert L.S., Chen A., Crupi M.J., Boulton S., Laroche G., Phan A., Rezaei R., Alluqmani N., Jirovec A., Acal A., Brown E.E., Singaravelu R., Petryk J., Idorn M., Potts K.G., Todesco H., John C., Mahoney D.J., Ilkow C.S., Giguère P., Alain T., Côté M., Paludan S.R., Olagnier D., Bell J.C., Azad T, & Diallo J.S. (2022). Identification of FDA-approved bifonazole as a SARS-CoV-2 blocking agent following a bioreporter drug screen. Molecular Therapy, 30(9), 2998-3016.

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Quantitative Analysis of Bifonazole

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TRAM-34 was purchased from Toronto Research Chemicals (Ontario, Canada). Bifonazole (Fig 1D, IS) and formic acid (FA) were purchased from Sigma-Aldrich (St. Louis, MO, USA). ACN, MeOH, and isopropanol (IPA) were of LC-MS grade and were purchased from JT Baker (Philipsburg, NJ, USA). Water was prepared using a Millipore Direct Q3 water purification system (Millipore, Billerica, USA).

Ye J.H, & Pao L.H. (2015). Using Visualized Matrix Effects to Develop and Improve LC-MS/MS Bioanalytical Methods, Taking TRAM-34 as an Example. PLoS ONE, 10(4), e0118818.

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Screening of Chemical Libraries

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The Prestwick Chemical Library, which contains 1,200 small molecules and FDA approved drugs, was acquired at Prestwick Chemicals (Illkirch-Graffenstaden, France). Fluvastatin, simvastatin and atorvastatin were provided by Prestwick Chemicals (Illkirch-Graffenstaden, France). Econazole, miconazole, tioconazole and bifonazole were acquired at Sigma (Sigma-Aldrich, St. Louis, MO, USA).

Andreux P.A., Mouchiroud L., Wang X., Jovaisaite V., Mottis A., Bichet S., Moullan N., Houtkooper R.H, & Auwerx J. (2014). A method to identify and validate mitochondrial modulators using mammalian cells and the worm C. elegans. Scientific Reports, 4, 5285.

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Comprehensive Chemical Characterization

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Acetonitrile (99.9%), ethyl acetate (99.8%) and n-hexane (95%) were of HPLC grade and acquired from Fisher Scientific (Lisbon, Portugal). Individual compounds were of HPLC or GC grade, and the fatty acids methyl ester (FAME) reference standard mixture 37 (standard 47885-U), individual organic acids and sugars standards were acquired from Sigma-Aldrich (St. Louis, MO, USA). Racemic tocol and tocopherols isoforms were acquired from Matreya, Pleasant Gap, (Pennsyivania, PA, USA). The standards trolox, streptomycin, ampicillin, ketoconazole, bifonazole, ellipticine and sulforhodamine B were acquired from Sigma-Aldrich, (St Louis, MO, USA). The phenolic compounds commercial standards were obtained from Extrasynthèse S.A. (Genay, France) and the human tumour cell lines were acquired from Leibniz-Institute DSMZ (Braunschweig, Germany). Other chemicals and solvents were of analytical grade purity and obtained from common suppliers. A Milli-Q water purification system (TGI Pure Water Systems, Greenville, SC, USA) was used to treat the water.

A. Petropoulos S., Fernandes Â., Dias M.I., Pereira C., Calhelha R.C., Chrysargyris A., Tzortzakis N., Ivanov M., D. Sokovic M., Barros L, & Ferreira I.C. (2020). Chemical Composition and Plant Growth of Centaurea raphanina subsp. mixta Plants Cultivated under Saline Conditions. Molecules, 25(9), 2204.

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Analytical Workflow for Bifonazole and CTZ

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Bifonazole and CTZ were obtained from Sigma-Aldrich Corp. (St. Louis, MO, USA). HPLC-grade methanol, acetonitrile, and formic acid (98%) were obtained from JT Baker. HPLC-grade dichloromethane was obtained from Merck (Darmstadt, Germany).
Malt extract, glucose, casein hydrolyzate, l-asparagine, adenine, vitamin B₆, and yeast extract were obtained from Sigma-Aldrich Corp. (St. Louis, MO, USA). Chemicals such as KH₂PO₄, MgSO₄·7H₂O, FeCl₃, MnSO₄·H₂O, NH₄Cl, CaCl₂·6H₂O, and ZnSO₄·7H₂O were obtained from PPH Golpharm (Kraków, Poland). Water (quadruple-distilled) with a conductivity of less than 1 µS cm⁻¹ was prepared using S2-97A2 distillation apparatus (ChemLand, Stargard Szczecin, Poland).

Kryczyk-Poprawa A., Żmudzki P., Maślanka A., Piotrowska J., Opoka W, & Muszyńska B. (2019). Mycoremediation of azole antifungal agents using in vitro cultures of Lentinula edodes. 3 Biotech, 9(6), 207.

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Antimicrobial Evaluation of Natural Extracts

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The extracts were redissolved in 5% dimethyl sulfoxide (DMSO) to a concentration of 10 mg/mL and further diluted. The microdilution method [58 (link)] was performed to assess the antimicrobial activity against the Gram-negative bacteria Escherichia coli (ATCC 25922), Salmonella typhimurium (ATCC 13311) and Enterobacter cloacae (ATCC 35030), and Gram-positive bacteria: Staphylococcus aureus (ATCC 11632), Bacillus cereus (clinical isolate), Listeria monocytogenes (NCTC 7973). For antifungal assays, six micromycetes were used: Aspergillus fumigatus (human isolate), Aspergillus niger (ATCC 6275), Aspergillus versicolor (ATCC11730), Penicillium funiculosum (ATCC 36839), Trichoderma viride (IAM 5061) and Penicillium verrucosum var. cyclopium (food isolate). The minimum extract concentrations that completely inhibited bacterial growth (MICs) were determined by a colorimetric microbial viability assay, and minimum bactericidal concentration (MBC) and minimum fungicidal concentration (MFC) were also calculated. Streptomycin, ampicillin, ketoconazole, and bifonazole (Sigma-Aldrich, St. Louis, MO, USA) were used as positive controls, and 5% DMSO was used as a negative control.

Kissanga R., Liberal Â., Diniz I., Rodrigues A.S., Baptista-Ferreira J.L., Batista D., Ivanov M., Soković M., Ferreira I.C., Fernandes Â., Barros L, & Catarino L. (2022). Biochemical and Molecular Profiling of Wild Edible Mushrooms from Huila, Angola. Foods, 11(20), 3240.

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Quantitative Determination of Antifungal Agents

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Bifonazole, butoconazole, clotrimazole, econazole, itraconazole, ketoconazole, miconazole, posaconazole, ravuconazole, terconazole, tioconazole, voriconazole and benzyl-4-hydroxybenzoate (Internal Standard, IS) (>98% purity grade), sodium phosphate monobasic and sodium phosphate dibasic (>99% purity grade), phosphoric acid (90% purity grade) and trichloroacetic acid (>99% purity grade) were purchased from Sigma-Aldrich (Milan, Italy).
The commercial drugs were obtained from a local Pharmacy after medical prescription. Both HPLC-grade Acetonitrile (AcN) and methanol (MeOH) were supplied by Carlo Erba (Milan, Italy) and were used without further purification. The water for HPLC analysis was generated by using a Millipore Milli-Q Plus water treatment system (Millipore Bedford Corp., Bedford, MA). Oasis HLB (1 mL, 30 mg) and Sep-Pak (1 mL, 50 mg) were obtained from Waters (Milford, MA), while Strata-X (1 mL, 30 mg) was purchased from Phenomenex (Torrance, CA). MEPS device (syringe) and replacement needle with C₁₈ stationary phase were purchased from SGE Analytical Science (Melbourne, Australia).

Campestre C., Locatelli M., Guglielmi P., De Luca E., Bellagamba G., Menta S., Zengin G., Celia C., Di Marzio L, & Carradori S. (2017). Analysis of imidazoles and triazoles in biological samples after MicroExtraction by packed sorbent. Journal of Enzyme Inhibition and Medicinal Chemistry, 32(1), 1053-1063.

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Prestwick Chemical Library Screening

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The Prestwick chemical library (1280 FDA approved compounds in 96-well plates) was purchased from Prestwick Chemical (Illkirch, France). Bifonazole, bromhexine HCl, clofazimine, lovastatin, meclozine 2HCL, and simvastatin were purchased from Sigma-Aldrich (Zwijndrecht, The Netherlands). The fibroblast growth factor (FGF)19 human enzyme-linked immunosorbent assay kit was purchased from BioVendor R&D (Brno, Czech Republic). [³H]-taurocholate and [¹⁴C]-inulin were purchased from Perkin Elmer (Groningen, The Netherlands).

van de Wiel S.M., de Waart D.R., Oude Elferink R.P, & van de Graaf S.F. (2017). Intestinal Farnesoid X Receptor Activation by Pharmacologic Inhibition of the Organic Solute Transporter α-β. Cellular and Molecular Gastroenterology and Hepatology, 5(3), 223-237.

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Metabolic Modulation in Jurkat T Cells

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Jurkat T cells were cultured in R10FBS supplemented with 2 mM glutamine. Chemicals and inhibitors used in this study were as follows: 2-DG (10 mM), Akti1/2 (10 μM), Osi-027 (10 μM), KU-0063794 (10 μM), Rotenone (1 μM), TTFA (200 μM), Antimycin A (2 μM), Oligomycin (0.1 or 1 μM) or 4-(trifluoromethoxy) phenylhydrazone (FCCP, 2 μM), Clotrimazol (25 μM), nocodazole (10 μM), oxamate (5 mM), methyl pyruvate (1 or 10 mM), bifonazole (25 µM), MB-3 (1, 10 µM), 2-NBDG (0.5 mM) and mitotempo (20 μM) (all from Sigma-Aldrich). TCS-2002 (10 µM), SB 204990 (3 µM) and garcinol (1, 10 µM) (Tocris) was used at 10 μM. VDAC peptides corresponding to loop 4 (LP4 - KKLETAVNLAWTAGNSN) flanked N-, and C-terminally by the tryptophan zipper motif for increased stability (SWTWE and KWTWK, respectively) were linked to tandem repeats of the DNP2 fusion peptide (KIKKVKKKGRKKIKKVKKKGRK). The complete sequence for the peptides used are: dNP2 (KIKKVKKKGRKKIKKVKKKGRKSWTWEKWTWK) and dNP2-VDAC (KIKKVKKKGRKKIKKVKKKGRKSWTWEKKLETAVNLAWTAGNSNKWTWK). Both peptides were synthesized by Biomatik.

Bantug G.R., Fischer M.G., Grählert J., Balmer M.L., Unterstab G., Develioglu L., Steiner R., Zhang L., da Costa A.S., Gubser P.M., Burgener A.V., Sauder U., Löliger J., Belle R., Dimeloe S., Lötscher J., Jauch A., Recher M., Hönger G., Hall M.N., Romero P., Frezza C, & Hess C. (2018). Mitochondria–ER contact sites are immunometabolic hubs that orchestrate the rapid recall response of memory CD8+ T cells. Immunity, 48(3), 542-555.e6.

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Antimicrobial and Antifungal Evaluation

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The extracts were redissolved in 5% dimethyl sulfoxide (DMSO) to a concentration of 10 mg/mL and further diluted. The microdilution method (Soković, Glamočlija, Marin, Brkić, & van Griensven, 2010) was performed to assess the antimicrobial activity against the Gram-negative bacteria Escherichia coli (ATCC 35210), Salmonella Typhimurium (ATCC 13311) and Enterobacter cloacae (ATCC 35030), and the Grampositive Staphylococcus aureus (ATCC 6538), Bacillus cereus (clinical isolate) and Listeria monocytogenes (NCTC 7973). The antifungal activity was assessed against Aspergillus fumigatus (ATCC 1022), Aspergillus ochraceus (ATCC 12066), Aspergillus niger (ATCC 6275), Penicillium funiculosum (ATCC 36839), Penicillium ochrochloron (ATCC 9112), and Penicillium aurantiogriseum (food isolate) (Corrêa et al., 2015) . The minimum extract concentrations that completely inhibited bacterial growth (MICs) were determined by a colorimetric microbial viability assay, and minimum bactericidal concentration (MBC) and minimum fungicidal concentration (MFC) were also calculated. Streptomycin, ampicillin, ketoconazole and bifonazole (Sigma-Aldrich, St. Louis, MO, USA) were used as positive controls, and 5% DMSO was used as a negative control.

Fernandes Â., Bancessi A., Pinela J., Dias M.I., Liberal Â., Calhelha R.C., Ćirić A., Soković M., Catarino L., Ferreira I.C.F.R, & Barros L. (2021). Nutritional and phytochemical profiles and biological activities of Moringa oleifera Lam. edible parts from Guinea-Bissau (West Africa). Food chemistry, 341(Pt 1).

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