Bifonazole

SKU: orb1309472

Description

Bifonazole (Bay H-4502) is an antifungal agent that inhibits fungal cytochrome P450 14α-demethylase (CYP51), disrupting ergosterol biosynthesis and compromising membrane integrity, leading to cell lysis. It is widely used in biochemical research to study antifungal mechanisms and has been utilized in both in vitro susceptibility assays and in vivo models of dermatophyte infections.

Research Area

Infectious Disease & Virology, Metabolism Research

Key Properties

• CAS Number: 60628-96-8
• MW: 310.39
• Purity: >99.99% (May vary between batches)
• Formula: C₂₂H₁₈N₂
• SMILES: C(C1=CC=C(C=C1)C2=CC=CC=C2)(N3C=CN=C3)C4=CC=CC=C4
• Target: Antibiotic,Cytochromes P450,Antifungal
• Solubility: Ethanol:16 mg/mL (51.55 mM);H2O:< 1 mg/mL (insoluble or slightly soluble);DMSO:1.55 mg/mL (4.99 mM);10% DMSO+40% PEG300+5% Tween 80+45% Saline:1 mg/mL (3.22 mM)

Bioactivity

• In Vivo:
  Bifonazole, but not clotrimazole, exhibits the characteristics of a peroxisome proliferator including hepatomegaly (increase in liver:body weight ratio), up to a 4-fold induction of lauric acid omega-hydroxylase activity and an 8-fold induction of palmitoyl-CoA oxidation by rat liver peroxisomes. Bifonazole also induces P402B1/2B2, P4503A and P4501A1, but not P4502E1.
• In Vitro:
  Bifonazole, a broad spectrum antifungal agent, inhibits monooxygenase activity and induces a type II binding spectrum in 2B4dH(H226Y), a modified enzyme previously crystallized in the presence of 4-(4-chlorophenyl)imidazole (CPI). Bifonazole (40 mM) releases Ca2+ from the store sensitive to 1 mM thapsigargin, an endopolasmic reticulum Ca2+ pump inhibitor. Bifonazole (40 mM) per se induces capacitative Ca2+ entry while reduces 1 mM thapsigargin-induced capacitative Ca2+ entry. Bifonazole is calmodulin antagonists which most effectively reduce glycolysis and ATP level in B16 melanoma cells. Bifonazole acts through allosteric regulation and detachment of glycolytic enzymes from cytoskeleton. Bifonazole blocks PGE2 formation induced by 2 μm and 4 μm arachidonic acid clearly better than at 6 or 10 μm of the agonist. Bifonazole shows the same characteristics in MC3T3-E1 and UMR-106 cells stimulated by ionomycin or various concentrations of arachidonic acid.

Storage & Handling

• Storage: Powder: -20°C for 3 years | In solvent: -80°C for 1 year | Shipping with blue ice/Shipping at ambient temperature.
• Expiration Date: 12 months from date of receipt.
• Disclaimer: For research use only

Alternative Names

Bifonazole, Bay H 4502, Bay H4502, Bay H-4502, Antibiotic, CYP51, Inhibitor, Fungal, inhibit

Compound Identifiers

PubChem CID

2378