Fluconazole

- Overview
  - Fluconazole is broad-spectrum fungistatic triazole antifungal. Fluconazole targets ergosterol synthesis in a wide range of fungal species such as Candida spp., Cryptococcus neoformans and dermatophytes. It is practically insoluble in water.
    
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    Background
    
    Fluconazole interferes with the conversion of lanosterol to ergosterol, an essential cell membrane component. The inhibition of ergosterol synthesis increases cell permeability which disrupts normal cellular function.
    Resistance to antifungals can include alteration in drug target, alteration in sterol biosynthesis, reduction in the intercellular concentration of target enzyme, or overexpression of the antifungal drug target (Ghannoum and Rice, 1999).
    It is a fungal cytochrome P-450 inhibitor, specifically sterile C-14-α-demethyllation. Resistance in C. albicans is due to mutations in the ERG11 gene which codes for C-14-α-demethyllation. Mutations in this gene prevent the compound from binding while still allowing binding to the enzyme’s natural substrate lanosterol.
    It also inhibits the human cytochrome P450 system, particularly the isozyme CYP2C9. Therefore, in theory, compounds that are metabolized by this enzyme tend to increase in concentration.
- Properties
  - CAS Number
    
    86386-73-4
    
    Molecular Formula
    
    C13H12F2N6O
    
    Molecular Weight
    
    306.27
    
    Appearance
    
    White or almost white crystalline powder
    
    Solubility
    
    Practically insoluble in water (0.001 mg/ml). Sparingly soluble in ethanol (20 mg/ml) and DMSO (33 mg/ml).
    
    Other Properties
    
    Source: Synthetic
    Assay: (On Dried Basis): 98.0-102.0%
    Residue On Ignition: ≤0.1%
    Loss on Drying: ≤0.5%
    Identification: Passes test
    
    Storage
    
    ≤30°C
    
    * For research use only
- Applications
  - Application Description
    
    Spectrum: Broad-spectrum including Candida spp. (excluding C. krusei and C. glabrata) and Cryptococcus neoformans. Also effective against dermatophytes such as Microsporum, Epidermophyton and Trichophyton.
    
    Microbiology Applications: Fluconazole is commonly used in clinical in vitro microbiological antimicrobial susceptibility tests (panels, discs, and MIC strips) against fungal isolates. Medical microbiologists use AST results to recommend antibiotic treatment options. Representative MIC values include: Blastomyces dermatidis 1 µg/ml – 64 µg/ml Candida albicans ≤ 0.0313 µg/mL - 8 µg/mL.
    Please note that MIC data are complicated by variability in testing methods and lack of standardized approaches, thus there is a wide range of MICs reported. Consequently, in vivo research models are more predictive (Saag and Dismukes, 1988).
    
    Eukaryotic Cell Culture Applications: There is no relationship between in vitro and in vivo activities for this compound, thus antifungal efficacy was mainly proved in animal models, and has low toxicity (Vincent-Ballereau et al, 1991).