• Fluconazole packaged and labeled.

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Description

Fluconazole is broad-spectrum fungistatic first-generation triazole antifungal developed and patented by Pfizer in 1981 in the UK.  It targets ergosterol synthesis in a wide range of fungal species such as Candida and Cryptococcus.  It differs from other azole antifungals in that it contains a friazole ring instead of an imidazole ring.   Fluconazole is practically insoluble in water but is sparingly soluble in organic solvents such as ethanol and DMSO.

    CAS Number

    86386-73-4

    Molecular Formula

    C13H12F2N6O

    Molecular Weight

    306.27

    Mechanism of Action

    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. 

    Storage Conditions

    ≤30°C

    Tariff Code

    2933.99.7500

    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.

Applications

    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).

    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

    For a representative list of Fluconazole MIC values, click here

    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).

Specifications

    Form

    Powder

    Appearance

    White or almost white crystalline powder

    Source

    Synthetic

    Impurity Profile

    Impurity A: Not more than 0.2%
    Impurity B: Not more than 0.1%
    Impurity C: Not more than 0.2%
    Total unknown impurities: Not more than 0.3%
    Total impurities: Not more than 1.5%

    Assay

    (On Dried Basis): 98.0-102.0%

    Loss on Drying

    ≤0.5%

    Residue On Ignition

    Not more than 0.1%

References

    References

    Ghannoum MA and Rice LB  (1999)  Antifungal agents: Mode of action, mechanisms of resistance, and correlation of these mechanisms with bacterial resistance.  Clin.  Microbiol. Rev. 12 (4):501-517  PMID 10515900

    Re JH et al (1997)  Development of interpretive breakpoints for antifungal susceptibility testing: Conceptual framework and analysis of in vitro-in vivo correlation data for fluconazole, itraconazole, and Candida Infections. Clin. Infect. Dis. 24(2):235–247

    Saag MS and Dismukes WE(1988)  Azole antifungal agents: Emphasis on new triazoles. Antimicrob. Agents. Chemother. 32(1):1-8

    Sobel, JD and Akins RA (2004)  Fungicidal activity of fluconazole against Candida albicans in a synthetic vagina-simulative medium.  Antimicrob. Agents Chemother. 48(1):161-167

    Vincent-Ballereau FN, Patey ON, Lafaix C (1991)  Fluconazole. Review and situation among antifungal drugs in the treatment of opportunistic mycoses of human immuno-deficiency virus infections.  Pharm Weekbl Sci. 13(2):45-57  PMID 1870943

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