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Phenylbutazone ionization kinetics.

V J Stella, J D Pipkin

    Journal of Pharmaceutical Sciences
    |August 1, 1976
    PubMed
    Summary
    This summary is machine-generated.

    Phenylbutazone exhibits nonclassical behavior due to its slow ionization kinetics. Understanding these ionization rates is crucial for accurate transport modeling of this carbon acid.

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    Area of Science:

    • Pharmacokinetics
    • Chemical Kinetics
    • Physical Chemistry

    Background:

    • Phenylbutazone shows bioavailability issues and nonclassical behavior in transport studies.
    • This behavior is partly due to phenylbutazone's noninstantaneous ionization kinetics as a carbon acid.
    • Diffusion-limited transport models often incorrectly assume instantaneous ionization reactions.

    Purpose of the Study:

    • To determine the ionization kinetics of phenylbutazone.
    • To investigate the mechanism of phenylbutazone ionization and protonation/deprotonation reactions.
    • To calculate kinetic parameters like pKaenol and pKadiketo.

    Main Methods:

    • Stopped-flow spectrophotometry was used to measure ionization kinetics.
    • Experiments were conducted at an ionic strength of 0.1 and 25°C.

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  • A log kobs versus pH profile was generated to elucidate the reaction mechanism.

    • Main Results:

    • The ionization kinetics of phenylbutazone were successfully determined.
    • A reaction mechanism consistent with the observed pH profile was postulated.
    • Kinetic calculations provided the percent enol/diketo forms and pKa values.
    • Protonation was acid-catalyzed, deprotonation was base-catalyzed, with water being a poor proton donor.

    Conclusions:

    • Phenylbutazone's noninstantaneous ionization kinetics contribute to its nonclassical behavior in transport.
    • The study provides a mechanistic understanding of phenylbutazone's ionization.
    • Accurate kinetic data are essential for reliable pharmacokinetic and transport modeling of phenylbutazone.