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Dissolution and ionization of warfarin.

V J Stella, K G Mooney, J D Pipkin

    Journal of Pharmaceutical Sciences
    |July 1, 1984
    PubMed
    Summary
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    Warfarin forms a cyclic hemiketal in aqueous solution, influencing its ionization and dissolution rates. This study quantifies warfarin

    Area of Science:

    • Pharmacology
    • Physical Chemistry
    • Drug Formulation

    Background:

    • Warfarin has been observed to exist as a cyclic hemiketal in solid states and nonaqueous solvents.
    • The implications of this cyclic hemiketal form on warfarin's behavior in aqueous solutions remain largely unexplored.

    Purpose of the Study:

    • To investigate the ionization and ionization kinetics of warfarin in aqueous solutions.
    • To confirm the existence of the cyclic hemiketal form of warfarin in water.
    • To determine how the cyclic hemiketal influences acyclic enol equilibrium, ionization kinetics, and dissolution rate.

    Main Methods:

    • Equilibrium aqueous solubility measurements at 25°C and ionic strength 0.5.
    • Determination of macroscopic pKα using potentiometric titration and spectrophotometric methods.

    Related Experiment Videos

  • Comparison with phenprocoumon to estimate the hemiketal-acyclic enol ratio.
  • Stop-flow spectrophotometry for ionization kinetics.
  • Rotating disk dissolution rate measurements under pH-stat conditions.

    • Main Results:

    • Equilibrium aqueous solubility of un-ionized warfarin acid was 1.28 x 10⁻⁵ M.
    • Observed macroscopic pKα ranged from 5.03 to 5.06.
    • The hemiketal-acyclic enol ratio was estimated to be approximately 20:1.
    • Warfarin ionization half-life was less than 1-2 x 10⁻³ s.
    • The dissolution rate profile was consistent with theoretical predictions for instantaneous ionizing acids.

    Conclusions:

    • Warfarin likely exists predominantly in the cyclic hemiketal form in aqueous solutions.
    • The cyclic hemiketal form does not significantly perturb the ionization and dissolution rate profiles from theoretical expectations.
    • The ionization and dissolution kinetics are primarily governed by the acyclic enol form and its pKα.