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Mechanisms by which moisture generates cocrystals.

Adivaraha Jayasankar1, David J Good, Naír Rodríguez-Hornedo

  • 1Department of Pharmaceutical Sciences, University of Michigan, Ann Arbor, Michigan 48109-1065, USA.

Molecular Pharmaceutics
|May 10, 2007
PubMed
Summary
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Moisture exposure can form pharmaceutical cocrystals from solid reactants through deliquescence. This process involves dissolution and recrystallization, influenced by humidity and reactant properties, offering control over cocrystal formation.

Area of Science:

  • Solid-state chemistry
  • Pharmaceutical science
  • Crystallization engineering

Background:

  • Cocrystals are solid forms with improved pharmaceutical properties.
  • Deliquescence, the absorption of atmospheric moisture leading to solution formation, is a critical factor in solid-state transformations.
  • Understanding cocrystal formation under deliquescent conditions is vital for drug formulation and stability.

Purpose of the Study:

  • To elucidate the mechanisms of cocrystal generation under deliquescent conditions.
  • To investigate the role of solution chemistry in cocrystallization during moisture uptake.
  • To establish models for predicting cocrystal formation based on solubility and reaction crystallization.

Main Methods:

  • Gravimetric vapor sorption (GVS) for moisture uptake analysis.

Related Experiment Videos

  • X-ray powder diffraction (XRPD) for phase identification.
  • On-line Raman spectroscopy for real-time crystallization monitoring.
  • Microscopy for visualizing transformation mechanisms.

    • Main Results:

    • Moisture uptake and deliquescence of solid reactant mixtures successfully generated cocrystals (e.g., carbamazepine-nicotinamide, carbamazepine-saccharin, caffeine/theophylline with dicarboxylic acids).
    • The transformation mechanism involves moisture uptake, dissolution of reactants, and subsequent cocrystal nucleation and growth.
    • Cocrystal formation rate and extent are dependent on relative humidity, moisture uptake, deliquescent additives, and reactant dissolution rates.

    Conclusions:

    • Deliquescence provides a viable pathway for cocrystal formation or even reversal of existing cocrystal forms under specific conditions.
    • The interplay between moisture uptake and dissolution kinetics governs liquid phase composition, supersaturation, and cocrystal formation rates.
    • Key indicators for cocrystal formation and stability include moisture uptake, cocrystal solubility, reactant solubility/dissolution, and transition concentration.