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Cocrystal or salt: does it really matter?

Christer B Aakeröy1, Meg E Fasulo, John Desper

  • 1Department of Chemistry, Kansas State University, Manhattan, Kansas 66506, USA. aakeroy@ksu.edu

Molecular Pharmaceutics
|May 15, 2007
PubMed
Summary
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Salt formation from carboxylic acids and N-heterocycles often yields unpredictable crystal structures. Molecular cocrystals, however, are more predictable, offering opportunities for diverse drug substance solid forms.

Area of Science:

  • Solid-state chemistry
  • Supramolecular chemistry
  • Crystallography

Background:

  • Salts and cocrystals are crucial for drug development, influencing properties like solubility and stability.
  • Predicting the solid-state structure of pharmaceutical compounds is vital for successful formulation.

Purpose of the Study:

  • To analyze the structural outcomes of salt and cocrystal formation between carboxylic acids and N-heterocycles.
  • To compare the predictability of crystal lattice composition for salts versus cocrystals.

Main Methods:

  • Structural analysis of over 80 synthesized salts and cocrystals.
  • Equimolar synthesis of carboxylic acids and N-heterocycles.
  • Assessment of lattice composition and stoichiometry.

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Main Results:

  • Salt formation via proton transfer frequently (45%) resulted in unpredictable lattice compositions (solvates or variable stoichiometry).
  • Molecular cocrystal formation (no proton transfer) rarely led to unexpected compositions (5%).
  • Proton transfer during salt formation significantly complicates structure prediction and targeted synthesis.

Conclusions:

  • Cocrystal formation offers greater predictability and control over crystal lattice composition compared to salt formation.
  • Cocrystals present a promising avenue for generating diverse solid forms of drug substances with desirable properties.
  • The formation of carboxylate anions during salt synthesis has significant structural implications, hindering predictable supramolecular assembly.