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Apremilast Cocrystals with Phenolic Coformers.

Yelizaveta Naumkina1,2, Bohumil Kratochvíl1, Elena Korotkova2

  • 1Department of Solid State Chemistry, University of Chemistry and Technology, Prague, Technicka 5, 16628 Prague, Czech Republic.

Molecules (Basel, Switzerland)
|January 8, 2025
PubMed
Summary
This summary is machine-generated.

Apremilast cocrystals were formed with phenolic coformers, but surprisingly showed little melting point variation. Apremilast

Keywords:
Apremilastcocrystalshydrogen bondsphenolic compoundsπ–π interactions

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Area of Science:

  • Materials Science
  • Pharmaceutical Chemistry
  • Crystallography

Background:

  • Apremilast (APR) is an anti-inflammatory drug used for psoriasis.
  • Enhancing APR solubility via cocrystallization is an active research area.
  • Phenolic coformers offer diverse hydrogen-bonding capabilities.

Purpose of the Study:

  • To investigate the cocrystallization of Apremilast with four phenolic coformers.
  • To characterize the resulting cocrystal structures and thermal properties.
  • To understand the influence of coformer hydroxyl group variations on cocrystal behavior.

Main Methods:

  • Synthesis and purification of four novel Apremilast cocrystal forms.
  • Characterization using X-Ray diffraction (XRD) and thermal analysis (DSC).
  • Analysis of molecular packing and intermolecular interactions via crystal structures and Hirshfeld surface analysis.

Main Results:

  • Four new Apremilast cocrystal forms were successfully synthesized.
  • Despite coformer differences, cocrystals showed minimal variation in melting points.
  • Crystal structures revealed that Apremilast's molecular packing restricts hydroxyl group interactions.

Conclusions:

  • The molecular structure of Apremilast limits the network-forming potential of phenolic coformers.
  • Cocrystallization did not significantly alter the thermal properties as expected.
  • Further studies are needed to fully understand Apremilast cocrystal behavior and solubility enhancement.