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Polymorphism on leflunomide: stability and crystal structures.

Daniel Vega1, Alicia Petragalli, Daniel Fernández

  • 1Unidad de Actividad Física, Comisión Nacional de Energía Atómica, Av. Gral. Paz 1499, 1650 San Martín, Buenos Aires, Argentina.

Journal of Pharmaceutical Sciences
|March 30, 2006
PubMed
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Two polymorphs of Leflunomide (form I and II) were identified and structurally characterized. Form I, the more stable polymorph, exhibits greater intermolecular interactions due to varied molecular conformations and pi-pi stacking.

Area of Science:

  • Solid-state chemistry
  • Crystallography
  • Materials science

Background:

  • Polymorphism is a critical factor influencing the physicochemical properties of active pharmaceutical ingredients.
  • Understanding crystal structures and intermolecular forces is essential for drug development and formulation.
  • Leflunomide, an immunosuppressive drug, has known polymorphic forms that require detailed investigation.

Purpose of the Study:

  • To identify and characterize distinct polymorphic forms of Leflunomide.
  • To elucidate the crystal structures and conformational differences between Leflunomide polymorphs.
  • To assess the thermodynamic stability and intermolecular interactions governing crystal cohesion.

Main Methods:

  • X-ray powder diffraction (XRPD) for phase identification and structural analysis.

Related Experiment Videos

  • Single-crystal X-ray diffraction for precise atomic arrangement determination.
  • Thermal analysis techniques, including differential scanning calorimetry (DSC), for thermodynamic stability assessment.

    • Main Results:

    • Two polymorphs of Leflunomide, designated form I and form II, were successfully identified and structurally solved.
    • Both forms crystallize in the monoclinic space group P2(1)/c, with distinct numbers of independent molecules per asymmetric unit.
    • Form I, identified as the more thermodynamically stable polymorph, displays cohesion through hydrogen bonding and pi-pi interactions, with differing molecular conformations.

    Conclusions:

    • The study successfully characterized two Leflunomide polymorphs, providing detailed structural and thermodynamic insights.
    • Differences in crystal packing, molecular conformations, and intermolecular interactions (H-bonding, pi-pi stacking) dictate the relative stability of Leflunomide forms.
    • This research contributes to a deeper understanding of Leflunomide's solid-state behavior, crucial for its pharmaceutical application.