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Zoledronic acid: monoclinic and triclinic polymorphs from powder diffraction data.

Vladimir V Chernyshev1, Sergey V Shkavrov, Ksenia A Paseshnichenko

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This study determined the crystal structures of zoledronic acid polymorphs using X-ray diffraction. Both forms exhibit layered structures stabilized by hydrogen bonds, with unique dimer formations in the monoclinic version.

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Area of Science:

  • Crystallography
  • Materials Science
  • Medicinal Chemistry

Background:

  • Zoledronic acid is a bisphosphonate drug used to treat bone diseases.
  • Understanding its crystalline forms (polymorphs) is crucial for drug formulation and efficacy.
  • Polymorphism can significantly impact a drug's physical and chemical properties.

Purpose of the Study:

  • To elucidate the crystal structures of the monoclinic and triclinic polymorphs of zoledronic acid.
  • To analyze the intermolecular interactions, particularly hydrogen bonding, in these polymorphs.
  • To compare the structural features and hydrogen bonding patterns between the two polymorphs.

Main Methods:

  • Laboratory powder X-ray diffraction was employed to collect crystallographic data.
  • Rietveld refinement was used to analyze the diffraction patterns and determine the crystal structures.
  • Analysis of hydrogen bond distances and coordination environments was performed.

Main Results:

  • The crystal structures of both monoclinic and triclinic zoledronic acid polymorphs were successfully determined.
  • Molecules exist as zwitterions (1-(2-hydroxy-2-phosphonato-2-phosphonoethyl)-1H-imidazol-3-ium) in both forms.
  • Strong intermolecular hydrogen bonds create layered structures in both polymorphs, with distinct layer orientations.
  • The monoclinic polymorph features unique hydrogen-bonded centrosymmetric dimers not observed in the triclinic form.

Conclusions:

  • The study provides detailed structural insights into zoledronic acid polymorphism.
  • Hydrogen bonding plays a critical role in stabilizing the distinct layered architectures of the monoclinic and triclinic forms.
  • Differences in hydrogen bonding, specifically the presence of dimers in the monoclinic form, highlight structural variations between polymorphs.