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Related Experiment Videos

Polymorphic forms of cilostazol.

Linda B Whittall1, Robert R Whittle, Grayson W Stowell

  • 1aaiPharma, 2320 Scientific Park Drive, Wilmington, North Carolina 28405, USA.

Acta Crystallographica. Section C, Crystal Structure Communications
|August 3, 2002
PubMed
Summary

Two distinct crystalline forms of cilostazol were identified. Differences in the butoxy chain conformation affect molecular interactions and crystal packing in these unique polymorphs.

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Thermally-prepared polymorphic forms of cilostazol.

Journal of pharmaceutical sciences·2002

Area of Science:

  • Crystallography
  • Solid-state chemistry
  • Medicinal chemistry

Background:

  • Cilostazol is a medication used to treat symptoms of intermittent claudication.
  • Polymorphism, the ability of a solid material to exist in multiple crystalline forms, can impact drug properties.
  • Understanding cilostazol's solid-state forms is crucial for its pharmaceutical development.

Purpose of the Study:

  • To discover and characterize novel polymorphic forms of cilostazol.
  • To elucidate the structural differences between cilostazol polymorphs.
  • To investigate the impact of conformational variations on crystal packing.

Main Methods:

  • Single-crystal X-ray structural analysis was employed to determine the molecular structures.
  • Crystallographic data were used to analyze conformational features and intermolecular interactions.
  • Comparison of distinct crystalline forms was performed.

Main Results:

  • Two unique conformational polymorphic forms of cilostazol were successfully isolated and characterized.
  • Both forms exhibit a chair conformation in the cyclohexyl ring and puckering in the quinolinone ring.
  • A key distinction lies in the rotational conformation of the butoxy chain, influencing intermolecular forces and crystal packing.

Conclusions:

  • The study identified two novel crystalline forms of cilostazol, highlighting conformational polymorphism.
  • Conformational variations in the butoxy chain are critical determinants of crystal packing in cilostazol.
  • Further investigation into the third polymorph is warranted, though crystallization challenges were encountered.

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