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Related Experiment Videos

Thermally-prepared polymorphic forms of cilostazol.

Grayson W Stowell1, Robert J Behme, Stacy M Denton

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

Journal of Pharmaceutical Sciences
|November 16, 2002
PubMed
Summary

Cilostazol, an antithrombotic drug, exhibits multiple crystalline forms (polymorphs) beyond the previously known Form A. These new forms, B and C, show higher solubility but rapidly convert to Form A in solvents.

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Area of Science:

  • Pharmaceutical Sciences
  • Solid-State Chemistry
  • Materials Science

Background:

  • Cilostazol is an antithrombotic drug.
  • Previously, only one crystalline form (Form A) of cilostazol was known, melting at ~159°C.
  • Heating cilostazol melts can form glasses that crystallize into new polymorphic forms.

Purpose of the Study:

  • To investigate the existence and properties of new crystalline polymorphic forms of cilostazol.
  • To characterize the thermodynamic relationships and solubility of different cilostazol forms.
  • To understand the crystallization behavior and stability of cilostazol polymorphs.

Main Methods:

  • Calorimetry (Differential Scanning Calorimetry, DSC) for thermal analysis and free-energy calculations.
  • Single crystal X-ray diffraction for structural analysis of Form A and Form C.

Related Experiment Videos

  • Intrinsic dissolution and Fourier transform-Raman spectroscopy for analyzing metastable forms.

    • Main Results:

    • Two new polymorphic forms of cilostazol, Form B (mp ~136°C) and Form C (mp ~146°C), were identified.
    • Free-energy diagrams indicate a monotropic relationship between all three forms (A, B, and C).
    • Form B and Form C exhibit significantly higher theoretical solubility than Form A at 37°C.
    • Forms B and C are unstable in solvents, rapidly converting to Form A via solvent-mediated transformation.

    Conclusions:

    • Cilostazol exists in at least three monotropically related crystalline forms.
    • The higher solubility of metastable Forms B and C is limited by their rapid conversion to the stable Form A in solution.
    • Understanding these polymorphic relationships is crucial for controlling cilostazol's solid-state properties and bioavailability.