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Thermodynamic relationships between nateglinide polymorphs.

G Bruni1, V Berbenni, C Milanese

  • 1C.S.G.I.-Dipartimento di Chimica Fisica M. Rolla, Università degli Studi di Pavia, Viale Taramelli 16, 27100 Pavia, Italy. bruni@matsci.unipv.it

Journal of Pharmaceutical and Biomedical Analysis
|July 3, 2009
PubMed
Summary
This summary is machine-generated.

Nateglinide polymorphs B, H, and S were characterized. The S form is the only stable polymorph, crystallizing from melt or via isothermal treatment of metastable B and H forms.

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Area of Science:

  • Solid-state chemistry
  • Pharmaceutical sciences
  • Materials science

Background:

  • Nateglinide is an antidiabetic agent.
  • Understanding nateglinide's polymorphic forms is crucial for drug formulation and efficacy.
  • Polymorphism significantly impacts drug properties, including stability and bioavailability.

Purpose of the Study:

  • To comprehensively characterize the physico-chemical properties of nateglinide polymorphs (B, H, and S).
  • To determine the relative stability and identify the most stable polymorphic form of nateglinide.
  • To elucidate the structural differences and similarities between the polymorphs.

Main Methods:

  • Thermal analysis (DSC/TGA)
  • X-ray diffraction (XRD) for crystal structure determination
  • Infrared (IR) spectroscopy for molecular structure analysis
  • Scanning electron microscopy (SEM) for microstructure examination

Main Results:

  • Three distinct polymorphs (B, H, S) of nateglinide were identified with different crystal structures.
  • IR spectroscopy indicated significant molecular structure differences between form B and forms H/S.
  • The S polymorph, the highest melting form, was identified as the only thermodynamically stable form.
  • Metastable B and H polymorphs can transform into the stable S form upon heating or isothermal treatment below their melting points.

Conclusions:

  • The S polymorph represents the stable crystalline form of nateglinide.
  • Metastable polymorphs (B and H) can convert to the stable S form, highlighting the importance of controlling polymorphic form during manufacturing and storage.
  • Physico-chemical characterization provides a basis for understanding nateglinide's solid-state behavior and optimizing its pharmaceutical applications.