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Comprehensive spectroscopic characterization of finasteride polymorphic forms. Does the form X exist?

Jadwiga Frelek1, Marcin Górecki, Alicja Dziedzic

  • 1Institute of Organic Chemistry, Polish Academy of Sciences, Warsaw, Poland.

Journal of Pharmaceutical Sciences
|February 5, 2015
PubMed
Summary

Researchers prepared and characterized three pure polymorphic forms of finasteride. Spectroscopic methods confirmed their distinct structures and identified finasteride "form X" as identical to form III, excluding its existence.

Keywords:
Calorimetry (DSC)FTIR (Fourier transform infrared spectroscopy)X-ray powder diffractometrychiralitycircular dichroismfinasteridepolymorphismsolid-state NMR

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Area of Science:

  • Solid-state chemistry
  • Pharmaceutical sciences
  • Spectroscopy

Background:

  • Polymorphism significantly impacts drug properties, including solubility and bioavailability.
  • Understanding and controlling finasteride's polymorphic forms is crucial for its therapeutic efficacy.
  • Previous studies have identified various finasteride forms, necessitating clear characterization.

Purpose of the Study:

  • To synthesize and unequivocally characterize the pure polymorphic forms I, II, and III of finasteride.
  • To differentiate these polymorphs using advanced spectroscopic techniques.
  • To clarify the identity of the reported finasteride 'form X' and assess its existence.

Main Methods:

  • Synthesis of finasteride polymorphic forms I, II, and III.
  • Purity confirmation using Fourier-transform infrared (FTIR) spectroscopy, differential scanning calorimetry (DSC), and X-ray powder diffraction (XRPD).
  • Structural analysis via carbon-13 (13C) and nitrogen-15 (15N) cross-polarization magic angle spinning (CP-MAS) nuclear magnetic resonance (NMR) spectroscopy.
  • Distinction of polymorphs using electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) spectroscopy.

Main Results:

  • Pure polymorphic forms I, II, and III of finasteride were successfully prepared and characterized.
  • Spectroscopic methods (FTIR, DSC, XRPD, 13C/15N CP-MAS NMR, VCD) confirmed the distinct nature of the three forms.
  • Vibrational circular dichroism (VCD) spectra effectively distinguished between the three finasteride polymorphs.
  • Analysis revealed one molecule per asymmetric unit in forms I and III, and two in form II.
  • Comparison with literature data confirmed finasteride 'form X' is identical to form III, thus excluding the existence of form X.

Conclusions:

  • The study successfully prepared and characterized three distinct polymorphic forms of finasteride.
  • A combination of spectroscopic techniques provides a robust method for differentiating finasteride polymorphs.
  • The existence of a separate finasteride 'form X' is refuted; it is identical to form III.