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Febuxostat ethanol monosolvate.

Thomas Gelbrich1, Volker Kahlenberg2, Verena Adamer3

  • 1University of Innsbruck, Institute of Pharmacy, Innrain 52, 6020 Innsbruck, Austria.

Acta Crystallographica. Section E, Crystallographic Communications
|June 12, 2020
PubMed
Summary

This study details the crystal structure of a febuxostat ethanol monosolvate, revealing helical chains formed by hydrogen bonds between the febuxostat molecule and ethanol. The structure is similar to a previously identified methanol analogue.

Keywords:
crystal structurehydrogen bondingisostructuralpharmaceuticalssolvate

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Area of Science:

  • Crystallography
  • Supramolecular Chemistry
  • Medicinal Chemistry

Background:

  • Febuxostat is a medication used to treat gout.
  • Understanding the solid-state structure of drug compounds is crucial for formulation and stability.
  • Solvates can exhibit different physical and chemical properties compared to the anhydrous form.

Purpose of the Study:

  • To characterize the crystal structure of 2-(3-cyano-4-iso-but-oxyphen-yl)-4-methyl-1,3-thia-zole-5-car-b-oxy-lic acid ethanol monosolvate.
  • To investigate the intermolecular interactions within the crystal lattice.
  • To compare the structure with related solvates.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of hydrogen bonding patterns and network topology.
  • Comparison with existing crystallographic data.

Main Results:

  • The title compound, a febuxostat ethanol monosolvate (C16H16N2O3S·C2H6O), was successfully synthesized and characterized.
  • Intermolecular O-H⋯O and O-H⋯N hydrogen bonds were observed between febuxostat and ethanol molecules.
  • These interactions lead to the formation of a helical hydrogen-bonded chain structure.
  • The determined structure is isostructural with the previously reported methanol analogue.

Conclusions:

  • The crystal structure of the febuxostat ethanol monosolvate reveals a specific hydrogen-bonding motif leading to helical chains.
  • The formation of solvates can influence the supramolecular assembly of drug molecules.
  • Isostructurality with the methanol analogue suggests potential similarities in solid-state behavior.