Febuxostat ethanol monosolvate

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.