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Related Experiment Videos

Fenofibric acid.

Nigam P Rath1, Wahajul Haq, Ganesaratnam K Balendiran

  • 1Department of Chemistry and Biochemistry, University of Missouri-St Louis, MO 63121, USA.

Acta Crystallographica. Section C, Crystal Structure Communications
|February 8, 2005
PubMed
Summary

Fenofibric acid, unlike fenofibrate, features a carboxylic acid group. This structural difference enables a rare hydrogen-bonding interaction, potentially aiding molecular recognition.

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Area of Science:

  • Crystallography
  • Medicinal Chemistry
  • Molecular Biology

Background:

  • Fenofibrate is a common lipid-lowering drug.
  • Fenofibric acid is the active metabolite of fenofibrate.
  • Understanding the structural differences between fenofibrate and fenofibric acid is crucial for drug design.

Purpose of the Study:

  • To characterize the crystal structure of fenofibric acid.
  • To investigate the role of the carboxylic acid moiety in molecular interactions.
  • To explore the implications of structural differences for molecular recognition.

Main Methods:

  • X-ray crystallography was used to determine the structure of fenofibric acid.
  • Analysis of intermolecular interactions, specifically hydrogen bonding.
  • Comparison of the crystal packing of fenofibric acid with related molecules.

Main Results:

  • Fenofibric acid crystallizes with a carboxylic acid group, unlike the ester in fenofibrate.
  • A rare acid-to-ketone hydrogen-bond-type packing interaction was observed.
  • The conformation of fenofibric acid, due to the absence of an isopropyl group, positions the carboxyl group favorably for this interaction.

Conclusions:

  • The carboxylic acid moiety and specific conformation of fenofibric acid are key to its distinct crystal packing.
  • These structural features may be important for differentiating fenofibric acid from fenofibrate in molecular recognition processes.
  • The findings provide insights into the structure-activity relationship of fenofibrate and its metabolite.

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