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Related Experiment Videos

Isomerism in iohexol and ioxilan. Analysis and implications.

S J Foster1, M Sovak

  • 1Biophysica Foundation, La Jolla, CA 92037.

Investigative Radiology
|September 1, 1988
PubMed
Summary

Contrast media like iohexol and ioxilan exist as unavoidable isomer mixtures. These hydrophilic mixtures are highly water-soluble, ensuring good biological tolerance for pharmacological use.

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Area of Science:

  • Pharmacology
  • Organic Chemistry
  • Analytical Chemistry

Background:

  • Pharmacologically useful contrast media (CM) require high water solubility for stable supersaturated solutions.
  • Iohexol and ioxilan are contrast agents with potential isomerism due to various structural features.

Purpose of the Study:

  • To investigate the isomeric composition of iohexol and ioxilan.
  • To assess the impact of isomerism on the physicochemical and pharmacological properties of these contrast media.

Main Methods:

  • High-pressure liquid chromatography (HPLC) was used to analyze isomer mixtures.
  • Nuclear magnetic resonance (NMR) spectroscopy (1H and 13C) was employed for structural identification.
  • Physicochemical properties like water solubility and hydrophilicity were evaluated.

Main Results:

  • Iohexol and ioxilan exist as mixtures of various isomers, including D,L isomers, carbamoyl rotamers, and N-acetyl isomers.
  • All identified isomers are highly water-soluble and hydrophilic.
  • N-acetyl isomers interconvert rapidly in water, forming stable, soluble mixtures.
  • Isomers are expected to exhibit low binding to biomacromolecules, suggesting high biological tolerance.

Conclusions:

  • The isomeric mixtures of iohexol and ioxilan are unavoidable and pharmacologically relevant entities.
  • The high hydrophilicity and water solubility of all isomers contribute to their expected low toxicity and high biological tolerance.
  • These findings support the use of iohexol and ioxilan as safe and effective contrast media.

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