Identification of a new isomer from a reversible isomerization of ceftriaxone in aqueous solution

J Pharm Biomed Anal. 2015 Jan:102:326-30. doi: 10.1016/j.jpba.2014.07.040. Epub 2014 Oct 2.

Abstract

A reversible isomerization of ceftriaxone in aqueous solution was observed, and the structure of the isomer was determined by mass spectrometry and various 1D and 2D NMR techniques. The mechanism of isomerization was also discussed. Finally, molecular docking simulations were performed and the antimicrobial activities of the isomers were measured. This showed that the biological activity of ceftriaxone was stronger than that of its isomer. The results reported in this article may be important to quality control requirements and to the stability of ceftriaxone products.

Keywords: Antibiotic; Biological activity; Ceftriaxone; Isomerization; Related substances.

MeSH terms

  • Anti-Bacterial Agents / analysis
  • Anti-Bacterial Agents / chemistry*
  • Ceftriaxone / analysis
  • Ceftriaxone / chemistry*
  • Chromatography, High Pressure Liquid / methods
  • Isomerism
  • Magnetic Resonance Spectroscopy / methods
  • Pharmaceutical Solutions / analysis
  • Pharmaceutical Solutions / chemistry*
  • Stereoisomerism
  • Water / analysis
  • Water / chemistry*

Substances

  • Anti-Bacterial Agents
  • Pharmaceutical Solutions
  • Water
  • Ceftriaxone