Structural elucidation of a dimeric impurity in the process development of ceftolozane using LC/HRMS and 2D-NMR

J Pharm Biomed Anal. 2019 Sep 10:174:242-247. doi: 10.1016/j.jpba.2019.05.057. Epub 2019 May 26.

Abstract

Ceftolozane is MSD's 5th generation cephalosporin antibiotic with broad-spectrum gram-negative activity. While refining the synthetic route to the drug substance, a dimeric impurity was observed in the final active pharmaceutical ingredient (API) of ceftolozane. Through impurity enrichment and preparative isolation, the structure of the impurity was subsequently established through LC/HRMS, HRMSMS, H/D exchange and 2D-NMR studies. A kinetic study of the impurity formation was conducted to determine the best conditions to control it in the final chemical process.

Keywords: Ceftolozane; HRMS; Impurity; Isolation; NMR; Stuctural elucidaton.

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Cephalosporins / analysis*
  • Chromatography, High Pressure Liquid
  • Chromatography, Liquid
  • Dimerization
  • Drug Contamination*
  • Gram-Negative Bacteria / drug effects
  • Kinetics
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Spectrophotometry, Ultraviolet
  • Technology, Pharmaceutical

Substances

  • Anti-Bacterial Agents
  • Cephalosporins
  • ceftolozane