Isolation, structural elucidation and characterization of impurities in Cefdinir

J Pharm Biomed Anal. 2007 Mar 12;43(4):1476-82. doi: 10.1016/j.jpba.2006.10.031. Epub 2006 Dec 15.

Abstract

Three unknown impurities in Cefdinir bulk drug at levels below 0.2% (ranging from 0.05 to 0.2%) have been detected by high performance liquid chromatography (HPLC). These impurities were isolated from crude sample of Cefdinir using preparative HPLC. Based on the spectral data (NMR, IR and MS) the structures of these impurities were characterized as (6R, 7R)-7-[(z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-8-oxo-3-vinyl-5-thia-1-azabicyclo [4.2.0] oct-2-ene-2-carboxylic acid-5-oxide (I). (6R, 7R)-7-[(z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-8-oxo-3-vinyl-5-thia-1-azabi-cyclo [4.2.0] oct-3-ene-2-carboxylic acid (II). (6R, 7R)-7-[(z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-8-oxo-3-methyl-5-thia-1-azabicyclo-[4.2.0]oct-2-ene-2-carboxylic acid (III), respectively. The origin and structural elucidation of all impurities have been discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / analysis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / standards
  • Cefdinir
  • Cephalosporins / analysis*
  • Cephalosporins / chemistry
  • Cephalosporins / standards
  • Chromatography, High Pressure Liquid
  • Drug Contamination*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Structure
  • Spectroscopy, Fourier Transform Infrared

Substances

  • Anti-Bacterial Agents
  • Cephalosporins
  • Cefdinir