title: Structural identification and characterization of impurities in ceftizoxime sodium.
abstract: Ceftizoxime sodium is a parenteral beta-lactamic antibacterial drug. In the synthesis of ceftizoxime sodium, eight process related impurities were detected in HPLC analysis. Pure impurities obtained by both synthesis and preparative HPLC were co-injected with ceftizoxime sample to confirm the retention times in HPLC. The impurities were characterized as, (6R,7R)-7-amino-3-cephem-4-carboxylic acid (impurity I); (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetamido]-3-cephem-1-oxo-4-carboxylic acid (impurity II); (4RS,6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino) acetamido]-3,4-dihydro-3-cephem-4-carboxylic acid (impurity III); (6R,7R)-7-[(E)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetamido]-3-cephem-4-carboxylic acid (impurity IV); (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetamido]-3-cephem-N-(3-cephem-4-carboxy-7-yl)-4-carboxamide (impurity V); (6R,7R)-7-[(Z)-2-[[(Z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetylamino]thiazol-4-yl]-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (impurity VI); 2-mercaptobenzothiazole (impurity VII) and 2-mercapto benzothiazolyl [(Z)-2-(2-amino-4-thiazolyl)-2-methoxyimino] acetate (impurity VIII). Structural elucidation of all impurities by spectral data ((1)H NMR, (13)C NMR, MS and IR) has been discussed.
authors.affiliation: A.P.L. Research Centre, 313, Bachupally, Hyderabad 500072, India.
authors.forename: Ch
authors.initials: Ch
authors.lastname: Bharathi
authors.forename: Ch S
authors.initials: ChS
authors.lastname: Prasad
authors.forename: D Vijaya
authors.initials: DV
authors.lastname: Bharathi
authors.forename: Rama
authors.initials: R
authors.lastname: Shankar
authors.forename: V Janardhana
authors.initials: VJ
authors.lastname: Rao
authors.forename: Ramesh
authors.initials: R
authors.lastname: Dandala
authors.forename: A
authors.initials: A
authors.lastname: Naidu
mesh_terms: D000900:Anti-Bacterial Agents / Q000032:analysis*; D015296:Ceftizoxime / Q000032:analysis*; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D004340:Drug Contamination; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D004364:Pharmaceutical Preparations / Q000737:chemistry / Q000592:standards; D011786:Quality Control; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods; D017550:Spectroscopy, Fourier Transform Infrared / Q000379:methods; D053719:Tandem Mass Spectrometry / Q000379:methods; D013678:Technology, Pharmaceutical
chemical_list: D000900:Anti-Bacterial Agents; D004364:Pharmaceutical Preparations; D015296:Ceftizoxime