Isolation and structural elucidation of urinary metabolites of ciprofloxacin

After oral administration of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-piperazine-1-ylquinoline++ +-3-carboxylic acid (ciprofloxacin, Bay o 9867; designated trademark: Ciprobay) four metabolites M1-M4 were isolated from human urine by Craig counter current distribution and semipreparative high-performance liquid chromatography. Their molecular structures were elucidated by nuclear magnetic resonance and mass spectrometry and confirmed by comparing their spectra with those of authentic synthetic reference compounds.