title: Chromatographic resolutions. XIV. Optical resolution of the racemic anticancer drug ifosfamide and other chiral oxazaphosphorines.
abstract: Ifosfamide, a chiral anticancer drug with phosphorus as chiral centre, was resolved into its enantiomers by chromatography on polyamides with bonded optically active substituents. Both enantiomers were isolated and characterized, the enantiomeric purity being at least 95% (31P nuclear magnetic resonance in the presence of an optically active shift reagent) and 99% (analytical chromatography), respectively. Experiments on the resolution of other oxazaphosphorines including the therapeutic drugs cyclophosphamide and trofosfamide are described.
mesh_terms: D000970:Antineoplastic Agents / Q000032:analysis*; D002853:Chromatography, Liquid; D003520:Cyclophosphamide / Q000031:analogs & derivatives* / Q000032:analysis; D007069:Ifosfamide / Q000032:analysis*; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; D003520:Cyclophosphamide; D007069:Ifosfamide