Bacterial induced infection is a major complication associated with the use of medical implants. Degradable antibacterial ciprofloxacin-polyurethanes (CFPU) have been synthesized in attempts to address this problem. It is supposed that the material may be sensitively hydrolyzed by inflammatory enzyme, cholesterol esterase (CE), and the drug could be released according to the state of infection. The enzyme biodegradation experiments showed an extra release of ciprofloxacin when CFPU was incubated by enzyme solutions than by phosphate-buffer saline (PBS). Results showed that the drug release was enhanced as the concentration of the enzyme increased. The antimicrobial activities of degradation solutions were tested by broth dilution assay. The enzyme degradation solutions exhibited an ability to kill bacteria. The cell cytotoxicity assay indicated that the degradation products were hypotoxicity to human beings according to the cytotoxicity grade of United States Pharmacopoeia (USP).