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Polyurethane/β-cyclodextrin/ciprofloxacin composite films have been prepared and structural and morphological behaviours reveal the progressive incorporation of the drug ciprofloxacin into polyurethane backbones. Spectral changes such as frequency shifts, band broadening and changes in the intensity are indicative of drug-polyurethane interactions. X-ray powder diffraction experiments demonstrate that ciprofloxacin retains its crystallinity in the polyurethane matrix. Electron microscopy and mercury porosimetry reveal open and interconnected macroporous pore morphology for the as-prepared polyurethane-drug films. Antimicrobial activity was evaluated by the agar disc diffusion method and the ciprofloxacin-polyurethane films demonstrate their potency as antibacterial medical systems. However, the ciprofloxacin-polyurethane films do not reveal antifungal properties.