Two new ciprofloxacin (CF) monomers, (ACF) and (MCF) were designed and synthesized. Both ACF and MCF were polymerized using a redox-initiated polymerization process, yielding the polymers PACF and PMCF, respectively. Three co-polymers were prepared by polymerizing ACF with acrylamide (AcA), acrylonitrile (AcN), or N-(thiazol-2-yl) acrylamide (NTA) monomers in a 1:3 molar ratio. Elemental analysis, X-ray, IR, 1 H and 13 C NMR, and mass spectrometry were used to characterize the obtained monomers, polymers, and co-polymers. The biological activities of the prepared monomers, polymers, and co-polymers against Gram-positive and Gram-negative bacteria were investigated. Newly prepared compounds had a severe-to-mild impact on the microorganisms that were tested. Additionally, CF-resistant bacteria were tested against newly prepared monomers and polyciprofloxacin. These data