The aim of this study was to prepare chitosan (CS) filaments incorporated with N-acetyl-D-Glucosamine (GlcNAc), using the wet spinning method, in order to combine the GlcNAc pharmacological properties with the CS biological properties for use as absorbable suture materials. The filaments were characterized by scanning electron microscopy (SEM), X-ray diffraction (XRD), uniaxial tensile testing, in vitro biodegradation, and through in vitro drug release and cytotoxicity studies. It was observed that the addition of GlcNAc did not alter the morphology of the filaments. The CS and CS/GlcNAc filaments presented diameters 145 µm and 148 µm, respectively, and the surfaces were homogeneous. Although the mechanical resistance of the chitosan filaments decreased with the incorporation of the GlcNAc drug, this property was greater than the mean values indicated in the U.S. Pharmacopeia (1.7 N) for suture number 6-0 (filament diameter of 100–149 μm). The biodegradation of the CS filaments was accelerated by the addition of GlcNAc. After 35 days, the CS/GlcNAc filaments degradability was at its total, and for the CS filaments it was acquired in 49 days. The in vitro kinetic of the release process was of the zero-order and Hopfenberg models, controlled by both diffusion and erosion process. The in vitro cytotoxicity data of the CS and CS/GlcNAc filaments toward L929 cells showed that these filaments are nontoxic to these cells. Thus, the GlcNAc-loaded CS filaments might be promising as absorbable suture materials. In addition, this medical device may be able to enhance healing processes, relieve pain, and minimize infection at the surgery site due the prolonged release of GlcNAc.