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First in-depth structural characterization of sulodexide by NMR, LC–MS, HP-SEC/TDA.Identification and quantification of sulodexide components, heparin and dermatan sulfate.Antithrombin affinity chromatography of sulodexide, 4 fractions isolated.Structural features of isolated heparin and dermatan sulfate components.Oligosaccharide profiling of components by heparinase digestion and LC_MS analysis.Sulodexide is a heparinoid which combines the properties of its components heparin and dermatan sulfate and is used not only for the prophylaxis and treatment of thromboembolic diseases but also for the treatment of diabetic nephropathy. Despite many clinical studies have been conducted to investigate its activity and safety, no data are available on the fine chemical characterization of its components. In this work, the in-depth investigation on the structural features of both the whole mixture and the isolated components was accomplished, involving the analysis of molecular weight distribution and of their mono, di and oligosaccharide composition by HP-SEC/TDA, 2D-NMR and HPLC–MS techniques. Moreover, also the separation of fractions endowed of graded affinity to antithrombin was achieved followed again by detailed structural analysis. The combination of different techniques permits to profile in depth the structural features of such a drug and offers a useful tool for possible analysis of batch production.