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Generally, NSAIDs are weakly soluble in water and contain both hydrophilic and hydrophobic groups. One of the most widely used NSAIDs is ibuprofen, which has a poor solubility and high permeability profile. By creating dynamic, non-covalent, water-soluble inclusion complexes, cyclodextrins (CDs) can increase the dissolution rate of low aqueous solubility drugs, operating as a drug delivery vehicle, additionally contributing significantly to the chemical stability of pharmaceuticals and to reducing drug-related irritability. In order to improve the pharmacological and pharmacokinetics profile of ibuprofen, new thiazolidin-4-one derivatives of ibuprofen (<b>4b</b>, <b>4g</b>, <b>4k</b>, <b>4m</b>) were complexed with <b>β-CD</b>, using co-precipitation and freeze-drying. The new <b>β-CD</b> complexes (<b>β-CD-4b</b>, <b>β-CD-4g</b>, <b>β-CD-4k</b>, <b>β-CD-4m</b>) were characterized using scanning electronic microscopy (SEM), differential scanning calorimetry (DSC), X-ray diffraction and a phase solubility test. Using the AutoDock-VINA algorithm included in YASARA-structure software, we investigated the binding conformation of ibuprofen derivatives to <b>β-CD</b> and measured the binding energies. We also performed an in vivo biological evaluation of the ibuprofen derivatives and corresponding <b>β-CD</b> complexes, using analgesic/anti-inflammatory assays, as well as a release profile. The results support the theory that <b>β-CD</b> complexes (<b>β-CD-4b</b>, <b>β-CD-4g</b>, <b>β-CD-4k</b>, <b>β-CD-4m</b>) have a similar effect to ibuprofen derivatives (<b>4b</b>, <b>4g</b>, <b>4k</b>, <b>4m</b>). Moreover, the <b>β-CD</b> complexes demonstrated a delayed release profile, which provides valuable insights into the drug-delivery area, focused on ibuprofen derivatives.