Objective: The synthesis, characterization, 15-LOX inhibition and molecular docking studies of a commercially available NSAID, flurbiprofen and its derivatives. Study Design: Experimental study. Place and Duration of Study: The study was carried out at Quaid-i-Azam University and Centre for Advanced Drug Research COMSATS University Islamabad, Abottabad Campus from March 2019 to February 2020. Materials and Methods: The structural elucidation of the compounds (2-5) was carried out using infrared, 1H and 13C NMR spectroscopic studies. The structure of 4-amino-5-(1-(2-fluorobiphenyl-4-yl)-ethyl)-4H-1,2,4triazole-3-thione (5) was also verified by single crystal X-ray diffraction (XRD) studies. Results: The most potent inhibitor for 15-LOX (2) has an IC50value of0.18 ± 0.01 µM. Molecular docking results of 1, 2, 3 and cognate ligand inside the active site of 15-LOX (PDB ID: 1IK3) revealed significant correlation. Conclusion: This work represents cost-effective, reproducible and facile conversion of an aromatic monocarboxylic acid into potent derivatives.The molecules 2-(2-fluorobiphenyl-4-yl) propanoic acid (1) and its derivatives (2-5) possess 15-LOX inhibition and can be a prospective therapeutic target for chronic obstructive pulmonary disease.