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The nonsteroidal anti-inflammatory drugs flurbiprofen and ibuprofen were modified in an attempt to alter the kinetics of inhibitor binding by COX-1. Contrary to prior predictions, a halogen substituent is not sufficient to confer slow tight-binding behavior. Conversion of the carboxylate moiety of flurbiprofen to an ester or amide abolishes slow tight-binding behavior, regardless of halogenation state.


Kushol Gupta, Carl J Kaub, Kristen N Carey, Eduard G Casillas, Barry S Selinsky, Patrick J Loll. Manipulation of kinetic profiles in 2-aryl propionic acid cyclooxygenase inhibitors. Bioorganic & medicinal chemistry letters. 2004 Feb 9;14(3):667-71

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PMID: 14741265

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