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NSAID Prodrugs with Improved Anti-inflammatory Activity and Low Ulcerogenicity: Wake Up Call to Pharmaceutical Companies and Health Authorities Open Access


Other title
Nitric Oxide
gastric toxicity
Type of item
Degree grantor
University of Alberta
Author or creator
Jain, Sarthak
Supervisor and department
Carlos A Velázquez (Faculty of Pharmacy and Pharmaceutical Sciences)
Examining committee member and department
Glen B. Baker (Department of Psychiatry)
Kamaljit Kaur (Faculty of Pharmacy and Pharmaceutical Sciences)
Faculty of Pharmacy and Pharmaceutical Sciences

Date accepted
Graduation date
Master of Science
Degree level
The objective of this work was to synthesize and evaluate the biological properties of a new series of nitric oxide-releasing non-steroidal anti-inflammatory drugs (NO-NSAIDs) possessing a tyrosol linker between the carboxylic acid present in classical NSAIDs and a NO-releasing group (PROLI/NO) derived from the naturally occurring amino acid L-proline; however, initial screening of ester intermediates without the PROLI/NO group showed the desired efficacy/safety ratio. The NSAID prodrugs were potent selective COX-2 inhibitors and showed equipotent anti-inflammatory activity compared to the corresponding parent NSAIDs, but showed a markedly reduced gastric toxicity. Furthermore, simple NSAID ester prodrugs were able to increase the activity of phase II carcinogen-metabolizing enzymes (NQO1); however, unlike NCX-4016 (NO-aspirin), NSAID esters were not effective inhibitors of platelet aggregation. These results provide complementary evidence to assume that the use of NO-releasing groups in hybrid NSAID prodrugs is not required to decrease the ulcerogenic profile of classical NSAIDs.
Permission is hereby granted to the University of Alberta Libraries to reproduce single copies of this thesis and to lend or sell such copies for private, scholarly or scientific research purposes only. Where the thesis is converted to, or otherwise made available in digital form, the University of Alberta will advise potential users of the thesis of these terms. The author reserves all other publication and other rights in association with the copyright in the thesis and, except as herein before provided, neither the thesis nor any substantial portion thereof may be printed or otherwise reproduced in any material form whatsoever without the author's prior written permission.
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