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Theoretical studies on nonsteroidal anti inflammatory drugs. Benoxaprofen, chlorpromazine, and piroxicam
Author(s) -
De Alencastro Ricardo Bicca,
Da Motta Neto Mjoaquim Delphino
Publication year - 1995
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.560560713
Subject(s) - piroxicam , nonsteroidal , chemistry , phototoxicity , chlorpromazine , tautomer , metabolite , quantum chemical , pharmacology , computational chemistry , stereochemistry , molecule , organic chemistry , biochemistry , medicine , alternative medicine , pathology , in vitro
We report quantum chemical semi‐empirical calculations of the geometries and the electronic structures (at AM1 and INDO /s levels) of three nonsteroidal antiinflammatory drugs ( NSAIDs ), namely, benoxaprofen, chlorpromazine and piroxicam, and a piroxicam metabolite, that have undesirable phototoxic effects. Our calculated electronic spectra in gas phase and in water fit reasonably well the observed spectral data. The wavelength of the absorption maxima are not significantly affected by changing from gas phase to water (at the SCRF level). We were able to assign the observed bands to the calculated transitions. We found also that the spectrum of the piroxicam metabolite actually responsible for the phototoxicity cannot be understood on the sole basis of one of the tautomers. We hope that these finding will be useful for the understanding of the photochemical events that lead ultimately to the biological effects. © 1995 John Wiley & Sons, Inc.