Comparative Theoretical Study of Stability, Lypophilicity, Dipole Moments, Acidity and Spectroscopic Properties of Non-Steroidal Anti-Inflammatory Drugs: Ibuprofen, Ketoprofen and Flurbiprofen
Assoma Amon Benjamine *
Laboratoire de Constitution et Réaction de la Matière, UFR SSMT, Université Felix Houphouët-Boigny, 22 BP 582 Abidjan 22, Côte d’Ivoire.
Atse Adepo Jacques
Laboratoire de Constitution et Réaction de la Matière, UFR SSMT, Université Felix Houphouët-Boigny, 22 BP 582 Abidjan 22, Côte d’Ivoire.
Kone Soleymane
Laboratoire de Constitution et Réaction de la Matière, UFR SSMT, Université Felix Houphouët-Boigny, 22 BP 582 Abidjan 22, Côte d’Ivoire.
Bamba El Hadji Sawaliho
Laboratoire de Constitution et Réaction de la Matière, UFR SSMT, Université Felix Houphouët-Boigny, 22 BP 582 Abidjan 22, Côte d’Ivoire.
*Author to whom correspondence should be addressed.
Abstract
A comparative theoretical study of some physicochemical properties of R and S enantiomers of ibuprofen, ketoprofen and flurbiprofen is undertaken in order to understand their reactivity. To do this, DFT and TD-DFT methods at the B3LYP/6-311G(d,p) level theory are used. The partition coefficient determined is 3.72 for ibuprofen, 2.81 for ketoprofen and 4.12. for flurbiprofen. That means that these NSAIDs are characterized by a high lipophilicity. The calculated Gibbs energies show that the R enantiomer is the most stable in the case of ibuprofen and the S enantiomer in the case of ketoprofen and flurbiprofen. The study of acidity shows that S enantiomer of ibuprofen and R enantiomers of ketoprofen and flurbiprofen are the most acidic enantiomers. TD-DFT calculations show that, the absorption maxima (λmax) of ibuprofen and flurbiprofen correspond to the HOMO→LUMO transition. For ketoprofen, these are associated with the transition HOMO→LUMO+1. These results elucidate the reactivity of the investigated NSAIDs and could help to establish a classification their efficacy.
Keywords: Ibuprofen, ketoprofen, flurbiprofen, acidity, B3LYP.