An Electronic Study for Metronidazole Metabolism

Abstract

The metronidazole metabolism has been explained by a mechanism involving single electron transfer using quantum chemistry calculations at the B3LYP theory level, together with the 6-31 + G(d, p) basis set. These methods were employed to obtain energy (E), ionization potential (IP), spin-density distribution, and LUMO and MEPs of the metronidazole. Our results using DFT/B3LYP/6-31+G(d, p) calculations show the ionization potential and spin densities of metronidazole can be used in oxidation or reduction prediction of its metabolism. The positive charge radical is stabilized by resonance. These properties were observed by spin density distribution. The bond dissociation energy is related with hydrogen abstraction and a possible hydroxylation via cytochrome P-450. An increase of spin distributions on C 7 < C 9 < C 8 < O 10 positions explain the azol ring participation in the stabilization.

Modeling the scavenging activity of ellagic acid and its methyl derivatives towards hydroxyl, methoxy, and nitrogen dioxide radicals

“…The atomic numbering scheme employed in the present work is shown in this figure. As the B3LYP functional is generally rated somewhat better than the B3PW91 functional [62][63][64], we considered the results obtained at the B3LYP/AUG-cc-pVDZ level to be more reliable than those obtained at the B3PW91/AUG-cc-pVDZ level in aqueous media. 1b, c, and d, respectively.…”