Structural Insights and Supramolecular Description of Gliclazide and its Impurity F
29 Pages Posted: 21 Mar 2022
Abstract
Gliclazide (GCZ) is an oral hyperglycemic antidiabetic drug of Biopharmaceutics Classification System Class II with low aqueous solubility and high permeability as mentioned in the WHO Model Lists of Essential Medicines. Gliclazide Impurity F (GCZ-IF), a specified impurity of gliclazide, is listed in the European Pharmacopoeia. The present study analyzed molecular conformation, supramolecular arrangement by Hirshfeld surface, and quantum theory calculations of atoms in the molecules to understand the physicochemical properties caused by the structural difference of the two compounds. Also, theoretical calculations were carried out by the density functional theory at the M062x/6-311++G** level to GCZ and GCZ-IF on the gas phase. The geometric properties were compared to experimental data. The frontier molecular orbitals (HOMO and LUMO) and the MEP maps indicate the electron density, electronic transition energies, and hydrogen bond donor capacities of both molecular systems, helpful to describe GCZ stability in pharmaceutical formulations.
Keywords: Gliclazide, Molecular modeling, M062x/6-311++G**, DFT, QTAIM
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