Structural Insights and Supramolecular Description of Gliclazide and its Impurity F

29 Pages Posted: 21 Mar 2022

See all articles by Marden Santos

Marden Santos

affiliation not provided to SSRN

Igor Borges

affiliation not provided to SSRN

Lauriane Santin

affiliation not provided to SSRN

Solemar Oliveira

affiliation not provided to SSRN

Lucimar Rosseto

affiliation not provided to SSRN

Loide Sallum

Universidade Evangélica de Goiás

Ademir Camargo

State University of Goias

James Fajemiroye

Federal University of Goias

Pal Perjesi

University of Pécs - Institute of Pharmaceutical Chemistry

Hamilton Napolitano

State University of Goias

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

Suggested Citation

Santos, Marden and Borges, Igor and Santin, Lauriane and Oliveira, Solemar and Rosseto, Lucimar and Sallum, Loide and Camargo, Ademir and Fajemiroye, James and Perjesi, Pal and Napolitano, Hamilton, Structural Insights and Supramolecular Description of Gliclazide and its Impurity F. Available at SSRN: https://ssrn.com/abstract=4030339 or http://dx.doi.org/10.2139/ssrn.4030339

Marden Santos

affiliation not provided to SSRN ( email )

No Address Available

Igor Borges

affiliation not provided to SSRN ( email )

No Address Available

Lauriane Santin

affiliation not provided to SSRN ( email )

No Address Available

Solemar Oliveira

affiliation not provided to SSRN ( email )

No Address Available

Lucimar Rosseto

affiliation not provided to SSRN ( email )

No Address Available

Loide Sallum

Universidade Evangélica de Goiás ( email )

Ademir Camargo

State University of Goias ( email )

James Fajemiroye

Federal University of Goias ( email )

Pal Perjesi

University of Pécs - Institute of Pharmaceutical Chemistry ( email )

Hungary

Hamilton Napolitano (Contact Author)

State University of Goias ( email )

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