Issue 28, 2022

Combined computational/experimental investigation of new cocrystals of the drug bosentan

Abstract

We report the discovery of new cocrystals of bosentan, a drug used in the treatment of pulmonary artery hypertension, with succinic acid, resorcinol, and 4-hydroxybenzoic acid through a combined virtual/experimental cocrystal screening. The X-ray structure of the bosentan/succinic acid cocrystal shows a network of H-bonds involving both components, which have been studied energetically using DFT calculations. The succinic acid molecules interact with one of the pyrazine rings of bosentan establishing an energetically significant lp⋯π interaction. Moreover, they form homodimers stabilized by antiparallel CO⋯CO interactions. This set of interactions has been rationalized using molecular electrostatic potential (MEP) surfaces, the quantum theory of “atoms-in-molecules” (QTAIM), and the noncovalent interaction plot (NCIplot).

Graphical abstract: Combined computational/experimental investigation of new cocrystals of the drug bosentan

Supplementary files

Article information

Article type
Paper
Submitted
26 Apr 2022
Accepted
12 Jun 2022
First published
13 Jun 2022

CrystEngComm, 2022,24, 5105-5111

Combined computational/experimental investigation of new cocrystals of the drug bosentan

R. Barbas, A. Portell, C. A. Hunter, R. Prohens and A. Frontera, CrystEngComm, 2022, 24, 5105 DOI: 10.1039/D2CE00581F

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