X-ray diffraction, vibrational and thermal study of dibenzazepinodione, a pharmacopeial impurity of oxcarbazepine

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dc.creatorFaudone, Sonia Nerina
dc.creatorPaschoa, Alexandre Rocha
dc.creatorCarvalho Júnior, Paulo de Sousa
dc.creatorAlcides Ellena, Javier
dc.creatorMartins, Felipe Terra
dc.creatorCuffini, Silvia Lucia
dc.creatorPedro Ayal, Alejandro
dc.creatorSperandeo, Norma Rebeca
dc.date.accessioned2023-11-24T11:19:11Z
dc.date.available2023-11-24T11:19:11Z
dc.date.issued2019
dc.description.abstractThe antiepileptic drug oxcarbazepine (OXC) was crystallized from various organic solvents, and mixtures of OXC crystals and red-orange particles were obtained. In view of the pharmaceutical relevance of OXC, this study focuses on the isolation and characterization of these red-orange crystals by structural [single crystal (SCXRD), powder X-ray diffraction (PXRD) and Hirshfeld surface analysis], vibrational [Fourier transform infrared (FT-IR), Fourier transform Raman (FT-Raman) and Density functional theory (DFT) calculations], and thermal methods of analysis [simultaneous thermogravimetry-differential thermal analysis (TG-DTA) and hot stage microscopy (HSM)]. According to SCXRD, the red-orange crystals corresponded to a recently codified impurity of OXC, referred as dibenzazepinodione (DBZ) or impurity D in the United States and European Pharmacopoeias respectively, which crystallized in the orthorhombic Pccn space group with a half-molecule in the asymmetric unit. Hirshfeld surface analysis revealed that weak intermolecular contacts played an important role in the stabilization of DBZ packing. DBZ was also characterized through its mid-infrared and Raman spectra and its vibrational bands were assigned based on DFT calculations with the hybrid B3LYP functional, coupled with the 6-311++g (d,p) basis set. The TG-DTA and HSM results shed light on the behaviour upon heating of DBZ, revealing that this impurity is an unsolvated solid with high thermal-oxidative stability, which sublimed, melted locally and decomposed above 320 °C. The obtained results demonstrated that slow crystallization of OXC from solvents such as ethanol and dimethylsulfoxide, at 20-25 °C, in the presence or absence of ambient light afforded DBZ. The X-ray pattern based on the SCXRD data for DBZ is presented as reliable reference for its identification.
dc.identifier.citationFAUDONE, Sonia N. et. al. X-ray diffraction, vibrational and thermal study of dibenzazepinodione, a pharmacopeial impurity of oxcarbazepine. Journal of Molecular Structure, Amsterdam, v. 1182, p. 204-212, 2019. DOI: 10.1016/j.molstruc.2019.01.032. Disponível em: https://www.sciencedirect.com/science/article/abs/pii/S0022286019300389?via%3Dihub. Acesso em: 20 nov. 2023.
dc.identifier.doi10.1016/j.molstruc.2019.01.032
dc.identifier.issne- 1872-8014
dc.identifier.issn0022-2860
dc.identifier.urihttps://www.sciencedirect.com/science/article/abs/pii/S0022286019300389?via%3Dihub
dc.language.isoeng
dc.publisher.countryHolanda
dc.publisher.departmentInstituto de Química - IQ (RMG)
dc.rightsAcesso Restrito
dc.titleX-ray diffraction, vibrational and thermal study of dibenzazepinodione, a pharmacopeial impurity of oxcarbazepine
dc.typeArtigo

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