Vibrational spectroscopic and Hirshfeld surface analysis of carvedilol crystal forms

被引:13
|
作者
Prado, Livia D. [1 ,2 ]
Santos, Alexandre B. X. [2 ]
Rocha, Helvecio V. A. [2 ]
Ferreira, Glaucio B. [1 ]
Resende, Jackson A. L. C. [1 ,3 ]
机构
[1] Univ Fed Fluminense, Programa Posgrad Quim, Outeiro Sao Joao Batista S-N, BR-24210130 Niteroi, RJ, Brazil
[2] Farmanguinhos Fiocruz, Lab Micro & Nanotecnol, Av Brasil 4036, BR-21040361 Rio De Janeiro, Brazil
[3] Univ Fed Mato Grosso, Inst Ciencias Exatas & Terra, Av Valdon Varjao 3690, BR-78600000 Barra Do Garcas, Mato Grosso, Brazil
关键词
Carvedilol; Polymorphism; Infrared spectroscopy; DFT; Hirshfeld surface; RAMAN-SPECTROSCOPY; SOLID FORMS; POLYMORPHS; SPECTRA; STATE; IR;
D O I
10.1016/j.ijpharm.2018.10.051
中图分类号
R9 [药学];
学科分类号
1007 ;
摘要
The drug carvedilol, used to treat cardiovascular conditions, is known to exist in distinct crystalline forms. Polymorphs II and III and the hydrate are characterized by variations in their molecular packing and conformation. This study deals with the spectroscopic (supported by quantum chemistry calculations) characterization of carvedilol structures. Band assignments were performed considering the isolated molecules and periodic calculations. We discuss the correlation between the vibrational modes and the intermolecular forces in the crystalline structures. Towards a better understanding of the intermolecular interactions, Hirshfeld surface was used. Besides band shifts related to stretching vibrations of N-H and O-H groups, differences between other modes have shown the possibility of using infrared spectroscopy to distinguish the crystal forms; technique routinely used in quality control of pharmaceutics. According to the spectroscopic analysis, the N-H groups participate in stronger bonds in the polymorph III, which contributes to its greater stability. With Hirshfeld surface we concluded that the bond with the nitrogen of the aliphatic chain participating as hydrogen acceptor in polymorph II is responsible for the pointy peaks in the fingerprint plot. This can explain why polymorph II shows lower dissolution in acid medium, as described in a previous work of our group.
引用
收藏
页码:261 / 271
页数:11
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