Conformational polymorphism of the antidiabetic drug chlorpropamide


Autoria(s): Ayala, A. P.; Caetano, M. W. C.; Honorato, S. B.; Mendes Filho, J.; Siesler, H. W.; Faudone, S. N.; Cuffini, S. L.; Martins, F. T.; da Silva, C. C. P.; Ellena, Javier
Contribuinte(s)

UNIVERSIDADE DE SÃO PAULO

Data(s)

23/08/2013

23/08/2013

2012

Resumo

In this paper, the main features of Raman spectroscopy, one of the first choice methods in the study of polymorphism in pharmaceuticals, are presented taking chlorpropamide as a case of study. The antidiabetic drug chlorpropamide (1-[4-chlorobenzenesulphonyl]-3-propyl urea), which belongs to the sulfonylurea class, is known to exhibit, at least, six polymorphic phases. These forms are characterized not only by variations in their molecular packing but also in their molecular conformation. In this study, the polymorphism of chlorpropamide is discussed on the basis of Raman scattering measurements and quantum mechanical calculations. The main spectroscopic features that fingerprint the crystalline forms are correlated with the corresponding crystalline structures. Using a theoretical approach on the energy dependence of the conformers, simulated molecular torsion angles are plotted versus the formation energy, which provides a satisfactory agreement between the torsion angles at the energy minima and the experimental values observed in the different solid forms of chlorpropamide. Copyright (C) 2011 John Wiley & Sons, Ltd.

CNPqProsul

CNPq-Prosul

FUNCAP

FUNCAP

CAPES

CAPES

FAPESP

FAPESP

CONICET

CONICET

Ministerio de Ciencia y Tecnologia (Argentina)

Ministerio de Ciencia y Tecnologia (Argentina)

Fundacion Sauberan

Fundacion Sauberan

Agencia Cordoba Ciencia

Agencia Cordoba Ciencia

CNPq

CNPq

CAPES-PNPD

CAPES PNPD

Identificador

JOURNAL OF RAMAN SPECTROSCOPY, MALDEN, v. 43, n. 2, supl. 4, Part 1, pp. 263-272, FEB, 2012

0377-0486

http://www.producao.usp.br/handle/BDPI/32697

10.1002/jrs.3012

http://dx.doi.org/10.1002/jrs.3012

Idioma(s)

eng

Publicador

WILEY-BLACKWELL

MALDEN

Relação

JOURNAL OF RAMAN SPECTROSCOPY

Direitos

restrictedAccess

Copyright WILEY-BLACKWELL

Palavras-Chave #CHLORPROPAMIDE #POLYMORPHISM #RAMAN SPECTROSCOPY #DFT #PHARMACEUTICAL SOLID POLYMORPHISM #RAMAN-SPECTROSCOPY #VIBRATIONAL SPECTROSCOPY #COMPRESSION #STATE #TEMPERATURE #SPECTRA #TRANSFORMATION #DENSITY #ENERGY #SPECTROSCOPY
Tipo

article

original article

publishedVersion