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Master's Dissertation
DOI
10.11606/D.9.2008.tde-04022009-195023
Document
Author
Full name
Ricardo Leite de Oliveira Rezende
E-mail
Institute/School/College
Knowledge Area
Date of Defense
Published
São Paulo, 2008
Supervisor
Committee
Santoro, Maria Inês Rocha Miritello (President)
Matos, Jivaldo do Rosário
Volpato, Nadia Maria
Title in Portuguese
Separação dos enatiômeros do cetoprofeno e do fenoprofeno por CLAE em fase estacionária quiral
Keywords in Portuguese
Cromatografia a líquido de alta eficiência (análise química)
Fármacos (controle da qualidade)
Medicamento (controle da qualidade)
Abstract in Portuguese
Durante muito tempo, os fármacos quirais de origem sintética foram comercializados predominantemente como racematos. Atualmente, sabe-se que os enantiômeros de um fármaco quiral podem apresentar propriedades farmacocinéticas, farmacodinâmicas e toxicológicas bastante distintas. Assim sendo, técnicas analíticas enantiosseletivas são fundamentais para a pesquisa e para o controle da qualidade desses fármacos. O cetoprofeno e o fenoprofeno são dois fármacos quirais, pertencentes à classe dos agentes antiinflamatórios não-esteróides derivados do ácido propiônico. Seus enantiômeros apresentam significativas diferenças farmacodinâmicas. Por essa razão, pretendeu-se desenvolver, no presente trabalho, métodos de separação enantiomérica para ambos os fármacos. Para tanto, utilizou-se a técnica de cromatografia a líquido de alta eficiência em fase estacionária quiral (coluna Whelk-O 1), nos modos normal e reverso. Abordagens uni- e multivariadas foram utilizadas para desenvolver e otimizar os métodos de separação. Pôde-se observar que a enantiosseletividade exibida pela coluna Whelk-O 1 em fase normal é superior àquela exibida em fase reversa. Empregando a CLAE em fase normal, foi possível desenvolver métodos de separação apropriados para os enantiômeros de ambos os fármacos. Em fase reversa, no entanto, apenas os enantiômeros do fenoprofeno puderam ser separados satisfatoriamente.
Title in English
Separation of ketoprofen and fenoprofen enantiomers by HPLC using chiral stationary phase
Keywords in English
Drug (quality control)
Drug product (quality control)
High-performance liquid chromatography (chemical analysis)
Abstract in English
For a long time, the synthetic chiral drugs were marketed mainly as racemates. Currently, it is known that enantiomers of chiral drugs may exhibit quite different pharmacokinetic, pharmacodynamic and toxicological properties. Therefore, enantioselective analytical techniques are critical to the research and quality control of these drugs. Ketoprofen and fenoprofen are two chiral drugs, belonging to the class of propionic acid-derived nonsteroidal anti-inflammatory agents. Their enantiomers show significant pharmacodynamic differences. For that reason, we aimed to develop, in this work, separation methods for the enantiomers of both drugs. In order to do so, it was used the high-performance liquid chromatography technique and the Whelk-O 1 column as the chiral stationary phase, under normal- and reversed-phase modes. Uni- and multivariate approaches were used to develop and optimize the separation methods. It was noted that the enantioselectivity exhibited by the Whelk-O 1 column under normal-phase mode is higher than that exhibited under reversed-phase mode. Under normal-phase mode, it was possible to achieve an appropriate separation for the enantiomers of both drugs. Under reversed-phase mode, however, only the enantiomers of fenoprofen could be successfully separated.
 
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RezendeRLO.pdf (6.36 Mbytes)
Publishing Date
2009-02-11
 
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