Caracterização e estudo do comportamento térmico dos adutos flunixina-meglumina e diclofenaco-meglumina
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Data
2010-06-28
Autores
Cassimiro, Douglas Lopes [UNESP]
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Universidade Estadual Paulista (Unesp)
Resumo
Aduto (do latin Adductus, “atraidos”) é o produto de uma adição direta de duas ou mais moléculas distintas, resultando em um produto de reação simples contendo todos os átomos de todos os componentes, com formação de duas ligações químicas e uma redução na multiplicidade da ligação em pelo menos um dos reagentes. Assim, aduto é uma nova espécie química resultante da união direta de moléculas individuais. A meglumina é um carboidrato que se caracteriza pela sua habilidade em formar adutos altamente solúveis em meio aquoso com ácidos carboxílicos. A indústria farmacêutica foi pioneira em explorar essa propriedade, aplicando-a no aperfeiçoamento de medicamentos já existentes. Diante desse contexto, os ácidos carboxílicos envolvidos na formação de adutos com a meglumina apresentam propriedades farmacológicas, mais especificadamente, pertencem à classe dos anti-inflamatórios não esteroidais (AINEs). Com relação à elucidação estrutural dessas espécies, um único trabalho é descrito na literatura o qual contempla o arranjo cristalino da flunixina-meglumina, primeiro aduto dessa classe a ser comercializado. Neste trabalho a flunixina-meglumina e o diclofenaco-meglumina, este último preparado como proposta do estudo, foram caracterizados a partir das técnicas Espectroscopia de Absorção na Região do Infravermelho (IV) e Ressonância Magnética Nuclear (RMN). O comportamento térmico da flunixina-meglumina e do diclofenaco-meglumina no estado sólido foi avaliado mediante as técnicas termoanalíticas Termogravimetria e Termogravimetria Derivada (TG/DTG); Termogravimetria e Análise Térmica Diferencial Simultânea (TG-DTA) e Calorimetria Exploratória Diferencial (DSC). Foi evidenciado que após a temperatura de fusão das respectivas amostras cristalinas, ocorre a formação de um material com comportamento polimérico sugerindo que os adutos...
An adduct (from the Latin adductus, drawn toward) is a product of a direct addition of two or more distinct molecules, resulting in a single reaction product containing all atoms of all components, with formation of two chemical bonds and a net reduction in bond multiplicity in at least one of the reactants.Thus, an adduct is a new chemical specie that results from the direct union of individual molecules. Meglumine is a carbohidrate characterized by its capability to form soluble adducts in aquous solutions with carboxilic acids. Pharmaceuticals industry was the first to explore this property, with application to enhance drugs that already exists. In this context, carboxylic acids related to adducts formation with meglumine present pharmacological properties and are included in the class of nonsteroidal anti-inflamatory drugs (NSAIDs). Actually, it is not well understood the structural and chemical characteristics about adducts formed by association of meglumine and carboxylic acids. Only one work in the literature describes the cristaline sctructure formed by flunixin-meglumine adducts, the first compound in this class to go to market. In this work, two adducts (flunixin-meglumine and diclofenac-meglumine) were characterized by Infrared Absortion Spectroscopy (IR) and Nuclear Magnetic Resonance (NMR). Results sugest that the adduct formation of carboxylic acid-meglumine occurs by deprotonation of carboxylic acid and protonation of meglumine. Both adducts in solid state studied in this work were analyzed by Thermogravimetry – Differential Thermal Analysis (TG-DTA) and Differential Scanning Calorimetry (DSC). The results for DSC curves presented two cristaline forms for both adducts. Besides, it was noted that after the melting temperature of the respectives cristalines compounds, they present an self-assembly process wich leads to supramolecular polymers... (Complete abstract click electronic access below)
An adduct (from the Latin adductus, drawn toward) is a product of a direct addition of two or more distinct molecules, resulting in a single reaction product containing all atoms of all components, with formation of two chemical bonds and a net reduction in bond multiplicity in at least one of the reactants.Thus, an adduct is a new chemical specie that results from the direct union of individual molecules. Meglumine is a carbohidrate characterized by its capability to form soluble adducts in aquous solutions with carboxilic acids. Pharmaceuticals industry was the first to explore this property, with application to enhance drugs that already exists. In this context, carboxylic acids related to adducts formation with meglumine present pharmacological properties and are included in the class of nonsteroidal anti-inflamatory drugs (NSAIDs). Actually, it is not well understood the structural and chemical characteristics about adducts formed by association of meglumine and carboxylic acids. Only one work in the literature describes the cristaline sctructure formed by flunixin-meglumine adducts, the first compound in this class to go to market. In this work, two adducts (flunixin-meglumine and diclofenac-meglumine) were characterized by Infrared Absortion Spectroscopy (IR) and Nuclear Magnetic Resonance (NMR). Results sugest that the adduct formation of carboxylic acid-meglumine occurs by deprotonation of carboxylic acid and protonation of meglumine. Both adducts in solid state studied in this work were analyzed by Thermogravimetry – Differential Thermal Analysis (TG-DTA) and Differential Scanning Calorimetry (DSC). The results for DSC curves presented two cristaline forms for both adducts. Besides, it was noted that after the melting temperature of the respectives cristalines compounds, they present an self-assembly process wich leads to supramolecular polymers... (Complete abstract click electronic access below)
Descrição
Palavras-chave
Quimica analitica, Analise termica, Estruturas supramoleculares, Thermal analysis
Como citar
CASSIMIRO, Douglas Lopes. Caracterização e estudo do comportamento térmico dos adutos flunixina-meglumina e diclofenaco-meglumina. 2010. 136 f. Dissertação (mestrado) - Universidade Estadual Paulista, Instituto de Química, 2010.