Mefenamic Acid Anti-Inflammatory Drug: Probing Its Polymorphs by Vibrational (IR and Raman) and Solid-State NMR Spectroscopies

Autor(es)

Cunha, Vanessa R. R. ^[1] ; Izumi, Celly M. S. ^[1] ; Petersen, Philippe A. D. ^[2] ; Magalhaes, Alvicler ^[3] ; Temperini, Marcia L. A. ^[1] ; Petrilli, Helena M. ^[2] ; Constantino, Vera R. L. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Sao Paulo, Inst Quim, Dept Quim Fundamental, BR-05508000 Sao Paulo - Brazil

^[2] Univ Sao Paulo, Inst Fis, Dept Fis Mat & Mecan, BR-05315970 Sao Paulo - Brazil

^[3] Univ Estadual Campinas, Inst Quim, Dept Quim Inorgan, BR-13083970 Campinas, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Journal of Physical Chemistry B; v. 118, n. 16, p. 4333-4344, APR 24 2014.
• Citações Web of Science: 17

Resumo

This work deals with the spectroscopic (supported by quantum chemistry calculations), structural, and morphological characterization of mefenamic acid (2-{[}(2,3-(dimethylphenyl)amino] benzoic acid) polymorphs, known as forms I and II. Polymorph I was obtained by recrystallization in ethanol, while form II was reached by heating form I up to 175 degrees C, to promote the solid phase transition. Experimental and theoretical vibrational band assignments were performed considering the presence of centrosymmetric dimers. Besides band shifts in the 3345-3310 cm(-1) range, important vibrational modes to distinguish the polymorphs are related to out-of-phase and in-phase N-H bending at 1582 (Raman)/1577 (IR) cm(-1) and 1575 (Raman)/1568 (IR) cm(-1) for forms I and II, respectively. In IR spectra, bands assigned to N-H bending out of plane are observed at 626 and 575 cm(-1) for polymorphs I and II, respectively. Solid-state C-13 NMR spectra pointed out distinct chemical shifts for the dimethylphenyl group: 135.8 to 127.6 ppm (carbon bonded to N) and 139.4 to 143.3 ppm (carbon bonded to methyl group) for forms I and II, respectively. (AU)

• Processo FAPESP: 11/50318-1 - Desenvolvimento de compostos com interesse farmacológico ou medicinal e de sistemas para seu transporte, detecção e reconhecimento no meio biológico
• Beneficiário: Ana Maria da Costa Ferreira
• Modalidade de apoio: Auxílio à Pesquisa - Temático
• Processo FAPESP: 12/12209-9 - Carregadores inorgânicos de substâncias bioativas: desenvolvimento, caracterização, estudos de toxicidade, de liberação in vitro e de absorção in vivo após administração oral
• Beneficiário: Vanessa Roberta Rodrigues da Cunha
• Modalidade de apoio: Bolsas no Brasil - Pós-Doutorado