Thermal behavior of naproxen and ketoprofen nonsteroidal anti-inflammatory drugs

Abstract

Nonsteroidal anti-inflammatory drugs naproxen (NAP) ((+)-(S)-2-(6-methoxynaphthalen-2-yl) propionic acid) and ketoprofen (KET) (RS)-(2-(3-benzoylphenyl)-propionic acid) were investigated by thermoanalytical techniques (TG/DTG/DTA, DSC and hot-stage microscopy) and evolved gas analysis (TG-FTIR) for evaluating their thermal behavior. In air, TG curve of NAP presented one mass loss step followed by the burning of carbonaceous material, with final residue of 1.5%, while in nitrogen, a single mass loss step was observed. After melting, if the sample is submitted to an isotherm it evaporates. According to DSC curve, NAP melts at 153.5 °C (∆Hfus = 31.6 kJ mol−1; ∆Sfus = 73.5 J K−1 mol−1) and recrystallizes in the cooling step. These events were confirmed by hot-stage microscopy. TG-FTIR studies revealed that NAP decomposes by releasing 2-methoxynaphthalene and propionic acid. Ketoprofen TG curves in both atmospheres presented a single mass loss. When the sample was kept under isotherm, after melting, it evaporated. From DSC data, the melting at 93.3 °C (∆Hfus=28.4 kJ mol−1, ∆Sfus = 76.9 J K−1 mol−1) was observed, without crystallization or cooling.

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Acknowledgements

The authors thank FAPESP (Fundação de Amparo à Pesquisa do Estado de São Paulo, Grant No. 2017/04211-7) and CNPq (Conselho Nacional de Desenvolvimento Científico e Tecnológico) for financial support.

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Medeiros, R.S., Ferreira, A.P.G. & Cavalheiro, E.T.G. Thermal behavior of naproxen and ketoprofen nonsteroidal anti-inflammatory drugs. J Therm Anal Calorim 142, 849–859 (2020). https://doi.org/10.1007/s10973-020-09389-1

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Keywords

  • Naproxen
  • Ketoprofen
  • Anti-inflammatory
  • Evolved gas analysis
  • Thermal behavior