Pharmaceutical salts of piroxicam and meloxicam with organic counterions

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Huang, Shan
Venables, Dean S.
Lawrence, Simon E.
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Piroxicam (PRM) and meloxicam (MEL) are two nonsteroidal anti-inflammatory drugs, belonging to the Biopharmaceutics Classification System Class II drugs. In this study, six novel pharmaceutical salts of PRM and MEL with three basic organic counterions, that is, 4-aminopyridine (4AP), 4-dimethylaminopyridine (4DMP), and piperazine (PPZ), were prepared by both slurrying and slow evaporation. These salts were characterized by single-crystal and powder X-ray diffraction, thermal analysis, and Fourier transform infrared spectroscopy. All six salts, especially MEL-4DMP and MEL-4AP, showed a significantly improved apparent solubility and dissolution rate in sodium phosphate solution compared with the pure APIs. Notably, PRM-4AP and PRM-4DMP salts exhibited enhanced fluorescence, and the PRMPPZ salt showed weaker fluorescence compared with that of pure PRM due to different luminescence mechanisms.
Aggregation-induced emission , Co-crystals , Solid-state , Quantitative analysis , Structural analysis , Chemical stability , Melt extrusion , Hydrogen bond , Solubility , Cocrystals
Huang, S., Venables, D. S. and Lawrence, S. E. (2022) 'Pharmaceutical salts of piroxicam and meloxicam with organic counterions', Crystal Growth and Design, 22(11), pp. 6504-6520. doi: 10.1021/acs.cgd.2c00722
© 2022, American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form Crystal Growth and Design, 22(11), pp. 6504-6520, after technical editing by the publisher. To access the final edited and published work see: 10.1021/acs.cgd.2c00722