Influence of environment on piroxicam polymorphism: vibrational spectroscopic study.
FTIR and FT-Raman spectroscopies were used to evaluate the mechanism of transformation of piroxicam into its different forms (alpha, beta, and monohydrate), depending on the environment. These vibrational techniques allowed us to identify the forms of piroxicam that crystallize from different solvents at different cooling rates and the conformation of the drug in some of its derivatives: piroxicam hydrochloride, piroxicam thallium and sodium salt hemihydrates, and piroxicam sodium salt. The usefulness of Raman spectroscopy in characterizing piroxicam:beta-cyclodextrin (PbetaCD) inclusion compounds was described. The Raman spectrum of 1:2 PbetaCD was discussed in comparison with that of the corresponding piroxicam sodium salt containing inclusion compound (1:2 PNabetaCD) in order to study the influence of the piroxicam derivative used on the structure of the inclusion compound. The Raman results showed that in both of the inclusion compounds the piroxicam mainly assumes the zwitterionic structure typical of a monohydrate; therefore, the kind of derivative used does not affect the conformation of the drug in its inclusion compound. The effect of the method of synthesis utilized (freeze-drying or freeze-thaw cycling) to obtain 1:2.5 PbetaCD was investigated. The inclusion compound obtained by freeze-thaw cycling proved to be more crystalline and to contain a higher amount of the beta form than the freeze-dried inclusion compound. Raman spectroscopy proved to be a useful technique for evaluating the effectiveness of the manufacturing process in relation to the pharmaceutical properties of the drug and to the nondestructive and noninvasive on-line quality control of the industrial products.
Taddei
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Dipartimento di Biochimica G. Moruzzi, Sezione di Chimica e Propedeutica Biochimica, University of Bologna, Via Belmeloro 8/2, 40126 Bologna, Italy. ptaddei@ciam.unibo.it
Torreggiani
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Simoni
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D003505:Cyclodextrins / Q000737:chemistry*; D015394:Molecular Structure; D010894:Piroxicam / Q000031:analogs & derivatives* / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared; D013059:Spectrum Analysis, Raman
D003505:Cyclodextrins; D010894:Piroxicam