Raman and solid state 13C-NMR investigation of the structure of the 1 : 1 amorphous piroxicam : beta-cyclodextrin inclusion compound.
The results of a Raman and solid state 13C-NMR spectroscopic investigation aimed at studying the conformation of piroxicam (P) and its interaction with beta-cyclodextrin (betaCD) in 1 : 1 amorphous PbetaCD inclusion compound are reported. The 1700-1200 cm(-1) FT-Raman and the 13C CP/MAS NMR spectra of 1 : 1 PbetaCD inclusion compound are discussed and assigned in comparison with those of the three main modifications of piroxicam (alpha, beta, and monohydrate). The FT-Raman and 13C-NMR results show that in 1 : 1 PbetaCD inclusion compound piroxicam mainly assumes the zwitterionic structure typical of monohydrate, even if the presence of a different structure, that is, beta form, is not excluded. Piroxicam monohydrate, differently from alpha and beta forms, is characterized by a zwitterionic structure with an internal proton transfer and an increased charge delocalization, as shown by our spectroscopic results. The charge delocalization characteristic of this zwitterionic structure gives rise to the interaction with betaCD via electrostatic and hydrogen bonds. The possibility of a host-guest interaction between piroxicam and betaCD is not excluded; the guest molecule can be accommodated in betaCD cavity by interaction via hydrophobic bonds.
Redenti
E
E
Chemical and Biopharmaceutical Department, Chiesi Farmaceutici S.p.A., Parma, Italy.
Zanol
M
M
Ventura
P
P
Fronza
G
G
Comotti
A
A
Taddei
P
P
Bertoluzza
A
A
D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry*; D002247:Carbon Isotopes; D003505:Cyclodextrins / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D010894:Piroxicam / Q000737:chemistry*; D013059:Spectrum Analysis, Raman; D047392:beta-Cyclodextrins
D000894:Anti-Inflammatory Agents, Non-Steroidal; D002247:Carbon Isotopes; D003505:Cyclodextrins; D047392:beta-Cyclodextrins; D010894:Piroxicam; C031215:betadex