Cyclodextrin Inclusion Complexes of the Central Analgesic Drug Nefopam

Abstract

Inclusion complexes of nefopam base (NEF) with various beta-cyclodextrins (betaCDs) were investigated. All tested betaCDs increased the apparent solubility of NEF according to a Higuchi AL type plot (except betaCD: AN type plot), which indicates the formation of 1:1 stoichiometry inclusion complexes. 1H-NMR and 13C-NMR experiments showed that complexation by CDs allowed an easy separation of the R and S enantiomers. Based on spectral data obtained from the two-dimensional rotating frame nuclear Overhauser effect spectroscopy (2D-ROESY), a reasonable geometry for the complexes could be proposed implicating the insertion of the benzoxazocine ring into the wide end of the torus cavity.

Effect of β-cyclodextrin and hydroxypropyl β-cyclodextrin complexation on physicochemical properties and antimicrobial activity of cefdinir

“…However, while forming inclusion complex with hydrophobic drugs, they do not alter their molecular structure and permeability characteristics [8]. Complexation with cyclodextrins has been extensively used to enhance the aqueous solubility and dissolution rate of poorly water-soluble drugs [9][10][11].…”

Improving the Solubility and Oral Bioavailability of a Novel Aromatic Aldehyde Antisickling Agent (PP10) for the Treatment of Sickle Cell Disease

“…Drug inclusion complex with cyclodextrins has attracted attention due to the hydrophilic nature of these carriers and their ability to form a stable complex with the hydrophobic guest molecule [ 30 ]. The inclusion complex is suggested to increase the aqueous drug solubility and dissolution rate, thereby enhancing diffusion across the biological membranes without changing the molecular structure or permeability characteristics [ 31 , 32 ]. Several studies show enhancement in the solubility, dissolution rate, and pharmacological activity of different drugs upon inclusion complexation with HP-β-CD [ 30 , 33 , 34 , 35 , 36 ].…”

The antitumor effects of an arsthinol–cyclodextrin complex in a heterotopic mouse model of glioma

“…A 2D-ROESY experiment was used to characterize the inclusion complex of STB and 2-hydroxypropyl-β-cyclodextrin. This technique is widely used and enables the identification of host-guest intermolecular interactions [33]. In our case, the overlapping of the STB peaks (b, c, d, g, Table 1) with those of cyclodextrin (between 3.5 and 4 ppm) and the variation of chemical shifts when passing from pure solution to complex and when changing the solvent made the identification of intermolecular cross peaks with the aromatic portion ambiguous (Fig.…”