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Binding of Sulfamethazine to β-cyclodextrin and Methyl-β-cyclodextrin

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Abstract

β-cyclodextrin (βCD) and methyl-β-cyclodextrin (MβCD) complexes with sulfamethazine (SMT) were prepared and characterized by different experimental techniques, and the effects of βCD and MβCD on drug solubility were assessed via phase-solubility analysis. The phase-solubility diagram for the drug showed an increase in water solubility, with the following affinity constants calculated: 40.4 ± 0.4 (pH 2.0) and 29.4 ± 0.4 (pH 8.0) M−1 with βCD and 56 ± 1 (water), 39 ± 3 (pH 2.0) and 39 ± 5 (pH 8.0) M−1 with MβCD. According to 1H NMR and 2D NMR spectroscopy, the complexation mode involved the aromatic ring of SMT included in the MβCD cavity. The complexes obtained in solid state by freeze drying were characterized by Fourier transform infrared spectroscopy, scanning electron microscopy, and thermal analysis. The amorphous complexes obtained in this study may be useful in the preparation of pharmaceutical dosage forms of SMT.

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ACKNOWLEDGMENTS

The authors thank the Fondo para la Investigación Científica y Tecnológica (FONCYT) Préstamo BID PICT 1376, the Secretaría de Ciencia y Técnica de la Universidad Nacional de Córdoba (SECyT), and the Consejo Nacional de Investigaciones Científicas y Tecnológicas de la Nación (CONICET) for financial support. We also thank Ferromet S.A. (agent of Roquette in Argentina) for its donation of βCD and MβCD. We are grateful to Dr. Gloria Bonetto for NMR measurements and for her helpful discussion of the 1H NMR spectra, and to Dr. Paul Hobson, native English speaker, for revision of the manuscript.

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  1. Departamento de Farmacia, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, 5000, Córdoba, Argentina

    Ariana Zoppi, Alicia Delrivo, Virginia Aiassa & Marcela Raquel Longhi

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  1. Ariana Zoppi
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  2. Alicia Delrivo
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  3. Virginia Aiassa
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  4. Marcela Raquel Longhi
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Correspondence to Marcela Raquel Longhi.

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Zoppi, A., Delrivo, A., Aiassa, V. et al. Binding of Sulfamethazine to β-cyclodextrin and Methyl-β-cyclodextrin. AAPS PharmSciTech 14, 727–735 (2013). https://doi.org/10.1208/s12249-013-9958-9

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