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Molecules 2010, 15(12), 8973-8987; doi:10.3390/molecules15128973
Article

Preparation and Properties of New Co-Crystals of Ibandronate with Gluco- or Galactopyranoside Derivatives

1,2, 3, 1,3, 3, 1, 1, 1, 1, 1, 1,3 and 1,3,*
1 Zentiva k.s., U Kabelovny 130, 102 37 Prague 10, Czech Republic 2 Department of Inorganic and Organic Chemistry, Faculty of Pharmacy in Hradec Kralove, Charles University in Prague, Heyrovskeho 1203, 500 05 Hradec Kralove, Czech Republic 3 Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackeho 1/3, 612 42 Brno, Czech Republic
Preliminary results were presented at the Thirteenth Electronic Conference on Synthetic Organic Chemistry (ECSOC-13, http://www.sciforum.net/presentation/201), 1-30 November 2009
* Author to whom correspondence should be addressed.
Received: 22 November 2010 / Revised: 3 December 2010 / Accepted: 7 December 2010 / Published: 8 December 2010
(This article belongs to the Special Issue ECSOC-13)
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Abstract

Mixtures of ibandronate monosodium salt with eleven gluco- and/or galacto-pyranoside derivatives as counterions were designed to prepare co-crystals with improved intestinal absorption. In general, gastrointestinal absorption of bisphosphonates after oral administration is approximately 1%. Co-crystals were generated by means of thermodynamically and/or kinetically controlled crystallization processes. Seventy-seven prepared samples were analyzed by means of FT-NIR, FT-Raman spectrometry and solid state NMR spectroscopy. New entities of ibandronate monosodium salt with phenyl-β-d-galactopyranoside were found and characterized. The absorption of these potential new co-crystals was investigated by means of PAMPA experiments. In the present study the relationships between the chemical structures of the studied compounds required for co-crystal generation are discussed.
Keywords: ibandronate; d-glucopyranosides; d-galactopyranosides; co-crystals; FT-NIR; FT-Raman; CP/MAS NMR; PAMPA ibandronate; d-glucopyranosides; d-galactopyranosides; co-crystals; FT-NIR; FT-Raman; CP/MAS NMR; PAMPA
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Oktabec, Z.; Kos, J.; Mandelova, Z.; Havelkova, L.; Pekarek, T.; Rezacova, A.; Placek, L.; Tkadlecova, M.; Havlicek, J.; Dohnal, J.; Jampílek, J. Preparation and Properties of New Co-Crystals of Ibandronate with Gluco- or Galactopyranoside Derivatives. Molecules 2010, 15, 8973-8987.

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