Molecules 2011, 16(5), 3740-3760; doi:10.3390/molecules16053740

Crystallization Products of Risedronate with Carbohydrates and Their Substituted Derivatives

1, 1, 1,2,3, 1,2, 1,2, 1, 1, 2, 2, 2, 2, 3, 2,4, 1,2 and 1,2,* email
Received: 7 February 2011; in revised form: 11 April 2011 / Accepted: 3 May 2011 / Published: 4 May 2011
(This article belongs to the Special Issue ECSOC-14)
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.
Abstract: The gastrointestinal absorption of bisphosphonates is in general only about 1%. To address this problem mixtures of risedronate monosodium salt with twelve varied sugar alcohols, furanoses, pyranoses and eight gluco-, manno- and galactopyranoside derivatives as counterions were designed in an effort to prepare co-crystals/new entities with improved intestinal absorption. Crystalline forms were generated by means of kinetically and/or thermodynamically controlled crystallization processes. One hundred and fifty-two prepared samples were screened by means of FT-NIR and FT-Raman spectroscopy. No co-crystal was prepared, but noteworthy results were obtained. A new solid phase of risedronate monosodium salt generated in the presence of phenyl-β-d-galactopyranoside under thermodynamically controlled crystallization conditions was found and also characterized using solid state NMR spectroscopy, X-ray powder diffraction and differential scanning calorimetry. This new polymorph was named as form P. Interactions between risedronate monosodium salt and both carbohydrates were confirmed by means of molecular dynamics simulation. In the present study the relationships between the chemical structures of the studied compounds required for crystalline form change are discussed.
Keywords: risedronate; phenyl-β-d-galactopyranoside; polymorph P; FT-NIR; FT-Raman; CP/MAS NMR; XRPD; DSC
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MDPI and ACS Style

Kos, J.; Pentakova, M.; Oktabec, Z.; Krejcik, L.; Mandelova, Z.; Harokova, P.; Hruskova, J.; Pekarek, T.; Dammer, O.; Tkadlecova, M.; Havlicek, J.; Vinsova, J.; Kral, V.; Dohnal, J.; Jampílek, J. Crystallization Products of Risedronate with Carbohydrates and Their Substituted Derivatives. Molecules 2011, 16, 3740-3760.

AMA Style

Kos J, Pentakova M, Oktabec Z, Krejcik L, Mandelova Z, Harokova P, Hruskova J, Pekarek T, Dammer O, Tkadlecova M, Havlicek J, Vinsova J, Kral V, Dohnal J, Jampílek J. Crystallization Products of Risedronate with Carbohydrates and Their Substituted Derivatives. Molecules. 2011; 16(5):3740-3760.

Chicago/Turabian Style

Kos, Jiri; Pentakova, Monika; Oktabec, Zbynek; Krejcik, Lukas; Mandelova, Zuzana; Harokova, Pavla; Hruskova, Jana; Pekarek, Tomas; Dammer, Ondrej; Tkadlecova, Marcela; Havlicek, Jaroslav; Vinsova, Jarmila; Kral, Vladimir; Dohnal, Jiri; Jampílek, Josef. 2011. "Crystallization Products of Risedronate with Carbohydrates and Their Substituted Derivatives." Molecules 16, no. 5: 3740-3760.

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