Dexketoprofen trometamol is the tromethamine salt of dexketoprofen [(2S)-2-(3-benzoylphenyl)propanoic acid-2-amino-2-(hydroxymethyl)propane-1,3-diol], a nonsteroidal anti-inflammatory drug (NSAID) used for the treatment of moderate-to strong-intensity acute pain. The crystal structure of the hitherto sole known hydrate phase of dexketoprofen trometamol (DK-T_2H2O), as determined by single-crystal X-ray diffraction, is presented. The water molecules are arranged in dimers included in isolated sites and sandwiched between piles of trometamol cations. The molecular and crystal structures of DK-T_2H2O are analyzed and compared to those of the parent anhydrous crystal form DK-T_A. In both the crystal structures, all the potential H-bond donors and acceptor of the dexketoprofen and trometamol ions are engaged, and both the species crystallize in the P21 space group. However, during the DK-T_A→DK-T_2H2O hydration process, the unique symmetry axis is not conserved, i.e., the ions are arranged in a different way with respect to the screw axis, even if the two crystal structures maintain structural blocks of DK anions and T cations. Quantum mechanical solid-state calculations provide some hints for the possible intermediate structure during the crystalline–crystalline hydration/dehydration process.

A combined crystallographic and computational study on dexketoprofen trometamol dihydrate salt / Rossi P.; Paoli P.; Milazzo S.; Chelazzi L.; Giovannoni M.P.; Guerrini G.; Ienco A.; Valleri M.; Conti L.. - In: CRYSTALS. - ISSN 2073-4352. - ELETTRONICO. - 10:(2020), pp. 1-14. [10.3390/cryst10080659]

A combined crystallographic and computational study on dexketoprofen trometamol dihydrate salt

Rossi P.;Paoli P.
;
Milazzo S.;Chelazzi L.;Giovannoni M. P.;Guerrini G.;Ienco A.;Valleri M.;Conti L.
2020

Abstract

Dexketoprofen trometamol is the tromethamine salt of dexketoprofen [(2S)-2-(3-benzoylphenyl)propanoic acid-2-amino-2-(hydroxymethyl)propane-1,3-diol], a nonsteroidal anti-inflammatory drug (NSAID) used for the treatment of moderate-to strong-intensity acute pain. The crystal structure of the hitherto sole known hydrate phase of dexketoprofen trometamol (DK-T_2H2O), as determined by single-crystal X-ray diffraction, is presented. The water molecules are arranged in dimers included in isolated sites and sandwiched between piles of trometamol cations. The molecular and crystal structures of DK-T_2H2O are analyzed and compared to those of the parent anhydrous crystal form DK-T_A. In both the crystal structures, all the potential H-bond donors and acceptor of the dexketoprofen and trometamol ions are engaged, and both the species crystallize in the P21 space group. However, during the DK-T_A→DK-T_2H2O hydration process, the unique symmetry axis is not conserved, i.e., the ions are arranged in a different way with respect to the screw axis, even if the two crystal structures maintain structural blocks of DK anions and T cations. Quantum mechanical solid-state calculations provide some hints for the possible intermediate structure during the crystalline–crystalline hydration/dehydration process.
2020
10
1
14
Goal 3: Good health and well-being for people
Rossi P.; Paoli P.; Milazzo S.; Chelazzi L.; Giovannoni M.P.; Guerrini G.; Ienco A.; Valleri M.; Conti L.
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/1208738
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