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.
Rossi, P., Paoli, P., Milazzo, S., Chelazzi, L., Giovannoni, M.P., Guerrini, G., et al. (2020). A combined crystallographic and computational study on dexketoprofen trometamol dihydrate salt. CRYSTALS, 10, 1-14 [10.3390/cryst10080659].
A combined crystallographic and computational study on dexketoprofen trometamol dihydrate salt
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
