Abstract
The molecular structure of esomeprazole magnesium derivative in the solid-state is reported for the first time, along with a simplified crystallization pathway. The structure was determined using the single crystal X-ray diffraction technique to reveal the bonding relationships between esomeprazole heteroatoms and magnesium. The esomeprazole crystallization process was carried out in 1-butanol and water was utilized as anti-solvent. The product proved to be esomeprazole magnesium tetrahydrate with two 1-butanol molecules that crystallized in P63 space group, in a hexagonal unit cell. Complete characterization of a sample after drying was conducted by the use of powder X-ray diffraction (PXRD), 1H-nuclear magnetic resonance (NMR), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), infrared spectroscopy (IR), and dynamic vapor sorption (DVS). Investigation by 1H-NMR and TGA has shown that the solvent content in the dried sample consists of two water molecules and 0.3 butanol molecules per esomeprazole magnesium molecule. This is different from the single crystal X-ray diffraction results and can be attributed to the loss of some water and 1-butanol molecules stabilized by intermolecular interactions. The title compound, after drying, is a true solvate in terms of water; conversely, 1-butanol fills the voids of the crystal lattice in non-stoichiometric amounts.
Highlights
Esomeprazole, the (S)-enantiomer of omeprazole, is the first single optical isomer proton pump inhibitor [1]
A novel form of esomeprazole magnesium has been characterized by single crystal X-ray diffraction, powder X-ray diffraction (PXRD), 1 H-nuclear magnetic resonance (NMR) spectroscopy, infrared spectroscopy (IR), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC) and dynamic vapor sorption (DVS)
Plate like single crystals were formed from a solution of amorphous esomeprazole magnesium in 1-butanol in the presence of water at 5 ̋ C after approximately three weeks
Summary
Esomeprazole, the (S)-enantiomer of omeprazole, is the first single optical isomer proton pump inhibitor [1] This eutomer forms an active inhibitor achiral sulphenamine when in the acidic compartment of the parietal cell. 6-methoxy tautomer is through the only crystallographic form present inanalysis the solid state It has derivative been state [11].the. A potential technique to stabilize esomeprazole is to form a solvate by incorporating solvent. A potential technique to stabilize is to to form molecules into the crystal lattice of the API via intermolecular forces. Pharmaceutical occur when water becomes incorporated the crystal lattice of an lattice of an API by means of intermolecular bonding [17]. In a study of esomeprazole magnesium hydrates, it was found that the stability order in water is trihydrate >. The solubility order in water was determined to be dihydrate form B > tetrahydrate > dihydrate form A > trihydrate [21]
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