Next Article in Journal
The Unusual Acid-Accumulating Behavior during Ripening of Cherimoya (Annona cherimola Mill.) is Linked to Changes in Transcription and Enzyme Activity Related to Citric and Malic Acid Metabolism
Next Article in Special Issue
New Aspects in the Formulation of Drugs Based on Three Case Studies
Previous Article in Journal
Highly Efficient Reproducible Perovskite Solar Cells Prepared by Low-Temperature Processing
Previous Article in Special Issue
The Effect of an Optimized Wet Milling Technology on the Crystallinity, Morphology and Dissolution Properties of Micro- and Nanonized Meloxicam

Crystallization of Esomeprazole Magnesium Water/Butanol Solvate

Department of Chemical and Biochemical Engineering, The University of Western Ontario, London, ON N6A 3K7, Canada
Apotex Pharmachem Inc., 34 Spalding Drive, Brantford, ON N3T 6B8, Canada
Author to whom correspondence should be addressed.
These authors contributed equally to this work.
Academic Editor: Derek J. McPhee
Molecules 2016, 21(4), 544;
Received: 15 March 2016 / Revised: 8 April 2016 / Accepted: 21 April 2016 / Published: 23 April 2016
(This article belongs to the Special Issue Crystallization of Pharmaceuticals)
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. View Full-Text
Keywords: pharmaceutical solvates; solid-state analysis; single crystal X-ray diffraction; thermal analysis; crystallization pharmaceutical solvates; solid-state analysis; single crystal X-ray diffraction; thermal analysis; crystallization
Show Figures

Graphical abstract

MDPI and ACS Style

Skieneh, J.; Khalili Najafabadi, B.; Horne, S.; Rohani, S. Crystallization of Esomeprazole Magnesium Water/Butanol Solvate. Molecules 2016, 21, 544.

AMA Style

Skieneh J, Khalili Najafabadi B, Horne S, Rohani S. Crystallization of Esomeprazole Magnesium Water/Butanol Solvate. Molecules. 2016; 21(4):544.

Chicago/Turabian Style

Skieneh, Jenna, Bahareh Khalili Najafabadi, Stephen Horne, and Sohrab Rohani. 2016. "Crystallization of Esomeprazole Magnesium Water/Butanol Solvate" Molecules 21, no. 4: 544.

Find Other Styles
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

Back to TopTop