Exploring the thermal behaviour of the solvated structures of Nifedipine
Jones, Eleanor C. L. and Goldsmith, Kate E. and Ward, Martin R. and Bimbo, Luis M. and Oswald, Iain D. H. (2023) Exploring the thermal behaviour of the solvated structures of Nifedipine. Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials, 79 (Part 2). pp. 164-175. ISSN 2052-5192 (https://doi.org/10.1107/s2052520623001282)
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Abstract
Understanding the solvation and desolvation of pharmaceutical materials is an important part of materials discovery and development. In situ structural data are vital to understand the changes to crystal form that may occur in the system. In this study, the isolation and characterization of seven solvates of the L-type calcium channel antagonist, nifedipine, is described using variable-temperature powder X-ray diffraction so that the structural evolution as a function of temperature can be followed. The solvates reported herein can be split into those that are structurally similar to the previously reported dimethyl sulfoxide (DMSO) and dioxane solvates and those that have a novel packing arrangement. Of particular note is the solvate with tetrahydrofuran (THF) which has a hydrogen-bonding motif between the nifedipine molecules very similar to that of metastable -nifedipine. In addition to variable-temperature X-ray diffraction, the stability of the solid forms was assessed using differential scanning calorimetry and thermogravimetric analysis and indicates that in all cases desolvation results in the thermodynamically stable -polymorph of nifedipine even with the THF solvate. From the diffraction data the pathway of desolvation during heating of the DMF solvate showed conversion to another likely 1:1 polymorph before desolvation to -nifedipine. The desolvation of this material indicated a two-stage process; first the initial loss of 90% of the solvent before the last 10% is lost on melting. The methanol solvate shows interesting negative thermal expansion on heating, which is rarely reported in organic materials, but this behaviour can be linked back to the winerack-type hydrogen-bonding pattern of the nifedipine molecules.
ORCID iDs
Jones, Eleanor C. L. ORCID: https://orcid.org/0000-0002-3926-6493, Goldsmith, Kate E., Ward, Martin R. ORCID: https://orcid.org/0000-0003-0013-5004, Bimbo, Luis M. and Oswald, Iain D. H. ORCID: https://orcid.org/0000-0003-4339-9392;-
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Item type: Article ID code: 84317 Dates: DateEvent30 April 2023Published9 March 2023Published Online12 February 2023AcceptedSubjects: Medicine > Pharmacy and materia medica > Pharmaceutical chemistry Department: Faculty of Science > Strathclyde Institute of Pharmacy and Biomedical Sciences
Technology and Innovation Centre > Continuous Manufacturing and Crystallisation (CMAC)Depositing user: Pure Administrator Date deposited: 21 Feb 2023 14:40 Last modified: 23 Oct 2024 00:39 Related URLs: URI: https://strathprints.strath.ac.uk/id/eprint/84317