Thermodynamic and molecular investigation into the solubility, stability and self-assembly of gabapentin anhydrate and hydrate

Wang, Yan; Du, Shichao; Wu, Songgu; Li, Long; Zhang, Dejiang; Chen, Yuanfu; Zhou, Lina; Bekele, Hibest kiflegiorgis; Gong, Junbo

doi:10.1016/j.jct.2017.05.041

Cited by 16 publications

(11 citation statements)

References 36 publications

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“…In GP, cyclopentane substitutes the isobutyl group but the supramolecular feature of the two molecules are essentially equivalent. Due to extensive polymorph screening, multiple anhydrous and hydrate forms of GP are reported (Braga et al, 2008;Reece & Levendis, 2008;Wang et al, 2017).…”

Section: Resultsmentioning

confidence: 99%

“…4). GP (CCDC refcode QIMKIG02) forms 1D chains (Reece & Levendis, 2008;Wang et al, 2017;Ibers, 2001;Vasudev et al, 2009), whereas the packing in the anhydrous form (CCDC refcode QIMKIG03) resembles those of the hydrate forms, GPH I and II (CCDC refcodes QIMKOM and QIMKOM02), and SPGH I and II, the zwitterionic groups being separated into two planes. Remarkably, despite structural similarities, only the hydrates undergo plastic bending, whereas all the anhydrous forms are brittle.…”

Section: Resultsmentioning

confidence: 99%

“…Crystallization of GP and GPH: GP and its hydrate crystals are reproduced by following the same procedure mentioned in the literature (Wang et al, 2017;Reece & Levendis, 2008).…”

Section: Methodsmentioning

confidence: 99%

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Plasticity in zwitterionic drugs: the bending properties of Pregabalin and Gabapentin and their hydrates

Khandavilli

Lusi

Frawley

2019

Int Union Crystallogr J

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The investigation of mechanical properties in molecular crystals is emerging as a novel area of interest in crystal engineering. Indeed, good mechanical properties are required to manufacture pharmaceutical and technologically relevant substances into usable products. In such endeavour, bendable single crystals help to correlate microscopic structure to macroscopic properties for potential design. The hydrate forms of two anticonvulsant zwitterionic drugs, Pregabalin and Gabapentin, are two examples of crystalline materials that show macroscopic plasticity. The direct comparison of these structures with those of their anhydrous counterparts, which are brittle, suggests that the presence of water is critical for plasticity. In contrast, structural features such as molecular packing and anisotropic distribution of strong and weak interactions seem less important.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Plasticity in zwitterionic drugs: the bending properties of Pregabalin and Gabapentin and their hydrates

Khandavilli

Lusi

Frawley

2019

Int Union Crystallogr J

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“…During hydrate examination, a specific accent must be put on the H-bonding investigation. This is because these are the H-bonds which are one of the main reasons for the structural alteration of a non-hydrate [ 128 , 129 ], as they are formed not only between water and API molecules, but also in the form of water bridges [ 130 ]. All these aspects contribute to the formation of complex H-bond networks.…”

Section: Hydrates Structural Analysis Selected Cases Within the Lmentioning

confidence: 99%

“…Especially excipients with high water-absorbing potential, like MC or HPC, can delay the start of a hydrate formation in an aqueous environment (e.g., wet granulation), as has been reported for piroxicam [ 116 ]. Nevertheless, sometimes, excipients also cause a stability decrease in formulations containing API hydrates [ 128 ].…”

Section: Influence Of Excipients On Api Hydratesmentioning

confidence: 99%

Pharmaceutical Hydrates Analysis—Overview of Methods and Recent Advances

et al. 2020

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This review discusses a set of instrumental and computational methods that are used to characterize hydrated forms of APIs (active pharmaceutical ingredients). The focus has been put on highlighting advantages as well as on presenting some limitations of the selected analytical approaches. This has been performed in order to facilitate the choice of an appropriate method depending on the type of the structural feature that is to be analyzed, that is, degree of hydration, crystal structure and dynamics, and (de)hydration kinetics. The presented techniques include X-ray diffraction (single crystal X-ray diffraction (SCXRD), powder X-ray diffraction (PXRD)), spectroscopic (solid state nuclear magnetic resonance spectroscopy (ssNMR), Fourier-transformed infrared spectroscopy (FT-IR), Raman spectroscopy), thermal (differential scanning calorimetry (DSC), thermogravimetric analysis (TGA)), gravimetric (dynamic vapour sorption (DVS)), and computational (molecular mechanics (MM), Quantum Mechanics (QM), molecular dynamics (MD)) methods. Further, the successful applications of the presented methods in the studies of hydrated APIs as well as studies on the excipients’ influence on these processes have been described in many examples.

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Machine learning-based solubility prediction and methodology evaluation of active pharmaceutical ingredients in industrial crystallization

Gao

Shi

et al. 2021

Front. Chem. Sci. Eng.

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Thermodynamic and molecular investigation into the solubility, stability and self-assembly of gabapentin anhydrate and hydrate

Cited by 16 publications

References 36 publications

Plasticity in zwitterionic drugs: the bending properties of Pregabalin and Gabapentin and their hydrates

Plasticity in zwitterionic drugs: the bending properties of Pregabalin and Gabapentin and their hydrates

Pharmaceutical Hydrates Analysis—Overview of Methods and Recent Advances

Machine learning-based solubility prediction and methodology evaluation of active pharmaceutical ingredients in industrial crystallization

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