Melt Crystallization of Celecoxib-Carbamazepine Cocrystals with the Synchronized Release of Drugs

Chen, An; Cai, Peishan; Luo, Minqian; Guo, Minshan; Cai, Ting

doi:10.1007/s11095-022-03427-3

Cited by 13 publications

(5 citation statements)

References 64 publications

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“…In our previous study, a carbamazepine−celecoxib (CBZ-CEL) cocrystal was prepared by melt crystallization, and the cocrystal growth kinetics of the coamorphous system were investigated both in the supercooled liquid and glassy states. 13 In the supercooled liquid, the growth rate of cocrystals decreased upon cooling, as predicted by diffusion theories for crystal growth. 14 However, in the glassy state, an anomalously fast growth mode (glass-to-crystal (GC) growth) was observed for the cocrystallization of CBZ-CEL, in which the crystal growth rate was orders of magnitude faster than those predicted by standard theories.…”

Section: Introductionmentioning

confidence: 75%

“…Generally, the bulk growth rate of CBZ-CEL cocrystals decreased upon cooling, but the trend showed a discontinuity near the T g . We have previously ascribed this sudden jump in growth rate at 323 K to the activation of GC growth, which can be much faster than diffusion-controlled crystal growth . Interestingly, when the PEO concentration was above 1% w/w, the GC growth mode of CBZ-CEL was no longer observed, and the bulk growth rate changed gradually as the temperature changed from 303 K ( T g – 29.5 K) to 373 K ( T g + 40.5 K).…”

Section: Resultsmentioning

confidence: 99%

“…We have previously ascribed this sudden jump in growth rate at 323 K to the activation of GC growth, which can be much faster than diffusion-controlled crystal growth. 13 Interestingly, when the PEO concentration was above 1% w/w, the GC growth mode of CBZ-CEL was no longer observed, and the bulk growth rate changed gradually as the temperature changed from 303 K (T g − 29.5 K) to 373 K (T g + 40.5 K). However, the GC growth of CBZ-CEL was not disrupted by the presence of various concentrations of PVP (0.5, 1, 2, or 3% w/w).…”

Section: Bulk and Surface Crystal Growth Of Cbz-cel Cocrystals From C...mentioning

confidence: 99%

“…In our previous study, a carbamazepine–celecoxib (CBZ-CEL) cocrystal was prepared by melt crystallization, and the cocrystal growth kinetics of the coamorphous system were investigated both in the supercooled liquid and glassy states . In the supercooled liquid, the growth rate of cocrystals decreased upon cooling, as predicted by diffusion theories for crystal growth .…”

Section: Introductionmentioning

confidence: 97%

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Effects of Polymers on Cocrystal Growth in a Drug–Drug Coamorphous System: Relations between Glass-to-Crystal Growth and Surface-Enhanced Crystal Growth

Luo,

Chen,

Huang

et al. 2024

Mol. Pharmaceutics

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Coamorphous and cocrystal drug delivery systems provide attractive crystal engineering strategies for improving the solubilities, dissolution rates, and oral bioavailabilities of poorly water-soluble drugs. Polymeric additives have often been used to inhibit the unwanted crystallization of amorphous drugs. However, the transformation of a coamorphous phase to a cocrystal phase in the presence of polymers has not been fully elucidated. Herein, we investigated the effects of low concentrations of the polymeric excipients poly(ethylene oxide) (PEO) and poly(vinylpyrrolidone) (PVP) on the growth of carbamazepine–celecoxib (CBZ-CEL) cocrystals from the corresponding coamorphous phase. PEO accelerated the growth rate of the cocrystals by increasing the molecular mobility of the coamorphous system, while PVP had the opposite effect. The coamorphous CBZ-CEL system exhibited two anomalously fast crystal growth modes: glass-to-crystal (GC) growth in the bulk and accelerated crystal growth at the free surface. These two fast growth modes both disappeared after doping with PEO (1–3% w/w) but were retained in the presence of PVP, indicating a potential correlation between the two fast crystal growth modes. We propose that the different effects of PEO and PVP on the crystal growth modes arose from weaker effects of the polymers on cocrystallization at the surface than in the bulk. This work provides a deep understanding of the mechanisms by which polymers influence the cocrystallization kinetics of a multicomponent amorphous phase and highlights the importance of polymer selection in stabilizing coamorphous systems or preparing cocrystals via solid-based methods.

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Section: Introductionmentioning

confidence: 75%

Section: Resultsmentioning

confidence: 99%

Section: Bulk and Surface Crystal Growth Of Cbz-cel Cocrystals From C...mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 97%

See 2 more Smart Citations

Effects of Polymers on Cocrystal Growth in a Drug–Drug Coamorphous System: Relations between Glass-to-Crystal Growth and Surface-Enhanced Crystal Growth

Luo,

Chen,

Huang

et al. 2024

Mol. Pharmaceutics

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“…The experimental details are similar to the procedures reported in the literature (Ou et al, 2020;Su et al, 2018;Chen et al, 2023). In brief, a small quantity of the sample was melted on a round coverslip at a specified temperature until a small single crystal remained.…”

Section: Melt Crystallization Of Paliperidone Derivativesmentioning

confidence: 97%

The role of alkyl chain length in the melt and solution crystallization of paliperidone aliphatic prodrugs

Chen,

Cai,

Peng

et al. 2024

Int Union Crystallogr J

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Fatty acid-derivative prodrugs have been utilized extensively to improve the physicochemical, biopharmaceutical and pharmacokinetic properties of active pharmaceutical ingredients. However, to our knowledge, the crystallization behavior of prodrugs modified with different fatty acids has not been explored. In the present work, a series of paliperidone aliphatic prodrugs with alkyl chain lengths ranging from C4 to C16 was investigated with respect to crystal structure, crystal morphology and crystallization kinetics. The paliperidone derivatives exhibited isostructural crystal packing, despite the different alkyl chain lengths, and crystallized with the dominant (100) face in both melt and solution. The rate of crystallization for paliperidone derivatives in the melt increases with alkyl chain length owing to greater molecular mobility. In contrast, the longer chains prolong the nucleation induction time and reduce the crystal growth kinetics in solution. The results show a correlation between difficulty of nucleation in solution and the interfacial energy. This work provides insight into the crystallization behavior of paliperidone aliphatic prodrugs and reveals that the role of alkyl chain length in the crystallization behavior has a strong dependence on the crystallization method.

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Advances in Carbamazepine Cocrystals: A Review

Kalantri,

Yadav

2024

Cryst. Res. Technol.

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Carbamazepine (CBZ), a widely used antiepileptic drug, is known for its therapeutic efficacy but exhibits suboptimal physicochemical characteristics, including limited bioavailability, low solubility, and poor dissolution rates. In recent years, cocrystallization has emerged as a promising approach to improve these properties and enhance the overall performance of CBZ. This review paper presents a comprehensive exploration of the advances in CBZ cocrystals, focusing on their role in enhancing bioavailability, solubility/dissolution rates, morphology, and stability compared to raw CBZ. It delves into the in‐depth examination of computational techniques, such as molecular modelling and crystal structure prediction, that play a pivotal role in the rational design and prediction of CBZ cocrystals, thereby expediting the development process. Additionally, the morphological attributes of CBZ cocrystals are discussed, shedding light on how the unique crystal structures affect their physical properties. Stability is another critical aspect addressed in this review, encompassing thermal, physical, and chemical stability. The thermal behavior of CBZ cocrystals is analyzed through differential scanning calorimetry (DSC), and their crystal structures are characterized by techniques such as X‐ray diffraction (XRD) and Fourier‐transform infrared spectroscopy (FTIR). These analyses reveal the stability and structural changes of CBZ cocrystals under various conditions, providing valuable insights for formulation and storage. In summary, this comprehensive review paper amalgamates the latest advancements in CBZ cocrystals, demonstrating their capacity to significantly improve bioavailability, solubility, dissolution rates, and stability.

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Melt Crystallization of Celecoxib-Carbamazepine Cocrystals with the Synchronized Release of Drugs

Cited by 13 publications

References 64 publications

Effects of Polymers on Cocrystal Growth in a Drug–Drug Coamorphous System: Relations between Glass-to-Crystal Growth and Surface-Enhanced Crystal Growth

Effects of Polymers on Cocrystal Growth in a Drug–Drug Coamorphous System: Relations between Glass-to-Crystal Growth and Surface-Enhanced Crystal Growth

The role of alkyl chain length in the melt and solution crystallization of paliperidone aliphatic prodrugs

Advances in Carbamazepine Cocrystals: A Review

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