Dissolution Profiles of Carbamazepine Cocrystals with Cis–Trans Isomeric Coformers

Omori, Maaya; Yamamoto, Hibiki; Matsui, Fumiya; Sugano, Kiyohiko

doi:10.1007/s11095-022-03209-x

Cited by 7 publications

(4 citation statements)

References 51 publications

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“…The reasons behind the improved dissolution rate could be attributed to the high solubility of MePRB with respect to CBZ and rapid cocrystal dissociation during the dissolution. Similar behavior has been reported in the literature for other CBZ cocrystals, and the use of pharmaceutically acceptable polymers has been proven to be an effective strategy for inhibiting the fast SMPT of cocrystals [81,83,84]. In the present study, the HPMC excipient was employed owing to its ability to prevent CBZ from precipitating in the bulk phase within a few hours [84].…”

Section: Aqueous Solubility and Dissolution Studies Of The [Cbz + Mep...supporting

confidence: 77%

“…This value represents the maximum theoretical supersaturation that can be generated by the [CBZ + MePRB] (1:1) cocrystal during the dissolution process in the aqueous solution. It is well known, however, that the cocrystal solubility advantage could be compromised due to rapid solution-mediated phase transformation (SMPT) and precipitation of a less soluble solid form, as observed for other cocrystals [ 80 , 81 , 82 ].…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Polymorphism of Carbamazepine Pharmaceutical Cocrystal: Structural Analysis and Solubility Performance

Surov,

Drozd,

Ramazanova

et al. 2023

Pharmaceutics

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Polymorphism is a common phenomenon among single- and multicomponent molecular crystals that has a significant impact on the contemporary drug development process. A new polymorphic form of the drug carbamazepine (CBZ) cocrystal with methylparaben (MePRB) in a 1:1 molar ratio as well as the drug’s channel-like cocrystal containing highly disordered coformer molecules have been obtained and characterized in this work using various analytical methods, including thermal analysis, Raman spectroscopy, and single-crystal and high-resolution synchrotron powder X-ray diffraction. Structural analysis of the solid forms revealed a close resemblance between novel form II and previously reported form I of the [CBZ + MePRB] (1:1) cocrystal in terms of hydrogen bond networks and overall packing arrangements. The channel-like cocrystal was found to belong to a distinct family of isostructural CBZ cocrystals with coformers of similar size and shape. Form I and form II of the 1:1 cocrystal appeared to be related by a monotropic relationship, with form II being proven to be the thermodynamically more stable phase. The dissolution performance of both polymorphs in aqueous media was significantly enhanced when compared with parent CBZ. However, considering the superior thermodynamic stability and consistent dissolution profile, the discovered form II of the [CBZ + MePRB] (1:1) cocrystal seems a more promising and reliable solid form for further pharmaceutical development.

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Section: Aqueous Solubility and Dissolution Studies Of The [Cbz + Mep...supporting

confidence: 77%

Section: Resultsmentioning

confidence: 99%

Polymorphism of Carbamazepine Pharmaceutical Cocrystal: Structural Analysis and Solubility Performance

Surov,

Drozd,

Ramazanova

et al. 2023

Pharmaceutics

View full text Add to dashboard Cite

show abstract

“…Cocrystallization offers the opportunity to adapt and improve the physiochemical properties (e.g., solubility, , dissolution, − and stability) of compounds without the need for covalent modification, an especially attractive strategy for drug delivery . Considering all of the different subsets of multicomponent solids containing CBZ, CBZ cocrystals are the most abundant in the CSD (69 structures of cocrystals and their solvates and hydrates).…”

Section: What Do We Know About Carbamazepine Solid Forms?mentioning

confidence: 99%

What Has Carbamazepine Taught Crystal Engineers?

Hall,

Cruz-Cabeza,

Steed

2024

Crystal Growth & Design

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The antiepilepsy drug carbamazepine is one of the most studied pharmaceuticals in the world. The rich story of its solid forms, cocrystals, and formulation is a microcosm of the topical world of pharmaceutical materials. Understanding carbamazepine has required time, money, and dedication from numerous researchers and pharmaceutical companies worldwide. This wealth of knowledge provides the opportunity to reflect on progress within the crystal engineering field in general. This Perspective covers the extensive solid form landscape of carbamazepine and applies these examples to discuss and answer fundamental questions in the discipline. The story encompasses screening methods, computational solid form discovery, the power and influence of crystal engineering in understanding and controlling crystals and the amorphous state, and the environmental legacy of modern pharmaceuticals. This broad but in-depth analysis of carbamazepine is a vehicle into modern crystal engineering, not only in its own right but across the spectrum of organic materials science and pharmaceutical formulation. Discoveries of carbamazepine demonstrate the potential richness in the materials chemistry of every drug.

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“…Surface precipitation is undesirable as it can severely restrict the cocrystal system from reaching the desired supersaturation target . Omori and co-workers studied this phenomenon extensively ,,− and showed that (1) the cocrystal may not generate any bulk supersaturation when the surface precipitation is excessive, (2) the surface precipitation rate is a strong function of the coformer type, (3) similar to bulk precipitation, the surface precipitation rate is also affected by the presence of dissolved polymers in the medium, and (4) different facets of a cocrystal may show different surface precipitation rates. These findings stress the importance of systematically selecting coformers, polymers, and surfactants to control the DSP behavior of cocrystal systems to maximize drug absorption through sustained levels of supersaturation.…”

Section: Introductionmentioning

confidence: 99%

An In Vitro Model for Cocrystal Dissolution with Simultaneous Surface and Bulk Precipitation

Mendis,

Lakerveld

2023

Mol. Pharmaceutics

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Cocrystals can be promising means of overcoming the poor aqueous solubility of many drugs. However, precipitation of the stable drug at the cocrystal surface or in the bulk medium is often provoked during cocrystal dissolution due to high drug supersaturation, which prevents sustaining high drug concentrations for enhanced bioavailability. There is a need for predictive in vitro models that can accurately describe this cocrystal dissolution−supersaturation−precipitation (DSP) process to aid drug development and formulation design. Consideration of surface precipitation is often essential for such models given the strong impact of surface precipitation on the drug concentration during cocrystal dissolution. However, DSP models that can explicitly account for the effect of surface precipitation are currently lacking. This work presents a population balance-based model to describe in vitro cocrystal DSP behavior, which accounts for cocrystal dissolution, surface precipitation, and bulk precipitation. Dissolution experiments with carbamazepine−succinic acid cocrystals are conducted for model development and validation. The developed model captures all of the principal experimental trends and predicts the dose-dependent DSP behavior outside the regression data set with reasonable accuracy. The results show that surface precipitation is an essential component of the model. Finally, the new model is integrated with numerical optimization to illustrate how it can be used to identify an optimal dose, particle size, and amount of predissolved coformer.

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Dissolution Profiles of Carbamazepine Cocrystals with Cis–Trans Isomeric Coformers

Cited by 7 publications

References 51 publications

Polymorphism of Carbamazepine Pharmaceutical Cocrystal: Structural Analysis and Solubility Performance

Polymorphism of Carbamazepine Pharmaceutical Cocrystal: Structural Analysis and Solubility Performance

What Has Carbamazepine Taught Crystal Engineers?

An In Vitro Model for Cocrystal Dissolution with Simultaneous Surface and Bulk Precipitation

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