Cocrystal Forms of the BCS Class IV Drug Sulfamethoxazole

Alsubaie, Moneerh; Aljohani, Marwah; Erxleben, Andrea; McArdle, Patrick

doi:10.1021/acs.cgd.8b00216

Cited by 30 publications

(25 citation statements)

References 41 publications

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“…Karki, et al [240] demonstrated that synthon analysis combined with Fabian's methodology was effective in prediction of possible co-formers for artemisinin. A series of co-crystals of sulfamethoxazole [241] and leflunomide [242] were synthesized using this approach. Prediction of possible H-bonded motifs between tyraminium cations and violurate anions also successfully predicted many of the bimolecular synthons experimentally observed in tyraminium violurate polymorphs and hydrates, but also demonstrated that none of the trimolecular synthons were predicted [243].…”

Section: Co-crystals Designmentioning

confidence: 99%

Intermolecular Interactions in Functional Crystalline Materials: From Data to Knowledge

Вологжанина

2019

Crystals

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Intermolecular interactions of organic, inorganic, and organometallic compounds are the key to many composition-structure and structure-property networks. In this review, some of these relations and the tools developed by the Cambridge Crystallographic Data Center (CCDC) to analyze them and design solid forms with desired properties are described. The potential of studies supported by the Cambridge Structural Database (CSD)-Materials tools for investigation of dynamic processes in crystals, for analysis of biologically active, high energy, optical, (electro)conductive, and other functional crystalline materials, and for the prediction of novel solid forms (polymorphs, co-crystals, solvates) are discussed. Besides, some unusual applications, the potential for further development and limitations of the CCDC software are reported. Crystals 2019, 9, 478 2 of 40 these fields, the manuscript cites only (i) recent works devoted to the analysis of correlations between intermolecular interactions and properties of a small molecule (for example its inclination to form polymorphs, solvates, and co-crystals), or a corresponding solid (from a well-known requirement for non-linear optical materials to crystallize in acentric space groups, to recent studies devoted to the effect of solvent presence on mechanical properties), and (ii) the corresponding software developed to investigate these correlations and to design novel solid forms with desired physicochemical properties. As the description of structure-property networks describes mainly the papers published in the last 10 years in the field of organic, organometallic, and coordination crystals, then the software under discussion will be limited with those developed by the Cambridge Crystallographic Data Centre (CCDC) for material chemistry and crystallography. Various examples of applications of the CCDC software to functional materials including their combination with other software, and restrictions found, will be given.First, the Cambridge Structural Database (CSD) and components of the CSD-Enterprise will be described in Section 2. Then, some properties related to the appearance of a given supramolecular associate, and the tools to search for an associate in the CSD will be reported in Section 3. The properties of solids dependent on the crystal morphology, the Bravais, Friedel, Donnay, and Harker (BFDH) tool for crystal morphology prediction and its' application to affect crystal morphology, polymorphism, and solvatomorphism will be reported in Section 4. Knowledge-based predictions of H-bonded polymorphism, co-crystal formation, mapping of likely intermolecular interactions, and conformer generation for the synthesis of novel functional materials will be discussed in Section 5, and the analysis of local connectivity and whole architectures of solvent molecules in Section 6. Finally, Section 7 contains information about Python API algorithms compatible with the CSD-Enterprise and about some examples of the successful combination of the CSD-Enterprise tools with exte...

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Section: Co-crystals Designmentioning

confidence: 99%

Intermolecular Interactions in Functional Crystalline Materials: From Data to Knowledge

Вологжанина

2019

Crystals

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“…Cocrystals, defined as “crystalline phase materials composed of two or more molecular and/or ionic compounds generally in a stoichiometric ratio”, show great potential in the pharmaceutical field . The formation of pharmaceutical cocrystals changes the fundamental molecular conformation and crystal-packing patterns, thereby modulating the physicochemical properties of the active pharmaceutical ingredient (API), such as solubility, dissolution rate, stability, and bioavailability. − Cooling and evaporation from solution are widely used crystallization methods in the laboratory to obtain cocrystals. However, experimental screening of cocrystals is usually time-consuming, labor-intensive, and expensive.…”

Section: Introductionmentioning

confidence: 99%

Machine-Learning-Guided Cocrystal Prediction Based on Large Data Base

Wang

Yang

Zhu

et al. 2020

Crystal Growth & Design

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A machine-learning model trained on the whole Cambridge Structural Database was developed to assist high-throughput cocrystal screening. With only 2D structures taken as inputs, the probability of cocrystal formation is returned for two given molecules. All of the cocrystal records in the CSD were used as positive samples, while negative samples were constructed by randomly combining different molecules into chemical pairs. Our model showed a prediction ability comparable with that of a widely used ab initio method in a head-to-head comparison test. Both experimental and virtual cocrystal screening against captopril were conducted at the same time to further validate the model. Two cocrystals of captopril with L-proline and sarcosine were obtained and characterized by PXRD, DSC, and FT-IR. These two coformers were also successfully predicted by our model. These results suggest that the tool we developed can be used to effectively guide coformer selection in the discovery of new cocrystals.

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“…It belongs to class IV of the Biopharmaceutics Classification System: i.e., it has low solubility and permeability . There are several known crystal forms of SMX, including five polymorphs, − a hemihydrate, , and a series of salts − and cocrystals. ,, Crystal structures of polymorphs I and II were determined in the early 1980s, , both of the monoclinic crystal system, with C 2/ c symmetry. In 2005, two new SMX polymorphs were discovered using different polymers as nucleation centers .…”

Section: Introductionmentioning

confidence: 99%

Hydrate vs Anhydrate under a Pressure-(De)stabilizing Effect of the Presence of Water in Solid Forms of Sulfamethoxazole

Patyk‐Kaźmierczak

Kaźmierczak

2021

Crystal Growth & Design

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An understanding of the structure–properties relationship of crystals is one of the principles of crystal engineering. It is well established that the physicochemical properties of solids, such as their temperature and pressure stability, can be modified by the diversification of the chemical composition: i.e., by the synthesis of multicomponent crystals. This method is widely used in the pharmaceutical industry in the search for novel crystal forms providing higher bioavailability and better processability during the manufacturing process. It is also crucial to thoroughly study, analyze, and compare multicomponent crystals with neat crystals to assess to what extent their properties were altered. In this work we investigate the effect of the presence of water molecules on the pressure stability of crystals, on an example of an antibiotic sulfamethoxazole in its neat form (polymorph I, SMX I) and as a hemihydrate (SMX·0.5H2O). The crystals were investigated under high pressure in a series of hydrostatic media up to ca. 4 GPa. SMX I was established to be the preferred and stable solid form of sulfamethoxazole under the studied conditions, while the compression of crystals of SMX·0.5H2O above 3.7 GPa led to a reversible isostructural solid-to-solid phase transition to phase II (named SMX hemihydrate-II). The difference between SMX hemihydrates I and II and a comparison of the pressure stability of the investigated forms of SMX are discussed in terms of intermolecular interactions, Full Interaction Maps (FIMs), structural voids, and changes in crystal density. It has been shown that lower density and less ordered molecular arrangement in crystals of SMX hemihydrate, a direct effect of the presence of water molecules, contribute to its lower pressure stability in comparison to crystals of SMX I.

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Cocrystal Forms of the BCS Class IV Drug Sulfamethoxazole

Cited by 30 publications

References 41 publications

Intermolecular Interactions in Functional Crystalline Materials: From Data to Knowledge

Intermolecular Interactions in Functional Crystalline Materials: From Data to Knowledge

Machine-Learning-Guided Cocrystal Prediction Based on Large Data Base

Hydrate vs Anhydrate under a Pressure-(De)stabilizing Effect of the Presence of Water in Solid Forms of Sulfamethoxazole

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