Solvent dependent 4-aminosalicylic acid-sulfamethazine co-crystal polymorph control

Salem, Ala’; Hagymási, Alexandra; Horváth, Barbara; Šafarik, Tatjana; Balić, Tomislav; Szabó, Péter; Gősi, Fruzsina; Nagy, Sándor; Pál, Szilárd; Kunsági‐Máté, Sándor; Széchenyi, Aleksandar

doi:10.1016/j.ejps.2020.105599

Cited by 13 publications

(5 citation statements)

References 27 publications

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“…Moreover, solvents can easily enter the crystal lattice to form solvated compounds. 9 , 13 − 15 Regarding the diversity of solvents used in the crystallization process, not only the solvent itself but also the volume of the solvent added influences the polymorphic outcome, as demonstrated by Hasa and co-workers during the liquid-assisted mechanochemical reactions. 16 …”

Section: Introductionmentioning

confidence: 99%

“…Solvents are one of those variables that have a considerable impact on the crystallization products ,, because the solute–solvent interactions are responsible for changing the molecular packing to form a different polymorph. Moreover, solvents can easily enter the crystal lattice to form solvated compounds. ,− Regarding the diversity of solvents used in the crystallization process, not only the solvent itself but also the volume of the solvent added influences the polymorphic outcome, as demonstrated by Hasa and co-workers during the liquid-assisted mechanochemical reactions …”

Section: Introductionmentioning

confidence: 99%

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Crystal Forms of the Antihypertensive Drug Irbesartan: A Crystallographic, Spectroscopic, and Hirshfeld Surface Analysis Investigation

Araya-Sibaja¹,

Fandaruff

Guevara-Camargo

et al. 2022

ACS Omega

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The design of new pharmaceutical solids with improved physical and chemical properties can be reached through in-detail knowledge of the noncovalent intermolecular interactions between the molecules in the context of crystal packing. Although crystallization from solutions is well-known for obtaining new solids, the effect of some variables on crystallization is not yet thoroughly understood. Among these variables, solvents are noteworthy. In this context, the present study aimed to investigate the effect of ethanol (EtOH), acetonitrile (MeCN), and acetone (ACTN) on obtaining irbesartan (IBS) crystal forms with 2,3-dibromosuccinic acid. Crystal structures were solved by single-crystal diffraction, and the intermolecular interactions were analyzed using the Hirshfeld surfaces analysis. The characterization of physicochemical properties was carried out by powder X-ray diffraction, Fourier transform infrared spectroscopy (FT-IR), thermal analysis, and solution-state NMR techniques. Two different IBS salts were obtained, one from MeCN and ACTN (compound 1 ) and a different one from EtOH (compound 2 ). The experimental results were in agreement with the findings obtained through quantum mechanics continuum solvation models. Compound 1 crystallized as a monoclinic system P 2 1 / c , whereas compound 2 in a triclinic system P 1̅. In both structures, a net of strong hydrogen bonds is present, and their existence was confirmed by the FT-IR results. In addition, the IBS cation acts as a H-bond donor through the N1 and N6 nitrogen atoms which interact with the bromide anion and the water molecule O1W in compound 1 . Meanwhile, N1 and N6 nitrogen atoms interact with the oxygen atoms provided by two symmetry-related 2,3-dibromo succinate anions in compound 2 . Solution-state NMR data agreed with the protonation of the imidazolone ring in the crystal structure of compound 1. Both salts presented a different thermal behavior not only in melting temperature but also in thermal stability.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Crystal Forms of the Antihypertensive Drug Irbesartan: A Crystallographic, Spectroscopic, and Hirshfeld Surface Analysis Investigation

Araya-Sibaja¹,

Fandaruff

Guevara-Camargo

et al. 2022

ACS Omega

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“…During solvent-based crystallization experiments, either for single components or potential cocrystal API-coformer pairs, the interactions between the dissolved components and the solvent molecules play a significant role in nucleation, crystal growth, solvate formation, and transformation to other polymorphic forms. − Therefore, the solvent selection process must be a focal point for solvent-based cocrystallization, taking into consideration not only the properties of the API but also those of the coformers, such as their solubility and possible interactions with solvent molecules. − Many essential parameters have been previously described for solvent-based (co)crystallizations, including the hydrogen bond acceptance ability of the solvent (δ hAcc ) or its polarity, as well as the effect of stirring and temperature conditions, cooling rate (if applicable), and seeding . Furthermore, Eddleston et al.…”

Section: Introductionmentioning

confidence: 99%

“… 6 − 9 Therefore, the solvent selection process must be a focal point for solvent-based cocrystallization, taking into consideration not only the properties of the API but also those of the coformers, such as their solubility and possible interactions with solvent molecules. 10 − 12 Many essential parameters have been previously described for solvent-based (co)crystallizations, including the hydrogen bond acceptance ability of the solvent (δ hAcc ) 13 or its polarity, 14 as well as the effect of stirring and temperature conditions, 15 cooling rate (if applicable), and seeding. 16 Furthermore, Eddleston et al.…”

Section: Introductionmentioning

confidence: 99%

Metronidazole Cocrystal Polymorphs with Gallic and Gentisic Acid Accessed through Slurry, Atomization Techniques, and Thermal Methods

Dyba,

Wiącek,

Nowak

et al. 2023

Crystal Growth & Design

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In this study, key features of metronidazole (MNZ) cocrystal polymorphs with gallic acid (GAL) and gentisic acid (GNT) were elucidated. Solvent-mediated phase transformation experiments in 30 solvents with varying properties were employed to control the polymorphic behavior of the MNZ cocrystal with GAL. Solvents with relative polarity (RP) values above 0.35 led to cocrystal I°, the thermodynamically stable form. Conversely, solvents with RP values below 0.35 produced cocrystal II, which was found to be only 0.3 kJ mol–1 less stable in enthalpy. The feasibility of electrospraying, including solvent properties and process conditions required, and spray drying techniques to control cocrystal polymorphism was also investigated, and these techniques were found to facilitate exclusive formation of the metastable MNZ-GAL cocrystal II. Additionally, the screening approach resulted in a new, high-temperature polymorph I of the MNZ-GNT cocrystal system, which is enantiotropically related to the already known form II°. The intermolecular energy calculations, as well as the 2D similarity between the MNZ-GAL polymorphs and the 3D similarity between MNZ-GNT polymorphs, rationalized the observed transition behaviors. Furthermore, the evaluation of virtual cocrystal screening techniques identified molecular electrostatic potential calculations as a supportive tool for coformer selection.

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“…Currently, the conventional polymorph regulation strategy involves adjusting experimental parameters such as solvents [8] , [9] , supersaturation [10] , [11] , temperature [12] , [13] , or adding crystal seed [14] , [15] , etc. However, these regulation strategies can’t achieve desired results for some drugs, as covering all possible crystallization conditions is not practicable.…”

Section: Introductionmentioning

confidence: 99%

Polymorph control by designed ultrasound application strategy: The role of molecular self-assembly

Zhao

Yang

et al. 2022

Ultrasonics Sonochemistry

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Solvent dependent 4-aminosalicylic acid-sulfamethazine co-crystal polymorph control

Cited by 13 publications

References 27 publications

Crystal Forms of the Antihypertensive Drug Irbesartan: A Crystallographic, Spectroscopic, and Hirshfeld Surface Analysis Investigation

Crystal Forms of the Antihypertensive Drug Irbesartan: A Crystallographic, Spectroscopic, and Hirshfeld Surface Analysis Investigation

Metronidazole Cocrystal Polymorphs with Gallic and Gentisic Acid Accessed through Slurry, Atomization Techniques, and Thermal Methods

Polymorph control by designed ultrasound application strategy: The role of molecular self-assembly

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