Investigation of solid–liquid phase diagrams of the sulfamethazine–salicylic acid co-crystal

Ahuja, Dipali; Svärd, Michael; Rasmuson, Åke C.

doi:10.1039/c9ce00124g

Cited by 32 publications

(48 citation statements)

References 55 publications

(71 reference statements)

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“…6 and experimental plots in Ahuja et al . 35 , some differences between experiments and the COSMO-SAC calculations were observed. The cocrystal region for SM/SA predicted by the COSMO-SAC is wider, while experimental data imply on the narrow region.…”

Section: Resultsmentioning

confidence: 88%

“…On the basis of Table 3, the octanol/water partition coefficients obtained from the Flory-Huggins model are farm from experimental data. In order to investigate a more complex system, a three-phases diagram of ternary system is explored by considering the sulfamethazine/salicylic acid cocrystal formation in methanol at 283.15 K, which studied by Ahuja et al 35 . Details of calculation and methods were described in "Cocrystal formation" section.…”

Section: Discussionmentioning

confidence: 99%

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Investigation of COSMO-SAC model for solubility and cocrystal formation of pharmaceutical compounds

Mahmoudabadi

Pazuki

2020

Sci Rep

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In this study, a predictive model named COSMO-SAC was investigated in solid/liquid equilibria for pharmaceutical compounds. The examined properties were the solubility of drug in the pure and mixed solvents, octanol/water partition coefficient, and cocrystal formation. The results of the original COSMO-SAC model (COSMO-SAC (2002)) was compared with a semi-predictive model named Flory–Huggins model and a revised version of the COSMO-SAC (COSMO-SAC (2010)). The results indicated the acceptable accuracy of the COSMO-SAC (2002) in the considered scope. The results emphasized on the suitability of the COSMO-SAC model for simple molecules containing C, H, and O by covalent and hydrogen bonding interactions. Applicability of the COSMO-SAC for more complicated molecules made of various functional groups such as COO and COOH doubly requires more modification in the COSMO-SAC.

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Section: Resultsmentioning

confidence: 88%

Section: Discussionmentioning

confidence: 99%

Investigation of COSMO-SAC model for solubility and cocrystal formation of pharmaceutical compounds

Mahmoudabadi

Pazuki

2020

Sci Rep

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“…Co‐crystallization techniques are feasible and applicable for pharmaceutical drug molecules and have been applied in the modulation of the physicochemical properties such as solubility, dissolution rate, bioavailability, stability, etc [1–4] . Co‐crystals are crystalline phases consisting of two or more stoichiometric neutral components that are chemically stable in pure form, and are held together in the crystal structure via the formation of various non‐covalent interactions [5,6] . For the formation of a pharmaceutical co‐crystal, an appropriate co‐former is required, which binds strongly through hydrogen (HB) and halogen (XB) bonding [7–9] interactions.…”

Section: Introductionmentioning

confidence: 99%

Interplay of Halogen and Hydrogen Bonding through Co–Crystallization in Pharmacologically Active Dihydropyrimidines: Insights from Crystal Structure and Energy Framework

et al. 2021

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A solvent‐assisted grinding method has been used to prepare co‐crystals in substituted dihydropyrimidines (DHPM) that constitutes pharmacologically active compounds. These were characterized using FT‐IR, PXRD, and single‐crystal X‐ray diffraction. In order to explore the possibility of formation of halogen (XB) and hydrogen bonding (HB) synthons in the solid state, co‐crystallization attempts of differently substituted DHPM molecules, containing nitro, hydoxy, and chloro substituents, with different co‐formers, such as 1,4‐diiodo tetrafluorobenzene (1,4 DITFB) and 3‐nitrobenzoic acid (3 NBA) were performed. The XB co‐crystals (C2aXB, C2bXB, and C2cXB) prefer the formation of C−I⋅⋅⋅O/C−I⋅⋅⋅S XB synthon, whereas the HB co‐crystal (C2dHB) is stabilized by N−H⋅⋅⋅O H‐bond formation. Hirshfeld surface analysis revealed that the percentage contribution of intermolecular interactions for XB co‐crystals prefer equal contribution of XB synthon along with HB synthon. Furthermore, the interaction energy was analyzed using energy frameworks, which suggests that their stability, a combination of electrostatics and dispersion, is enhanced through XB/HB in comparison to the parent DHPMs.

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“…where R denotes the gas constant, T temperature of the measurement, while C pm APR and C cocr APR are the concentration of APR from dissolution of a physical mixture and a cocrystal, respectively (Zhang et al, 2017;Ahuja et al, 2019). Since all enthalpies of formation of the studied cocrystals have positive values, negative Gibbs free energies indicate that the formation of cocrystals is indeed entropy driven.…”

Section: Stabilizing Role Of Disorder?mentioning

confidence: 99%

Understanding the formation of apremilast cocrystals

Dudek

Wielgus

Paluch

et al. 2019

Acta Crystallogr Sect B

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Apremilast (APR), an anti‐psoriatic agent, easily forms isostructural cocrystals and solvates with aromatic entities, often disobeying at the same time Kitaigorodsky's rule as to the saturation of possible hydrogen‐bonding sites. In this paper the reasons for this peculiar behavior are investigated, employing a joint experimental and theoretical approach. This includes the design of cocrystals with coformers having a high propensity towards the formation of both aromatic–aromatic and hydrogen‐bonding interactions, determination of their structure, using solid‐state NMR spectroscopy and X‐ray crystallography, as well as calculations of stabilization energies of formation of the obtained cocrystals, followed by crystal structure prediction calculations and solubility measurements. The findings indicate that the stabilization energies of cocrystal formation are positive in all cases, which results from strain in the APR conformation in these crystal forms. On the other hand, solubility measurements show that the Gibbs free energy of formation of the apremilast:picolinamide cocrystal is negative, suggesting that the formation of the studied cocrystals is entropy driven. This entropic stabilization is associated with the disorder observed in almost all known cocrystals and solvates of APR.

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Investigation of solid–liquid phase diagrams of the sulfamethazine–salicylic acid co-crystal

Abstract: Ternary phase diagrams for sulfamethazine–salicylic acid co-crystal have been constructed in three solvent systems.

Cited by 32 publications

References 55 publications

Investigation of COSMO-SAC model for solubility and cocrystal formation of pharmaceutical compounds

Investigation of COSMO-SAC model for solubility and cocrystal formation of pharmaceutical compounds

Interplay of Halogen and Hydrogen Bonding through Co–Crystallization in Pharmacologically Active Dihydropyrimidines: Insights from Crystal Structure and Energy Framework

Understanding the formation of apremilast cocrystals

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