Polymorphic solvates, ionic cocrystals and C–N bond formation to form ionic cocrystals in sulfamethoxazole and sulfathiazole-derived urea

Baruah, Jubaraj B.; Nath, Jitendra

doi:10.1039/d1ce01731d

Cited by 3 publications

(1 citation statement)

References 71 publications

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“…SMX is classified as a BCS II drug due to its poor solubility (∼0.5 mg/mL) and poor dissolution properties . Several approaches, like salt formation, , cocrystals, , supersaturating drug delivery systems, and solid dispersions, have been reported to overcome these poor physicochemical properties of SMX.…”

Section: Introductionmentioning

confidence: 99%

Study on Sulfamethoxazole–Piperazine Salt: A Mechanistic Insight into Simultaneous Improvement of Physicochemical Properties

Roy,

Chakraborty,

Pandey

et al. 2023

Mol. Pharmaceutics

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Multidrug salts represent more than one drug in a crystal lattice and thus could be used to deliver multiple drugs in a single dose. It showcases unique physicochemical properties in comparison to individual components, which could lead to improved efficacy and therapeutic synergism. This study presents the preparation and scale-up of sulfamethoxazole−piperazine salt, which has been thoroughly characterized by X-ray diffraction and thermal and spectroscopic analyses. A detailed mechanistic study investigates the impact of piperazine on the microenvironmental pH of the salt and its effect on the speciation profile, solubility, dissolution, and diffusion profile. Also, the improvement in the physicochemical properties of sulfamethoxazole due to the formation of salt was explored with lattice energy contributions. A greater ionization of sulfamethoxazole (due to pH changes contributed by piperazine) and lesser lattice energy of sulfamethoxazole−piperazine contributed to improved solubility, dissolution, and permeability. Moreover, the prepared salt addresses the stability issues of piperazine and exhibits good stability behavior under accelerated stability conditions. Due to the improvement of physicochemical properties, the sulfamethoxazole−piperazine salt demonstrates better pharmacokinetic parameters in comparison to sulfamethoxazole and provides a strong suggestion for the reduction of dose. The following study suggests that multidrug salts can concurrently enhance the physicochemical properties of drugs and present themselves as improved fixed-dose combinations.

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Section: Introductionmentioning

confidence: 99%

Study on Sulfamethoxazole–Piperazine Salt: A Mechanistic Insight into Simultaneous Improvement of Physicochemical Properties

Roy,

Chakraborty,

Pandey

et al. 2023

Mol. Pharmaceutics

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Development of sulfamethoxazole-succinimide cocrystal by mechanochemical cocrystallization – An insight into spectroscopic, electronic, chemical conformation and physicochemical properties

Roy

Pandey

Kumari

et al. 2022

Chemical Engineering Research and Design

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Assemblies of Sulfathiazole- and Sulfamethazine-Derived Thiourea: Polymorphs, Solvates, and Fluoride Detection

Nath,

Baruah

2024

Crystal Growth & Design

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Hydrogen-bonded assemblies of a series of thiourea derivatives of sulfa-drugs, 4-(3-arylthioureido)-N-(thiazol-2(3H)-ylidene) benzenesulfonamide (aryl = phenyl, 4-methoxyphenyl, 4-nitrophenyl, 2,3or 2,4-or 3,4-dichlorophenyl), and their polymorphs and solvates were investigated. All forms of the 4-(3-arylthioureido)-N-(thiazol-2(3H)ylidene)benzenesulfonamides studied here, other than a dimethyl sulfoxide (1:2) solvate, had homodimeric hydrogen-bonded units. The 4-(3-phenylthioureido)-N-(thiazol-2(3H)-ylidene)benzenesulfonamide provided two polymorphs, one having a hairpinlike structure and other a stretched structure. The projections of the −SO 2 − groups in the respective homodimer as well as the orientations of the thiourea part of the polymorphs were different. In the respective self-assembly, 2,3-or 2,4-or 3,4-dichlorophenylthiourea derivatives of sulfathiazole (positional isomers), the types of chlorine-chlorine interactions were dependent on the position of chloro groups on the phenyl ring. The theoretically calculated energy of the homodimers of the positional isomers had showed a predictable trend in the melting point in the respective series. The dimethylformamide hydrate as well as the dimethylacetamide solvate of N-(4,6-dimethylpyrimidin-2(1H)-ylidene)-4-(3-(4-nitrophenyl)thioureido)benzenesulfonamide had similar unit cell dimensions. This fact shows that the water molecule in the former case had compensated the space in the lattice required for an additional methyl group present in the dimethylacetamide than the dimethylformamide to achieve tight packing. The 4-nitrophenylthiourea derived compounds could selectively detect fluoride ions by visual means.

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Polymorphic solvates, ionic cocrystals and C–N bond formation to form ionic cocrystals in sulfamethoxazole and sulfathiazole-derived urea

Cited by 3 publications

References 71 publications

Study on Sulfamethoxazole–Piperazine Salt: A Mechanistic Insight into Simultaneous Improvement of Physicochemical Properties

Study on Sulfamethoxazole–Piperazine Salt: A Mechanistic Insight into Simultaneous Improvement of Physicochemical Properties

Development of sulfamethoxazole-succinimide cocrystal by mechanochemical cocrystallization – An insight into spectroscopic, electronic, chemical conformation and physicochemical properties

Assemblies of Sulfathiazole- and Sulfamethazine-Derived Thiourea: Polymorphs, Solvates, and Fluoride Detection

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