Mechanochemical Reaction of Sulfathiazole with Carboxylic Acids: Formation of a Cocrystal, a Salt, and Coamorphous Solids

Hu, Yun; Gniado, Katarzyna; Erxleben, Andrea; McArdle, Patrick

doi:10.1021/cg401673z

Cited by 71 publications

(68 citation statements)

References 47 publications

(85 reference statements)

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“…Co-milling of solids have been reported to cause solid phase reactions, either physically or chemically (Boldyrev, 2004;Hu et al, 2014). Cocrystal phase formation between two crystalline solids by solid state milling method has been recognized as an alternative method (Friscic and Jones, 2009;Lin, 2016).…”

Section: Discussionmentioning

confidence: 99%

“…The 2-aminopyrimidine group of the trimethoprim is hydrogen bonded to the N(heteroatom)-C-NH(sulfonamide) moiety of sulfamethoxazole (Caira, 2007;Zaini et al, 2010). The solid state form of drug substances significantly affects physical properties such as solubility, dissolution rate, stability and bioavailability (Huang and Tong, 2004). Pharmaceutical co-crystal has gained more interest from pharmaceutical industries because they offer multiple opportunities for modification of the chemical and or physical properties of drug substances without making or breaking any covalent bonds.…”

Section: Introductionmentioning

confidence: 99%

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Formation and Characterization of Sulfamethoxazole-Trimethoprim Cocrystal by Milling Process

2017

J App Pharm Sci

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The purpose of this study was to describe and characterize co-crystal formation of sulfamethoxazole and trimethoprim. The co-crystal formation was carried out by solid state milling process. Co-crystal by solution cocrystallization and physical mixture were also prepared as a comparison. The potential co-crystalline phase was characterized by powder X-ray Diffraction (PXRD), thermal analysis differential scanning calorimetry (DSC), scanning electron microscope (SEM), and Fourier transform Infrared (FT-IR) spectroscopy. Effect of milling time on formation of co-crystal sulfamethoxazole and trimethoprim was investigated by DSC and PXRD analysis. The study showed that the milling process of sulfamethoxazole and trimethoprim in equimolar yielded the co-crystal. Intact co-crystal was obtained by solution co-crystallization with methanol. Prolongation of milling time accelerated the formation of co-crystal. Physical characterization showed that sulfamethoxazole and trimethoprim co-crystal demonstrated a unique powder X-ray diffraction, thermal and spectroscopic properties. The study concludes that the milling process induces equimolar co-crystal formation between sulfamethoxazole and trimethoprim. The transformation to co-crystalline phase is affected by milling time.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Formation and Characterization of Sulfamethoxazole-Trimethoprim Cocrystal by Milling Process

2017

J App Pharm Sci

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“…Mechanochemistry, due to its non-equilibrium nature, is often employed to produce polymorphs 6 and co-crystals 53 Co-milled 1 and g (HP) in a 1:1 ratio results in a new XRPD pattern ( Figure S13, SI) suggesting the formation of a new co-crystalline adduct. This is further supported by the thermal analysis ( Figure S14, SI) where the material shows an endothermic peak at 187 °C, followed by melting at 202 °C.…”

Section: Ball Millingmentioning

confidence: 99%

Tailoring Cocrystal and Salt Formation and Controlling the Crystal Habit of Diflunisal

Pallipurath

Civati

Eziashi

et al. 2016

Crystal Growth & Design

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Crystal habit modification of the drug diflunisal that normally grows into extremely thin, long needles has been achieved by breaking the stacking effect with the help of co-formers. Eight new co-crystals are reported, along with three crystal structures. In all cases, ortho F disorder, often a feature in diflunisal structures was absent due to the presence of CH…F interactions. Co-milling diflunisal with oxalic acid produced 1:1 and 2:1 co-crystals. In contrast, in solution crystallisation oxalic acid played the role of an additive resulting in the crystallisation of diflunisal form I rather than form III. To rationalize co-crystal formation a statistical analysis of the CCDC data base for aromatic o-hydroxy carboxylic acids was carried out. All co-crystals of o-hydroxy carboxylic acids with the COOH dimer motif have an electron-withdrawing group on one of the acids. COOH…Nar motifs are formed preferentially over carboxylic homo-dimers in the presence of an Nar co-former. AbstractCrystal habit modification of the drug diflunisal that normally grows into extremely thin, long needles has been achieved by breaking the stacking effect with the help of co-formers. Eight new co-crystals are reported, along with three crystal structures. In all cases, ortho F disorder, often a feature in diflunisal structures was absent due to the presence of CH…F interactions. Co-milling diflunisal with oxalic acid produced 1:1 and 2:1 co-crystals. In contrast, in solution crystallisation oxalic acid played the role of an additive resulting in the crystallisation of diflunisal form I rather than form III. To rationalize co-crystal formation a statistical analysis of the CCDC data base for aromatic o-hydroxy carboxylic acids was carried out. All co-crystals of o-hydroxy carboxylic acids with the COOH dimer motif have an electron-withdrawing group on one of the acids. COOH…Nar motifs are formed preferentially over carboxylic homo-dimers in the presence of an Nar co-former.

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“…Coamorphous systems of the polymorphic sulfa-drug sulfathiazole and a range of multifunctional carboxylic acids as coformers were studied by NIRS [237]. L-tartaric acid and citric acid were shown to stabilize amorphous sulfathiazole for up to one month at low RH.…”

Section: Savolainen Et Al Reported An Example Where In Situmentioning

confidence: 99%

Application of Vibrational Spectroscopy to Study Solid-state Transformations of Pharmaceuticals

Erxleben

2016

CPD

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Understanding the properties, stability and transformations of the solid-state forms of an active pharmaceutical ingredient (API) in the development pipeline is of crucial importance for process-development, formulation development and FDA approval. Investigation of the polymorphism and polymorphic stability is a routine part of the preformulation studies. Vibrational spectroscopy allows the real-time in situ monitoring of phase transformations and probes intermolecular interactions between API molecules, between API and polymer in amorphous solid dispersions or between API and coformer in cocrystals or coamorphous systems and thus plays a major role in efforts to gain a predictive understanding of the relative stability of solid-state forms and formulations. Infrared (IR), near-infrared (NIR) and Raman spectroscopies, alone or in combination with other analytical methods, are important tools for studying transformations between different crystalline forms, between the crystalline and amorphous form, between hydrate and anhydrous form and for investigating solid-state cocrystal formation. The development of simple-to-use and cost-effective instruments on the one hand and recent technological advances such as access to the low-frequency Raman range down to 5 cm-1, on the other, have led to an exponential growth of the literature in the field. This review discusses the application of IR, NIR and Raman spectroscopies in the study of solid-state transformations with a focus on the literature published over the last eight years.

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Mechanochemical Reaction of Sulfathiazole with Carboxylic Acids: Formation of a Cocrystal, a Salt, and Coamorphous Solids

Cited by 71 publications

References 47 publications

Formation and Characterization of Sulfamethoxazole-Trimethoprim Cocrystal by Milling Process

Formation and Characterization of Sulfamethoxazole-Trimethoprim Cocrystal by Milling Process

Tailoring Cocrystal and Salt Formation and Controlling the Crystal Habit of Diflunisal

Application of Vibrational Spectroscopy to Study Solid-state Transformations of Pharmaceuticals

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