A new polymorph of ciprofloxacin saccharinate: Structural characterization and pharmaceutical profile

Singh, Pawanpreet; Chadha, Renu

doi:10.1016/j.jpba.2017.07.036

Cited by 14 publications

(7 citation statements)

References 30 publications

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“…Theoretical calculations , and solid-state NMR − are often used to overcome such drawbacks. Among these techniques, the simplest method is to validate the structure using the root-mean-square deviation (RMSD) of the optimized structure obtained by dispersion-corrected density functional theory (DFT-D) calculations, as in the study by van de Streek et al…”

Section: Introductionmentioning

confidence: 99%

New Salt and Cocrystal of Mequitazine: Impact of Coformer Flexibility and Hydrogen Bond Donors on Polymorphism

Okura

Uchiyama

Kadota

et al. 2020

Crystal Growth & Design

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New multicomponent crystals of mequitazine (MQZ) with succinic acid (SUC), fumaric acid (FUM), glycolic acid (GLC), and glycolamide (GLA) were obtained after liquidassisted grinding. The hydrate/anhydrate availability in the crystals differed owing to slight differences in the coformer structure. Therefore, the causes of these differences in the crystal structure were investigated. The structures of crystals, for which single crystals were difficult to obtain, were obtained using powder diffraction crystal structure analyses. The crystal structures, including the disordered structure and the structure in which the H atom position could not be identified, were validated via dispersion-corrected density functional theory calculations using the Quantum ESPRESSO code. MQZ-SUC and MQZ-FUM formed isostructural anhydrates, but only MQZ-SUC formed a hydrate by twisting the alkyl straight chain; hence, the difference between the dihedral angles that the coformer can form led to a small change in polymorphism. MQZ-GLC hydrate and MQZ-GLA anhydrate had no isomorphic crystals, MQZ-GLC formed a hydrate, and MQZ-GLA formed an anhydrate. Differences in the number of hydrogen bond donors in the coformer led to major changes in polymorphism. The results of this study might be useful for coformer selection and controlling multicomponent crystal polymorphism.

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Section: Introductionmentioning

confidence: 99%

New Salt and Cocrystal of Mequitazine: Impact of Coformer Flexibility and Hydrogen Bond Donors on Polymorphism

Okura

Uchiyama

Kadota

et al. 2020

Crystal Growth & Design

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“…In recent years, mechanochemistry has been increasingly exploited for the screening of polymorphic forms of single- and multicomponent crystals. − In the case of fluoroquinolone salts, it has been shown that mechanochemical synthesis of pharmaceutical salt of ciprofloxacin with maleic acid resulted in the formation of three distinct polymorphic modifications of the ciprofloxacin maleate . In addition, the third polymorph of the ciprofloxacin saccharinate has been recently discovered entirely due to the application of the mechanochemical approach . These examples indicate that mechanochemistry is the suitable tool to explore the polymorphic potential of the fluoroquinolone multicomponent crystals.…”

Section: Introductionmentioning

confidence: 99%

Solid Forms of Ciprofloxacin Salicylate: Polymorphism, Formation Pathways, and Thermodynamic Stability

Surov

Vasilev

Churakov³

et al. 2019

Crystal Growth & Design

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The crystallization of ciprofloxacinan antibacterial fluoroquinolone compoundwith salicylic acid resulted in the isolation of five distinct solid forms of the drug, namely, an anhydrous salt, two polymorphic forms of the salt monohydrate, methanol and acetonitrile solvates, and the salt-cocrystal hydrate. The salicylate salts were investigated by different analytical techniques ranging from powder and single crystal X-ray diffractometry, differential scanning calorimetry, thermogravimetric analysis, variable temperature powder X-ray diffraction, dynamic vapor sorption analysis, dissolution, and solubility investigations. Real-time in situ Raman spectroscopy was used to investigate the mechanochemical formation pathways of the different solid polymorphs of ciprofloxacin salicylate. The mechanism of the phase transformation between the crystalline forms was evaluated under mechanochemical conditions. It was found that the formation pathway and kinetics of the grinding process depend on the form of the starting material and reaction conditions. The analysis of the solid-state thermal evolution of the hydrated salts revealed the two-step mechanism of dehydration process, which proceeds through a formation of the distinct intermediate crystalline products.

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“…In some cases it is plainly stated that the proper designation of the hydrogen positions would not be possible at all, unless the combination of DFT and ssNMR had been used [203]. an excellent agreement of obtained spectra with the experimental results [192][193][194]. Calculation-derived spectra help to clarify the conflicting assignment of peaks [195] and often play a decisive role when only coarse PXRD data are available [196].…”

Section: Solid State Nmrmentioning

confidence: 90%

“…Most commonly NMR parameters calculations are performed for 1 H and 13 C or 15 N [188] and 35 Cl nuclei [189] but this methodology gives a reasonable result for many other isotopes like: 23 Na [190] or 31 P [191]. Numerous studies have already reported an excellent agreement of obtained spectra with the experimental results [192][193][194]. Calculation-derived spectra help to clarify the conflicting assignment of peaks [195] and often play a decisive role when only coarse PXRD data are available [196].…”

Section: Solid State Nmrmentioning

confidence: 99%

Periodic DFT Calculations—Review of Applications in the Pharmaceutical Sciences

2020

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In the introduction to this review the complex chemistry of solid-state pharmaceutical compounds is summarized. It is also explained why the density functional theory (DFT) periodic calculations became recently so popular in studying the solid APIs (active pharmaceutical ingredients). Further, the most popular programs enabling DFT periodic calculations are presented and compared. Subsequently, on the large number of examples, the applications of such calculations in pharmaceutical sciences are discussed. The mentioned topics include, among others, validation of the experimentally obtained crystal structures and crystal structure prediction, insight into crystallization and solvation processes, development of new polymorph synthesis ways, and formulation techniques as well as application of the periodic DFT calculations in the drug analysis.

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A new polymorph of ciprofloxacin saccharinate: Structural characterization and pharmaceutical profile

Cited by 14 publications

References 30 publications

New Salt and Cocrystal of Mequitazine: Impact of Coformer Flexibility and Hydrogen Bond Donors on Polymorphism

New Salt and Cocrystal of Mequitazine: Impact of Coformer Flexibility and Hydrogen Bond Donors on Polymorphism

Solid Forms of Ciprofloxacin Salicylate: Polymorphism, Formation Pathways, and Thermodynamic Stability

Periodic DFT Calculations—Review of Applications in the Pharmaceutical Sciences

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