Rietveld Method in the Analysis of Polymorphism in Mebendazole Tablets Acquired in Brazil's Drugstores

Salvi, S. T. B.; Antônio, Selma Gutierrez; Ferreira, Fábio Furlan; Paiva-Santos, C. O.

doi:10.5935/0103-5053.20150151

Cited by 2 publications

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“…Since the L1 powder was the source of subsequent tests shown in this work, this characterization is crucial. To perform X-ray powder diffraction, L1 was mounted on a zero-background cell, and the pattern was determined in a Bruker D8 Advance diffractometer equipped with a LynxEye position-sensitive detector [ 33 ]. Using the corrected diffraction data of L1 (C 20 H 27 N 3 O, M = 325.45 g/mol), accurate unit-cell parameters were obtained with a = 17.0520 Å, b = 10.6445 Å, c = 10.5946 Å, β = 102.12°, V =1880.1 (Å 3 ) and density 1.15 g cm −3 .…”

Section: Resultsmentioning

confidence: 99%

“…The lower window of the detector electronics was increased using Si-Einkristalle at the default value of 0.11–0.19 V to minimize the effects of fluorescence. The Rietveld refinement technique [ 83 , 84 , 85 ] with software suite Diffrac TOPAS 4.2 [ 33 , 86 , 87 , 88 ] was used to determine the L1 structure. The single-crystal structure of L1 , used to compare our results, has been previously reported [ 34 ].…”

Section: Methodsmentioning

confidence: 99%

“…The parameter fundamentals (profile function #1) were used for the refinements [ 4 , 89 ]. Background function #0 (shifted Chebyshev function with 3 terms) in combination with the CW X-ray profile (functions #1) were used for the refinements [ 33 , 90 , 91 , 92 ]. (Breger et al, 2005; Hunger et al, 1999; Liu et al, 2011; Salvi et al, 2015).…”

Section: Methodsmentioning

confidence: 99%

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Structural Characterization, DFT Calculation, NCI, Scan-Rate Analysis and Antifungal Activity against Botrytis cinerea of (E)-2-{[(2-Aminopyridin-2-yl)imino]-methyl}-4,6-di-tert-butylphenol (Pyridine Schiff Base)

et al. 2020

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Botrytis cinerea is a ubiquitous necrotrophic filamentous fungal phytopathogen that lacks host specificity and can affect more than 1000 different plant species. In this work, we explored L1 [(E)-2-{[(2-aminopyridin-2-yl)imino]-methyl}-4,6-di-tert-butylphenol], a pyridine Schiff base harboring an intramolecular bond (IHB), regarding their antifungal activity against Botrytis cinerea. Moreover, we present a full characterization of the L1 by NMR and powder diffraction, as well as UV–vis, in the presence of previously untested different organic solvents. Complementary time-dependent density functional theory (TD-DFT) calculations were performed, and the noncovalent interaction (NCI) index was determined. Moreover, we obtained a scan-rate study on cyclic voltammetry of L1. Finally, we tested the antifungal activity of L1 against two strains of Botrytis cinerea (B05.10, a standard laboratory strain; and A1, a wild type strains isolated from Chilean blueberries). We found that L1 acts as an efficient antifungal agent against Botrytis cinerea at 26 °C, even better than the commercial antifungal agent fenhexamid. Although the antifungal activity was also observed at 4 °C, the effect was less pronounced. These results show the high versatility of this kind of pyridine Schiff bases in biological applications.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Structural Characterization, DFT Calculation, NCI, Scan-Rate Analysis and Antifungal Activity against Botrytis cinerea of (E)-2-{[(2-Aminopyridin-2-yl)imino]-methyl}-4,6-di-tert-butylphenol (Pyridine Schiff Base)

et al. 2020

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“…Furthermore, the polymorphic composition of the bulk drug and formulations marketed in different countries (South Africa, Brazil, Germany) has been analyzed [21,30,[33][34][35]. These studies revealed that all three polymorphic forms of MEB are found in the market.…”

Section: Introductionmentioning

confidence: 99%

“…1). In addition, variable temperature X-ray powder diffraction was employed to study the transformation of Form C into the most stable Form A [20], and the Rietveld method has been used for analysis of MEB polymorphism in commercial tablets of the drug [21].…”

Section: Introductionmentioning

confidence: 99%

Mebendazole crystal forms in tablet formulations. An ATR-FTIR/chemometrics approach to polymorph assignment

Calvo

Kaufman

Maggio

2016

Journal of Pharmaceutical and Biomedical Analysis

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a b s t r a c tStructural polymorphism of active pharmaceutical ingredients (API) is a relevant concern for the modern pharmaceutical industry, since different polymorphic forms may display dissimilar properties, critically affecting the performance of the corresponding drug products. Mebendazole (MEB) is a widely used broad spectrum anthelmintic drug of the benzimidazole class, which exhibits structural polymorphism (Forms A-C). Form C, which displays the best pharmaceutical profile, is the recommended one for clinical use. The polymorphs of MEB were prepared and characterized by spectroscopic, calorimetric and microscopic means. The polymorphs were employed to develop a suitable chemometrics-assisted sample display model based on the first two principal components of their ATR-FTIR spectra in the 4000-600 cm −1 region. The model was internally and externally validated employing the leave-one-out procedure and an external validation set, respectively. Its suitability for revealing the polymorphic identity of MEB in tablets was successfully assessed analyzing commercial tablets under different physical forms (whole, powdered, dried, sieved and aged). It was concluded that the ATR-FTIR/PCA (principal component analysis) association is a fast, efficient and non-destructive technique for assigning the solid-state forms of MEB in its drug products, with minimum sample pre-treatment.

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Rietveld Method in the Analysis of Polymorphism in Mebendazole Tablets Acquired in Brazil's Drugstores

Cited by 2 publications

References 1 publication

Structural Characterization, DFT Calculation, NCI, Scan-Rate Analysis and Antifungal Activity against Botrytis cinerea of (E)-2-{[(2-Aminopyridin-2-yl)imino]-methyl}-4,6-di-tert-butylphenol (Pyridine Schiff Base)

Structural Characterization, DFT Calculation, NCI, Scan-Rate Analysis and Antifungal Activity against Botrytis cinerea of (E)-2-{[(2-Aminopyridin-2-yl)imino]-methyl}-4,6-di-tert-butylphenol (Pyridine Schiff Base)

Mebendazole crystal forms in tablet formulations. An ATR-FTIR/chemometrics approach to polymorph assignment

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