Mechanochemical synthesis, characterization, and thermal behavior of meloxicam cocrystals with salicylic acid, fumaric acid, and malic acid

Fernandes, Richard Perosa; Nascimento, André Ferreira do; Carvalho, Ana Carina Sobral; Teixeira, J. A.; Ionashiro, Massao

doi:10.1007/s10973-019-08118-7

Cited by 27 publications

(8 citation statements)

References 27 publications

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“…The DTG curve (Fig. 2) suggests that the thermal decomposition mechanism in air occurs in more than one stage, as previously seen in the degradation of other oxicam drugs [6,20]. In both atmospheres an initially sharp, exothermic, mass loss occurs over the range of 205 to 360 °C with a m of 63.02% (air) and 63.97% (N2).…”

Section: Tg/dtg-dscsupporting

confidence: 63%

Lornoxicam drug—A new study of thermal degradation under oxidative and pyrolysis conditions using the thermoanalytical techniques, DRX and LC-MS/MS

et al. 2019

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In the present work, the thermal behavior of Lornoxicam drug was studied under oxidizing (air) and pyrolysis (N2) atmospheres using simultaneous thermogravimetry and differential scanning calorimetry (TG-DSC), differential scanning calorimetry (DSC), Hot Stage Microscopy (HSM) and Evolved Gas Analysis (EGA) in the form of thermogravimetry coupled to infrared spectroscopy (TG-FTIR) and mass spectrometry (TG-MS). The thermal degradation product formed at different temperatures were examined using liquid chromatography coupled to mass spectrometry (LC-MS) and Powder X-Ray Diffraction (PXRD). The thermal study showed that the drug does not melt, partially amorphized on heating, it is thermally stable to 205 °C and undergoes thermal decomposition in two overlapping mass loss steps. Furthermore, the DSC and MS techniques suggest that thermal degradation processes are very complex, which occur with the release of gaseous products HCN, SO2, COS, CO2, N2O and CO and formation of three intermediate in the thermal residue.

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Section: Tg/dtg-dscsupporting

confidence: 63%

Lornoxicam drug—A new study of thermal degradation under oxidative and pyrolysis conditions using the thermoanalytical techniques, DRX and LC-MS/MS

et al. 2019

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“…The co-crystallization of active pharmaceutical ingredients (APIs) with coformers offers a unique way to improve key physicochemical properties without changing the chemical nature and pharmacological activity of APIs [ 1 , 2 ]. Solubility, dissolution rate, bioavailability [ 3 , 4 , 5 , 6 , 7 , 8 ], melting point [ 9 ], stability [ 10 , 11 , 12 ], tabletability [ 13 ], taste [ 6 ], and other properties can undergo change during co-crystallization. Orally disintegrating tablets consisting of gabapentin co-crystals (antiepileptic and analgesic agent) with saccharin (sweetener) have shown a number of benefits in comparison to the same formulation with a physical mixture of starting components [ 6 ].…”

Section: Introductionmentioning

confidence: 99%

Structural Characterization of Co-Crystals of Chlordiazepoxide with p-Aminobenzoic Acid and Lorazepam with Nicotinamide by DSC, X-ray Diffraction, FTIR and Raman Spectroscopy

et al. 2020

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The low water solubility of benzodiazepines seriously affects their bioavailability and, in consequence, their biological activity. Since co-crystallization has been found to be a promising way to modify undesirable properties in active pharmaceutical ingredients, the objective of this study was to prepare co-crystals of two benzodiazepines, chlordiazepoxide and lorazepam. Using different co-crystallization procedures, slurry evaporation and liquid-assisted grinding, co-crystals of chlordiazepoxide with p-aminobenzoic acid and lorazepam with nicotinamide were prepared for the first time. Confirmation that co-crystals were obtained was achieved through a comparison of the data acquired for both co-crystals using differential scanning calorimetry (DSC), powder X-ray diffraction (PXRD), Fourier-transform infrared (FTIR) and Raman spectroscopy, with comparisons acquired for the physical mixtures of both benzodiazepines and coformers. The compatibility of PXRD patterns of both benzodiazepines co-crystals with those contained in the base Powder Diffraction File (PDF-4+) suggests that new crystal structures were indeed created under the co-crystallization procedure. Single-crystal X-ray diffraction revealed that a chlordiazepoxide co-crystal with p-aminobenzoic acid and a lorazepam co-crystal with nicotinamide crystallized in the monoclinic P21/n and P21/c space group, respectively, with one molecule of benzodiazepine and one of coformer in the asymmetric unit. FTIR and Raman spectroscopy corroborated that benzodiazepine and coformer are linked by a hydrogen bond without proton exchange. Furthermore, a DSC study revealed that single endothermic DSC peaks assigned to the melting of co-crystals differ slightly depending on the co-crystallization procedures and solvent used, as well as differing from those of starting components.

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“…The v CO confirmed that TMA of the cocrystal exists in neutral form. The weak sharp band at 3124 cm –1 was ascribed to v N–H of THEO with slight shifts of 1–2 cm –1 in the cocrystal, THEO-TMA. − …”

Section: Results and Discussionmentioning

confidence: 98%

Trimesic acid–Theophylline and Isopthalic acid–Caffeine Cocrystals: Synthesis, Characterization, Solubility, Molecular Docking, and Antimicrobial Activity

Abosede

Gordon

Dembaremba

et al. 2020

Crystal Growth & Design

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The preparation of cocrystals from active pharmaceutical ingredients (APIs) and biologically relevant coformers offers the opportunity of obtaining compounds with more desirable physicochemical and biological properties. This work focuses on theophylline–trimesic acid, caffeine–isophthalic acid, and caffeine–trimesic acid cocrystals. All the cocrystals were produced via slow evaporation and were characterized using Fourier transform infrared, differential scanning calorimetry, thermogravimetric analysis, and single-crystal X-ray diffraction. Structural characterization revealed that interactions such as CO···H, N···H···O, π–π, and C–H···π between the APIs and coformers significantly contribute to crystal packing. Density functional theory studies further revealed the electronic properties of cocrystals, as well as the functional groups that enhance their solubility. Drug activity through the weak groove-binding mode was realized through docking studies of the cocrystals with the DNA structure (Protein Data Bank identifier 1ZEW). Similarly, major interactions, including hydrogen bonding and π-π bonding, were observed between cocrystals and 4HL2, a New Delhi metallo-β-lactamase-1 produced by resistant clinical strains of K. pneumoniae. Biological studies revealed cocrystals with antimicrobial properties, particularly against clinically relevant gram-negative bacterial pathogens (Acinetobacter baumannii, Escherichia coli, Klebsiella pneumoniae, and Pseudomonas aeruginosa). So, these compounds represent a novel promising group of anti-infective agents.

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Mechanochemical synthesis, characterization, and thermal behavior of meloxicam cocrystals with salicylic acid, fumaric acid, and malic acid

Cited by 27 publications

References 27 publications

Lornoxicam drug—A new study of thermal degradation under oxidative and pyrolysis conditions using the thermoanalytical techniques, DRX and LC-MS/MS

Lornoxicam drug—A new study of thermal degradation under oxidative and pyrolysis conditions using the thermoanalytical techniques, DRX and LC-MS/MS

Structural Characterization of Co-Crystals of Chlordiazepoxide with p-Aminobenzoic Acid and Lorazepam with Nicotinamide by DSC, X-ray Diffraction, FTIR and Raman Spectroscopy

Trimesic acid–Theophylline and Isopthalic acid–Caffeine Cocrystals: Synthesis, Characterization, Solubility, Molecular Docking, and Antimicrobial Activity

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