Pharmaceutical salts/cocrystals of enoxacin with dicarboxylic acids: Enhancing in vitro antibacterial activity of enoxacin by improving the solubility and permeability

Liu, Lixin; Zou, Dongyu; Zhang, Yunan; Zhang, Qiang; Feng, Yanru; Guo, Yingxue; Liu, Yingli; Cheng, Guangdong; Wang, Chaoxing; Zhang, Lei; Wu, Lili; Chang, Liang; Su, Xin; Yu, Da‐Gang; Zhang, Yanfei; Liu, Moqi

doi:10.1016/j.ejpb.2020.06.018

Cited by 42 publications

(36 citation statements)

References 60 publications

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“…Based on these results, this higher absorption of PEL-T was caused by the increased solubility and permeability. Similarly, many reports have demonstrated that the absorption enhancement can generally be correlated with the solubility and/or permeability of a drug [ 29 , 30 , 31 ]. According to the BCS evaluation guidelines by the Food and Drug Administration (FDA), the solubility, rapid dissolution ability, and biological permeability of a drug are the main factors that affect its bioavailability [ 32 ].…”

Section: Resultsmentioning

confidence: 99%

“…According to the BCS evaluation guidelines by the Food and Drug Administration (FDA), the solubility, rapid dissolution ability, and biological permeability of a drug are the main factors that affect its bioavailability [ 32 ]. Three pharmaceutical salts/cocrystals of enoxacin (EX) with oxalic acid, malonic acid, and fumaric acid could enhance the antibacterial activity of the corresponding parent compound (EX) by improving its solubility and permeability [ 30 ]. As fenofibrate is highly lipophilic, virtually insoluble in water, and poorly absorbed, coadministration with meals is necessary to maximize the bioavailability of older formulations [ 31 ].…”

Section: Resultsmentioning

confidence: 99%

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Development of Pelubiprofen Tromethamine with Improved Gastrointestinal Safety and Absorption

Park

et al. 2021

Pharmaceutics

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Pelubiprofen (PEL), which is a commercialized non-steroidal anti-inflammatory drug (NSAID), is associated with the risk of gastrointestinal (GI) adverse events following long-term exposure and has poor water-soluble properties. Here, a new pelubiprofen tromethamine (PEL-T) with improved solubility, permeability, GI safety, and absorption, compared to PEL, has been developed. The nuclear magnetic resonance spectroscopy (NMR), differential scanning calorimetry (DSC), and Fourier transform infrared spectroscopy (FT-IR) results confirmed that the PEL-T was well formed. The powder of PEL-T showed the presence of additional 6H protons at δ 3.66–3.61 in the 1H NMR spectrum, and shifted the sharp endothermic peaks at 129 °C in DSC, and the spectrum of distinct absorption peaks in FT-IR. In addition, compared with PEL, PEL-T showed a significantly improved solubility in various media and an increased permeability coefficient (Kp) in Caco-2 cells. Furthermore, compared to PEL oral administration, PEL-T was found to significantly reduce the damaged area in an acute gastric damage rat model. The pharmacokinetic study of the PEL-T powder showed higher maximum plasma concentration (Cmax) and area under the plasma concentration–time curve from 0 h to the last time point (AUCt) than those of the PEL powder. Taken together, our data suggest that PEL-T is a recommendable candidate with enhanced gastrointestinal safety and better absorption compared with commercial PEL.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Development of Pelubiprofen Tromethamine with Improved Gastrointestinal Safety and Absorption

Park

et al. 2021

Pharmaceutics

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“…Because of this, many different strategies were proposed to address this limitation. This includes amorphization [ 28 , 29 ], formation of monocrystals [ 30 , 31 ], micronization [ 32 ] and solid dispersion formation [ 33 ], complexation with cyclodextrins [ 34 , 35 ], salts [ 36 , 37 ] and cocrystals [ 38 , 39 ] formation. Another way of improving solubility involves cosolvation techniques in which a particular amount of a solvent is added to the primary solvent [ 40 , 41 , 42 ] resulting in elevated solubility.…”

Section: Introductionmentioning

confidence: 99%

Quantification of Caffeine Interactions in Choline Chloride Natural Deep Eutectic Solvents: Solubility Measurements and COSMO-RS-DARE Interpretation

Jeliński¹,

Cysewski²

2022

IJMS

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Solubility of active pharmaceutical ingredients is an important aspect of drug processing and formulation. Although caffeine was a subject of many studies aiming to quantify saturated solutions, many applied solvents suffer from not being environmentally friendly. This work fills this gap by presenting the results of solubility measurements in choline chloride natural deep eutectic solvents, ccNADES, comprising one of seven of the following polyalcohols: glycerol, sorbitol, xylitol, glucose, sucrose, maltose and fructose. The ratio of ccNADES components was optimized for maximizing caffeine solubility at room temperature. Additionally, temperature dependent solubility was measured for the first four systems exhibiting the highest solubility potential, both in their neat forms and in mixtures with water. Results were used for intermolecular interactions assessments using the COSMO-RS-DARE approach, which led to a perfect match between experimental and computed solubility values. An important methodological discussion was provided for an appropriate definition of the systems. Surprising linear trends were observed between the values of fitting parameters and water-ccNADES composition. In addition, comments on selection of the values of the fusion thermodynamic parameters were provided, which led to the conclusion that COSMO-RS-DARE solubility computations can effectively compensate for the inaccuracies of these important physicochemical properties.

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“…In recent decades, great efforts have been made to improve solubility, permeability, or bioavailability of poorly water-soluble drugs by inserting a more soluble coformer in the crystal lattice leading to a reduced solvation barrier ( Cysewski, 2018 ; Dalpiaz et al, 2018 ; Liu et al, 2016 ; Wen et al, 2005 ). Cocrystals can also enhance membrane permeation and diffusion due to the induced supersaturated drug concentration ( Ferretti et al, 2015 ; Guo et al, 2018 ; Liu et al, 2020b ).…”

Section: Introductionmentioning

confidence: 99%

Preparation, characterization, and pharmacokinetics of rivaroxaban cocrystals with enhanced in vitro and in vivo properties in beagle dogs

Meng¹,

Tan²,

Yao³

et al. 2022

International Journal of Pharmaceutics: X

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Pharmaceutical salts/cocrystals of enoxacin with dicarboxylic acids: Enhancing in vitro antibacterial activity of enoxacin by improving the solubility and permeability

Cited by 42 publications

References 60 publications

Development of Pelubiprofen Tromethamine with Improved Gastrointestinal Safety and Absorption

Development of Pelubiprofen Tromethamine with Improved Gastrointestinal Safety and Absorption

Quantification of Caffeine Interactions in Choline Chloride Natural Deep Eutectic Solvents: Solubility Measurements and COSMO-RS-DARE Interpretation

Preparation, characterization, and pharmacokinetics of rivaroxaban cocrystals with enhanced in vitro and in vivo properties in beagle dogs

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