The Use Of N-Methylpyrrolidone as a Cosolvent and Oxidant in Pharmaceutical Stress Testing

Reynolds, Dan W.; Galvani, Marina; Hicks, Simon R.; Joshi, Biren J.; Kennedy-Gabb, Sonya; Kleinman, Mark H.; Parmar, Paresh Z.

doi:10.1002/jps.22793

Cited by 28 publications

(18 citation statements)

References 29 publications

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“…[2] Glycerol and N-methyl-2-pyrrolidone were added to water for enhancing the solubility of low water-soluble pharmaceuticals and also used as their individual or mixtures for various purposes. [3][4][5][6][7][8][9][10][11] The viscosity and/or surface tension of glycerol [12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27] and N-methyl-2-pyrrolidone [28][29][30][31][32][33] have been reported in the literature. To the best of our knowledge, there is no report on the properties of glycerol + N-methyl-2-pyrrolidone mixtures in the literature.…”

Section: Introductionmentioning

confidence: 99%

Viscosity and surface tension of glycerol + N-methyl-2-pyrrolidone mixtures from 293 to 323 K

Bandarkar

Khattab

Martínez

et al. 2014

Physics and Chemistry of Liquids

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2015) Viscosity and surface tension of glycerol + N-methyl-2-pyrrolidone mixtures from 293The viscosity and surface tension of binary mixtures of glycerol (1) + N-methyl-2-pyrrolidone (2) at T = 293, 298, 303, 308, 313, 318, and 323 K and at atmospheric pressure are reported. The Jouyban-Acree model was used for mathematical correlation of measured data. The average percentage deviation was used as an accuracy criterion. Derived properties from measured thermophysical properties, including deviations in viscosity and surface tension; the enthalpy, entropy and Gibbs energy of flow activation; standard enthalpy and entropy of surface formation data were reported.

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Section: Introductionmentioning

confidence: 99%

Viscosity and surface tension of glycerol + N-methyl-2-pyrrolidone mixtures from 293 to 323 K

Bandarkar

Khattab

Martínez

et al. 2014

Physics and Chemistry of Liquids

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“…For instance, PSf is stable for thermo-oxidative destruction for an extended period (more than a year) even at temperature 140 • C. Whereas, other components of casting solution such as NMP and PEG possess lower stability towards degradation at elevated temperatures. It was shown that NMP reacts in the presence of atmospheric oxygen at the temperature of 60-80 • C with the formation of peroxides [24], upon the destruction of which N-methylsuccinimide and atomic oxygen are formed. Thereby, NMP does not only undergo thermal degradation but can also act as a promoter of further oxidation of other components in the common solution [24].…”

Section: Introductionmentioning

confidence: 99%

“…It was shown that NMP reacts in the presence of atmospheric oxygen at the temperature of 60-80 • C with the formation of peroxides [24], upon the destruction of which N-methylsuccinimide and atomic oxygen are formed. Thereby, NMP does not only undergo thermal degradation but can also act as a promoter of further oxidation of other components in the common solution [24]. Furthermore, PEG can also be oxidized in the presence of atmospheric oxygen forming formic acid, while PEG end groups can transform from the hydroxyl to the carbonyl, carboxyl, or ester groups [25][26][27].…”

Section: Introductionmentioning

confidence: 99%

Effect of Temperature Exposition of Casting Solution on Properties of Polysulfone Hollow Fiber Membranes

Borisov

Vasilevsky

Matveev

et al. 2019

Fibers

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It was shown for the first time that the conditions of thermal treatment of the casting solution significantly affect the morphology and transport properties of porous, flat, and hollow fiber polysulfone (PSf) membranes. It is ascertained that the main solution components that are subjected to thermo-oxidative destruction are the pore-forming agent polyethylene glycol (PEG) and solvent N-methyl-2-pyrrolidone (NMP). It is proved that hydroxyl groups of PEG actively react in the process of the casting solution thermo-oxidative destruction. It is shown that despite the chemical conversion taking place in the casting solution, their stability towards coagulation virtually does not change. The differences in the membrane morphology associated with the increase of thermal treatment time at 120 °C are not connected to the thermodynamic properties of the casting solutions, but with the kinetics of the phase separation. It is revealed that the change of morphology and transport properties of membranes is connected with the increase of the casting solution viscosity. The rise of solution viscosity resulted in the slowdown of the phase separation and formation of a more densely packed membrane structure with less pronounced macropores. It is determined experimentally that with the increase of casting solution thermal treatment time, the membrane selective layer thickness increases. This leads to the decrease of gas permeance and the rise of the He/CO2 selectivity for flat and hollow fiber membranes. In the case of hollow fibers, the fall of gas permeance is also connected with the appearance of the sponge-like layer at the outer surface of membranes. The increase of selectivity and decline of permeance indicates the reduction of selective layer pore size and its densification, which agrees well with the calculation results of the average membrane density. The results obtained are relevant to any polymeric casting solution containing NMP and/or PEG and treated at temperatures above 60 °C.

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“…12,13 For this reason, oxidation is associated with a high risk of generating potentially genotoxic impurities. Many previous studies have described approaches for studying oxidative mechanisms, including autoxidation prediction using free radical initiators, [14][15][16][17] the use of N-methylpyrrolidone 18 and Tween80/Fe 3+ , 19 nucleophilic/ electrophilic oxidation prediction with peroxides, 3,4,20,21 electron transfer oxidation prediction with transition metals, 5 electro-oxidation prediction with voltammetry, 22 and prediction of photochemically induced oxidation with a photosensitizer. 6 Indeed, these approaches have been used in the pharmaceutical industry, often producing useful information relating to oxidation susceptibility that has been helpful in pharmaceutical development.…”

Section: Introductionmentioning

confidence: 99%

Realistic Prediction of Solid Pharmaceutical Oxidation Products by Using a Novel Forced Oxidation System

Ueyama

Tamura

Mizukawa

et al. 2014

Journal of Pharmaceutical Sciences

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The Use Of N-Methylpyrrolidone as a Cosolvent and Oxidant in Pharmaceutical Stress Testing

Cited by 28 publications

References 29 publications

Viscosity and surface tension of glycerol + N-methyl-2-pyrrolidone mixtures from 293 to 323 K

Viscosity and surface tension of glycerol + N-methyl-2-pyrrolidone mixtures from 293 to 323 K

Effect of Temperature Exposition of Casting Solution on Properties of Polysulfone Hollow Fiber Membranes

Realistic Prediction of Solid Pharmaceutical Oxidation Products by Using a Novel Forced Oxidation System

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