Solubility of paracetamol in binary mixtures of biodegradable betaine/ethylene glycol deep eutectic solvent and water: measurement and correlation

References

• Williams RO. Solubility and solubilization in aqueous media. Samuel H, Yalkowsky. edited By. (University of Arizona). Oxford University Press: 1999 : New York.
   Google Scholar
• Sanghvi R, Narazaki R, Machatha SG, et al. Solubility improvement of drugs using N-methyl pyrrolidone. AAPS Pharm Sci Tech. 2008;9(2):366–376.
   PubMed Web of Science ®Google Scholar
• Martinez F, Jouyban A, Acree JWE. Pharmaceuticals solubility is still nowadays widely studied everywhere. Pharm Sci. 2017;23(1):1–2.
   Google Scholar
• Jouyban A. Handbook of solubility data for pharmaceuticals. 1st ed. CRC Press: Taylor and Francis Group; 2010.
   Google Scholar
• KolaY P, Shen JW, Tsuboi A, et al. Solvent selection for pharmaceuticals. Fluid Phase Equilib. 2002;194:771–782.
   Web of Science ®Google Scholar
• Duncan CW, Watson DP, Stein A. Diagnosis and management of headache in adults: summary of SIGN guideline. BMJ. 2008;337:2329.
   PubMedGoogle Scholar
• Kalantzi L, Reppas C, Dressman JB, et al. Biowaiver monographs for immediate release solid oral dosage forms: acetaminophen (paracetamol). J Pharm Sci. 2006;95(1):4–14.
   PubMed Web of Science ®Google Scholar
• Jimenez JA, and Martinez F Thermodynamic magnitudes of mixing and solvation of acetaminophen in ethanol + water cosolvent mixtures . Rev. Aad. Colomb.Cienc 2006; 30: 87–99 .
   Google Scholar
• Hojjati H, and Rohani S. Measurement and prediction of solubility of paracetamol in water−isopropanol solution. part 2. prediction Org. Process Res. Dev 2006;10(6):1110–1118
   Web of Science ®Google Scholar
• Jouyban A, Soltanpour S, Acree JWE. Solubility of acetaminophen and ibuprofen in the mixtures of polyethylene glycol 200 or 400 with ethanol and water and the density of solute-free mixed solvents at 298.2 K. J Chem Eng Data. 2010;55(11):5252–5257.
   Web of Science ®Google Scholar
• Ahumada EA, Delgado DR, Martinez F. Solution thermodynamics of acetaminophen in some PEG 400+water mixtures. Fluid Phase Equilib. 2012;332:120–127.
   Web of Science ®Google Scholar
• Soltanpour S, Jouyban A. Solubility of acetaminophen and ibuprofen in polyethylene glycol 600, propylene glycol and water mixtures at 25°C. J Mol Liq. 2010;155(2–3):80–84.
   Web of Science ®Google Scholar
• Soltanpour S, Jouyban A. Solubility of acetaminophen and ibuprofen in polyethylene glycol 600n-methyl pyrrolidone and water mixtures. J Sol Chem. 2011;40:2032–2045.
   Web of Science ®Google Scholar
• Munoz MM, Jouyban A, Martinez F. Solubility and preferential solvation of Acetaminophen in methanol + water mixtures at 298.15 K, Phys. Chem Liq. 2016;54(4):515–528.
   Web of Science ®Google Scholar
• Shakeel F, Alanazi FA, Alsarra IA, et al. Solubilization behavior of paracetamol in transcutol–water mixtures at (298.15 to 333.15) K. J Chem Eng Data. 2013;58(12):3551–3556.
   Web of Science ®Google Scholar
• Bustamante P, Romero S, Pena A, et al. Enthalpy-entropy compensation for the solubility of drugs in solvent mixtures: paracetamol, acetanilide, and nalidixic acid in dioxane-water. J Pharm Sci. 1998;87:1590–1596.
   PubMed Web of Science ®Google Scholar
• Romdhani A, Martinez F, Almanza OA, et al. Solubility of Acetaminophen in (ethanol + propylene glycol + water) mixtures: measurement, correlation, thermodynamics, and volumetric contribution at saturation. J Mol Liq. 2020;318:114065.
   Web of Science ®Google Scholar
• Pourkarim F, Mirheydari SN, Martinez F, et al. Solubility of Acetaminophen in 1-propanol + water mixtures at T = 293.2–313.2 K. Phys Chem Liq. 2020;58(4):456–472.
   Web of Science ®Google Scholar
• Rahimpour R. Mazaher Haji Agha E, Martinez F, Barzegar-Jalali M, Jouyban A. Solubility study of acetaminophen in the mixtures of acetonitrile and water at different temperatures. J Mol Liq. 2021;324:114708.
   Web of Science ®Google Scholar
• Hajebrahimi S, Roosta A. Solubility of acetaminophen in aqueous solutions of three natural deep eutectic solvents (NADESs) and individual components of the NADESs. J Mol Liq. 2020;316:113867.
   Web of Science ®Google Scholar
• Shekaari H, Zafarani-Moattar MT, Shayanfar A, et al. Effect of choline chloride/ethylene glycol or glycerol as deep eutectic solvents on the solubility and thermodynamic properties of Acetaminophen. J Mol Liq. 2018;249:1222–1235.
   Web of Science ®Google Scholar
• Shekaari H, Zafarani-Moattar MT, Mokhtarpour M. Experimental determination and correlation of acetaminophen solubility in aqueous solutions of choline chloride based deep eutectic solvents at various temperatures. Fluid Phase Equilib. 2018;462:100–110.
   Web of Science ®Google Scholar
• Abbott AP, Capper G, Davies DL, et al. Novel solvent properties of choline chloride/urea mixtures. Chem Commun. 2003;1(1):70–71.
   Google Scholar
• Smith EL, Abbott AP, Ryder KS. Deep Eutectic Solvents (DESs) and their applications. Chem Rev. 2014;114(21):11060–11082.
   PubMed Web of Science ®Google Scholar
• Francisco M, Bruinhorst AV, Kroon MC. Low-Transition-Temperature Mixtures (LTTMs): a new generation of designer solvents. Ang Chem Int Ed. 2013;52:3074–3085.
   PubMed Web of Science ®Google Scholar
• Dai Y, Spronsen J. van, Witkamp GJ, Verpoorte R, Choi YH. Natural deep eutectic solvents as new potential media for green technology. Anal Chim Acta. 2013;766:61–68.
   PubMed Web of Science ®Google Scholar
• Yang B, Zhang Q, Fei F, et al. Biodegradable betaine-based aprotic task-specific ionic liquids and their application in efficient SO 2 absorption. Green Chem. 2015;17(7):3798–3805.
   Web of Science ®Google Scholar
• Jelinski T, Przybylek M, Cysewski M. Natural deep eutectic solvents as agents for improving solubility, stability and delivery of curcumin. Pharm Res. 2019;36:116.
   PubMed Web of Science ®Google Scholar
• Daneshjou S, Khodaverdian S, Dabirmanesh B, et al. Improvement of chondroitinases ABCI stability in natural deep eutectic solvents. J Mol Liq. 2017;227:21–25.
   Web of Science ®Google Scholar
• Radosevic K, Canak I, Panic M, et al. Antimicrobial, cytotoxic and antioxidative evaluation of natural deep eutectic solvents. Environ Sci Pollut Res Int. 2018;25:14188–14196.
   PubMed Web of Science ®Google Scholar
• Hayyan M, Looi CY, Hayyan A, et al. In vitro and in vivo toxicity profiling of ammonium-based deep eutectic solvents. PLOS ONE. 2015;10(2):0117934.
   PubMed Web of Science ®Google Scholar
• Rodrigues LA, Cardeira M, Leonardo IC, et al. Deep eutectic systems from betaine and polyols – physicochemical and toxicological properties. J Mol Liq. 2021;335:116201.
   Web of Science ®Google Scholar
• Rogosic M, Kristo A, and Kucan KZ. Deep eutectic solvents based on betaine and propylene glycol as potential denitrification agents: a liquid-liquid equilibrium study. Braz J Chem Eng. 2021; 36:1703–1716.
   Web of Science ®Google Scholar
• Fakhree MAA, Jouyban A. Experimental, computational methods pertaining to drug solubility. Toxicity Drug Test. 2012;
   Google Scholar
• Sanchez PB, Gonzalez B, Salgado J, et al. Physical properties of seven deep eutectic solvents based on l-proline or betaine. J Chem Thermodyn. 2019;131:517–523.
   Web of Science ®Google Scholar
• Jouyban A, Acree JWE. Mathematical derivation of the jouyban-acree model to represent solute solubility data in mixed solvents at various temperatures. J Mol Liq. 2018;256:541–547.
   Web of Science ®Google Scholar
• Jouyban A, Khoubnasabjafari M, Chan HK, et al. Mathematical representation of solubility of amino acids in binary aqueous-organic solvent mixtures at various temperatures using the jouyban-acree model. Pharmazie. 2006;61(9):789–792.
   PubMed Web of Science ®Google Scholar
• Fathi-Azarbayjani A, Abbasi M, Vaez-Gharamaleki J, et al. Measurement and correlation of deferiprone solubility: investigation of solubility parameter and application of van’t Hoff equation and Jouyban-Acree model. J Mol Liq. 2016;215:339–344.
   Web of Science ®Google Scholar
• Acree JWE. Mathematical representation of thermodynamic properties: part 2. derivation of the combined nearly ideal binary solvent (NIBS)/Redlich-Kister mathematical representation from a two-body and three-body interactional mixing model. Thermochim Acta. 1992;198:71–79.
   Web of Science ®Google Scholar
• Jouyban-Gharamaleki A. The modified Wilson model and predicting drug solubility in water-cosolvent mixtures. Chem Pharma Bull. 1998;46(6):1058–1061.
   Web of Science ®Google Scholar
• Prausnitz JM, Lichtenthaler RN, and de Azevedo EG. Molecular thermodynamics of fluid-phase equilibria. Amazon: Pearson Education; 1998.
   Google Scholar
• Chen CC, Britt HI, Boston JF, et al. Local composition model for excess Gibbs energy of electrolyte systems. Part I: single solvent, single completely dissociated electrolyte systems. AIChE J. 1982;28:588–596.
   Web of Science ®Google Scholar
• Wilson GM. Vapor-liquid equilibrium XI, New A. Expression for the excess free energy of mixing. J Am Chem Soc. 1964;86(2):127–130.
   Web of Science ®Google Scholar
• Renon H, Prausnitz JM. Local compositions in thermodynamic excess functions for liquid mixtures. AIChE J. 1968;14(1):135–144.
   Web of Science ®Google Scholar
• Yao G, Xia Z, Li Z. Thermodynamic study of solubility for 2-amino-4-chloro-6-methoxypyrimidine in twelve organic solvents at temperatures from 273.15 K to 323.15 K. J Chem Thermodyn. 2017;105:187–197.
   Web of Science ®Google Scholar
• Moradi M, Mazaher Haji Agha E, Hemmati S, et al. Solubility of 5-aminosalicylic acid in {N-methyl-2-pyrrolidone + ethanol} mixtures at T = (293.2 to 313.2) K. J Mol Liq. 2020;306:112774.
   Web of Science ®Google Scholar
• Li W, Chen J, Han S, et al. Thermodynamic solubility of tetraethyl ranelate in ten organic solvents at different temperatures. J Mol Liq. 2016;216:771–780.
   Web of Science ®Google Scholar
• Krug RR, Hunter WG, Grieger RA. Enthalpy-entropy compensation. 2. Separation of the chemical from the statistical effect. J Phys Chem. 1976;80(21):2341–2351.
   Web of Science ®Google Scholar
• Martinez F, Gomez A. Thermodynamic study of the solubility of some sulfonamides in octanol, water, and the mutually saturated solvents. J Sol Chem. 2001;30:909–923.
   Web of Science ®Google Scholar
• Perlovich GL, Kurkov SV, Kinchin AN, et al. Thermodynamics of solutions III: comparison of the solvation of (+)-naproxen with other NSAIDs. Eur J Pharm Biopharm. 2004;57(2):411–420.
   PubMed Web of Science ®Google Scholar
• Hojjati H, Rohani S. Measurement and prediction of solubility of paracetamol in water−isopropanol solution. part 1. measurement and data analysis. Org Process Res Dev. 2006;10(6):1101–1109.
   Google Scholar
• Picciochi R, Diogo HP, Minas da Piedade ME. Minas da Piedade ME. Thermochemistry of paracetamol. J Thermal Anal Cal. 2010;100(2):391–401
   Web of Science ®Google Scholar
• Zafarni-Moattar MT, Shekaari H, Mokhtarpour M. Experimental determination and correlation of Acetaminophen solubility in aqueous solutions of choline chloride based deep eutectic solvents at various temperatures. Fluid Phase Equilib. 2018;462:100–110.
   Web of Science ®Google Scholar
• Bustamante P, Romero S, Pena A, et al. Enthalpy-entropy compensation for the solubility of drugs in solvent mixtures: paracetamol, acetanilide, and nalidixic acid in dioxane-water. J Pharm Sci. 1998;87:1590–1596.
   PubMed Web of Science ®Google Scholar
• Granberg RA, Rasmuson AC. Solubility of paracetamol in pure solvents. J Chem Eng Data. 1999;44(6):1391–1395.
   Web of Science ®Google Scholar
• Hojjati H, Rohani S. Measurement and prediction of solubility of paracetamol in water-isopropanol solution. part 1. measurement and data analysis. Org Process Res Dev. 2006;10(6):1101–1109.
   Web of Science ®Google Scholar
• Soltanpour S, Jouyban A, Acree JWE. Solubility of Acetaminophen and ibuprofen in the mixtures of polyethylene glycol 200 or 400 with ethanol and water and the density of solute-free mixed solvents at 298.2 K. J Chem Eng Data. 2010;55(11):5252–5257.
   Web of Science ®Google Scholar
• Smith KB, Bridson RH, Leeke GA. Solubilities of pharmaceutical compounds in ionic liquids. J Chem Eng Data. 2011;56(5):2039–2043.
   Web of Science ®Google Scholar
• Shakeel F, Alanazi FK, Alsarra IA, et al. Solubilization behavior of paracetamol in transcutol-water mixtures at (298.15 to 333.15) K. J Chem Eng Data. 2013;58(12):3551–3556.
   Web of Science ®Google Scholar
• Mehrdad A, Miri AH. Influence of 1-butyl-3-methyl imidazolium bromide, ionic liquid as co-solvent on aqueous solubility of Acetaminophen. J Mol Liq. 2016;221:1162–1167.
   Web of Science ®Google Scholar
• Barzegar-Jalali M, Jafari P, and Jouyban A. Thermodynamic study of the aqueous pseudo-binary mixtures of betaine-based deep eutectic solvents at T = (293.15 to 313.15) K. Phys Chem Liq. 2022; 60:2024539.
   Web of Science ®Google Scholar
• Soltanpour S, Jouyban A. Solubility of acetaminophen and ibuprofen in binary and ternary mixtures of polyethylene glycol 600, ethanol and water. Chem Pharm Bull. 2010;58(2):219–224.
   PubMed Web of Science ®Google Scholar