Solubilization, Hansen solubility parameters, and thermodynamic studies of delafloxacin in (transcutol + 1-butyl-3-methyl imidazolium hexafluorophosphate) mixtures

References

• Ray GT, Suaya JA, Baxter R. Incidence, microbiology, and patient characteristics of skin and soft-tissue infections in a U.S. population: a retrospective population based study. BMC Infect Dis. 2013;13(1):E252.
   PubMedGoogle Scholar
• Falcone M, Concia E, Giusti M, et al. Acute bacterial skin and skin structure infections in internal medicine wards: old and new drugs. Intern Emerg Med. 2016;11(5):637–648.
   PubMed Web of Science ®Google Scholar
• Markham A. Delafloxacin: first global approval. Drugs. 2017;77(13):1481–1486.
   PubMed Web of Science ®Google Scholar
• Cho JC, Crotty MP, White BP, et al. What is old is new again: delafloxacin, a modern fluoroquinolone. Pharmacotherapy. 2018;38(1):108–121.
   PubMed Web of Science ®Google Scholar
• Hatoum HT, Akhras KS, Lin SJ. The attributable clinical and economic burden of skin and skin structure infections in hospitalized patients: a matched cohort study. Diagn Microbiol Infect Dis. 2009;64(3):305–310.
   PubMed Web of Science ®Google Scholar
• Thabit AK, Crandon JL, Nicolau DP. Pharmacodynamic and pharmacokinetic profiling of delafloxacin in a murine lung model against community-acquired respiratory tract pathogens. Int J Antimicrob Agents. 2016;48(5):535–541.
   PubMed Web of Science ®Google Scholar
• Flamm RK, Rhomberg PR, Huband MD, et al. In vitro activity of delafloxacin tested against isolates of Streptococcus pneumoniae, Haemophilus influenzae, and Moraxella catarrhalis. Antimicrob Agents Chemother. 2016;60(10):6381–6385.
   PubMed Web of Science ®Google Scholar
• Carda-Broch S, Berthod A, Armstrong DW. Solvent properties of the 1-butyl-3-methylimidazolium hexafluorophosphate ionic liquid. Anal Bioanal Chem. 2003;375(2):191–199.
   PubMed Web of Science ®Google Scholar
• Welton T. Room-temperature Ionic Liquids. Solvents for Synthesis and Catalysis. Chem Rev. 1999;99(8):2071–2083.
   PubMed Web of Science ®Google Scholar
• Plechkova NV, Seddon KR. Applications of ionic liquids in the chemical industry. Chem Soc Rev. 2008;37(1):123–150.
   PubMed Web of Science ®Google Scholar
• Marrucho IM, Branco LC, Rebelo LP. Ionic liquids in pharmaceutical applications. Annu Rev Chem Biomol Eng. 2014;5:527–546.
   PubMed Web of Science ®Google Scholar
• Jaitely V, Karatas A, Florence AT. Water-immiscible room temperature ionic liquids (RTILs) as drug reservoirs for controlled release. Int J Pharm. 2008;354(1-2):168–173.
   PubMedGoogle Scholar
• Mizuuchi H, Jaitely V, Murdan S, et al. Room temperature ionic liquids and their mixtures: Potential pharmaceutical solvents. Eur J Pharm Sci. 2008;33(4-5):326–331.
   PubMed Web of Science ®Google Scholar
• Santos ADD, Morais ARC, Melo C, et al. Solubility of pharmaceutical compounds in ionic liquids. Fluid Phase Equilib. 2013;356:18–29.
   Web of Science ®Google Scholar
• Anwer MK, Muqtader M, Iqbal M, et al. Estimating the solubility, solution thermodynamics, and molecular interaction of aliskiren hemifumarate in alkylimidazolium based ionic liquids. Molecules. 2019;24(15):2807.
   PubMed Web of Science ®Google Scholar
• Berton P, Mishra MK, Choudhary H, et al. Solubility studies of cyclosporine using ionic liquids. ACS Omega. 2019;4(5):7938–7943.
   PubMed Web of Science ®Google Scholar
• Singh SK. Solubility of lignin and chitin in ionic liquids and their biomedical applications. Int J Biol Macromol. 2019;132:265–277.
   PubMed 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
• Lotfi M, Moniruzzaman M, Sivapragasam M, et al. Solubility of acyclovir in non-toxic and biodegradable ionic liquids: COSMO-RS prediction and experimental verification. J Mol Liq. 2017;243:124–131.
   Web of Science ®Google Scholar
• Faria RAM, Vieira TFM, Melo CI, et al. Solubility data as a response for a challenge for formulation chemists: imidazolium based ionic liquids and antitubercular antibiotic medicines. J Chem Eng Data. 2016;61(9):3116–3126.
   Web of Science ®Google Scholar
• Resende de Azevedo J, Letourneau J-J, Espitalier F, et al. Solubility of a new cardioactive prototype drug in ionic liquids. J Chem Eng Data. 2014;59(6):1766–1773.
   Web of Science ®Google Scholar
• Barzegar-Jalali M, Jouyban A, Martinez F, et al. Solubility and thermodynamics of lamotrigine in ternary mixtures of ionic liquids ([OMIm][Br] + [HMIm][Br] + water) at different temperatures. Chin J Chem Eng. 2020;28(1):198–207.
   Web of Science ®Google Scholar
• Shakeel F, Haq N, Alanazi FK, et al. Solubility and thermodynamic function of apremilast in different (Transcutol + water) cosolvent mixtures: measurement, correlation and molecular interactions. J Ind Eng Chem. 2017; 56:99–107.
   Web of Science ®Google Scholar
• Alshehri S, Shakeel F. Solubility determination, various solubility parameters and solution thermodynamics of sunitinib malate in some co-solvents, water and various (transcutol + water) mixtures. J Mol Liq. 2020;307:112970.
   Web of Science ®Google Scholar
• Shakeel F, Alshehri S, Imran M, et al. Experimental and computational approaches for solubility measurement of pyridazinone derivative in binary (DMSO + water) systems. Molecules. 2019;25(1):171.
   Web of Science ®Google Scholar
• Shakeel F, Imran M, Abida , et al. Solubility and thermodynamic/solvation behavior 6-phenyl-4,5-dihydropyridazin-3(2H)-one in different (transcutol + water) mixtures. J Mol Liq. 2017;230:511–517.
   Web of Science ®Google Scholar
• Anwer MK, Iqbal M, Muharram MM, et al. Development of lipomer nanoparticles for the enhancement of drug release, antimicrobial activity and bioavailability of delafloxacin. Pharm. 2020;12(3):252.
   Google Scholar
• Anwer MK, Mohammad M, Khalil NY, et al. Solubility, thermodynamics and molecular interaction studies of delafloxacin in environmental friendly ionic liquids. J Mol Liq. 2020;305:112854.
   Web of Science ®Google Scholar
• Higuchi T, Connors KA. Phase-solubility techniques. Adv Anal Chem Inst. 1965;4:117–122.
   Google Scholar
• Pinho SP, Macedo EA. Solubility of NaCl, NaBr, and KCl in water, methanol, ethanol, and their mixed solvents. J Chem Eng Data. 2005;50(1):29–32.
   Web of Science ®Google Scholar
• Zhu QN, Wang Q, Hu YB, et al. Practical determination of the solubility parameters of 1-alkyl-3-methylimidazolium bromide ([CnC1im]Br, n = 5, 6, 7, 8) ionic liquids by inverse gas chromatography and the Hansen solubility parameter. Molecules. 2019;24(7):1346.
   PubMed Web of Science ®Google Scholar
• Kalam MA, Alshehri S, Alshamsan A, et al. Solubility measurement, Hansen solubility parameters and solution thermodynamics of gemfibrozil in different pharmaceutically used solvents. Drug Dev Ind Pharm. 2019;45(8):1258–1264.
   PubMed Web of Science ®Google Scholar
• Shakeel F, Haq N, Alsarra IA, et al. Solubility, Hansen solubility parameters and thermodynamic behavior of emtricitabine in various (polyethylene glycol-400 + water) mixtures: computational modeling and thermodynamics. Molecules. 2020;25(7):1559.
   Web of Science ®Google Scholar
• Wan Y, He H, Huang Z, et al. Solubility, thermodynamic modeling and Hansen solubility parameter of 5-norbornene-2,3-dicarboximide in three binary solvents (methanol, ethanol, ethyl acetate + DMF) from 278.15 K to 323.15 K. J Mol Liq. 2020;300:112097.
   Web of Science ®Google Scholar
• Ruidiaz MA, Delgado DR, Martínez F, et al. Solubility and preferential solvation of indomethacin in 1,4-dioxane + water solvent mixtures. Fluid Phase Equilib. 2010;299(2):259–265.
   Web of Science ®Google Scholar
• Shakeel F, Haq N, Siddiqui NA. Thermodynamic solubility and solvation behavior of ferulic acid in different (PEG-400 + water) binary solvent mixtures. Drug Dev Ind Pharm. 2019;45(9):1468–1476.
   PubMed Web of Science ®Google Scholar
• Wang J, Xie C, Yin Q, et al. Measurement and correlation of solubility of cefmenoxime hydrochloride in pure solvents and binary solvent mixtures. J Chem Thermodyn. 2016;95:63–71.
   Web of Science ®Google Scholar
• Zhao K, Yang P, Du S, et al. Measurement and correlation of solubility and thermodynamics of mixing of 4-aminobutyric acid in mono-solvents and binary solvent mixtures. J Chem Thermodyn. 2016;102:276–286.
   Web of Science ®Google Scholar
• Holguín AR, Rodríguez GA, Cristancho DM, et al. Solution thermodynamics of indomethacin in propylene glycol + water mixtures. Fluid Phase Equilib. 2012;314:134–139.
   Web of Science ®Google Scholar
• Krug RR, Hunter WG, Grieger RA. Enthalpy-entropy compensation. 2. Separation of the chemical from the statistic effect. J Phys Chem. 1976;80(21):2341–2351.
   Web of Science ®Google Scholar
• Apelblat A, Manzurola E. Solubilities of o-acetylsalicylic, 4-aminosalicylic, 3,5-dinitrosalicylic and p-toluic acid and magnesium-DL-aspartate in water from T = (278–348) K. J Chem Thermodyn. 1999;31(1):85–91.
   Web of Science ®Google Scholar
• Manzurola E, Apelblat A. Solubilities of L-glutamic acid, 3-nitrobenzoic acid, acetylsalicylic, p-toluic acid, calcium-L-lactate, calcium gluconate, magnesium-DL-aspartate, and magnesium-L-lactate in water. J Chem Thermodyn. 2002;34(7):1127–1136.
   Web of Science ®Google Scholar
• Yalkowsky SH, Roseman TJ. Solubilization of drugs by cosolvents. In: SH Yalkowsky, editor. Techniques of solubilization of drugs. New York: Marcel Dekker Inc; 1981. p. 91–134.
   Google Scholar
• Jouyban A. Review of the cosolvency models for predicting solubility of drugs in water-cosolvent mixtures. J Pharm Pharm Sci. 2008;11(1):32–58.
   PubMed Web of Science ®Google Scholar
• Sotomayor RG, Holguín AR, Romdhani A, et al. Solution thermodynamics of piroxicam in some ethanol + water mixtures and correlation with the Jouyban–Acree model. J Solution Chem. 2013;42(2):358–371.
   Web of Science ®Google Scholar
• Babaei M, Shayanfar A, Rahimpour E, et al. Solubility of bosentan in {propylene glycol + water} mixtures at various temperatures: experimental data and mathematical modeling. Phys Chem Liq. 2019;57(3):338–348.
   Web of Science ®Google Scholar
• Jouyban A, Chan HK, Chew NY, et al. Solubility prediction of paracetamol in binary and ternary solvent mixtures using Jouyban-Acree model. Chem Pharm Bull (Tokyo). 2006;54(4):428–431.
   PubMed Web of Science ®Google Scholar
• Jouyban A, Acree WE. Jr. In silico prediction of drug solubility in water-ethanol mixtures using Jouyban-Acree model. J Pharm Pharm Sci. 2006;9:262–269.
   PubMed Web of Science ®Google Scholar
• Khoubnasabjafari M, Shayanfar A, Martínez F, et al. Generally trained models to predict solubility of drugs in carbitol + water mixtures at various temperatures. J Mol Liq. 2016;219:435–438.
   Web of Science ®Google Scholar
• Jouyban A, Acree WE. Mathematical derivation of the Jouyban-Acree model to represent solute solubility data in mixed solvents at various temperatures. J Chem Eng Data. 2018;256:541–547.
   Google Scholar
• Jouyban-Gharamaleki A, Hanaee J. A novel method for improvement of predictability of the CNIBS/R-K equation. Int J Pharm. 1997;154(2):245–247.
   Google Scholar