Solvation dynamics of furazolidone in pure organic solvents and aqueous EDTA disodium salt mixtures: molecular interactions and thermodynamic insights

doi:10.5246/jcps.2024.10.065

Abstract

Abstract:

This study systematically examined the dissolution behavior of furazolidone in 12 different pure solvents and in aqueous solutions containing ethylenediaminetetraacetic acid disodium salt (EDTA-2Na). The solubility data indicated that polar aprotic solvents demonstrated a marginally higher solubility of furazolidone compared to alcohols and water. Interestingly, a co-solvency effect was observed in the aqueous solutions of EDTA-2Na, where the solubility of furazolidone initially increased and then decreased with the gradual addition of EDTA-2Na, peaking at a mass fraction of 0.03 (1.949 × 10^–5 at 323.15 K). The analysis using the Kamlet-Abboud-Taft Linear Solvation Energy Relationship (KAT-LSER) model suggested that the dissolution of furazolidone in these systems was predominantly influenced by non-specific solute-solvent and solvent-solvent interactions. Furthermore, Hansen solubility parameter calculations revealed that N,N-dimethylformamide (DMF) and N,N-dimethylacetamide (DMAC) exhibited superior dissolution capabilities compared to other solvents. It was also found that the partial solubility parameters played a crucial role in determining the overall solubility behavior.

Key words: Furazolidone, Solubility, Co-solvency phenomenon, Correlation of thermodynamic models

Supporting: /attached/file/20241104/20241104005827_401.pdf

Yufang Wu, Qingzhi Guo, Rui Li, Shikun Zhang. Solvation dynamics of furazolidone in pure organic solvents and aqueous EDTA disodium salt mixtures: molecular interactions and thermodynamic insights[J]. Journal of Chinese Pharmaceutical Sciences, 2024, 33(10): 906-917.

Figures/Tables 8

Table 1. Experimental and calculated mole fraction solubility of furazolidone in the solvent at the temperature range from T = (283.15 to 323.15) K under 101.1 kPa.a

Table 2. Hildebrand solubility parameters (δH) and solvatochromic parameters α, β, and π* for the selected solvents.a

Table 3. Values of solvents polarity, HSPs of furazolidone, and selected solvents.a

Table 4. The apparent dissolution thermodynamics parameters of furazolidone in pure and mixed solvents at mean harmonic temperature (302.60 K).

References 44

[1]	Silva, K.M.M.N.; de Carvalho, D.É.L.; Valente, V.M.M.; Campos Rubio, J.C.; Faria, P.E.; Silva-Caldeira, P.P. Concomitant and controlled release of furazolidone and bismuth(III) incorporated in a cross-linked sodium alginate-carboxymethyl cellulose hydrogel. Int. J. Biol. Macromol. 2019, 126, 359–366.
[2]	Eisig, J.N.; Silva, F.M.; Rodriguez, T.N.; Hashimoto, C.L.; Barbuti, R.C. A furazolidone-based quadruple therapy for Helicobacter pylori retreatment in patients with peptic ulcer disease. Clinics. (Sao Paulo). 2005, 60, 485–488.
[3]	Raether, W.; Hänel, H. Nitroheterocyclic drugs with broad spectrum activity. Parasitol. Res. 2003, 90, S19–S39.
[4]	Upcroft, P.; Upcroft, J.A. Drug targets and mechanisms of resistance in the anaerobic protozoa. Clin. Microbiol. Rev. 2001, 14, 150–164.
[5]	Li, D.; Zang, M.W.; Wang, S.W.; Zhang, K.H.; Zhang, Z.Q.; Li, X.M.; Li, J.C.; Guo, W.P. Food fraud of rejected imported foods in China in 2009–2019. Food Contr. 2022, 133, 108619.
[6]	Tawiah, B.; Badoe, W.; Fu, S. Advances in the development of animicrobial agents for texiles: the quest for natural products. Fibres Tex. East. Eur. 2018, 24, 136-149.
[7]	https://www.nmpa.gov.cn/xxgk/ggtg/ypggtg/ypqtggtg/ 20190215114101621.html.
[8]	Wu, X. D.; Chou, F. J. Furazolidone synthesis and purification method. CN 101450944 June 10, 2009.
[9]	Shuai, F.W.; Wang, X.F.; Zhang, J.W. Production method of medicinal furazolidone. CN Patent 108069953 May 25, 2018.
[10]	Badu-Tawiah, A.; Bland, C.; Campbell, D.I.; Cooks, R.G. Non-aqueous spray solvents and solubility effects in desorption electrospray ionization. J. Am. Soc. Mass Spectrom. 2010, 21, 572–579.
[11]	Li, R.R.; Yin, X.F.; Jin, Y.X.; Chen, X.L.; Zhao, B.; Wang, W.; Zhong, S.Y.; Han, D.M. The solubility profile and dissolution thermodynamic properties of minocycline hydrochloride in some pure and mixed solvents at several temperatures. J. Chem. Thermodyn. 2021, 157, 106399.
[12]	Chen, X.; Xu, Q.Q.; Liu, Z.Y.; Zhu, X.L.; Zheng, H.L.; Zhao, J.; Li, R.R.; Han, D.M. Solubility determination, model correlation, and solvent effect analysis of nisoldipine in different solvent systems at a series of temperature. J. Chem. Eng. Data. 2020, 65, 1627–1635.
[13]	Li, R.R.; Jin, Y.X.; Yu, B.B.; Xu, Q.Q.; Chen, X.L.; Han, D.M. Solubility determination and thermodynamic properties calculation of macitentan in mixtures of ethyl acetate and alcohols. J. Chem. Thermodyn. 2021, 156, 106344.
[14]	Chen, X.L.; Zhao, B.; Tang, T.; Yin, X.F.; Li, R.R.; Han, D.M. The co-solvency and thermodynamic properties of camptothecin in mixtures of (ethyl acetate + methanol/ethanol). J. Chem. Thermodyn. 2021, 163, 106592.
[15]	Li, R.R.; Tang, T.; Yin, X.F.; Yao, L.S.; Lin, Z.P.; Zhang, L.; Gao, X.; Xu, X.J.; Zhao, J.; Han, D.M. Solubility of naftopidil in pure and mixed solvents at 273.15–313.15 K and its correlation with the Jouyban-Acree and CNIBS/R-K models. J. Chem. Thermodyn. 2020, 145, 105969.
[16]	Wu, Y.; Di, Y.C.; Zhang, X.L.; Zhang, Y.T. Solubility determination and thermodynamic modeling of 3-methyl-4-nitrobenzoic acid in twelve organic solvents from T = (283.15–318.15) K and mixing properties of solutions. J. Chem. Thermodyn. 2016, 102, 257–269.
[17]	Wu, Y.; Qin, Y.; Bai, L.; Kang, Y.; Zhang, Y.T. Determination and thermodynamic modelling for 4-nitropyrazole solubility in (methanol+water), (ethanol+water) and (acetonitrile+water) binary solvent mixtures from T = (278.15 to 318.15) K. J. Chem. Thermodyn. 2016, 103, 276–284.
[18]	Marian, E.; Jurca, T.; Kacso, I.; Miclaus, M.; Bratu, I. Interactions analysis between furazolidone and excipients used in pharmaceutical forms. Rev. De Chim. 2013, 64, 1275–1278.
[19]	Smallwood, I.M. Handbook of organic solvent properties. Amoled: London, 1996.
[20]	Mohammad, M.A.; Alhalaweh, A.; Velaga, S.P. Hansen solubility parameter as a tool to predict cocrystal formation. Int. J. Pharm. 2011, 407, 63–71.
[21]	He, Z.C.; Zhang, J.Y.; Gao, X.; Tang, T.; Yin, X.F.; Zhao, J.; Li, R.R.; Han, D.M. Solubility determination, correlation, and solute-solvent molecular interactions of 5-aminotetrazole in various pure solvents. J. Chem. Eng. Data. 2019, 64, 3988–3993.
[22]	Kamlet, M.J.; Abboud, J.L.M.; Taft, R.W. An examination of linear solvation energy relationships. Prog. Phys. Org. Chem. 2007, 13, 485–630.
[23]	Zheng, M.; Farajtabar, A.; Zhao, H.K. Solute-solvent and solvent-solvent interactions and preferential solvation of hesperidin in aqueous cosolvent mixtures of ethanol, isopropanol, propylene glycol and n-propanol. J. Mol. Liq. 2018, 264, 285–291.
[24]	Li, R.R.; Chen, X.L.; He, G.H.; Wu, C.L.; Gan, Z.X.; He, Z.C.; Zhao, J.; Han, D.M. The dissolution behaviour and thermodynamic properties calculation of praziquantel in pure and mixed organic solvents. J. Chem. Thermodyn. 2020, 144, 106062.
[25]	Marcus, Y. The properties of organic liquids that are relevant to their use as solvating solvents. Chem. Soc. Rev. 1993, 22, 409–416.
[26]	Du, C.B.; Li, R.R.; Chen, L. Dissolution thermodynamic properties calculation and intermolecular interaction analysis of diacerein in different pure and mixed solvents. J. Chem. Thermodyn. 2022, 173, 106850.
[27]	Du, C.B.; Luo, Y.L.; Huang, C.Y.; Li, R.R. Solubility measurement and thermodynamic model correlation of baclofen in 12 pure organic solvents. J. Chem. Eng. Data. 2022, 67, 2655–2661.
[28]	Williams, D.; Kuklenz, K. A determination of the Hansen solubility parameters of hexanitrostilbene (HNS). Propellants Explos. Pyrotech. 2009, 34, 452–457.
[29]	Hansen, C.M. Hansen Solubility Parameters: A User’s Handbook, Second Edition. CRC Press. 2007.
[30]	Belmares, M.; Blanco, M.; Goddard, W.A. 3rd, Ross, R.B.; Caldwell, G.; Chou, S.H.; Pham, J.; Olofson, P.M.; Thomas, C. Hildebrand and Hansen solubility parameters from molecular dynamics with applications to electronic nose polymer sensors. J. Comput. Chem. 2004, 25, 1814–1826.
[31]	Mohammad Azmin, S.N.H.; Mustaffa, A.A.; Wan Alwi, S.R.; Manan, Z.A.; Chua, L.S. Solubility parameter prediction for Kacip Fatimah herb using group contribution-based models. Comput. Aided Chem. Eng. Amsterdam: Elsevier. 2014, 33, 1225–1230.
[32]	Just, S.; Sievert, F.; Thommes, M.; Breitkreutz, J. Improved group contribution parameter set for the application of solubility parameters to melt extrusion. Eur. J. Pharm. Biopharm. 2013, 85, 1191–1199.
[33]	Manzurola, E.; Apelblat, A. Solubilities of L-glutamic acid, 3-nitrobenzoic acid, p-toluic acid, calcium-L-lactate, calcium gluconate, magnesium-DL-aspartate, and magnesium-L-lactate in water. J. Chem. Thermodyn. 2002, 34, 1127–1136.
[34]	Li, R.R.; Wang, W.; Chen, X.L.; Chen, H.; Bao, H.H.; Zhu, Y.W.; Zhao, J.; Han, D.M. Equilibrium solubility determination and correlation of monobenzone in fifteen monosolvents at a series of temperatures. J. Chem. Eng. Data. 2020, 65, 2300–2309.
[35]	Li, R.R.; Ye, S.F.; Chen, Y.F.; Jiang, M.; Jin, Y.X.; Jia, W.P.; Chen, X.Y.; Zhan, S.Y.; Han, D.M. Solubility of sulfachloropyridazine in pure and binary solvent mixtures and investigation of intermolecular interactions. J. Chem. Eng. Data. 2018, 63, 2002–2008.
[36]	Buchowski, H.; Ksiazczak, A.; Pietrzyk, S. Solvent activity along a saturation line and solubility of hydrogen-bonding solids. J. Phys. Chem. 1980, 84, 975–979.
[37]	Li, R.R.; Zhan, S.Y.; Chen, G.; Jin, Y.X.; Yu, B.B.; Zhao, J.; Han, D.M.; Fan, H.J. Equilibrium solubility, model correlation, and solvent effect of indole-3-acetic acid in twelve pure solvents. J. Chem. Eng. Data. 2019, 64, 1802–1808.
[38]	Chen, X.Y.; Zhan, S.Y.; Chen, Y.F.; Jin, Y.X.; Zeng, L.L.; Zhao, J.; Li, R.R.; Han, D.M. Solubility measurement and modeling of 1-(3-nitrophenyl)ethanone and 1-(4-nitrophenyl)ethenone in nine pure organic solvents from T = (278.15 to 318.15) K and mixing properties of solutions. J. Chem. Eng. Data. 2018, 63, 2875–2887.
[39]	Jouyban, A.; Acree, W.E.; Martínez, F. Dissolution thermodynamics and preferential solvation of ketoconazole in some{ethanol (1) + water (2)} mixtures. J. Mol. Liq. 2020, 313, 113579.
[40]	Romdhani, A.; Martínez, F.; Almanza, O.A.; Jouyban, A.; Acree, W.E. Solubility of acetaminophen in (ethanol + propylene glycol + water) mixtures: measurement, correlation, thermodynamics, and volumetric contribution at saturation. J. Mol. Liq. 2020, 318, 114065.
[41]	Li, R.R.; Yin, X.F.; Zhang, J.Y.; Tang, T.; Fang, X.C.; Zhang, L.B.; Xu, W.J.; Zhao, J.; Han, D.M. Improving the solubility of temozolomide by cosolvent and its correlation with the Jouyban-Acree and CNIBS/R-K models. J. Chem. Thermodyn. 2019, 139, 105875.
[42]	Wu, X.Y.; Yin, X.F.; Tang, T.; Zheng, H.L.; Xu, W.J.; Lin, Z.P.; Chen, X.L.; Li, R.R.; Zhao, J.; Han, D.M. Solubility of edaravone in four mixed solvents at 273.15–313.15 K and correlation of jouyban-acree and CNIBS/R-K models. J. Chem. Eng. Data. 2020, 65, 1460–1467.
[43]	Chen, Y.H.; Luo, Z.Y.; Ren, Z.X.; Shen, L.B.; Li, R.R.; Chen, L.; Du, C.B. The interactions and thermodynamic parameters of lenvatinib mesylate in pure and mixed solvents at several temperatures. J. Chem. Thermodyn. 2023, 176, 106922.
[44]	Wan, Y.M.; He, H.X.; Zhang, P.S.; Huang, Z.B.; Zhao, R.; Sha, J.; Li, T.; Ren, B.Z. Solid-liquid equilibrium solubility and thermodynamic properties of cis-5-norbornene-endo-2,3-dicarboxylic anhydride in fourteen pure solvents and three binary solvents at various temperatures. J. Mol. Liq. 2020, 297, 111396.