Modeling solubility of oxaprozin and irbesartan in biorelevant complex solutions based on a combination of pH-dependent and micellar solubilization models

doi:10.1016/j.cjche.2024.03.025

中国化学工程学报 ›› 2024, Vol. 72 ›› Issue (8): 34-43.DOI: 10.1016/j.cjche.2024.03.025

Modeling solubility of oxaprozin and irbesartan in biorelevant complex solutions based on a combination of pH-dependent and micellar solubilization models

Chen Shen, Yuanhui Ji

Jiangsu Province Hi-Tech Key Laboratory for Biomedical Research, School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, China

收稿日期:2023-11-28 修回日期:2024-03-05 出版日期:2024-08-28 发布日期:2024-10-17
通讯作者: Yuanhui Ji,E-mail:yuanhui.ji@seu.edu.cn,yuanhuijinj@163.com.Tel.:+86 13951907361
基金资助:
This work received the financial support from the National Natural Science Foundation of China (22278070, 21978047, 21776046).

Modeling solubility of oxaprozin and irbesartan in biorelevant complex solutions based on a combination of pH-dependent and micellar solubilization models

Chen Shen, Yuanhui Ji

Jiangsu Province Hi-Tech Key Laboratory for Biomedical Research, School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, China

Received:2023-11-28 Revised:2024-03-05 Online:2024-08-28 Published:2024-10-17
Contact: Yuanhui Ji,E-mail:yuanhui.ji@seu.edu.cn,yuanhuijinj@163.com.Tel.:+86 13951907361
Supported by:
This work received the financial support from the National Natural Science Foundation of China (22278070, 21978047, 21776046).

摘要/Abstract

摘要： Biological solubility is one of the important basic parameters in the development process of poorly soluble drugs, but the current measurement methods are mainly based on a large number of experiments, which are time-consuming and cost-intensive. There is still a lack of effective theoretical models to accurately describe and predict the biological solubility of drugs to reduce costs. Therefore, in this study, osaprazole and irbesartan were selected as model drugs, and their solubility in solutions containing surfactants and biorelevant media was measured experimentally. By calculating the parameters of each component using the perturbed-chain statistical associating fluid theory (PC-SAFT) model, combined with pH-dependent and micellar solubilization models, the thermodynamic phase behavior of the two drugs was successfully modeled, and the predicted results were in good agreement with the experimental values. These results demonstrate that the model combination used provides important basic parameters and theoretical guidance for the development and screening of poorly soluble drugs and related formulations.

关键词: Biorelevant media, pH-dependent solubility, Micellar solubilization, PC-SAFT, Active pharmaceutical ingredients

Abstract: Biological solubility is one of the important basic parameters in the development process of poorly soluble drugs, but the current measurement methods are mainly based on a large number of experiments, which are time-consuming and cost-intensive. There is still a lack of effective theoretical models to accurately describe and predict the biological solubility of drugs to reduce costs. Therefore, in this study, osaprazole and irbesartan were selected as model drugs, and their solubility in solutions containing surfactants and biorelevant media was measured experimentally. By calculating the parameters of each component using the perturbed-chain statistical associating fluid theory (PC-SAFT) model, combined with pH-dependent and micellar solubilization models, the thermodynamic phase behavior of the two drugs was successfully modeled, and the predicted results were in good agreement with the experimental values. These results demonstrate that the model combination used provides important basic parameters and theoretical guidance for the development and screening of poorly soluble drugs and related formulations.

Key words: Biorelevant media, pH-dependent solubility, Micellar solubilization, PC-SAFT, Active pharmaceutical ingredients

Chen Shen, Yuanhui Ji. Modeling solubility of oxaprozin and irbesartan in biorelevant complex solutions based on a combination of pH-dependent and micellar solubilization models[J]. 中国化学工程学报, 2024, 72(8): 34-43.

参考文献

[1] S. Stegemann, F. Leveiller, D. Franchi, H. de Jong, H. Linden, When poor solubility becomes an issue: from early stage to proof of concept, Eur. J. Pharm. Sci. 31 (5) (2007) 249-261.
[2] D.M. Mudie, G.L. Amidon, G.E. Amidon, Physiological parameters for oral delivery and in vitro testing, Mol. Pharm. 7 (5) (2010) 1388-1405.
[3] E. Galia, E. Nicolaides, D. Horter, R. Lobenberg, C. Reppas, J.B. Dressman, Evaluation of various dissolution media for predicting in vivo performance of class I and II drugs, Pharm. Res. 15 (5) (1998) 698-705.
[4] B. Hens, Y. Tsume, M. Bermejo, P. Paixao, M.J. Koenigsknecht, J.R. Baker, W.L. Hasler, R. Lionberger, J.H. Fan, J. Dickens, K. Shedden, B. Wen, J. Wysocki, R. Loebenberg, A. Lee, A. Frances, G. Amidon, A. Yu, G. Benninghoff, N. Salehi, A. Talattof, D.X. Sun, G.L. Amidon, Low buffer capacity and alternating motility along the human gastrointestinal tract: implications for in vivo dissolution and absorption of ionizable drugs, Mol. Pharm. 14 (12) (2017) 4281-4294.
[5] L. Klumpp, K. Nagasekar, O. McCullough, A. Seybert, M. Ashtikar, J. Dressman, Stability of biorelevant media under various storage conditions, Dissolution Technol. 26 (2) (2019) 6-18.
[6] C. Markopoulos, C.J. Andreas, M. Vertzoni, J. Dressman, C. Reppas, In-vitro simulation of luminal conditions for evaluation of performance of oral drug products: Choosing the appropriate test media, Eur. J. Pharm. Biopharm. 93 (2015) 173-182.
[7] B. Yang, C.N. Wu, B. Ji, X.Y. Ai, X. Kuang, M.R. Wu, M.C. Sun, C. Luo, Z.G. He, J. Sun, The biorelevant concentration of Tween 80 solution is a simple alternative medium to simulated fasted state intestinal fluid, RSC Adv. 5 (127) (2015) 104846-104853.
[8] A. Pobudkowska, U. Domanska, Study of pH-dependent drugs solubility in water, Chem. Ind. Chem. Eng. Q. 20 (1) (2014) 115-126.
[9] A. Niederquell, M. Kuentz, Biorelevant drug solubility enhancement modeled by a linear solvation energy relationship, J. Pharm. Sci. 107 (1) (2018) 503-506.
[10] K. Dong, F. Huo, S.J. Zhang, Thermodynamics at microscales: 3D→2D, 1D and 0D, Green Energy Environ. 5 (3) (2020) 251-258.
[11] N.T. Hansen, I. Kouskoumvekaki, F.S. Joergensen, S. Brunak, S.O. Jonsdottir, Prediction of pH-dependent aqueous solubility of druglike molecules, J. Chem. Inf. Model. 46 (6) (2006) 2601-2609.
[12] M.A. McDonald, A.S. Bommarius, R.W. Rousseau, Enzymatic reactive crystallization for improving ampicillin synthesis, Chem. Eng. Sci. 165 (2017) 81-88.
[13] J.B. Gao, P. Wang, Z.K. Wang, C.L. Li, S.Q. Sun, S.Q. Hu, Self-assembly of DCPD-loaded cross-linked micelle from triblock copolymers and its pH-responsive behavior: a dissipative particle dynamics study, Chem. Eng. Sci. 195 (2019) 325-334.
[14] M.J. Abdekhodaie, J. Cheng, X.Y. Wu, Effect of formulation factors on the bioactivity of glucose oxidase encapsulated chitosan-alginate microspheres: in vitro investigation and mathematical model prediction, Chem. Eng. Sci. 125 (2015) 4-12.
[15] C.A.S. Bergstrom, K. Luthman, P. Artursson, Accuracy of calculated pH-dependent aqueous drug solubility, Eur. J. Pharm. Sci. 22 (5) (2004) 387-398.
[16] E. Fuguet, X. Subirats, C. Rafols, E. Bosch, A. Avdeef, Ionizable drug self-associations and the solubility dependence on pH: detection of aggregates in saturated solutions using mass spectrometry (ESI-Q-TOF-MS/MS), Mol. Pharm. 18 (6) (2021) 2311-2321.
[17] Y.W. Wardhana, E.N. Aisyah, I. Sopyan, T. Rusdiana, In vitro solubility and release profile correlation with pKa value of efavirenz polymorphs, Dissolution Technol. 28 (3) (2021) 14-22.
[18] A.T.M. Serajuddin, Salt Formation to improve drug solubility, Adv. Drug Deliv. Rev. 59 (7) (2007) 603-616.
[19] L.W. Dittert, T. Higuchi, D.R. Reese, Phase solubility technique in studying the formation of complex salts of triamterene, J. Pharm. Sci. 53 (1964) 1325-1328.
[20] J. Lakra, D. Tikariha, T. Yadav, M.L. Satnami, K.K. Ghosh, Study of solubility efficiency of polycyclic aromatic hydrocarbons in single surfactant systems, J. Surfactants Deterg. 16 (6) (2013) 957-966.
[21] I. Ullah, M.K. Baloch, G.F. Durrani, Solubility of LIDOCAINE in ionic, nonionic and zwitterionic surfactants, J. Solut. Chem. 41 (2) (2012) 215-222.
[22] X.J. Liang, M.L. Zhang, C.L. Guo, S. Abel, X.Y. Yi, G.N. Lu, C. Yang, Z. Dang, Competitive solubilization of low-molecular-weight polycyclic aromatic hydrocarbons mixtures in single and binary surfactant micelles, Chem. Eng. J. 244 (2014) 522-530.
[23] J. Wei, G.H. Huang, H. Yu, C.J. An, Efficiency of single and mixed Gemini/conventional micelles on solubilization of phenanthrene, Chem. Eng. J. 168 (1) (2011) 201-207.
[24] R. Nagarajan, E. Ruckenstein, Theory of surfactant self-assembly: a predictive molecular thermodynamic approach, Langmuir 7 (12) (1991) 2934-2969.
[25] A. Khoshnood, B. Lukanov, A. Firoozabadi, Temperature effect on micelle formation: molecular thermodynamic model revisited, Langmuir 32 (9) (2016) 2175-2183.
[26] E. Jantratid, N. Janssen, C. Reppas, J.B. Dressman, Dissolution media simulating conditions in the proximal human gastrointestinal tract: an update, Pharm. Res. 25 (7) (2008) 1663-1676.
[27] J. Gross, G. Sadowski, Perturbed-chain SAFT: an equation of state based on a perturbation theory for chain molecules, Ind. Eng. Chem. Res. 40 (4) (2001) 1244-1260.
[28] J. Gross, G. Sadowski, Application of the perturbed-chain SAFT equation of state to associating systems, Ind. Eng. Chem. Res. 41 (22) (2002) 5510-5515.
[29] C. Held, T. Reschke, S. Mohammad, A. Luza, G. Sadowski, ePC-SAFT revised, Chem. Eng. Res. & Des. 92 (2014) 2884-2897.
[30] J.P. Wolbach, S.I. Sandler, Using molecular orbital calculations to describe the phase behavior of cross-associating mixtures, Ind. Eng. Chem. Res. 37 (8) (1998) 2917-2928.
[31] J. Cassens, A. Prudic, F. Ruether, G. Sadowski, Solubility of pharmaceuticals and their salts As a function of pH, Ind. Eng. Chem. Res. 52 (7) (2013) 2721-2731.
[32] P. Tosco, B. Rolando, R. Fruttero, Y. Henchoz, S. Martel, P.A. Carrupt, A. Gasco, Physicochemical profiling of sartans: a detailed study of ionization constants and distribution coefficients, Helv. Chim. Acta 91 (3) (2008) 468-482.
[33] Y.Y. Jiang, K. Ge, Y.H. Ji, Modeling and prediction of thermodynamic phase behaviors of oxaprozin and irbesartan in biorelevant media, Fluid Phase Equilib. 571 (2023) 113806.
[34] L.A. Moreira, A. Firoozabadi, Thermodynamic modeling of the duality of linear 1-alcohols as cosurfactants and cosolvents in self-assembly of surfactant molecules, Langmuir 25 (20) (2009) 12101-12113.
[35] K. Ge, R. Paus, V. Penner, G. Sadowski, Y.H. Ji, Theoretical modeling and prediction of biorelevant solubility of poorly soluble pharmaceuticals, Chem. Eng. J. 444 (2022) 136678.
[36] L. Moreira, A. Firoozabadi, Molecular thermodynamic modeling of specific ion effects on micellization of ionic surfactants, Langmuir 26 (19) (2010) 15177-15191.
[37] W.F. McDevit, F.A. Long, The activity coefficient of benzene in aqueous salt solutions, J. Am. Chem. Soc. 74 (7) (1952) 1773-1777.
[38] K. Ge, Y.H. Ji, X.H. Lu, A novel interfacial thermodynamic model for predicting solubility of nanoparticles coated by stabilizers, Chin. J. Chem. Eng. 31 (2021) 103-112.
[39] D. Kumar, M.A. Rub, Effect of anionic surfactant and temperature on micellization behavior of promethazine hydrochloride drug in absence and presence of urea, J. Mol. Liq. 238 (2017) 389-396.
[40] C.A. Ericsson, O. Soderman, V.M. Garamus, M. Bergstrom, S. Ulvenlund, Effects of temperature, salt, and deuterium oxide on the self-aggregation of alkylglycosides in dilute solution. 1. n-nonyl-beta-D-glucoside, Langmuir 20 (4) (2004) 1401-1408.
[41] H.M. Cassel, Critical concentration of micelle solutions, J. Chem. Phys. 61 (1) (1974) 430.
[42] F. Gadelle, W.J. Koros, R.S. Schechter, Solubilization isotherms of aromatic solutes in surfactant aggregates, J. Colloid Interface Sci. 170 (1) (1995) 57-64.
[43] N. Salehi, J. Al-Gousous, D.M. Mudie, G.L. Amidon, R.M. Ziff, G.E. Amidon, Hierarchical mass transfer analysis of drug particle dissolution, highlighting the hydrodynamics, pH, particle size, and buffer effects for the dissolution of ionizable and nonionizable drugs in a compendial dissolution vessel, Mol. Pharm. 17 (10) (2020) 3870-3884.
[44] K. Ge, Y.H. Ji, A thermodynamic approach for predicting thermodynamic phase behaviors of pharmaceuticals in biorelevant media, Chem. Eng. Sci. 261 (2022) 117973.
[45] S. Chakraborty, D. Shukla, A. Jain, B. Mishra, S. Singh, Assessment of solubilization characteristics of different surfactants for carvedilol phosphate as a function of pH, J. Colloid Interface Sci. 335 (2) (2009) 242-249.
[46] Y. Wu, Y. Wang, T. Lei, Y. Xia, The solubilization capability of polycyclic aromatic hydrocarbons enhanced by biosurfactant saponin mixed with conventional chemical surfactants, Petrol. Sci. Technol. 32 (1) (2014) 108-115.
[47] S. Tiwari, J. Ma, S. Rathod, P. Bahadur, Solubilization of quercetin in P123 micelles: Scattering and NMR studies, Colloids Surf. A Physicochem. Eng. Aspects 621 (2021) 126555.
[48] P.A. Bhat, A. Dar, G.M. Rather, Solubilization capabilities of some cationic, anionic, and nonionic surfactants toward the poorly water-soluble antibiotic drug erythromycin, J. Chem. & Eng. Data 53 (2008) 1271-1277.

Modeling solubility of oxaprozin and irbesartan in biorelevant complex solutions based on a combination of pH-dependent and micellar solubilization models

Modeling solubility of oxaprozin and irbesartan in biorelevant complex solutions based on a combination of pH-dependent and micellar solubilization models

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 1

编辑推荐

Metrics

本文评价