Ternary phase diagrams and solvate transformation thermodynamics of omeprazole sodium in different solvent mixtures

doi:10.1016/j.cjche.2018.07.016

Abstract

Abstract: Omeprazole sodium (OMS), a typical non-hydrogen bond donors API, is only available in solvates so far, including monohydrate, ethanol solvate and methanol solvate. The methanol solvate was found for the first time. Solvate transformation thermodynamics of OMS was studied in this paper. First, the ternary phase diagrams forming two solvates for OMS in binary solvent mixtures including methanol + water, ethanol + water, and methanol + ethanol were measured at temperature ranging of T=(278.15 to 313.15) K under atmospheric pressure. Further, the standard equilibrium constants of the solvate transformation reactions were evaluated according to the chemical reaction isothermal equation. The standard molar Gibbs free energy, the standard molar enthalpy, and the standard molar entropy of solvate transformation reactions were then calculated based on van't Hoff equation. Moreover, the thermodynamic stability of the OMS solvate was analyzed based on phase diagram. The results are of great importance to develop a crystallization process for manufacturing OMS solvate, and could be helpful to other solvate transformation research.

Key words: Omeprazole sodium, Solvate, Phase equilibria, Ternary phase diagram, Chemical reaction, Thermodynamics

摘要： Omeprazole sodium (OMS), a typical non-hydrogen bond donors API, is only available in solvates so far, including monohydrate, ethanol solvate and methanol solvate. The methanol solvate was found for the first time. Solvate transformation thermodynamics of OMS was studied in this paper. First, the ternary phase diagrams forming two solvates for OMS in binary solvent mixtures including methanol + water, ethanol + water, and methanol + ethanol were measured at temperature ranging of T=(278.15 to 313.15) K under atmospheric pressure. Further, the standard equilibrium constants of the solvate transformation reactions were evaluated according to the chemical reaction isothermal equation. The standard molar Gibbs free energy, the standard molar enthalpy, and the standard molar entropy of solvate transformation reactions were then calculated based on van't Hoff equation. Moreover, the thermodynamic stability of the OMS solvate was analyzed based on phase diagram. The results are of great importance to develop a crystallization process for manufacturing OMS solvate, and could be helpful to other solvate transformation research.

关键词: Omeprazole sodium, Solvate, Phase equilibria, Ternary phase diagram, Chemical reaction, Thermodynamics

Meitang Jin, Zhao Xu, Ying Bao, Long Li, Liping Wang, Haijiao Lu, Chuang Xie, Hongxun Hao. Ternary phase diagrams and solvate transformation thermodynamics of omeprazole sodium in different solvent mixtures[J]. Chin.J.Chem.Eng., 2019, 27(2): 362-368.

References

[1] B. Bechtloff, S. Nordhoff, J. Ulrich, Pseudopolymorphs in Industrial Use, Cryst. Res. Technol. 36(2001) 1315-1328.

[2] H.G. Brittain, Polymorphism and Solvatomorphism 2010, J. Pharm. Sci. 101(2010) 464-484.

[3] Sudha R. Vippagunta, H.G. Brittain, D.J.W. Grant, Crystalline solids, Adv. Drug Deliv. Rev. 48(2001) 3-26.

[4] J. van de Streek, All series of multiple solvates (including hydrates) from the Cambridge Structural Database, CrystEngComm 9(2007) 350-352.

[5] S. Mittapalli, G. Bolla, S. Perumalla, A. Nangia, Can we exchange water in a hydrate structure:a case study of etoricoxib, CrystEngComm 18(2016) 2825-2829.

[6] P. Grobelny, A. Mukherjee, G.R. Desiraju, Polymorphs and hydrates of Etoricoxib, a selective COX-2 inhibitor, CrystEngComm 14(2012) 5785-5794.

[7] F.S. Murakami, K.L. Lang, C. Mendes, A.P. Cruz, M.A.S. Carvalho, M.A.S. Silva, Physicochemical solid-state characterization of omeprazole sodium:Thermal, spectroscopic and crystallinity studies, J. Pharm. Biomed. Anal. 49(2009) 72-80.

[8] L. Vranicar Savanovic, Z. Ham, J. Rzen, Crystalline solvate of omeprazole sodium, WO Pat., 200613138-A2, 2006.

[9] L. Li, Study on the Preparation of Omeprazole Sodium Solvates, Master's Thesis, TianJin University, TianJin, 2016.

[10] Y. Bao, L. Tao, L. Li, H. Hao, J. Lv, B. Hou, New omeprazole sodium 1, 2-propylene glycol solvate contains 1,2-propylene glycol in preset molar ratio, CN Pat., 104844572-A, 2015.

[11] C. Liu, L. Dang, W. Bai, R. Wang, H. Wei, Solid-liquid equilibrium of theophylline in solvent mixtures, J. Chem. Eng. Data 59(2014) 263-268.

[12] Y. Wei, X. Zhang, L. Dang, H. We, Solubility and pseudopolymorphic transitions in mixed solvent:Meropenem in methanol-water solution, Fluid Phase Equilib. 349(2013) 25-30.

[13] Y. Li, P.S. Chow, R.B.H. Tan, S.N. Black, Effect of water activity on the transformation between hydrate and anhydrate of carbamazepine, Org. Process. Res. Dev. 12(2008) 264-270.

[14] K.J. Chavez, R.W. Rousseau, Solubility and pseudopolymorphic transitions in mixed solvents:sodium naproxen in methanol-water and ethanol-water solutions, Cryst. Growth Des. 10(2010) 3802-3807.

[15] X. Wang, L. Dang, S. Black, X. Zhang, H. Wei, Influence of polymorphs on the transformation water activity of theophylline, Ind. Eng. Chem. Res. 51(2012) 2789-2796.

[16] F. Tian, H. Qu, A. Zimmermann, T. Munk, A.C. Jorgensen, J. Rantanen, Factors affecting crystallization of hydrates, J. Pharm. Pharmacol. 62(2010) 1534-1546.

[17] T.N.P. Nguyen, K.J. Kim, Transformation of monohydrate into anhydrous form of risedronate monosodium in methanol-water mixture, Ind. Eng. Chem. Res. 49(2010) 4842-4849.

[18] C. Liu, L. Dang, W. Bai, R. Wang, H. Wei, Facile method for the prediction of anhydrate/hydrate transformation point, Ind. Eng. Chem. Res. 52(2013) 16506-16512.

[19] N. Variankaval, C. Lee, J. Xu, R. Calabria, N. Tsou, R. Ball, Water activity-mediated control of crystalline phases of an active pharmaceutical ingredient, Org. Process. Res. Dev. 11(2007) 229-236.

[20] H. Qu, M. Louhi-Kultanen, J. Rantanen, J. Kallas, Solvent-mediated phase transformation kinetics of an anhydrate/hydrate system, Cryst. Growth Des. 6(2006) 2053-2060.

[21] C. Liu, L. Dang, Y. Tong, H. Wei, influence of polymorphs on the transformation water activity of theophylline, Ind. Eng. Chem. Res. 52(2013) 14979-14983.

[22] M.D. Ticehurst, R.A. Storey, C. Watt, Application of slurry bridging experiments at controlled water activities to predict the solid state conversion between anhydrous and hydrated forms using theophylline as a model drug, Int. J. Pharm. 247(2002) 1-10.

[23] A. Jayasankar, L. Roy, N. Rodriguez-Hornedo, Transformation pathways of cocrystal hydrates when coformer modulates water activity, J. Pharm. Sci. 99(2010) 3977-3985.

[24] H. Zhu, D.J.W. Grant, Influence of water activity in organic solvent + water mixtures on the nature of the crystallizing drug phase.2. Ampicillin, Int. J. Pharm. 139(1996) 33-43.

[25] Y. Wang, P. Sun, S. Xu, S. Du, T. Zhang, B. Yu, S. Zhang, Y. Wang, B. Gong, Solution-meditated phase transformation of argatroban:ternary phase diagram, rate-determining step, and transformation kinetics, Ind. Eng. Chem. Res. 56(2017) 4539-4548.

[26] K. Kiyofumi, N. Mikiyoshi, K. Kazuo, Isobaric vapor-liquid equilibria for methanol + ethanol + water and the three constituent binary systems, J. Chem. Eng. Data 38(1993) 446-449.

[27] A. Ainouz, J.R. Authelin, P. Billot, H. Lieberman, Modeling and prediction of cocrystal phase diagrams, Int. J. Pharm. 374(2009) 82-89.

[28] K. Jarring, T. Larsson, B. Stensland, I. Ymen, Thermodynamic stability and crystal structures for polymorphs and solvates of formoterol fumarate, J. Pharm. Sci. 95(2006) 1144-1161.

[29] J. Zhang, Y. Wang, G. Wang, H. Hao, H. Wang, Q. Luan, C. Jiang, Determination and correlation of solubility of spironolactone form Ⅱ in pure solvents and binary solvent mixtures, J. Chem. Thermodyn. 79(2014) 61-68.

[30] X. Wang, Y. Qin, T. Zhang, W. Tang, B. Ma, J. Gong, Measurement and correlation of solubility of azithromycin monohydrate in five pure solvents, J. Chem. Eng. Data 59(2014) 784-791.

[31] Z. Sun, H. Hao, C. Xie, Z. Xu, Q. Yin, Y. Bao, B. Hou, Y. Wang, Thermodynamic properties of Form A and Form B of florfenicol, Ind. Eng. Chem. Res. 53(2014) 13506-13512.

[32] D. Zhang, Y. Wang, S. Ma, S. Wu, H. Hao, Determination of solubility and induction time of ceftazidime, J. Chem. Eng. Data 58(2013) 176-182.

[33] L. Chen, L. Song, Y. Gao, A. Zhu, D. Cao, Experimental determination of solubilities and supersolubilities of 2,2',4,4',6,6'-hexanitrostilbene in different organic solvents, Chin. J. Chem. Eng. 25(2017) 809-814.

[34] Q. Xia, P. Ma, Measurement and correlation for solubility of dimethyl-2,6-naphthalene dicarboxylate in organic solvents, Chin. J. Chem. Eng. 15(2007) 215-220.