Solubility Determination and Correlation of Warfarin Sodium 2-Propanol Solvate in Pure, Binary, and Ternary Solvent Mixtures

George De La Rosa, M. V.; Santiago, R.; Malavé Romero, J.; Duconge, J.; Monbaliu, Jean-Christophe; López-Mejías, V.; Stelzer, T.

doi:10.1021/acs.jced.8b00977

Article (Scientific journals)

Solubility Determination and Correlation of Warfarin Sodium 2-Propanol Solvate in Pure, Binary, and Ternary Solvent Mixtures

George De La Rosa, M. V.; Santiago, R.; Malavé Romero, J. et al.

2019 • In Journal of Chemical and Engineering Data, 64 (4), p. 1399-1413

Peer Reviewed verified by ORBi

Permalink
https://hdl.handle.net/2268/237053

DOI
10.1021/acs.jced.8b00977

Files (1)Send to Details Statistics Bibliography Similar publications

Files

Full Text

19JCED1399.pdf

Publisher postprint (2.63 MB)

Request a copy

All documents in ORBi are protected by a user license.

Send to

RIS BibTex APA Chicago Permalink X Linkedin

Details

Keywords :

Acetone; Binary mixtures; Drug products; Ethanol; Heptane; Hexane; Sodium; Solubility; Binary solvent mixtures; Experimental solubility datum; Increasing temperatures; Pharmaceutical crystallizations; Polythermal methods; Relative deviations; Solubility determination; Ternary solvent mixture; Organic solvents

Abstract :

[en] The solubility of warfarin sodium isopropanol solvate (WS·IPA), a widely used anticoagulant, was determined at temperatures ranging from 278.15 to 333.15 K in four pure solvents (acetone, ethanol, IPA, and water), five binary solvent mixtures (IPA + acetone, IPA + ethanol, IPA + water, IPA + heptane, and IPA + hexane), and five ternary solvent mixtures (IPA + acetone + heptane, IPA + acetone + hexane, IPA + ethanol + heptane, IPA + ethanol + hexane, and IPA + water + heptane) using the polythermal method. It was demonstrated that the solubility of WS·IPA increases with increasing temperature in the pure solvents and at constant solvent composition in the solvent mixtures. In addition, the solubility of WS·IPA in IPA increases with increasing content of acetone, ethanol, and water, which act as cosolvents, and decreases with increasing content of heptane and hexane, which act as antisolvents. The experimental solubility data of WS·IPA in pure solvents and binary and ternary solvent mixtures were correlated using the modified Apelblat and λh model equations. The correlated solubility data agree with the experimental data based on the relative deviation and the average relative deviation (ARD %) values. Thus, the correlated and experimentally derived solubility data of WS·IPA provide a pathway to engineer advanced pharmaceutical crystallization processes for WS·IPA. © 2019 American Chemical Society.

Disciplines :

Chemistry

Author, co-author :

George De La Rosa, M. V.; Department of Pharmaceutical Sciences, University of Puerto Rico, Medical Sciences Campus, San Juan, PR 00936, United States, Crystallization Design Institute, Molecular Sciences Research Center, University of Puerto Rico, San Juan, PR 00926, United States

Santiago, R.; Crystallization Design Institute, Molecular Sciences Research Center, University of Puerto Rico, San Juan, PR 00926, United States, Department of Mathematics, University of Puerto Rico, Río Piedras Campus, San Juan, PR 00931, United States

Malavé Romero, J.; Crystallization Design Institute, Molecular Sciences Research Center, University of Puerto Rico, San Juan, PR 00926, United States, Department of Biology, University of Puerto Rico, Bayamón Campus, Bayamón, PR 00959, United States

Duconge, J.; Department of Pharmaceutical Sciences, University of Puerto Rico, Medical Sciences Campus, San Juan, PR 00936, United States

Monbaliu, Jean-Christophe ; Université de Liège - ULiège > Département de chimie (sciences) > Synthèse organique appliquée

López-Mejías, V.; Crystallization Design Institute, Molecular Sciences Research Center, University of Puerto Rico, San Juan, PR 00926, United States, Department of Chemistry, University of Puerto Rico, Río Piedras Campus, San Juan, PR 00931, United States

Stelzer, T.; Department of Pharmaceutical Sciences, University of Puerto Rico, Medical Sciences Campus, San Juan, PR 00936, United States, Crystallization Design Institute, Molecular Sciences Research Center, University of Puerto Rico, San Juan, PR 00926, United States

Language :

English

Title :

Solubility Determination and Correlation of Warfarin Sodium 2-Propanol Solvate in Pure, Binary, and Ternary Solvent Mixtures

Publication date :

2019

Journal title :

Journal of Chemical and Engineering Data

ISSN :

0021-9568

eISSN :

1520-5134

Publisher :

American Chemical Society

Volume :

Issue :

Pages :

1399-1413

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 19 June 2019

Statistics

Number of views

39 (3 by ULiège)

Number of downloads

0 (0 by ULiège)

More statistics

Scopus citations^®

Scopus citations^®
without self-citations

OpenCitations

OpenAlex citations

Bibliography

(2018) WHO Model List of Essential Medicines - 19th List (April 2015), , http://www.who.int/medicines/publications/pharmacopoeia, World Health Organization. (accessed Mar 19)
(2018) Drugs.com. Warfarin for Injection, , https://www.drugs.com/drugshortages/%0Dwarfarin-for-injection-1110, (accessed Mar 19)
(2018) Drugs.com. Warfarin Sodium Tablets, , https://www.drugs.com/drugshortages/%0Dwarfarin-sodium-tablets-908, (accessed Mar 19)
(2018) Warfarin for Injection, ASHP-Pharmacists Advancing Healthcare, , https://www.ashp.org/drug-shortages/current-shortages/drug-shortageslist?%0Dpage=CurrentShortages, ASHP. (accessed Mar 19)
Zhangazha, W., (2015) Zim Hit by A Massive Drug Shortage, , Zimbabwe Independent, May
Moore, T.J., Furberg, C.D., Mattison, D.R., Cohen, M.R., (2015) Quarter Watch: Monitoring FDA MedWatch Reports, pp. 1-21
(2018) Underlying Cause of Death 1999-2013 on CDC WONDER Online Database, , https://wonder.cdc.gov/ucdicd10.%0Dhtml, Centers for Disease Control and Prevention (CDC). (accessed Mar 19)
Adamo, A., Beingessner, R.L., Behnam, M., Chen, J., Jamison, T.F., Jensen, K.F., Monbaliu, J.-C.M., Zhang, P., On-Demand Continuous-Flow Production of Pharmaceuticals in a Compact, Reconfigurable System (2016) Science, 352, pp. 61-67
Monbaliu, J.-C.M., Stelzer, T., Revalor, E., Weeranoppanant, N., Jensen, K.F., Myerson, A.S., Compact and Integrated Approach for Advanced End-to-End Production, Purification, and Aqueous Formulation of Lidocaine Hydrochloride (2016) Org. Process Res. Dev., 20, pp. 1347-1353
Zhang, P., Weeranoppanant, N., Thomas, D.A., Tahara, K., Stelzer, T., Russell, M.G., O'Mahony, M., Adamo, A., Advanced Continuous Flow Platform for On-Demand Pharmaceutical Manufacturing (2018) Chem. - Eur. J., 24, pp. 2776-2784
Porta, R., Benaglia, M., Puglisi, A., Flow Chemistry: Recent Developments in the Synthesis of Pharmaceutical Products (2016) Org. Process Res. Dev., 20, pp. 2-25
Hessel, V., Novel Process Windows - Gate to Maximizing Process Intensification via Flow Chemistry (2009) Chem. Eng. Technol., 32, pp. 1655-1681
Van Gerven, T., Stankiewicz, A., Structure, Energy, Synergy, Time - The Fundamentals of Process Intensification (2009) Ind. Eng. Chem. Res., 48, pp. 2465-2474
Jiménez-González, C., Poechlauer, P., Broxterman, Q.B., Yang, B.-S., Am Ende, D., Baird, J., Bertsch, C., Manley, J., Key Green Engineering Research Areas for Sustainable Manufacturing A Perspective from Pharmaceutical and Fine Chemicals Manufacturers (2011) Org. Process Res. Dev., 15, pp. 900-911
(2011) COUMADIN-Warfarin Sodium Injection, Powder, Lyophilized, for Solution, pp. 1-39. , Bristol-Myers Squibb. Dly. Med
Rahman, Z., Korang-Yeboah, M., Siddiqui, A., Mohammad, A., Khan, M.A., Understanding Effect of Formulation and Manufacturing Variables on the Critical Quality Attributes of Warfarin Sodium Product (2015) Int. J. Pharm., 495, pp. 19-30
Kasim, N.A., Whitehouse, M., Ramachandran, C., Bermejo, M., Lennernäs, H., Hussain, A.S., Junginger, H.E., Amidon, G.L., Molecular Properties of WHO Essential Drugs and Provisional Biopharmaceutical Classification (2004) Mol. Pharm., 1, pp. 85-96
Sheth, A.R., Young, V.G., Grant, D.J.W., Warfarin Sodium 2-Propanol Solvate (2002) Acta Crystallogr., Sect. E: Struct. Rep. Online, 58, pp. m197-m199
Sheth, A.R., Brennessel, W.W., Young, V.G., Muller, F.X., Grant, D.J.W., Solid-State Properties of Warfarin Sodium 2-Propanol Solvate (2004) J. Pharm. Sci., 93, pp. 2669-2680
Hilfiker, R., (2006) Polymorphism in the Pharmaceutical Industry, , Wiley-VCH
Hiskey, C.F., Melnitchenko, V., Clathrates of Sodium Warfarin (1965) J. Pharm. Sci., 54, pp. 1298-1302
Karusala, N.R., Kishore, J.A., Bandari, M., Gorantla, S.R., (2007) A Process for the Preparation of Warfarin Sodium, , U.S. Patent 044,246 A2, October 9
(2018) Warfarin Full Prescribing Information, , http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/009218s107lbl.pdf, Bristol-Myers-Squibb. (accessed Feb 22)
Weldele, M., Delmarre, D., Gao, D., El-Khateeb, M.A., Centeno, C.-J.S., Pathak, S.R., (2007) Stable Warfarin Sodium Liquid Formulation and Method of Making Same, , U.S. Patent 7,259,185 B2
(2015) Warfarin Sodium for Injection, 38, pp. 5802-5804. , United States Pharmacopeia. USP
Long, B., Li, J., Song, Y., Du, J., Temperature Dependent Solubility of R-Form L -Glutamic Acid in Selected Organic Solvents: Measurements and Thermodynamic Modeling (2011) Ind. Eng. Chem. Res., 50, pp. 8354-8360
Reus, M.A., Van Der Heijden, A.E.D.M., Ter Horst, J.H., Solubility Determination from Clear Points upon Solvent Addition (2015) Org. Process Res. Dev., 19, pp. 1004-1011
Gao, D., Maurin, M.B., Physical Chemical Stability of Warfarin Sodium (2001) AAPS PharmSci, 3, p. 18
(2018) ThermoLit: NIST Literature Report Builder for Thermochemical Property Measurements, , https://trc.nist.gov/thermolit/main/home.html#property/syssel:2:info
warfarin_sodi%0Dum:info
2-propanol:form/props:3:0:0, National Institute of Standards and Technology. (accessed Mar 24)
Hong, M., Xu, L., Ren, G., Chen, J., Qi, M., Solubility of Lansoprazole in Different Solvents (2012) Fluid Phase Equilib., 331, pp. 18-25
Omar, W., Effect of Solvent Composition on Crystallization Process of Ascorbic Acid (2006) Chem. Eng. Technol., 29, pp. 119-123
Rosbottom, I., Ma, C.Y., Turner, T.D., O'Connell, R.A., Loughrey, J., Sadiq, G., Davey, R.J., Roberts, K.J., Influence of Solvent Composition on the Crystal Morphology and Structure of p-Aminobenzoic Acid Crystallized from Mixed Ethanol and Nitromethane Solutions (2017) Cryst. Growth Des., 17, pp. 4151-4161
Lee, T., Kuo, C.S., Chen, Y.H., Solubility, Polymorphism, Crystallinity, and Crystal Habit of Acetaminophen and Ibuprofen by Initial Solvent Screening (2006) Pharm. Technol., 10, pp. 72-92
Mirza, S., Miroshnyk, I., Heinämäki, J., Christiansen, L., Karjalainen, M., Yliruusi, J., Influence of Solvents on the Variety of Crystalline Forms of Erythromycin (2003) AAPS PharmSci, 5, p. 39
Shekunov, B.Y., York, P., Crystallization Processes in Pharmaceutical Technology and Drug Delivery Design (2000) J. Cryst. Growth, 211, pp. 122-136
Chekal, B.P., Campeta, A.M., Abramov, Y.A., Feeder, N., Glynn, P.P., McLaughlin, R.W., Meenan, P.A., Singer, R.A., The Challenges of Developing an API Crystallization Process for a Complex Polymorphic and Highly Solvating System. Part i (2009) Org. Process Res. Dev., 13, pp. 1327-1337
Nývlt, J., Kinetics of Nucleation in Solutions (1968) J. Cryst. Growth, 3, pp. 377-383
Kaemmerer, H., Jones, M.J., Lorenz, H., Seidel-Morgenstern, A., Selective Crystallisation of a Chiral Compound-Forming System-Solvent Screening, SLE Determination and Process Design (2010) Fluid Phase Equilib., 296, pp. 192-205
Vellema, J., Hunfeld, N.G.M., Van Den Akker, H.E.A., Ter Horst, J.H., Avoiding Crystallization of Lorazepam during Infusion (2011) Eur. J. Pharm. Sci., 44, pp. 621-626
Zorrilla-Veloz, R.I., Stelzer, T., López-Mejías, V., Measurement and Correlation of the Solubility of 5-Fluorouracil in Pure and Binary Solvents (2018) J. Chem. Eng. Data, 63, pp. 3809-3817
(2017) Guidance for Industry Q3C, 9765, pp. 1-8. , International Council for Harmonisation. US Health & Human Services Department- Food and Drug Adminsitration
Croker, D.M., Kelly, D.M., Horgan, D.E., Hodnett, B.K., Lawrence, S.E., Moynihan, H.A., Rasmuson, Å.C., Demonstrating the Influence of Solvent Choice and Crystallization Conditions on Phenacetin Crystal Habit and Particle Size Distribution (2015) Org. Process Res. Dev., 19, pp. 1826-1836
Chen, E.C., McGuire, G., Lee, H.Y., Solubility Isotherm of the Ferric Chloride-Magnesium Chloride-Hydrogen Chloride-Water System (1970) J. Chem. Eng. Data, 15, pp. 448-449
Cabrera, A.L., Toledo, A.R., Del Valle, J.M., De La Fuente, J.C., Measuring and Validation for Isothermal Solubility Data of Solid 2-(3,4-Dimethoxyphenyl)-5,6,7,8-Tetramethoxychromen-4-One (Nobiletin) in Supercritical Carbon Dioxide (2015) J. Chem. Thermodyn., 91, pp. 378-383
Shiflett, M.B., Harmer, M.A., Junk, C.P., Yokozeki, A., Solubility and Diffusivity of 1,1,1,2-Tetrafluoroethane in Room-Temperature Ionic Liquids (2006) Fluid Phase Equilib., 242, pp. 220-232
Wang, S., Wang, J., Yin, Q., Measurement and Correlation of Solubility of 7-Aminocephalosporanic Acid in Aqueous Acetone Mixtures (2005) Ind. Eng. Chem. Res., 44, pp. 3783-3787
Mohan, R., Lorenz, H., Myerson, A.S., Solubility Measurement Using Differential Scanning Calorimetry (2002) Ind. Eng. Chem. Res., 41, pp. 4854-4862
Wei, T., Wang, C., Du, S., Wu, S., Li, J., Gong, J., Measurement and Correlation of the Solubility of Penicillin v Potassium in Ethanol + Water and 1-Butyl Alcohol + Water Systems (2015) J. Chem. Eng. Data, 60, pp. 112-117
Guo, L., Wang, Y., Tu, L., Li, J., Thermodynamics and Phase Equilibrium of the System CsCl-MgCl2-H2O at 298.15 K (2017) J. Chem. Eng. Data, 62, pp. 1397-1402
Shakeel, F., Shazly, G.A., Haq, N., Solubility of Metoclopramide Hydrochloride in Six Green Solvents at (298.15 to 338.15) K (2014) J. Chem. Eng. Data, 59, pp. 1700-1703
Dwyer, L., Kulkarni, S., Ruelas, L., Myerson, A., Two-Stage Crystallizer Design for High Loading of Poorly Water-Soluble Pharmaceuticals in Porous Silica Matrices (2017) Crystals, 7, p. 131
Roa Engel, C.A., Ter Horst, J.H., Pieterse, M., Van Der Wielen, L.A.M., Straathof, A.J.J., Solubility of Fumaric Acid and Its Monosodium Salt (2013) Ind. Eng. Chem. Res., 52, pp. 9454-9460
Smallwood, I.M., (1996) Handbook of Organic Solvent Properties, , Arnold: London, Great Britain
Guo, Y., Yin, Q., Hao, H., Zhang, M., Bao, Y., Hou, B., Chen, W., Cong, W., Measurement and Correlation of Solubility and Dissolution Thermodynamic Properties of Furan-2-Carboxylic Acid in Pure and Binary Solvents (2014) J. Chem. Eng. Data, 59, pp. 1326-1333
Pascual, G.K., Donnellan, P., Glennon, B., Kamaraju, V.K., Jones, R.C., Experimental and Modeling Studies on the Solubility of 2-Chloro-N-(4-Methylphenyl)Propanamide (S1) in Binary Ethyl Acetate + Hexane, Toluene + Hexane, Acetone + Hexane, and Butanone + Hexane Solvent Mixtures Using Polythermal Method (2017) J. Chem. Eng. Data, 62, pp. 3193-3205
Wang, X., Qin, Y., Zhang, T., Tang, W., Ma, B., Gong, J., Measurement and Correlation of Solubility of Azithromycin Monohydrate in Five Pure Solvents (2014) J. Chem. Eng. Data, 59, pp. 784-791
Rahman, Z., Mohammad, A., Akhtar, S., Siddiqui, A., Korang-Yeboah, M., Khan, M.A., Chemometric Model Development and Comparison of Raman And13C Solid-State Nuclear Magnetic Resonance-Chemometric Methods for Quantification of Crystalline/Amorphous Warfarin Sodium Fraction in the Formulations (2015) J. Pharm. Sci., 104, pp. 2550-2558
Ahuja, S., Scypinski, S., (2011) Handbook of Modern Pharmaceutical Analysis, 10. , 2 nd ed. Academic Press: Amsterdam
Brittain, H.G., (2009) Polymorphism in Pharmaceutical Solids, , 2 nd ed. Informa Healthcare, USA, Inc
Tian, Y., Booth, J., Meehan, E., Jones, D.S., Li, S., Andrews, G.P., Construction of Drug-Polymer Thermodynamic Phase Diagrams Using Flory-Huggins Interaction Theory: Identifying the Relevance of Temperature and Drug Weight Fraction to Phase Separation within Solid Dispersions (2013) Mol. Pharm., 10, pp. 236-248
Giron, D., Thermal Analysis and Calorimetric Methods in the Characterisation of Polymorphs and Solvates (1995) Thermochim. Acta, 248, pp. 1-59
Yan, H., Wang, Z., Wang, J., Correlation of Solubility and Prediction of the Mixing Properties of Capsaicin in Different Pure Solvents (2012) Ind. Eng. Chem. Res., 51, pp. 2808-2813
Buchowski, H., Ksiazczak, A., Pietrzyk, S., Solvent Activity along a Saturation Line and Solubility of Hydrogen-Bonding Solids (1980) J. Phys. Chem., 84, pp. 975-979
Filippa, M.A., Gasull, E.I., Ibuprofen Solubility in Pure Organic Solvents and Aqueous Mixtures of Cosolvents: Interactions and Thermodynamic Parameters Relating to the Solvation Process (2013) Fluid Phase Equilib., 354, pp. 185-190
Millard, J.W., Alvarez-Núnez, F.A., Yalkowsky, S.H., Solubilization by cosolvents (2002) Int. J. Pharm., 245, pp. 153-166
Jouyban, A., Review of the Cosolvency Models for Predicting Solubility of Drugs in Water-Cosolvent Mixtures (2008) J. Pharm. Pharm. Sci., 11, pp. 32-58