Thermodynamic Characteristics of Phenacetin in Solid State and Saturated Solutions in Several Neat and Binary Solvents - Publication - Bridge of Knowledge

Your account

login

Search

Thermodynamic Characteristics of Phenacetin in Solid State and Saturated Solutions in Several Neat and Binary Solvents

Abstract

The thermodynamic properties of phenacetin in solid state and in saturated conditions in neat and binary solvents were characterized based on differential scanning calorimetry and spectroscopic solubility measurements. The temperature-related heat capacity values measured for both the solid and melt states were provided and used for precise determination of the values for ideal solubility, fusion thermodynamic functions, and activity coefficients in the studied solutions. Factors affecting the accuracy of these values were discussed in terms of various models of specific heat capacity difference for phenacetin in crystal and super-cooled liquid states. It was concluded that different properties have varying sensitivity in relation to the accuracy of heat capacity values. The values of temperature-related excess solubility in aqueous binary mixtures were interpreted using the Jouyban–Acree solubility equation for aqueous binary mixtures of methanol, DMSO, DMF, 1,4-dioxane, and acetonitrile. All binary solvent systems studied exhibited strong positive non-ideal deviations from an algebraic rule of mixing. Additionally, an interesting co-solvency phenomenon was observed with phenacetin solubility in aqueous mixtures with acetonitrile or 1,4-dioxane. The remaining three solvents acted as strong co-solvents. 

Citations

  • 1 2

    CrossRef

  • 0

    Web of Science

  • 1 1

    Scopus

Authors (5)

Cite as

Full text

download paper
downloaded 24 times
Publication version
Submitted Version
License
Creative Commons: CC-BY-NC-ND open in new tab

Keywords

Details

Category:
Magazine publication
Type:
Magazine publication
Published in:
MOLECULES no. 26, edition 13,
ISSN: 1420-3049
Publication year:
2021
DOI:
Digital Object Identifier (open in new tab) 10.3390/molecules26134078
Bibliography: test
  1. Clissold, S.P. Paracetamol and Phenacetin. Drugs 1986, 32, 46-59. [CrossRef] open in new tab
  2. Chandrasekharan, N.V.; Dai, H.; Roos, K.L.T.; Evanson, N.K.; Tomsik, J.; Elton, T.S.; Simmons, D.L. COX-3, a cyclooxygenase-1 variant inhibited by acetaminophen and other analgesic/antipyretic drugs: Cloning, structure, and expression. Proc. Natl. Acad. Sci. USA 2002, 99, 13926-13931. [CrossRef] [PubMed] open in new tab
  3. Jensen, C.B.; Jollow, D.J. The role of N-hydroxyphenetidine in phenacetin-induced hemolytic anemia. Toxicol. Appl. Pharmacol. 1991, 111, 1-12. [CrossRef] open in new tab
  4. Peters, G.; Baechtold-Fowler, N.; Bonjour, J.P.; Chométy-Diézi, F.; Filloux, B.; Guidoux, R.; Guignard, J.P.; Peters-Haefeli, L.; Roch-Ramel, F.; Schelling, J.L.; et al. General and renal toxicity of phenacetin, paracetamol and some anti-mitotic agents in the rat. Arch. Toxicol. 1972, 28, 225-269. [CrossRef] open in new tab
  5. Easley, J.L.; Condon, B.F. Phenacetin-induced Methemoglobinemia and Renal Failure. Anesthesiology 1974, 41, 99-100. [CrossRef] open in new tab
  6. McLaughlin, J.K.; Mandel, J.S.; Blot, W.J.; Schuman, L.M.; Mehl, E.S.; Fraumeni, J.F. A Population-Based Case-Control Study of Renal Cell Carcinoma. J. Natl. Cancer Inst. 1984, 72, 275-284. [CrossRef] [PubMed] open in new tab
  7. McCredie, M.; Ford, J.; Stewart, J. Risk Factors for Cancer of the Renal Parenchyma. J. Urol. 1989, 141, 1272-1273. [CrossRef] open in new tab
  8. Khan, S.; Batchelor, H.; Hanson, P.; Perrie, Y.; Mohammed, A.R. Physicochemical characterisation, drug polymer dissolution and in vitro evaluation of phenacetin and phenylbutazone solid dispersions with polyethylene glycol 8000. J. Pharm. Sci. 2011, 100, 4281-4294. [CrossRef] [PubMed] open in new tab
  9. Wu, X.; Yi, J.-M.; Liu, Y.-J.; Liu, Y.-B.; Zhang, P.-L. Solubility and micronisation of phenacetin in supercritical carbon dioxide. Chem. Pap. 2013, 67, 517-525. [CrossRef] open in new tab
  10. Ismail, S.; Shawky, S.; Hafez, E. A New Approach for Enhancing the Dissolution Rate of Phenacetin. Drug Dev. Ind. Pharm. 1987, 13, 2147-2158. [CrossRef] open in new tab
  11. Kim, S.; Thiessen, P.A.; Bolton, E.E.; Chen, J.; Fu, G.; Gindulyte, A.; Han, L.; He, J.; He, S.; Shoemaker, B.A.; et al. PubChem substance and compound databases. Nucleic Acids Res. 2016, 44, D1202-D1213. [CrossRef] open in new tab
  12. Junyaprasert, V.B.; Morakul, B. Nanocrystals for enhancement of oral bioavailability of poorly water-soluble drugs. Asian J. Pharm. Sci. 2015, 10, 13-23. [CrossRef] open in new tab
  13. Fulas, O.A.; Laferrière, A.; Ayoub, G.; Gandrath, D.; Mottillo, C.; Titi, H.M.; Stein, R.S.; Friščić, T.; Coderre, T.J. Drug-nutraceutical co-crystal and salts for making new and improved bi-functional analgesics. Pharmaceutics 2020, 12, 1144. [CrossRef] open in new tab
  14. Grant, D.; Mehdizadeh, M.; Chow, A.-L.; Fairbrother, J. Non-linear van't Hoff solubility-temperature plots and their pharmaceuti- cal interpretation. Int. J. Pharm. 1984, 18, 25-38. [CrossRef] open in new tab
  15. 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 to 348) K. J. Chem. Thermodyn. 1999, 31, 85-91. [CrossRef] open in new tab
  16. 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. [CrossRef] open in new tab
  17. 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. [CrossRef] open in new tab
  18. Wilson, G.M. Vapor-Liquid Equilibrium. XI. A New Expression for the Excess Free Energy of Mixing. J. Am. Chem. Soc. 1964, 86, 127-130. [CrossRef] open in new tab
  19. Renon, H.; Prausnitz, J.M. Local compositions in thermodynamic excess functions for liquid mixtures. AIChE J. 1968, 14, 135-144. [CrossRef] open in new tab
  20. Jouyban, A.; Acree, W. Prediction of drug solubility in ethanol-ethyl acetate mixtures at various temperatures using the Jouyban- Acree model. J. Drug Deliv. Sci. Technol. 2007, 17, 159-160. [CrossRef] open in new tab
  21. Aydi, A.; Ayadi, C.; Ghachem, K.; Al-Khazaal, A.Z.; Delgado, D.R.; Alnaief, M.; Kolsi, L. Solubility, Solution Thermodynamics, and Preferential Solvation of Amygdalin in Ethanol + Water Solvent Mixtures. Pharmaceuticals 2020, 13, 395. [CrossRef] open in new tab
  22. Przybyłek, M.; Walczak, P.; Ziółkowska, D.; Grela, I.; Cysewski, P. Studies on the solid-liquid equilibria and intermolecular interactions Urea binary mixtures with Sulfanilamide and Sulfacetamide. J. Chem. Thermodyn. 2021, 153, 106308. [CrossRef] open in new tab
  23. Shakeel, F.; Haq, N.; Alsarra, I.; Alshehri, S. Solubility Data, Solubility Parameters and Thermodynamic Behavior of An Antiviral Drug Emtricitabine in Different Pure Solvents: Molecular Understanding of Solubility and Dissolution. Molecules 2021, 26, 746. [CrossRef] open in new tab
  24. Cysewski, P.; Walczak, P.; Ziółkowska, D.; Grela, I.; Przybyłek, M. Experimental and theoretical studies on the Sulfamethazine- Urea and Sulfamethizole-Urea solid-liquid equilibria. J. Drug Deliv. Sci. Technol. 2021, 61, 102186. [CrossRef] open in new tab
  25. Jeliński, T.; Bugalska, N.; Koszucka, K.; Przybyłek, M.; Cysewski, P. Solubility of sulfanilamide in binary solvents containing water: Measurements and prediction using Buchowski-Ksiazczak solubility model. J. Mol. Liq. 2020, 319, 114342. [CrossRef] open in new tab
  26. Ravi, M.; Julu, T.; Kim, N.A.; Park, K.E.; Jeong, S.H. Solubility Determination of c-Met Inhibitor in Solvent Mixtures and Mathematical Modeling to Develop Nanosuspension Formulation. Molecules 2021, 26, 390. [CrossRef] [PubMed] open in new tab
  27. Abbott, S. Solubility Science: Principles and Practice; Destech Publications: Lancaster, PA, USA, 2017; ISBN 9781605954844.
  28. Pappa, G.D.; Voutsas, E.C.; Magoulas, K.; Tassios, D.P. Estimation of the Differential Molar Heat Capacities of Organic Compounds at Their Melting Point. Ind. Eng. Chem. Res. 2005, 44, 3799-3806. [CrossRef] open in new tab
  29. Martínez, F.; Gomez, A. Thermodynamic Study of the Solubility of Some Sulfonamides in Octanol, Water, and the Mutually Saturated Solvents. J. Solut. Chem. 2001, 30, 909-923. [CrossRef] open in new tab
  30. Perlovich, G.; Kurkov, S.V.; Kinchin, A.N.; Bauer-Brandl, A. Thermodynamics of solutions III: Comparison of the solvation of (+)-naproxen with other NSAIDs. Eur. J. Pharm. Biopharm. 2004, 57, 411-420. [CrossRef] [PubMed] open in new tab
  31. Sha, J.; Ma, T.; Zhao, R.; Zhang, P.; Sun, R.; Jiang, G.; Wan, Y.; He, H.; Yao, X.; Li, Y.; et al. The dissolution behaviour and apparent thermodynamic analysis of doxifluridine in twelve pure solvents at various temperatures. J. Chem. Thermodyn. 2020, 144, 106073. [CrossRef] open in new tab
  32. Shakeel, F.; Alshehri, S.; Ibrahim, M.A.; Altamimi, M.; Haq, N.; Elzayat, E.M.; Shazly, G.A. Solubilization and thermody- namic properties of simvastatin in various micellar solutions of different non-ionic surfactants: Computational modeling and solubilization capacity. PLoS ONE 2021, 16, e0249485. [CrossRef] open in new tab
  33. Sadeghi, M.; Rasmuson, Å.C. On the estimation of crystallization driving forces. CrystEngComm 2019, 21, 5164-5173. [CrossRef] open in new tab
  34. Camacho, D.M.; Roberts, K.J.; More, I.; Lewtas, K.; Lewtas, K. Solubility and Nucleation of Methyl Stearate as a Function of Crystallization Environment. Energy Fuels 2018, 32, 3447-3459. [CrossRef] open in new tab
  35. Baena, Y.; Pinzón, J.A.; Barbosa, H.J.; Martínez, F. Temperature-dependence of the solubility of some acetanilide derivatives in several organic and aqueous solvents. Phys. Chem. Liq. 2004, 42, 603-613. [CrossRef] open in new tab
  36. Chang, Q.-L.; Li, Q.-S.; Wang, S.; Tian, Y.-M. Solubility of Phenacetinum in Methanol, Ethanol, 1-Propanol, 1-Butanol, 1-Pentanol, Tetrahydrofuran, Ethyl Acetate, and Benzene between 282.65 K and 333.70 K. J. Chem. Eng. Data 2007, 52, 1894-1896. [CrossRef] open in new tab
  37. Cárdenas, Z.J.; Almanza, O.A.; Jouyban, A.; Martínez, F.; Acree, W.E., Jr. Solubility and preferential solvation of phenacetin in methanol + water mixtures at 298.15 K. Phys. Chem. Liq. 2018, 56, 16-32. [CrossRef] open in new tab
  38. Peña, M.; Escalera, B.; Reíllo, A.; Sánchez, A.; Bustamante, P. Thermodynamics of Cosolvent Action: Phenacetin, Salicylic Acid and Probenecid. J. Pharm. Sci. 2009, 98, 1129-1135. [CrossRef] [PubMed] open in new tab
  39. Mantheni, D.R.; Maheswaram, M.P.K.; Munigeti, R.; Perera, I.; Riga, A.; Alexander, K.S. Solid-and liquid-state studies of a wide range of chemicals by isothermal and scanning dielectric thermal analysis. J. Therm. Anal. Calorim. 2013, 115, 2253-2260. [CrossRef] open in new tab
  40. Umnahanant, P.; Chickos, J. Vaporization and Sublimation Enthalpies of Acetanilide and Several Derivatives by Correlation Gas Chromatography. J. Chem. Eng. Data 2012, 57, 1331-1337. [CrossRef] open in new tab
  41. Baird, J.A.; Van Eerdenbrugh, B.; Taylor, L. A Classification System to Assess the Crystallization Tendency of Organic Molecules from Undercooled Melts. J. Pharm. Sci. 2010, 99, 3787-3806. [CrossRef] open in new tab
  42. Miyako, Y.; Khalef, N.; Matsuzaki, K.; Pinal, R. Solubility enhancement of hydrophobic compounds by cosolvents: Role of solute hydrophobicity on the solubilization effect. Int. J. Pharm. 2010, 393, 48-54. [CrossRef] open in new tab
  43. Vecchio, S.; Tomassetti, M. Vapor pressures and standard molar enthalpies, entropies and Gibbs energies of sublimation of three 4-substituted acetanilide derivatives. Fluid Phase Equilibria 2009, 279, 64-72. [CrossRef] open in new tab
  44. Wassvik, C.M.; Holmén, A.G.; Draheim, R.; Artursson, P.; Bergström, C.A.S. Molecular characteristics for solid-state limited solubility. J. Med. Chem. 2008, 51, 3035-3039. [CrossRef] [PubMed] open in new tab
  45. Wassvik, C.M.; Holmén, A.G.; Bergström, C.A.S.; Zamora, I.; Artursson, P. Contribution of solid-state properties to the aqueous solubility of drugs. Eur. J. Pharm. Sci. 2006, 29, 294-305. [CrossRef] [PubMed] open in new tab
  46. Vecchio, S.; Catalani, A.; Rossi, V.; Tomassetti, M. Thermal analysis study on vaporization of some analgesics. Acetanilide and derivatives. Thermochim. Acta 2004, 420, 99-104. [CrossRef] open in new tab
  47. Manzo, R.H.; Ahumada, A.A. Effects of Solvent Medium on Solubility. V: Enthalpic and Entropic Contributions to the Free Energy Changes of Di-substituted Benzene Derivatives in Ethanol: Water and Ethanol: Cyclohexane Mixtures. J. Pharm. Sci. 1990, 79, 1109-1115. [CrossRef] open in new tab
  48. Nordström, F.L.; Rasmuson, Å.C. Determination of the activity of a molecular solute in saturated solution. J. Chem. Thermodyn. 2008, 40, 1684-1692. [CrossRef] open in new tab
  49. Svärd, M.; Valavi, M.; Khamar, D.; Kuhs, M.; Rasmuson, Å.C. Thermodynamic Stability Analysis of Tolbutamide Polymorphs and Solubility in Organic Solvents. J. Pharm. Sci. 2016, 105, 1901-1906. [CrossRef] open in new tab
  50. Svärd, M.; Hjorth, T.; Bohlin, M.; Rasmuson, Å.C. Calorimetric Properties and Solubility in Five Pure Organic Solvents of N-Methyl-d-Glucamine (Meglumine). J. Chem. Eng. Data 2016, 61, 1199-1204. [CrossRef] open in new tab
  51. Neau, S.H.; Flynn, G.L. Solid and Liquid Heat Capacities of n-Alkyl Para-aminobenzoates Near the Melting Point. Pharm. Res. 1990, 7, 1157-1162. [CrossRef] open in new tab
  52. Hojjati, H.; Rohani, S. Measurement and Prediction of Solubility of Paracetamol in Water−Isopropanol Solution. Part 2. Prediction. Org. Process. Res. Dev. 2006, 10, 1110-1118. [CrossRef] open in new tab
  53. Yalkowsky, S.H.; Wu, M. Estimation of the ideal solubility (crystal-liquid fugacity ratio) of organic compounds. J. Pharm. Sci. 2010, 99, 1100-1106. [CrossRef] open in new tab
  54. Alvarez, V.H.; Saldaña, M.D.A. Modeling Solubility of Polycyclic Aromatic Compounds in Subcritical Water. Ind. Eng. Chem. Res. 2011, 50, 11396-11405. [CrossRef] open in new tab
  55. Prausintz, J.M.; Lichtenthaler, R.N.; de Azevedo, E.G. Molecular Thermodynamics of Fluid-Phase Equilibria, 3rd ed.; Prentice Hall: Englewood Cliffs, NJ, USA, 1999.
  56. Bondi, A. Estimation of Heat Capacity of Liquids. Ind. Eng. Chem. Fundam. 1966, 5, 442-449. [CrossRef] open in new tab
  57. Mackay, D.; Bobra, A.; Chan, D.W.; Shiu, W.Y. Vapor-pressure correlations for low-volatility environmental chemicals. Environ. Sci. Technol. 1982, 16, 645-649. [CrossRef] open in new tab
  58. Mishra, D.S.; Yalkowsky, S.H. Ideal Solubility of a Solid Solute: Effect of Heat Capacity Assumptions. Pharm. Res. 1992, 9, 958-959. [CrossRef] [PubMed] open in new tab
  59. Hildebrandt, J.H.; Prausnitz, J.M.; Scott, R.L. Regular and Related Solutions; Van Nostrand Reinhold: New York, NY, USA, 1970.
  60. Neau, S.H.; Bhandarkar, S.V.; Hellmuth, E.W. Differential Molar Heat Capacities to Test Ideal Solubility Estimations. Pharm. Res. 1997, 14, 601-605. [CrossRef] open in new tab
  61. Jia, R.; Sun, K.; Li, R.; Zhang, Y.; Wang, W.; Yin, H.; Fang, D.; Shi, Q.; Tan, Z. Heat capacities of some sugar alcohols as phase change materials for thermal energy storage applications. J. Chem. Thermodyn. 2017, 115, 233-248. [CrossRef] open in new tab
  62. Mealey, D.; Svärd, M.; Rasmuson, Å.C. Thermodynamics of risperidone and solubility in pure organic solvents. Fluid Phase Equilibria 2014, 375, 73-79. [CrossRef] open in new tab
  63. Bustamante, C.; Bustamante, P. Nonlinear Enthalpy-Entropy Compensation for the Solubility of Phenacetin in Dioxane-Water Solvent Mixtures. J. Pharm. Sci. 1996, 85, 1109-1111. [CrossRef] open in new tab
  64. Jouyban, A. Handbook of Solubility Data for Pharmaceuticals; CRC Press: Boca Raton, FL, USA, 2009. open in new tab
  65. Jouyban, A.; Fakhree, M.A.A. Experimental and Computational Methods Pertaining to Drug Solubility. In Toxicity and Drug Testing; open in new tab
  66. Acree, W.E., Ed.; InTech: Rijeka, Croatia, 2012; pp. 187-218, ISBN 978-953-51-0004-1.
  67. Jouyban, A. Review of the cosolvency models for predicting solubility of drugs in water-cosolvent mixtures. J. Pharm. Pharm. Sci. 2008, 11, 32-58. [CrossRef] open in new tab
  68. Cysewski, P.; Jeliński, T.; Procek, D.; Dratwa, A. Solubility of Sulfanilamide and Sulfacetamide in neat solvents: Measurements and interpretation using theoretical predictive models, first principle approach and artificial neural networks. Fluid Phase Equilibria 2021, 529, 112883. [CrossRef] open in new tab
  69. Svärd, M.; Ahuja, D.; Rasmuson, Å.C. Calorimetric Determination of Cocrystal Thermodynamic Stability: Sulfamethazine- Salicylic Acid Case Study. Cryst. Growth Des. 2020, 20, 4243-4251. [CrossRef] open in new tab
  70. Svärd, M.; Zeng, L.; Valavi, M.; Krishna, G.R.; Rasmuson, Å.C. Solid and Solution State Thermodynamics of Polymorphs of Butamben (Butyl 4-Aminobenzoate) in Pure Organic Solvents. J. Pharm. Sci. 2019, 108, 2377-2382. [CrossRef] [PubMed] open in new tab
  71. Cheuk, D.; Svärd, M.; Rasmuson, Å.C. Thermodynamics of the Enantiotropic Pharmaceutical Compound Benzocaine and Solubility in Pure Organic Solvents. J. Pharm. Sci. 2020, 109, 3370-3377. [CrossRef] [PubMed] open in new tab
  72. Yang, H.; Thati, J.; Rasmuson, Å.C. Thermodynamics of molecular solids in organic solvents. J. Chem. Thermodyn. 2012, 48, 150-159. [CrossRef] open in new tab
  73. Chase, M. NIST-JANAF Thermochemical Tables, 4th ed.; American Institute of Physics: College Park, MD, USA, 1998. open in new tab
  74. Grønvold, F. Heat capacity of indium from 300 to 1000 K. J. Therm. Anal. Calorim. 1978, 13, 419-428. [CrossRef] open in new tab
Verified by:
No verification

seen 88 times

Recommended for you

Thermodynamics and Intermolecular Interactions of Nicotinamide in Neat and Binary Solutions: Experimental Measurements and COSMO-RS Concentration Dependent Reactions Investigations

2021

Experimental and Theoretical Screening for Green Solvents Improving Sulfamethizole Solubility

2021

New Screening Protocol for Effective Green Solvents Selection of Benzamide, Salicylamide and Ethenzamide

2022

Solubility Characteristics of Acetaminophen and Phenacetin in Binary Mixtures of Aqueous Organic Solvents: Experimental and Deep Machine Learning Screening of Green Dissolution Media

2022
Meta Tags