An evaluation of thermodynamic models for the prediction of drug and drug-like molecule solubility in organic solvents

Fluid Phase Equilibria

Volumn 309, Issue 1, 2011, Pages 36-52

  Bouillot, Baptiste ^a   Teychené, Sébastien ^a   Biscans, Béatrice ^a  

^a LABORATOIRE DE GÉNIE CHIMIQUE   (France)

Author keywords

Activity coefficient; COSMO SAC; Crystallization; NRTL SAC; Solubility prediction; Thermodynamics; UNIFAC

Indexed keywords

4-AMINOBENZOIC ACID; ACTIVE PHARMACEUTICAL INGREDIENTS; BENZOIC ACID; COSMO-SAC; CRYSTALLIZATION PROCESS; DIFFERENT SOLVENTS; DRUG DEVELOPMENT; EQUILIBRIUM EQUATION; EXPERIMENTAL DETERMINATION; LIQUID LIQUID EQUILIBRIUM; MIXED SOLVENT; MODEL ERRORS; MODEL PARAMETERS; NRTL-SAC; QUANTITATIVE PREDICTION; SALICYLIC ACIDS; SOLID LIQUID EQUILIBRIUM; SOLID-STATE PROPERTIES; SOLUBILITY DATA; SOLUBILITY ESTIMATION; SOLUBILITY PREDICTION; THERMODYNAMIC MODEL; THREE ORDERS OF MAGNITUDE; UNIFAC; UNIFAC MODEL;

AMINO ACIDS; C (PROGRAMMING LANGUAGE); CARBOXYLIC ACIDS; CRYSTALLIZATION; ERRORS; FORECASTING; FUNCTIONAL GROUPS; HYDROGEN BONDS; LIQUIDS; MOLECULES; ORGANIC SOLVENTS; SOLVENTS; THERMODYNAMIC PROPERTIES;

SOLUBILITY;

EID: 80051576618     PISSN: 03783812     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.fluid.2011.06.032     Document Type: Article

References (58)

1. Morissete S., Almarsson O., Peterson M., Remenar J., Read M., Lemmo A., Ellis S., Cima M., Gardner C. High-throughput crystallization: polymorphs, salts, co-crystals and solvates of pharmaceutical solids. Advanced Drug Delivery Reviews 2003, 56:275-300.
2. Laval P., Lisai N., Salmon J.-B., Joanicot M. A microfluidic device based on droplet storage for screening solubility diagrams. Lab on a Chip 2007, 7:829-834.
3. Noyes A.A., Whitney W.R. Physical Chemistry 1909, 23:689.
4. Gmehling J.G., Anderson T.F., Prausnitz J.M. Solid-liquid equilibria using UNIFAC. Industrial & Engineering Chemistry Fundamentals 1978, 17:269-273.
5. Gracin S., Brinck T., Rasmuson A. Prediction of solubility of solid organic compounds in solvents by UNIFAC. Industrial & Engineering Chemistry Research 2002, 41:5114-5124.
6. Mullins E., Liu Y., Ghaderi A., Fast S.D. Sigma profile database for predicting solid solubility in pure and mixed solvent mixtures for organic pharmacological compounds with COSMO-based thermodynamic methods. Industrial & Engineering Chemistry Research 2008, 47:1707-1725.
7. Mota F.L., Carneiro A.P., Pinho S.P., Macedo E.A. Temperature and solvent effect in solubility of some pharmaceutical compounds: measurements and modelling. European Journal of Pharmaceutical Science 2009, 37:499-507.
8. Hahnenkamp I., Graubner G., Gmehling J. Measurement and prediction of solubilities of active pharmaceutical ingredients. International Journal of Pharmaceutics 2010, 388:73-81.
9. Mullin J. Crystallization-3 Rev 1993, Oxford.
10. Brown M., Glass B. Decomposition of solids accompanied by melting-Bawn kinetics. International Journal of Pharmaceutics 2003, 254:255-261.
11. Fredenslund A., Jones R., Prausnitz J. Group-contribution estimation of activity-coefficients in nonideal liquid-mixtures. AIChE Journal 1975, 21:1086-1099.
12. Weidlich U., Gmehling J. A modified UNIFAC model. 1. Prediction of VLE, HE, and gamma-infinity. Industrial & Engineering Chemistry Research 1987, 26:1372-1381.
13. Klamt A., Schuurmann G. COSMO-a new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient. Journal of the Chemical Society-Perkin Transactions 1993, 2:799-805.
14. Klamt A., Jonas V., Burger T., Lohrenz J. Refinement and parametrization of COSMO-RS. Journal of Physical Chemistry A 1998, 102:5074-5085.
15. Lin S., Sandler S. A priori phase equilibrium prediction from a segment contribution solvation model. Industrial & Engineering Chemistry Research 2002, 41:899-913.
16. Mullins E., Oldland R., Liu Y., Wang S., Sandler S.I., Chen C.-C., Zwolak M., Seavey K.C. Sigma-profile database for using COSMO-based thermodynamic methods. Industrial & Engineering Chemistry Research 2006, 45:4389-4415.
17. Chen C.-C., Song Y. Solubility modeling with a nonrandom two-liquid segment activity coefficient model. Industrial & Engineering Chemistry Research 2004, 43:8354-8362.
18. Renon H., Prausnitz J. Local composition in thermodynamic excess functions for liquid mixtures. AIChE Journal 1968, 14:135-144.
19. Chen C.-C. A segment-based local composition model for the Gibbs energy of polymer solutions. Fluid Phase Equilibria 1993, 83:301.
20. Garzon L.C., Martinez F. Temperature dependence of solubility for ibuprofen in some organic and aqueous solvents. Journal of Solution Chemistry 2004, 33:1379-1395.
21. Gracin S., Rasmuson A. Solubility of phenylacetic acid, p-hydroxyphenylacetic acid, p-aminophenylacetic acid, p-hydroxybenzoic acid, and ibuprofen in pure solvents. Journal of Chemical and Engineering Data 2002, 47:1379-1383.
22. Granberg R., Rasmuson A. Solubility of paracetamol in pure solvents. Journal of Chemical and Engineering Data 1999, 44:1391-1395.
23. De Fina K., Sharp T., Roy L., Acree W. Solubility of 8-hydroxybenzoic acid in select organic solvents at 298.15K. Journal of Chemical and Engineering Data 1999, 44:1262-1264.
24. Fung H., Higuchi T. Molecular interactions and solubility of polar nonelectrolytes in nonpolar solvents. Journal of Pharmaceutical Sciences 1971, 60:1782-1788.
25. Nordstrom F.L., Rasmuson A.C. Solubility and melting properties of salicylic acid. Journal of Chemical and Engineering Data 2006, 51:1668-1671.
26. Paruta A., Sciarrone B., Lordi N. Solubility of salicylic acid as a function of dielectric constant. Journal of Pharmaceutical Sciences 1964, 53:1349-1353.
27. Shalmashi A., Eliassi A. Solubility of salicylic acid in water, ethanol, carbon tetrachloride, ethyl acetate, and xylene. Journal of Chemical and Engineering Data 2008, 53:199-200.
28. Acree W., Bertrand G. Thermochemical investigations of nearly ideal binary solvents. 7. Monomer and dimer models for solubility of benzoic-acid in simple binary and ternary solvents. Journal of Pharmaceutical Sciences 1981, 70:1033-1036.
29. Beerbower A., Wu P., Martin A. Expanded solubility parameter approach. 1. Naphthalene and benzoic-acid in individual solvents. Journal of Pharmaceutical Sciences 1984, 73:179-188.
30. Li D., Liu D., Wang F. Solubility of 4-methylbenzoic acid between 288K and 370K. Journal of Chemical and Engineering Data 2001, 46:234-236.
31. Lin H., Nash R. An experimental method for determining the Hildebrand solubility parameter of organic nonelectrolytes. Journal of Pharmaceutical Sciences 1993, 82:1018-1025.
32. Yalkowski S., Valvani S., Roseman T. Solubility and partitioning vi: octanol solubility and octanol-water partition coefficients. Journal of Pharmaceutical Science 1983, 72:866-870.
33. Hancock C., Pawlowski J., Idoux J. Journal of Organic Chemistry 1966, 31:3801.
34. Daniels C., Charlton A., Wold R., Moreno R., Acree W., Abraham M. Mathematical correlation of 4-aminobenzoic acid solubilities in organic solvents with the Abraham solvation parameter model. Physics and Chemistry of Liquids 2004, 42:633-641.
35. Cepeda E., Gomez B. Solubility of anthracene and anthraquinone in some pure and mixed solvents. Journal of Chemical Engineering Data 1989, 34:273-275.
36. Cepeda E., Diaz M. Solubility of anthracene and anthraquinone in acetonitrile, methyl ethyl ketone, isopropyl alcohol and their mixtures. Fluid Phase Equilibria 1996, 121:267-272.
37. Al-Sharrah G., Ali S., Fahim M. Solubility of anthracene in two binary solvents containing toluene. Fluid Phase Equilibria 2002, 193:191-201.
38. Powell J., Acree W. Solubility of anthracene in binary alcohol+dibutyl ether solvent mixtures. Journal of Chemical Engineering Data 1995, 40:914-916.
39. Zvaigzne A., Acree W. Thermochemical investigations of molecular complexation. Estimation of anthracene-ethyl acetate and anthracene-diethyl adipate association parameters from measured solubility data. Physics & Chemistry of Liquids 1991, 24:31-42.
40. Andrews D., Lynn G., Johnston J. The heat capacities and heat of crystallization of some isomeric aromatic compounds. Journal of American Chemical Society 1926, 48:1274-1287.
41. David D. Determination of specific heat and heat of fusion by differential thermal analysis. study of theory and operating parameters. Analysis Chemistry 1964, 36:2162-2166.
42. Ginnings D., Furukawa G. Heat capacity standards for the range 14 to 1200. Journal of American Chemical Society 1953, 75:522-527.
43. Grant D., Mehdizadeh M., Chow A., Fairbrother J. Nonlinear van't Hoff solubility-temperature plots and their pharmaceutical interpretation. International Journal of Pharmaceutics 1984, 18:25-38.
44. Li D., Liu J., Liu D., Wang F. Solubilities of terephthalaldehydic, p-toluic, benzoic, terephthalic and isophthalic acids in n,n-dimethylformamide from 294.75 to 370.45K. Fluid Phase Equilibria 2002, 200:69-74.
45. Manzo R., Ahumada A. Effects of solvent medium on solubility. 5. Enthalpic and entropic contributions to the free-energy changes of disubstituted benzene-derivatives in ethanol water and ethanol cyclohexane mixtures. Journal of Pharmaceutical Sciences 1990, 79:1109-1115.
46. Neau S., Bhandarkar S., Hellmuth E. Differential molar heat capacities to test ideal solubility estimations. Pharmaceutical Research 1997, 14:601-605.
47. Nielsen T., Abildskov J., Harper P., Papaeconomou I., Gani R. The CAPEC database. Journal of Chemical and Engineering Data 2001, 46:1041-1044.
48. Qingzhu J., Peisheng M., Shouzhi Y., Qiang W., Chan W., Guiju L. Solubilities of benzoic acid, p-methylbenzoic acid, m-methylbenzoic acid, o-methylbenzoic acid, p-hydrobenzoic acid, and o-nitrobenzoic acid in 1-octanol. Journal of Chemical and Engineering Data 2008, 53:1278-1282.
49. Romero S., Reillo A., Escalera B., Bustamante P. The behaviour of paracetamol in mixtures of amphiprotic and amphiprotic-aprotic solvents. Relationship of solubility curves to specific and nonspecific interactions. Chemical & Pharmaceutical Bulletin 1996, 44:1061-1064.
50. Sacchetti M. Thermodynamic analysis of DSC data for acetaminophen polymorphs. Journal of Thermal Analysis and Calorimetry 2001, 63:345-350.
51. Weast R., Astle M. CRC Handbook of Data on Organic Compounds 1985, CRC Press, Boca Raton, FL.
52. Wu M., Yalkowsky S. Estimation of the molar heat capacity change on melting of organic compounds. Industrial & Engineering Chemical Research 2009, 48:1063-1066.
53. Xu F., Sun L., Tan Z., Liang J., Li R. Thermodynamic study of ibuprofen by adiabatic calorimetry and thermal analysis. Thermochimica Acta 2004, 412:33-37.
54. Van Duyne R., Taylor Self-association and hydration of benzoic acid in benzene. Journal of Physics Chemistry 2009, 48:1063-1066.
55. Chen C.-C., Song Y. Extension of nonrandom two-liquid segment activity coefficient model for electrolytes. Industrial & Engineering Chemistry Research 2005, 44:8909-8921.
56. Chen C.-C., Crafts P.A. Correlation and prediction of drug molecule solubility in mixed solvent systems with the nonrandom two-liquid segment activity coefficient (NRTL-SAC) model. Industrial & Engineering Chemistry Research 2006, 45:4816-4824.
57. Tsivintzelis I., Dritsas G., Panayiotou C. An alternative approach to nonrandomness in solution thermodynamics. Industrial & Engineering Chemistry Research 2006, 7264-7274.
58. Gross J., Sadowski G. Perturbed-chain saft: an equation of state based on a perturbation theory for chain molecules. Industrial & Engineering Chemistry Research 2001, 40:1244-1260.