Major source of error in QSPR prediction of intrinsic thermodynamic solubility of drugs: Solid vs nonsolid state contributions?

Molecular Pharmaceutics

Volumn 12, Issue 6, 2015, Pages 2126-2141

  Abramov, Yuriy A ^a  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

crystal packing contribution; error propagation; free energy of fusion; free energy of mixing; QSPR QSAR; thermodynamic intrinsic aqueous solubility

Indexed keywords

ACETAZOLAMIDE; ALPRENOLOL; ASTEMIZOLE; ATROPINE; BENZOCAINE; CARVEDILOL; CHLORPROPAMIDE; CHLORPROTHIXENE; CIMETIDINE; CINNARIZINE; CIPROFLOXACIN; CLOZAPINE; DANAZOL; DIAZEPAM; DIAZOXIDE; DICLOFENAC; FELODIPINE; FLUFENAMIC ACID; GLIBENCLAMIDE; GLICLAZIDE; GLIMEPIRIDE; GRISEOFULVIN; HYDROCHLOROTHIAZIDE; IBUPROFEN; INDOMETACIN; ITRACONAZOLE; KETOPROFEN; MEFENAMIC ACID; PARACETAMOL; UNINDEXED DRUG;

ALGORITHM; AQUEOUS SOLUTION; ARTICLE; CRYSTAL STRUCTURE; DRUG INDUSTRY; DRUG SOLUBILITY; ENVIRONMENTAL TEMPERATURE; MATERIAL STATE; MEASUREMENT ACCURACY; PREDICTION; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; QUANTITATIVE STRUCTURE PROPERTY RELATION; SOLID STATE; SOLUBILIZATION; THERMODYNAMICS; WORKFLOW; SOLUBILITY; THEORETICAL MODEL;

ALGORITHMS; MODELS, THEORETICAL; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; SOLUBILITY; THERMODYNAMICS;

EID: 84930657068     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/acs.molpharmaceut.5b00119     Document Type: Article

References (63)

1. Yu, L. X.; Amidon, G. L.; Polli, J. E.; Zhao, H.; Mehta, M. U.; Conner, D. P.; Shah, V. P.; Lesko, L. J.; Chen, M.-L.; Lee, V. H. Biopharmaceutics classification system: the scientific basis for biowaiver extensions Pharm. Res. 2002, 19 (7) 921-925
2. Di, L.; Kerns, E. H.; Carter, G. T. Drug-like property concepts in pharmaceutical design Curr. Pharmaceut. Des. 2009, 15 (19) 2184-2194
3. Docherty, R. P.; Pencheva, K.; Abramov, Y. A. Low solubility in drug development: de-convoluting the relative importance of solvation and crystal packing J. Pharm. Pharm. 2015, 10.1111/jphp.12393
4. Jorgensen, W. L.; Duffy, E. M. Prediction of drug solubility from structure Adv. Drug Delivery Rev. 2002, 54 (3) 355-366
5. Gudmundsson, O.; Venkatesh, S. Strategies for in silico and experimental screening of physicochemical properties Biotechnol.: Pharm. Aspects 2004, 1, 393-412
6. Delaney, J. S. Predicting aqueous solubility from structure Drug Discovery Today 2005, 10 (4) 289-295
7. Johnson, S. R.; Zheng, W. Recent progress in the computational prediction of aqueous solubility and absorption AAPS J. 2006, 8 (1) E27-E40
8. Johnson, S. R.; Chen, X.-Q.; Murphy, D.; Gudmundsson, O. A computational model for the prediction of aqueous solubility that includes crystal packing, intrinsic solubility, and ionization effects Mol. Pharmaceutics 2007, 4 (4) 513-523
9. Balakin, K. V.; Savchuk, N. P.; Tetko, I. V. In silico approaches to prediction of aqueous and DMSO solubility of drug-like compounds: trends, problems and solutions Curr. Med. Chem. 2006, 13 (2) 223-241
10. Wang, J.; Hou, T. Recent advances on aqueous solubility prediction Comb. Chem. High Throughput Screening 2011, 14 (5) 328-338
11. Salahinejad, M.; Le, T. C.; Winkler, D. A. Aqueous solubility prediction: Do crystal lattice interactions help? Mol. Pharmaceutics 2013, 10 (7) 2757-2766
12. Abramov, Y. A.; Pencheva, K. Thermodynamics and relative solubility prediction of polymorphic systems. In Chemical Engineering in the Pharmaceutical Industry: R&D to Manufacturing; am Ende, D. J., Ed.; John Wiley and Sons: 2011; pp 477-490.
13. Palmer, D. S.; Mitchell, J. B. Is experimental data quality the limiting factor in predicting the aqueous solubility of druglike molecules? Mol. Pharmaceutics 2014, 11 (8) 2962-2972
14. Palmer, D. S.; Llinàs, A.; Morao, I.; Day, G. M.; Goodman, J. M.; Glen, R. C.; Mitchell, J. B. Predicting intrinsic aqueous solubility by a thermodynamic cycle Mol. Pharmaceutics 2008, 5 (2) 266-279
15. Palmer, D. S.; McDonagh, J. L.; Mitchell, J. B.; van Mourik, T.; Fedorov, M. V. First-Principles Calculation of the Intrinsic Aqueous Solubility of Crystalline Druglike Molecules J. Chem. Theory Comput. 2012, 8 (9) 3322-3337
16. McDonagh, J. L.; Nath, N.; De Ferrari, L.; Van Mourik, T.; Mitchell, J. B. Uniting Cheminformatics and Chemical Theory To Predict the Intrinsic Aqueous Solubility of Crystalline Druglike Molecules J. Chem. Inf. Model. 2014, 54 (3) 844-856
17. Abramov, Y. A. Computational modeling of drug solubility. IQPC Improving Solubility Forum, Princeton, NJ, USA, 2008
18. Grant, D. J.; Higuchi, T. Solubility behavior of organic compounds; Wiley: New York, 1990.
19. Zielenkiewicz, X.; Perlovich, G.; Wszelaka-Rylik, M. The vapour pressure and the enthalpy of sublimation: determination by inert gas flow method J. Therm. Anal. Calorim. 1999, 57 (1) 225-234
20. Clas, S.-D.; Dalton, C. R.; Hancock, B. C. Differential scanning calorimetry: applications in drug development Pharm. Sci. Technol. Today 1999, 2 (8) 311-320
21. Taylor, J. Introduction to error analysis, the study of uncertainties in physical measurements; University Science Books: 1997.
22. Hoffman, J. D. Thermodynamic driving force in nucleation and growth processes J. Chem. Phys. 1958, 29 (5) 1192-1193
23. Llinàs, A.; Glen, R. C.; Goodman, J. M. Solubility challenge: can you predict solubilities of 32 molecules using a database of 100 reliable measurements? J. Chem. Inf. Model. 2008, 48 (7) 1289-1303
24. Hopfinger, A. J.; Esposito, E. X.; Llinàs, A.; Glen, R. C.; Goodman, J. M. Findings of the challenge to predict aqueous solubility J. Chem. Inf. Model. 2008, 49 (1) 1-5
25. Comer, J.; Judge, S.; Matthews, D.; Towes, L.; Falcone, B.; Goodman, J.; Dearden, J. The intrinsic aqueous solubility of indomethacin ADMET and DMPK 2014, 2 (1) 18-32
26. Bergström, C. A.; Wassvik, C. M.; Johansson, K.; Hubatsch, I. Poorly soluble marketed drugs display solvation limited solubility J. Med. Chem. 2007, 50 (23) 5858-5862
27. Wassvik, C. M.; Holmén, A. G.; Bergström, C. A.; Zamora, I.; Artursson, P. Contribution of solid-state properties to the aqueous solubility of drugs Eur. J. Pharm. Sci. 2006, 29 (3) 294-305
28. Carhart, R. E.; Smith, D. H.; Venkataraghavan, R. Atom pairs as molecular features in structure-activity studies: definition and applications J. Chem. Inf. Comput. Sci. 1985, 25 (2) 64-73
29. Sheridan, R. P.; Feuston, B. P.; Maiorov, V. N.; Kearsley, S. K. Similarity to molecules in the training set is a good discriminator for prediction accuracy in QSAR J. Chem. Inf. Comput. Sci. 2004, 44 (6) 1912-1928
30. Rai, U.; Pandey, P.; Rai, R. Physical chemistry of binary organic eutectic and monotectic alloys; 1, 2, 4, 5-tetrachlorobenzene-α-naphthol and TCB-resorcinol systems Mater. Lett. 2002, 53 (1) 83-90
31. Yu, L. Inferring thermodynamic stability relationship of polymorphs from melting data J. Pharm. Sci. 1995, 84 (8) 966-974
32. Baraldi, C.; Gamberini, M.; Tinti, A.; Palazzoli, F.; Ferioli, V. Vibrational study of acetazolamide polymorphism J. Mol. Struct. 2009, 918 (1) 88-96
33. Li, Z. J.; Zell, M. T.; Munson, E. J.; Grant, D. J. Characterization of racemic species of chiral drugs using thermal analysis, thermodynamic calculation, and structural studies J. Pharm. Sci. 1999, 88 (3) 337-346
34. Domanska, U.; Pobudkowska, A.; Pelczarska, A.; Gierycz, P. pKa and Solubility of Drugs in Water, Ethanol, and 1-Octanol J. Phys. Chem. B 2009, 113 (26) 8941-8947
35. Wassvik, C. M.; Holmén, A. G.; Draheim, R.; Artursson, P.; Bergström, C. A. Molecular characteristics for solid-state limited solubility J. Med. Chem. 2008, 51 (10) 3035-3039
36. Domalski, E. S.; Hearing, E. D. Heat capacities and entropies of organic compounds in the condensed phase. Volume III J. Phys. Chem. Ref. Data 1996, 25 (1) 1-525
37. Crafts, P. The role of solubility modeling and crystallization in the design of active pharmaceutical ingredients Comput.-Aided Chem. Eng. 2007, 23, 23-85
38. Yu, X.; Zipp, G. L.; Davidson, G. R., III The effect of temperature and pH on the solubility of quinolone compounds: estimation of heat of fusion Pharm. Res. 1994, 11 (4) 522-527
39. Surov, A. O.; Voronin, A. P.; Manin, A. N.; Manin, N. G.; Kuzmina, L. G.; Churakov, A. V.; Perlovich, G. L. Pharmaceutical Cocrystals of Diflunisal and Diclofenac with Theophylline Mol. Pharmaceutics 2014, 11 (10) 3707-3715
40. Perlovich, G. L.; Surov, A. O.; Bauer-Brandl, A. Thermodynamic properties of flufenamic and niflumic acids - Specific and non-specific interactions in solution and in crystal lattices, mechanism of solvation, partitioning and distribution J. Pharm. Biomed. Anal. 2007, 45 (4) 679-687
41. Henck, J. O.; Kuhnert-Brandstatter, M. Demonstration of the terms enantiotropy and monotropy in polymorphism research exemplified by flurbiprofen J. Pharm. Sci. 1999, 88 (1) 103-108
42. Surov, A. O.; Terekhova, I. V.; Bauer-Brandl, A.; Perlovich, G. L. Thermodynamic and structural aspects of some fenamate molecular crystals Cryst. Growth Des. 2009, 9 (7) 3265-3272
43. Romero, S.; Bustamante, P.; Escalera, B.; Mura, P.; Cirri, M. Influence of solvent composition on the solid phase at equilibrium with saturated solutions of quinolones in different solvent mixtures J. Pharm. Biomed. Anal. 2004, 35 (4) 715-726
44. Oliveira, P.; Bernardi, L.; Murakami, F.; Mendes, C.; Silva, M. A. Thermal characterization and compatibility studies of norfloxacin for development of extended release tablets J. Therm. Anal. Calorim. 2009, 97 (2) 741-745
45. Sabbah, R.; Perez, L. étude thermodynamique des acides phtalique, isophtalique et téréphtalique Can. J. Chem. 1999, 77 (9) 1508-1513
46. Perlovich, G. L.; Volkova, T. V.; Bauer-Brandl, A. Thermodynamic study of sublimation, solubility, solvation, and distribution processes of atenolol and pindolol Mol. Pharmaceutics 2007, 4 (6) 929-935
47. Pena, M.; Escalera, B.; Reíllo, A.; Sánchez, A.; Bustamante, P. Thermodynamics of cosolvent action: phenacetin, salicylic acid and probenecid J. Pharm. Sci. 2009, 98 (3) 1129-1135
48. Martínez, F.; Gómez, A. Estimation of the solubility of sulfonamides in aqueous media from partition coefficients and entropies of fusion Phys. Chem. Liq. 2002, 40 (4) 411-420
49. Muela, S.; Escalera, B.; Pena, M. á.; Bustamante, P. Influence of temperature on the solubilization of thiabendazole by combined action of solid dispersions and co-solvents Int. J. Pharm. 2010, 384 (1) 93-99
50. Chickos, J. S.; Braton, C. M.; Hesse, D. G.; Liebman, J. F. Estimating entropies and enthalpies of fusion of organic compounds J. Org. Chem. 1991, 56 (3) 927-938
51. Breiman, L. Random Forests Mach. Learn. 2001, 45, 5-32
52. Quinlan, J. R. In Combining Instance-Based and Model-Based Learning; ICML: 1993; pp 236-243.
53. Gao, H.; Yao, L.; Mathieu, H. W.; Zhang, Y.; Maurer, T. S.; Troutman, M. D.; Scott, D. O.; Ruggeri, R. B.; Lin, J. In silico modeling of nonspecific binding to human liver microsomes Drug Metab. Dispos. 2008, 36 (10) 2130-2135
54. Gupta, R. R.; Gifford, E. M.; Liston, T.; Waller, C. L.; Hohman, M.; Bunin, B. A.; Ekins, S. Using open source computational tools for predicting human metabolic stability and additional absorption, distribution, metabolism, excretion, and toxicity properties Drug Metab. Dispos. 2010, 38 (11) 2083-2090
55. Palmer, D. S.; OBoyle, N. M.; Glen, R. C.; Mitchell, J. B. Random forest models to predict aqueous solubility J. Chem. Inf. Model. 2007, 47 (1) 150-158
56. Svetnik, V.; Liaw, A.; Tong, C.; Culberson, J. C.; Sheridan, R. P.; Feuston, B. P. Random forest: a classification and regression tool for compound classification and QSAR modeling J. Chem. Inf. Comput. Sci. 2003, 43 (6) 1947-1958
57. Lee, P. H.; Cucurull-Sanchez, L.; Lu, J.; Du, Y. J. Development of in silico models for human liver microsomal stability J. Comput.-Aided Mol. Des. 2007, 21 (12) 665-673
58. Tu, M. L. D. An in Silico Model to Predict P-gp Substrate; The World Pharmaceutical Congress. Cambridge Healthtech Institute: Needham, MA, Philadelphia, PA, 2004.
59. Hughes, L. D.; Palmer, D. S.; Nigsch, F.; Mitchell, J. B. Why are some properties more difficult to predict than others? A study of QSPR models of solubility, melting point, and Log P J. Chem. Inf. Model. 2008, 48 (1) 220-232
60. Charlton, M. H.; Docherty, R.; Hutchings, M. G. Quantitative structure-sublimation enthalpy relationship studied by neural networks, theoretical crystal packing calculations and multilinear regression analysis J. Chem. Soc., Perkin Trans. 2 1995, 11) 2023-2030
61. Ouvrard, C.; Mitchell, J. B. Can we predict lattice energy from molecular structure? Acta Crystallogr., Sect. B: Struct. Sci. 2003, 59 (5) 676-685
62. Salahinejad, M.; Le, T. C.; Winkler, D. A. Capturing the crystal: prediction of enthalpy of sublimation, crystal lattice energy, and melting points of organic compounds J. Chem. Inf. Model. 2013, 53 (1) 223-229
63. Abramov, Y. A. QSPR modeling of chemical and physical stability of pharmaceuticals, 20th EuroQSAR symposium, St. Petersburg, Russia. 2014.