An investigation into the influence of counterion on the properties of some amorphous organic salts

Molecular Pharmaceutics

Volumn 5, Issue 6, 2008, Pages 946-955

  Towler, Christopher S ^a   Li, Tonglei ^b   Wikstrom, Håkan ^a   Remick, David M ^c   Sanchez Felix, Manuel V ^c   Taylor, Lynne S ^a  

^a PURDUE UNIVERSITY   (United States)

^b University of Kentucky   (United States)

^c ELI LILLY AND COMPANY   (United States)

Author keywords

Amorphous; Counterion; Glass transition; Pk a; Salts

Indexed keywords

ACETIC ACID; BASE; BENZOIC ACID; BESYLATE; CHLORIDE; CITRIC ACID; COUNTERION; INORGANIC SALT; MESYLIC ACID; NICARDIPINE; OXALIC ACID; PHOSPHATE; PROPRANOLOL; SULFATE; TARTARIC ACID; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL PHENOMENA; CRYSTALLIZATION; GLASS TRANSITION TEMPERATURE; MOISTURE SORPTION BEHAVIOR; MULTIVARIATE ANALYSIS; PRIORITY JOURNAL;

ADSORPTION; CHEMISTRY, PHARMACEUTICAL; CRYSTALLIZATION; GLASS; HUMANS; HUMIDITY; MOLECULAR STRUCTURE; MULTIVARIATE ANALYSIS; NICARDIPINE; ORGANIC CHEMICALS; PHARMACEUTICAL PREPARATIONS; PROPRANOLOL; SALTS; SOLUBILITY; TECHNOLOGY, PHARMACEUTICAL; TEMPERATURE; TRANSITION TEMPERATURE; WATER;

EID: 64649101109     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp8000342     Document Type: Article

References (57)

1. Lipinski, C. A. Drug-like properties and the causes of poor solubility and poor permeability. J. Pharmacol. Toxicol. Methods 2000, 44 (1), 235-249.
2. Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Delivery Rev. 1997, 23 (1-3), 3-25.
3. Muller, R. H.; Jacobs, C.; Kayser, O. Nanosuspensions as particulate drug formulations in therapy Rationale for development and what we can expect for the future. Adv. Drug Delivery Rev. 2001, 47 (1), 3-19.
4. Berge, S. M.; Bighley, L. D.; Monkhouse, D. C. Pharmaceutical Salts. J. Pharm. Sci. 1977, 66 (1), 1-19.
5. Higuchi, W. I.; Bernardo, P. D.; Mehta, S. C. Polymorphism and Drug Availability. 2. Dissolution Rate Behavior of Polymorphic Forms of Sulfathiazole and Methylprednisolone. J. Pharm. Sci. 1967, 56 (2), 200.
6. Hancock, B. C.; Parks, M. What is the true solubility advantage for amorphous pharmaceuticals. Pharm. Res. 2000, 17 (4), 397-404.
7. Basavoju, S.; Bostrom, D.; Velaga, S. P. Pharmaceutical cocrystal and salts of norfloxacin. Cryst. Growth Des. 2006, 6 (12), 2699-2708.
8. Singhal, D.; Curatolo, W. Drug polymorphism and dosage form design: a practical perspective. Adv. Drug Delivery Rev. 2004, 56 (3), 335-347.
9. Hancock, B. C.; Carlson, G. T.; Ladipo, D. D.; Langdon, B. A.; Mullarney, M. P. Comparison of the mechanical properties of the crystalline and amorphous forms of a drug substance. Int. J. Pharm. 2002, 241 (1), 73-85.
10. Hancock, B. C.; Zografi, G. Characteristics and significance of the amorphous state in pharmaceutical systems. J. Pharm. Sci. 1997, 86 (1), 1-12.
11. Ahlneck, C.; Zografi, G. The Molecular-Basis of Moisture Effects on the Physical and Chemical-Stability of Drugs in the Solid- State. Int. J. Pharm. 1990, 62 (2-3), 87-95.
12. Kaushal, A. M.; Gupta, P.; Bansal, A. K. Amorphous Drug Delivery Systems: Molecular Aspects, Design, and Performance. Crit. Rev. Ther. Drug Carrier Syst. 2004, 21 (3), 113-193.
13. Leuner, C.; Dressman, J. Improving drug solubility for oral delivery using solid dispersions. Eur. J. Pharm. Biopharm. 2000, 50 (1), 47-60.
14. Serajuddin, A. T. M. Solid dispersion of poorly water-soluble drugs: Early promises, subsequent problems, and recent break-throughs. J. Pharm. Sci. 1999, 88 (10), 1058-1066.
15. Simonelli, A. P.; Mehta, S. C.; Higuchi, W. I. Dissolution Rates of High-Energy Sulfathiazole-Povidone Coprecipitates. 2. Char-acterization of Form of Drug Controlling Its Dissolution Rate Via Solubility Studies. J. Pharm. Sci. 1976, 65 (3), 355-361.
16. Chiou, W. L.; Riegelman, S. Pharmaceutical Applications of Solid Dispersion Systems. J. Pharm. Sci. 1971, 60 (9), 1281-1302.
17. Handbook of Pharmaceutical Salts; Wiley-VCH: New York, 2002.
18. Gould, P. L. Salt Selection for Basic Drugs. Int. J. Pharm. 1986, 33 (1-3), 201-217.
19. Tong, P.; Zografi, G. Solid-state characteristics of amorphous sodium indomethacin relative to its free acid. Pharm. Res. 1999, 16 (8), 1186-1192.
20. Tong, P.; Taylor, L. S.; Zografi, G. Influence of alkali metal counterions on the glass transition temperature of amorphous indomethacin salts. Pharm. Res. 2002, 19 (5), 649-654.
21. Consani, K.; Devlin, J. P.; Ray, A.; Farrar, H.; Wilson, E. W. Simple Amorphous Salts - Spectra and Glass-Transition Tem-peratures. J. Chem. Phys. 1981, 74 (9), 4774-4779.
22. Exarhos, G. J.; Miller, P. J.; Risen, W. M. Interionic Vibrations and Glass Transitions in Ionic Oxide Metaphosphate Glasses. J. Chem. Phys. 1974, 60 (11), 4145-4155.
23. Weuts, I.; Kempen, D.; Verreck, G.; Peeters, J.; Brewster, M.; Blaton, N.; Van den Mooter, G. Salt formation in solid dispersions consisting of polyacrylic acid as a carrier and three basic model compounds resulting in very high glass transition temperatures and constant dissolution properties upon storage. Eur. J. Pharm. Sd. 2005, 25 (4-5), 387-393.
24. Sjostrom, M.; Wold, S.; Lindberg, W.; Persson, J. A.; Martens, H. A Multivariate Calibration-Problem in Analytical-Chemistry Solved by Partial Least-Squares Models in Latent-Variables. Anal. Chim. Acta 1983, 150 (1), 61-70.
25. Wold, S.; Martens, H.; Wold, H. The Multivariate Calibration-Problem in Chemistry Solved by the PLS Method. Lect. Notes Math. 1983, No. 973, 286-293.
26. Dunn, W. J. Quantitative Structure-Activity Relationships (QSAR). Chemom. Intell. Lab. Syst. 1989, (6), 181-190.
27. Hellberg, S.; Sjostrom, M.; Wold, S. The Prediction of Bradykinin Potentiating Potency of Pentapeptides. An Example of a Peptide Quantitative Structure-Activity Relationship. Acta Chem. Scand. 1986, B40, 135-140.
28. Wold, S.; Dunn, W. J. Multivariate Quantitative Structure Activity Relationships (QSAR) - Conditions for Their Applicability. J. Chem. Inf. Comput. Sci. 1983, 23 (1), 6-13.
29. Becke, A. D. Density-Functional Exchange-Energy Approximation with Correct Asymptotic-Behavior. Phys. Rev.A1988, 38 (6), 3098-3100.
30. Lee, C. T.; Yang, W. T.; Parr, R. G. Development of the Colle-Salvetti Correlation-Energy Formula Into A Functional of the Electron-Density. Phys. Rev.B1988, 37 (2), 785-789.
31. Gaussian 03; Gaussian Inc.: Wallingfort, CT, 2004.
32. Eriksson, L.; Johansson, N.; Kettaneh-Wold, N.; Wold, S. InMulti- and mega-variate data analysis; Umetrics Academy: Umeå, Sweden, 2001; p 329.
33. Gift, A. D.; Taylor, L. S. Hyphenation of Raman spectroscopy with gravimetric analysis to interrogate water-solid interactions in pharmaceutical systems. J. Pharm. Biomed. Anal. 2007, 43 (1), 14-23.
34. Serajuddin, A. T. M.; Sheen, P. C.; Augustine, M. A. Improved Dissolution of A Poorly Water-Soluble Drug from Solid Disper-sions in Polyethylene-Glycol - Polysorbate-80 Mixtures. J. Pharm. Sci. 1990, 79 (5), 463-464.
35. Serajuddin, A. T. M. Salt formation to improve drug solubility. Adv. Drug Delivery Rev. 2007, 59 (7), 603-616.
36. Eisenberg, A.; Shen, M. C. Glass Transitions in Polymers. Prog. Solid State Chem. 1966, (3), 407-481.
37. Eisenberg, A.; Shen, M. C. Recent Advances in Glass Transitions in Polymers. Rubber Chem. Technol. 1970, (43), 156-170.
38. Hohenberg, P.; Kohn, W. Inhomogeneous Electron Gas. Phys. Rev.B1964, 136 (3B), B864.
39. Kohn, W.; Becke, A. D.; Parr, R. G. Density functional theory of electronic structure. J. Phys. Chem. 1996, 100 (31), 12974-12980.
40. Parr, R. G.; Yang, W. T. Density-Functional Theory of the Electronic-Structure of Molecules. Annu. Rev. Phys. Chem. 1995, 46, 701-728.
41. Alba-Simionesco, C.; Fan, J.; Angell, C. A. Thermodynamic aspects of the glass transition phenomenon. II. Molecular liquids with variable interactions. J. Chem. Phys. 1999, 110 (11), 5262-5272.
42. Klopman, G. Chemical Reactivity and Concept of Charge- and Frontier-Controlled Reactions. J. Am. Chem. Soc. 1968, 90 (2), 223.
43. Parr, R. G.; Pearson, R. G. Absolute Hardness - Companion Parameter to Absolute Electronegativity. J. Am. Chem. Soc. 1983, 105 (26), 7512-7516.
44. Parr, R. G.; Donnelly, R. A.; Levy, M.; Palke, W. E. Electrone-gativity - Density Functional Viewpoint. J. Chem. Phys. 1978, 68 (8), 3801-3807.
45. Yang, W. T.; Parr, R. G. Hardness, Softness, and the Fukui Function in the Electronic Theory of Metals and Catalysis. Proc. Natl. Acad. Sci. U.S.A. 1985, 82 (20), 6723-6726.
46. Parr, R. G.; Von Szentpaly, L.; Liu, S. B. Electrophilicity index. J. Am. Chem. Soc. 1999, 121 (9), 1922-1924.
47. Ayers, P. W.; Levy, M. Perspective on "Density functional approach to the frontier-electron theory of chemical reactivity" - Parr RG, Yang W (1984) J Am Chem Soc 106: 4049-4050. Theor. Chem. Acc. 2000, 103 (3-4), 353-360.
48. Geerlings, P.; De Proft, F.; Langenaeker, W. Conceptual density functional theory. Chem. Rev. 2003, 103 (5), 1793-1873.
49. Parr, R. G.; Yang, W. T. Density Functional-Approach to the Frontier-Electron Theory of Chemical-Reactivity. J. Am. Chem. Soc. 1984, 106 (14), 4049-4050.
50. Yang, W.; Parr, R. G.; Pucci, R. Electron-Density, Kohn-Sham Frontier Orbitals, and Fukui Functions. J. Chem. Phys. 1984, 81 (6), 2862-2863.
51. Ayers, P. W.; Parr, R. G.; Pearson, R. G. Elucidating the hard/ soft acid/base principle: A perspective based on half-reactions. J. Chem. Phys. 2006, 124 (19), 194107-1-194107-8.
52. Chattaraj, P. K.; Lee, H.; Parr, R. G. Hsab Principle. J. Am. Chem. Soc. 1991, 113 (5), 1855-1856.
53. Pearson, R. G. Hard and Soft Acids and Bases. J. Am. Chem. Soc. 1963, 85 (22), 3533.
54. Pearson, R. G. Acids and Bases. Science 1966, 151 (3707), 172.
55. Anderson, J. S. M.; Melin, J.; Ayers, P. W. Conceptual density- functional theory for general chemical reactions, including those that are neither charge- nor frontier-orbital-controlled. 1. Theory and derivation of a general-purpose reactivity indicator. J. Chem. Theor. Comput. 2007, 3 (2), 358-374.
56. Berkowitz, M. Density Functional-Approach to Frontier Controlled Reactions. J. Am. Chem. Soc. 1987, 109 (16), 4823-4825.
57. Avdeef, A. Adsorption and Drug Development: Solubility, Permeability and Charge State, 1st ed.; John Wiley and Sons Inc.: Hoboken, NJ, 2003.