Assessment of the amorphous "solubility" of a group of diverse drugs using new experimental and theoretical approaches

Molecular Pharmaceutics

Volumn 12, Issue 2, 2015, Pages 484-495

  Almeida E Sousa, Luis ^a   Reutzel Edens, Susan M ^b   Stephenson, Gregory A ^b   Taylor, Lynne S ^a  

^a PURDUE UNIVERSITY   (United States)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

amorphous "solubility"; phase separation; supersaturation

Indexed keywords

ACETONE; DICLOFENAC; FLUORESCENT DYE; GRISEOFULVIN; IBUPROFEN; METHANOL; N,N DIMETHYLFORMAMIDE; PHENYLBUTAZONE; SORAFENIB; TOLNAFTATE; WATER;

ARTICLE; COOLING; CRYSTAL STRUCTURE; CRYSTALLIZATION; DIFFERENTIAL SCANNING CALORIMETRY; DISPERSION; DRUG BIOAVAILABILITY; DRUG SOLUBILITY; ENTHALPY; ENTROPY; EXPOSURE; FLUORESCENCE SPECTROSCOPY; GLASS TRANSITION TEMPERATURE; HEAT; LIQUID; PH; PHASE SEPARATION; PHYSICAL CHEMISTRY; PREDICTION; PRIORITY JOURNAL; SOLVENT EFFECT; THEORETICAL STUDY; ULTRAVIOLET SPECTROPHOTOMETRY; MEDICINAL CHEMISTRY; PROCEDURES; SOLUBILITY; THEORETICAL MODEL;

CHEMISTRY, PHARMACEUTICAL; MODELS, THEORETICAL; SOLUBILITY;

EID: 84961289883     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp500571m     Document Type: Article

References (26)

1. Fahr, A.; Liu, X. Drug delivery strategies for poorly water-soluble drugs Expert Opin. Drug Delivery 2007, 4 (4) 403-416
2. Williams, H. D.; Trevaskis, N. L.; Charman, S. A.; Shanker, R. M.; Charman, W. N.; Pouton, C. W.; Porter, C. J. H. Strategies to address low drug solubility in discovery and development Pharmacol. Rev. 2013, 65 (1) 315-499
3. Ilevbare, G. A.; Taylor, L. S. Liquid-liquid phase separation in highly supersaturated aqueous solutions of poorly water-soluble drugs: Implications for solubility enhancing formulations Cryst. Growth Des. 2013, 13 (4) 1497-1509
4. Murdande, S. B.; Pikal, M. J.; Shanker, R. M.; Bogner, R. H. Solubility advantage of amorphous pharmaceuticals: I. A thermodynamic analysis J. Pharm. Sci. 2010, 99 (3) 1254-1264
5. Pudipeddi, M.; Serajuddin, A. T. M. Trends in solubility of polymorphs J. Pharm. Sci. 2005, 94 (5) 929-939
6. Johari, G. P.; Shanker, R. M. On the solubility advantage of a pharmaceuticals glassy state over the crystal state, and of its crystal polymorphs Thermochim. Acta 2014, 598 (0) 16-27
7. Murdande, S.; Pikal, M.; Shanker, R.; Bogner, R. Solubility advantage of amorphous pharmaceuticals: II. Application of quantitative thermodynamic relationships for prediction of solubility enhancement in structurally diverse insoluble pharmaceuticals Pharm. Res. 2010, 27 (12) 2704-2714
8. Shah, N.; Sandhu, H.; Choi, D.; Kalb, O.; Page, S.; Wyttenbach, N. Structured development approach for amorphous systems. In Formulating Poorly Water Soluble Drugs; Williams, R. O., III; Watts, A. B.; Miller, D. A., Eds.; Springer: New York, 2012; Vol. 3, pp 267-310.
9. Elamin, A. A.; Ahlneck, C.; Alderborn, G.; Nyström, C. Increased metastable solubility of milled griseofulvin, depending on the formation of a disordered surface structure Int. J. Pharm. 1994, 111 (2) 159-170
10. Ozaki, S.; Kushida, I.; Yamashita, T.; Hasebe, T.; Shirai, O.; Kano, K. Evaluation of drug supersaturation by thermodynamic and kinetic approaches for the prediction of oral absorbability in amorphous pharmaceuticals J. Pharm. Sci. 2012, 101 (11) 4220-4230
11. Hoffman, J. D. Thermodynamic driving force in nucleation and growth processes J. Chem. Phys. 1958, 29 (5) 1192-1193
12. Kalyanasundaram, K.; Thomas, J. K. Environmental effects on vibronic band intensities in pyrene monomer fluorescence and their application in studies of micellar systems J. Am. Chem. Soc. 1977, 99 (7) 2039-2044
13. Lianos, P.; Cremel, G. Environmental effects on the electronic spectral properties of 1-pyrenecarboxaldehyde and their application in probing biological structures Photochem. Photobiol. 1980, 31 (5) 429-434
14. Magrassi, L.; Purves, D.; Lichtman, J. Fluorescent probes that stain living nerve terminals J. Neurosci. 1987, 7 (4) 1207-1214
15. Raina, S. PhD Thesis; Purdue University: 2014.
16. 3 alloy Thermochim. Acta 1985, 85, 175-178
17. Perepezko, J. H.; Paik, J. S. Thermodynamic properties of undercooled liquid metals J. Non-Cryst. Solids 1984, 61-62 (Part 1) 113-118
18. Marsac, P.; Konno, H.; Taylor, L. A Comparison of the physical stability of amorphous felodipine and nifedipine systems Pharm. Res. 2006, 23 (10) 2306-2316
19. Turnbull, D. Formation of crystal nuclei in liquid metals J. Appl. Phys. 1950, 21 (10) 1022-1028
20. Jones, D. R. H.; Chadwick, G. A. An expression for the free energy of fusion in the homogeneous nucleation of solid from pure melts Philos. Mag. 1971, 24 (190) 995-998
21. Thompson, C. V.; Spaepen, F. On the approximation of the free energy change on crystallization Acta Metall. 1979, 27 (12) 1855-1859
22. Dubey, K. S.; Ramachandrarao, P. On the free energy change accompanying crystallisation of undercooled melts Acta Metall. 1984, 32 (1) 91-96
23. Singh, H. B.; Holz, A. Stability limit of supercooled liquids Solid State Commun. 1983, 45 (11) 985-988
24. Miura, H.; Isa, S.; Omuro, K. Estimation of free energies of crystallization of amorphous alloys J. Non-Cryst. Solids 1984, 61-62 (Part 1) 163-168
25. Atkins, P.; de Paula, J. Atkins Physical Chemistry; OUP: Oxford, 2010.
26. Box, K. J.; Comer, J. E. Using measured pKa, LogP and solubility to investigate supersaturation and predict BCS class Curr. Drug Metab. 2008, 9 (9) 869-78