Effect of micellar solubilization on cocrystal solubility and stability

Crystal Growth and Design

Volumn 10, Issue 5, 2010, Pages 2050-2053

  Huang, Neal ^a   Rodríguez Hornedo, Naír ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77952086944     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg1002176     Document Type: Article

References (26)

1. Rodríguez-Hornedo, N.; Nehm, S. J.; Jayasankar, A. Cocrystals: Design, Properties and Formation Mechanisms. Encyclopedia of Pharmaceutical Technology, 3 rd ed.; 2006; pp 615-635.
2. Rodríguez-Hornedo, N. Cocrystals: Molecular design of pharmaceutical materials Mol. Pharmaceutics 2007, 4 (3) 299-300 (Pubitemid 46983945)
3. Stahly, G. P. A Survey of Cocrystals Reported Prior to 2000 Cryst. Growth Des. 2009, 9 (10) 4212-4229
4. Aakeroy, C. B.; Desper, J.; Fasulo, M.; Hussain, I.; Levin, B.; Schultheiss, N. Ten years of co-crystal synthesis; the good, the bad, and the ugly CrystEngComm 2008, 10 (12) 1816-1821
5. Shan, N.; Zaworotko, M. J. The role of cocrystals in pharmaceutical science Drug Discovery Today 2008, 13 (9-10) 440-446
6. Trask, A. V. An overview of pharmaceutical cocrystals as intellectual property Mol. Pharmaceutics 2007, 4 (3) 301-309 (Pubitemid 46983946)
7. McNamara, D. P.; Childs, S. L.; Giordano, J.; Iarriccio, A.; Cassidy, J.; Shet, M. S.; Mannion, R.; O'Donnell, E.; Park, A. Use of a glutaric acid cocrystal to improve oral bioavailability of a low solubility API Pharm. Res. 2006, 23 (8) 1888-1897 (Pubitemid 44200553)
8. Bak, A.; Gore, A.; Yanez, E.; Stanton, M.; Tufekcic, S.; Syed, R.; Akrami, A.; Rose, M.; Surapaneni, S.; Bostick, T.; King, A.; Neervannan, S.; Ostovic, D.; Koparkar, A. The co-crystal approach to improve the exposure of a water-insoluble compound: AMG 517 sorbic acid co-crystal characterization and pharmacokinetics J. Pharm. Sci. 2008, 97 (9) 3942-3956
9. Good, D. J.; Rodríguez-Hornedo, N. Solubility Advantage of Pharmaceutical Cocrystals Cryst. Growth Des. 2009, 9 (5) 2252-2264
10. Bethune, S. J.; Huang, N.; Jayasankar, A.; Rodriguez-Hornedo, N. Understanding and Predicting the Effect of Cocrystal Components and pH on Cocrystal Solubility Cryst. Growth Des. 2009, 9 (9) 3976-3988
11. Christian, S. D.; Scamehorn, J. F. Solubilization in Surfactant Aggregates; Marcel Dekker, Inc.: 1995; Vol. 55.
12. Reddy, L. S.; Bethune, S. J.; Kampf, J. W.; Rodriguez-Hornedo, N. Cocrystals and Salts of Gabapentin: pH Dependent Cocrystal Stability and Solubility Cryst. Growth Des. 2009, 9 (1) 378-385
13. Tucker, E. E.; Christian, S. D. Solubilization of benzene by aqueous sodium octylsulfate: Effect of added sodium chloride J. Colloid Interface Sci. 1985, 104 (2) 562-568
14. Christian, S. D.; Tucker, E. E.; Lane, E. H. Precise vapor pressure measurements of the solubilization of cyclohexane by sodium octyl sulfate and sodium octyl sulfate micelles J. Colloid Interface Sci. 1981, 84 (2) 423-432
15. Moroi, Y. Micelles: Theoretical and Applied Aspects; Plenum Press: 1992.
16. Rizzo, V. Hydrophilic molecules solubilized in water-in-oil microemulsions: Distribution of species in a chemical equilibrium J. Colloid Interface Sci. 1986, 110 (1) 110-113 (Pubitemid 16520570)
17. Li, P.; Tabibi, S. E.; Yalkowsky, S. H. Combined effect of complexation and pH on solubilization J. Pharm. Sci. 1998, 87 (12) 1535-1537 (Pubitemid 28559637)
18. Jain, A.; Ran, Y. Q.; Yalkowsky, S. H. Effect of pH-sodium lauryl sulfate combination on solubilization of PG-300995 (an anti-HIV agent): A technical note AAPS PharmSciTech 2004, 5 (3) 65-67 (Pubitemid 41086235)
19. Chiarella, R. A.; Davey, R. J.; Peterson, M. L. Making co-crystals-The utility of ternary phase diagrams Cryst. Growth Des. 2007, 7 (7) 1223-1226
20. Blagden, N.; Berry, D. J.; Parkin, A.; Javed, H.; Ibrahim, A.; Gavan, P. T.; De Matos, L. L.; Seaton, C. C. Current directions in co-crystal growth New J. Chem. 2008, 32 (10) 1659-1672
21. Rodríguez-Hornedo, N.; Murphy, D. Surfactant-facilitated crystallization of dihydrate carbamazepine during dissolution of anhydrous polymorph J. Pharm. Sci. 2004, 93 (2) 449-460 (Pubitemid 38174265)
22. Williams, R. J.; Phillips, J. N.; Mysels, K. J. The critical micelle concentration of sodium lauryl sulphate at 25° C Trans. Faraday Soc. 1955, 51, 728-737
23. Nordström, F. L.; Rasmuson, ̊. C. Solubility and Melting Properties of Salicylic Acid J. Chem. Eng. Data 2006, 51 (5) 1668-1671 (Pubitemid 44562515)
24. Papadopoulos, N.; Avranas, A. Dissociation of salicylic acid, 2,4,2,5-and 2,6-dihydroxybenzoic acids in 1-propanol-water mixtures at 25° C J. Solution Chem. 1991, 20 (3) 293
25. Good, D. J.; Rodríguez-Hornedo, N. Cocrystal Eutectic Constants and Prediction of Solubility Behavior Cryst. Growth Des. 2010, 10 (3) 1028-1032
26. Wang, Y.; LoBrutto, R.; Wenslow, R. W.; Santos, I. Eutectic Composition of a Chiral Mixture Containing a Racemic Compound Org. Process Res. Dev. 2005, 9 (5) 670-676 (Pubitemid 41422494)