Preformulation aspects of insoluble compounds

Water-Insoluble Drug Formulation, Second Edition

Volumn , Issue , 2008, Pages 61-90

  Tong, Wei Qin ^a   Wen, Hong ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85123271228     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (83)

1. Albers, E. and Muller, B.W. (1995). Cyclodextrin derivatives in pharmaceutics, Crit. Rev. Therap. Drug Carrier Syst., 12, 311-337.
2. Albert, A. and Serjeant, E.P. (1984). The Determination of Ionization Constants: A Laboratory Manual. (3rd ed.). Metheren Inc., New York, NY, 150 pp.
3. Amidon, G.L., Lennernaes, H., Shah, V.P., and Crison, J.R. (1995). A theoretical basis for a biopharmaceutic drug classification: the correlation of in vitro drug product dissolution and in vivo bioavailability. Pharm. Res., 12, 413-120.
4. Austin, R.P., Davis, A.M., and Manners, C.N. (1995). Partitioning of ionizing molecules between aqueous buffers and phospholipid vesicles, J. Pharm. Sci., 84, 1180-1183.
5. Avdeef A. (1993). Applications and Theory Guide to pH-Metric pKa and logP Determination, Sirius Analytical Instruments Ltd., Forest Row, East Sussex RH18 5AF, England.
6. Avdeef, A., Box, K.J., Comer, J.E.A., Hibbert, C., and Tam, K.Y. (1998). pH-Metric logP 10. Determination of liposomal membrane-water partition coefficients of ionizable drugs, Pharm. Res., 15, 209-215.
7. Beall, H.D., Getz, J.J., and Sloan, K.B. (1993). The estimation of relative water solubility for prodrugs that are unstable in water, Int. J. Pharm., 93, 37-17.
8. Berger, R., Friebe, M., Pietzsch, H.J., Scheunemann, M., Noll, B., Fietz, T., Spies, H., and Johannsen, B. (1997). Lipophilicity and ionization properties of some amine-bearing technetium and rhenium "3 + 1" mixed ligand chelates of the same ligand structure, Institute for Bioinorganic and Radiopharmaceutical Chemistry, Annual Report, pp. 43-47.
9. Byrn, S., Pfeiffer, R., Ganey, M., Hoiberg, C., and Poochilian, G. (1995). Pharmaceutical solids: a strategic approach to regulatory considerations, Pharm. Res., 12, 945-954.
10. Cakiryildiz, C., Mehta, P.J., Rahmen, W., and Schoenleber, D. (1975). Dissolution studies with a multichannel continuous-flow apparatus, J. Pharm. Sci., 64, 1692-1697.
11. Callahan, J.C., Cleary, G.W., Elefant, M., Kaplan, G., Kensler, T., and Nash, R.A. (1982). Equilibrium moisture content of pharmaceutical excipients, Drug Dev. Ind. Pharm., 8, 355-369.
12. Carstensen, J.T. (2002). Preformulation, Drugs Pharm. Sci., 121 (Modern Pharmaceutics, 4th ed.), 167-185.
13. Chemical Sciences (July, 2001). Pharmaceutical Profiling User's Guide. Version 1.0.
14. Connors, K.A., Amidon, G.L., and Stella, V.J. (1986). Chemical Stability of Pharmaceuticals, A Handbook for Pharmacists (2nd ed.). John Wiley & Sons, Inc., New York, NY, 847 pp.
15. Corrigan, O.I. (1991). Co-solvent systems in dissolution testing theoretical considerations, Drug. Dev. Ind. Pharm., 17, 695-708.
16. Curatolo, W.J. (1996). Screening Studies for Transport Properties, Proceeding for 38th Annual International Industrial Pharmaceutical Research and Development Conference, Merrimac, WI.
17. Davis, S.S., Higuchi, T., and Rytting, J.H. (1974). Determination of thermodynamics of functional groups in solutions of drug molecules, Advances in Pharmaceutical Sciences, Vol. 4, Bean, H.S., Beckett, A.H., and Carless, J.E. eds., Academic Press, London, England, pp. 73-261.
18. Dearden, J.C. and Bresnen, G.M. (1988). The measurement of partition coefficents, Quant. Struct.-Act. Relat., 7, 133-144.
19. De Smidt, J.H., Fokkens, J.G., Grijseels, H., and Crommelin, D.J.A. (1986). Dissolution of theophylline monohydrate and anhydrous theophylline in buffer solutions, J. Pharm. Sci., 75, 497-501.
20. Dodge, A. and Gould, P.L. (1987). Dissolution of chlorpropamide tablets in a methanol-water binary solvent system, Drug. Dev. Ind. Pharm., 13, 1817-1826.
21. Dressman, J.B., Amidon, G.L., Reppas, C., and Shah, V.P. (1998). Dissolution testing as a prognostic tool for oral drug absorption: immediate release dosage forms, Pharm. Res., 15, 11-22.
22. Dressman, J.B., Fleisher, D. and Amidon, G.L. (1984). Physicochemical model for dose-dependent drug absorption, J. Pharm. Sci., 73, 1274-1279.
23. Dressman, J.B. and Fleisher, D. (1986). Mixing-tank model for predicting dissolution rate control of oral absorption, J. Pharm. Sci., 75, 109-116.
24. Elworthy, P.H., Florence, A.T., and Macfarlane, C.B. (1965). Solubilization by Surface-Active Agents, Chapman and Hall, London.
25. Fendler, J.H. and Fendler, E.J. (1975). Catalysis in Micellar and Macromolecular Systems, Academic Press, New York, pp. 98-100.
26. Fiese, E.F. and Hagen, T.A. (1986). Preformulation, The Theory and Practice of Industrial Pharmacy, Lea & Febiger, Philadelphia, PA, Chapter 8.
27. Finholt, P. (1974). Influence of formulation on dissolution rate, Dissolution Technology, Lesson, L.J. and Carstensen, J.T., eds., Washington, DC, Academy of Pharmaceutical Sciences, p. 106.
28. Flora, K.P., Smith, S.L., and Cradock, J.C. (1997). Application of simple high-performance liquid chromatographic method for the determination of melphalan in the presence of its hydrolysis products. J. Chromatogr., 177, 91-97.
29. Formelova, J., Breier, A., Gemeiner, P., and Kurillova, L. (1991). Trypsin entrapped within liposomes. Partition of a low-molecular-mass substrate as the main factor in kinetic control of hydrolysis. Coll. Czech. Chem. Comm., 56, 712-717.
30. Goldberg, A.H., Gibaldi, M., Kanig, J.L., and Shanker, J. (1965). Method for determining dissolution rates of multiparticulate systems, J. Pharm. Sci., 54, 1722-1725.
31. Grant, D.J.W. and Higuchi, T. (1990). Techniques of Chemistry, Vol. 21: Solubility Behavior of Organic Compounds. Wiley, New York, NY, 600 pp.
32. Hamid, I.A. and Parrott, E.L. (1971). Effect of temperature on solubilization and hydrolytic degradation of solubilized benzocaine and homatropine, J. Pharm. Sci., 60, 901-906.
33. Hellwich, U. and Schubert, R. (1995). Concentration-dependent binding of the chiral B-blocker oxprenolol to isoelectric or negatively charged unilamellar vesicles, Biochem. Pharmacol., 49, 511-517.
34. Hersey, A., Hill, A.P., Hyde, R.M., and Livingstone, D.J. (1989). Principles of method selection in partition studies, Quant. Struct.-Act. Relat., 8, 288-296.
35. Higuchi, T., Shih, F.L., Kimura, T., and Rytting, J.H. (1979). Solubility determination of barely aqueous soluble organic solids, J. Pharm. Sci., 68, 1267-1272.
36. James, K.C. (1986). Drugs andthe Pharmaceutical Sciences, Vol. 28: Solubility and Related Properties. Marcel Dekker Inc., New York, NY, 425 pp.
37. Junquera, E., Tardajos, G., and Aicart, E. (1993). Effect of the presence of B-cyclodexdtrin on micellization process of sodium dodecyl sulfate or sodium perfluorooctanoate in water, Langmuir, 9, 1212-1219.
38. Kearney, A.S., Mehta, S.C. and Radebaugh, G.W. (1994). Preformulation studies to aid in the development of an injectable formulation of PD 144872, a radiosensitizing anticancer agent. Int. J. Pharm., 102, 63-70.
39. Koljonen, M., Hakala, K.S., Antola-Satila, T., Laitinen, L., Kostiainen, R., Kotiaho, T., Kaukonen, A.M. and Hirvonen, J. (2006). Evaluation of cocktail approach to standardize Caco-2 permeability experiements. Eur. J. Pharm. Biopharm., 64, 379-387.
40. Kramer, S.F. and Flynn, G.L. (1972). Solubility of organic hydrochlorides. J. Pharm. Sci., 61, 1896-1904.
41. Kraus, C., Mehnert, W., Frömming, K.-H. (1991). Interactions of B-cyclodextrin with Solutol HS 15 and their influence on diazepam solubilization, Pharm. Ztg. Wiss., Nr. 1.4./136. Jahrgang, 11-15.
42. Kuhnvelten, W.N. (1991). Thermodynamics and modulation of progesterone microcompartmentation and hydrophobic interaction with cytochrome P450XVII based on quantification of local ligand concentrations in a complex multi-component system, Eur. J. Biochem., 197, 381-390.
43. Law, D., Schmitt, E.A., Marsh, K.C., Everitt, E.A., Wang, W., Fort, J.J., Krill, S.L., and Qiu, Y. (2004). Ritonavir-PEG 8000 amorphous solid dispersions: in vitro and in vivo evaluations. J. Pharm. Sci., 93, 563-570.
44. Leo, A., Hansch, C., and Elkins, D. (1971). Partition coefficients and their uses, Chem. Rev., 71, 525-616.
45. Lipinski, C.A., Lombardo, F., Dominy, B.W., and Feeney, P.J. (1997). Experimental and Computational approaches to estimate solubility and permeability in drug discovery and development settings, Adv. Drug Delivery Rev., 23, 3-25.
46. Lötter, A.P., Flanagan, D.R., Jr., Palepu, N.R., and Guillory, J.K. (1983). A simple reproducible method for determining dissolution rates of hydrophobic powders, Pharm. Technol., 4, 56-66.
47. Madan, D.K. and Cadwallader, D.E. (1973). Solubility of cholesterol and hormone drugs in water, J. Pharm. Sci., 62, 1567-1569.
48. Marini, A., Berbenni, V., Bruni, G., Cofrancesco, P., Giordano, F., and Villa, M. (2003). Physico-chemical characterization of drugs and drug forms in the solid state, Curr. Medicinal Chem.: Anti-Infective Agents, 2, 303-321.
49. Miyazaki, J., Hideg, K., and Marsh, D. (1992). Interfacial ionization and partitioning of membrane-bound local anaesthetics, Biochim. Biophys. Acta, 1103, 62-68.
50. Mooney, K.G., Mintun, M.A., Himmelstein, K.J., and Stella, V.J. (1981a). Dissolution kinetics of carboxylic acids I: Effect of pH under unbuffered conditions, J. Pharm. Sci., 70, 13-22.
51. Mooney, K.G., Mintun, M.A., Himmelstein, K.J., and Stella, V.J. (1981b). Dissolution kinetics of carboxylic acids II: Effect of buffers, J. Pharm. Sci., 70, 22-32.
52. Muller, B.W. and Albers, E. (1991). Effect of hydrotropic substances on the complexation of sparingly soluble drugs with cyclodextrin derivatives and the influence of cyclodextrin complexation on the pharmacokinetics, J. Pharm. Sci., 80, 599.
53. Ni, N., Sanghvi, T., and Yalkowsky, S.H. (2002). Solubilization and preformulation of carbendazim. Int. J. Pharm., 244, 257-264.
54. Pan, L., Ho, Q., Tsutsui, K., and Takahashi, L. (2001). Comparison of chromatographic and spectroscopic methods used to rank compounds for aqueous solubility, J. Pharm. Sci., 90, 521-529.
55. Pauletti, G.M. and Wunderli-Allenspach, H. (1994). Partition coefficients in vitro: Artificial membranes as a standardized distribution model, Eur. J. Pharm. Sci., 1, 273-282.
56. a Prediction for Organic Acids and Bases, Chapman and Hall in association with Methuen, Inc., New York, NY.
57. Ping, L., Vishnuvajjala, R., Tabibi, S.E., and Yalkowsky, S.H. (1998). Evaluation of in vitro precipitation methods, J. Pharm. Sci., 87, 196-199.
58. Ramette, R.W. (1981). Coulometric study of cadmium iodate solubility equilibriums, Anal. Chem., 53, 2244-2246.
59. Ran, Y., Jain, A., and Yalkowsky, S.H. (2005). Solubilization and preformulation studies on PG-300995 (an anti-HIV drug). J. Pharm. Sci., 94, 297-303.
60. Ravin, L.J. and Radebaugh, G.W. (1990). Preformulation, Remington's Pharmaceutical Sciences, 18th ed., edited by Gennaro, A.R., Mack Publishing Company, Easton, PA, Chapter 75.
61. Rogers, J.A. and Choi, Y.W. (1993). The liposome partitioning system for correlating biological activities of imidazolidine derivatives, Pharm. Res., 10, 913-917.
62. Rosen, M.J. (1979). Surfactants and Interfacial Phenomena, John Wiley & Son, New York.
63. Ruan, J., Tattersall, P., Lozano, R., and Shah, P. (2006). The role of forced degradation studies in stability indicating HPLC method development. Am. Pharm. Rev., 9, 46-53.
64. Rubino, J.T. (1987). The effect of cosolvents on the action of pharmaceutical buffers, J. Parenter. Sci. Technol., 41, 45-49.
65. Saha, P. and Kou, J.H. (2000). Effect of solubilizing excipients on permeation of poorly water-soluble compounds across Caco-2 cell monolayers, Eur. J. Pharm. Biopharm., 50, 403-411.
66. Sims, J.L., Roberts, J.K., Bateman, A.G., Carreira, J.A., and Hardy, M.J. (2002). An automated workstation for forced degradation of active pharmaceutical ingredients, J. Pharm. Sci., 91, 884-892.
67. Strickley, R.G. (2004). Solubilizing excipients in oral and injectable formulations, Pharm. Res., 21, 201-230.
68. Suzuki, A., Higuchi, W.I., and Ho, N.F. (1970). Theoretical model studies of drug absorption and transport in the gastrointestinal tract I, J. Pharm. Sci., 59, 644-651.
69. Swenson, E.S., Milisen, W.B., and Curatolo, W. (1994). Intestinal permeability enhancement: Efficacy, acute local toxicity, and reversibility, Pharm. Res., 11, 1132-1142.
70. Szejtli, J. (1982). Inclusion Compounds and Their Complexes, Akademiai Kiado, Budapest.
71. Tang, L., Khan, S.U., and Muhammad, N.A. (2001). Evaluation and selection of bio-relevant dissolution media for a poorly water-soluble new chemical entity, Pharm. Dev. Technol., 6, 531-540.
72. Todd, D. and Winnike, R.A. (1994). A rapid method for generating pH-solubility profiles for new chemical entities, Pharm. Res., 11, S-271.
73. Tong, W.Q., Wells, M.L., and Williams, S.O. (1994). Solubility behavior of GF120918A, Pharm. Res., 11, S-269.
74. Tong, W.Q. and Whitesell, G. (1998). In situ salt screening-A useful technique for discovery support and preformulation studies, Pharm. Dev. Tech., 3, 215-223.
75. Tong, W.Q., Adkison, K., Ott, R., McNulty, M., Brown, K.K., Lenhard, J., and Lightfoot, R. (1998). Feasibility studies of using TPGS/PG solutions as a universal oral formulation for insoluble compounds for pharmacokinetics, in vivo efficacy and toxicological studies during the early stages of drug discovery, Pharm. Res., 15.
76. Valko, K., Bevan, C., and Reynolds, D. (1997). Chromatographic hydrophobicity index by fast-gradient RP-HPLC: a high-throughput alternative to log P/log D, Anal. Chem., 69, 2022-2029.
77. Venkatesh, S., Li, J.M., Xu, Y.H., Vishnuvajjala, R., and Anderson, B.D. (1996). Intrinsic solubility estimation and pH-solubility behavior of cosalane (NSC 658586), an extremely hydrophobic diprotic acid, Pharm. Res., 15, 1453-1459.
78. Von Raumer, M., Dannappel, J., and Hilfiker, R. (2006). Polymorphism, salts, and crystallization: The relevance of solid-state development. Chimica Oggi., 24, 41-44.
79. Ward, G.H. and Yalkowsky, S.H. (1993). Studies in phlebitis VI: Dilution-induced precipitation of amiodarone HCL. J. Parenter. Sci. Technol., 47, 161-165.
80. Wells, J.I. (1988). Pharmaceutical Preformulation: The Physicochemical Properties of Drug Substances, Ellis Horwood Ltd.
81. Yalkowsky, S.H. and Valvani, S.C. (1980). Solubility and partitioning. I: Solubility of nonelectrolytes in water, J. Phar. Sci., 69, 912-922.
82. Yalkowsky, S.H. and Roseman, T.J. (1981). Solubilization of drugs by cosolvents, Techniques of Solubilization of Drugs, Yalkowsky, S.H. ed., Marcel Dekker, Inc.
83. Yalkowsky, S.H., Valvani, S.C., and Johnson, B.W. (1983). In vitro method for detecting precipitation of parenteral formulation after injection, J. Pharm. Sci., 72, 1014-1017.