Evaluation of the structural determinants of polymeric precipitation inhibitors using solvent shift methods and principle component analysis

Molecular Pharmaceutics

Volumn 10, Issue 8, 2013, Pages 2823-2848

  Warren, Dallas B ^a   Bergström, Christel A S ^a,b   Benameur, Hassan ^c   Porter, Christopher J H ^a   Pouton, Colin W ^a  

^a MONASH UNIVERSITY   (Australia)

^b UPPSALA UNIVERSITY   (Sweden)

^c CAPSUGEL   (France)

Author keywords

crystallization; inhibition; lipid formulation; metastable; polymer; supersaturation

Indexed keywords

AMIDE; AMIODARONE; CARBAMAZEPINE; CARBOXYLIC ACID; CELLULOSE DERIVATIVE; DANAZOL; DRUG VEHICLE; ETHINYLESTRADIOL; HALOFANTRINE; HYDROXYL GROUP; ITRACONAZOLE; LIPID; MECLOFENAMIC ACID; MEFENAMIC ACID; POLYMER; POLYMERIC PRECIPITATION INHIBITOR; SOLVENT; TOLFENAMIC ACID; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL STRUCTURE; CRYSTALLIZATION; DIGESTION; DRUG DELIVERY SYSTEM; DRUG FORMULATION; DRUG SOLUBILITY; LIQUID; MOLECULAR WEIGHT; PHYSICAL CHEMISTRY; PHYSICAL PHASE; POLYMERIZATION; PRECIPITATION; PRINCIPAL COMPONENT ANALYSIS; PRIORITY JOURNAL; SELF EMULSIFYING DRUG DELIVERY SYSTEM; SOLID STATE; SOLUBILITY; THERMODYNAMICS;

MOLECULAR STRUCTURE; MOLECULAR WEIGHT; POLYMERS; PRINCIPAL COMPONENT ANALYSIS; SOLVENTS;

EID: 84881322355     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp300576u     Document Type: Article

References (66)

1. 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, 315-499
2. Porter, C. J. H.; Anby, M. U.; Warren, D. B.; Williams, H. D.; Benameur, H.; Pouton, C. W. Lipid based formulations: Exploring the link between in vitro Supersaturation and in vivo exposure Bull. Tech. Gattefossé 2011, 104, 61-69
3. Gao, P.; Rush, B. D.; Pfund, W. P.; Huang, T.; Bauer, J. M.; Morozowich, W.; Kuo, M.-S.; Hageman, M. J. Development of a supersaturable SEDDS (S-SEDDS) formulation of paclitaxel with improved oral bioavailability J. Pharm. Sci. 2003, 92 (12) 2386-2398
4. Anby, M. U.; Williams, H. D.; McIntosh, M.; Benameur, H.; Edwards, G. A.; Pouton, C. W.; Porter, C. J. H. Lipid Digestion as a Trigger for Supersaturation: Evaluation of the Impact of Supersaturation Stabilization on the in Vitro and in Vivo Performance of Self-Emulsifying Drug Delivery Systems Mol. Pharmaceutics 2012, 9 (7) 2063-2079
5. Guzman, H. R.; Tawa, M.; Zhang, Z.; Ratanabanangkoon, P.; Shaw, P.; Gardner, C. R.; Chen, H.; Moreau, J. P.; Almarsson, O.; Remenar, J. F. Combined use of crystalline salt forms and precipitation inhibitors to improve oral absorption of celecoxib from solid oral formulations J. Pharm. Sci. 2007, 96 (10) 2686-2702
6. Brouwers, J.; Brewster, M. E.; Augustijns, P. Supersaturating drug delivery systems: The answer to solubility-limited oral bioavailability? J. Pharm. Sci. 2009, 98 (8) 2549-2572
7. Yamashita, K.; Nakate, T.; Okimoto, K.; Ohike, A.; Tokunaga, Y.; Ibuki, R.; Higaki, K.; Kimura, T. Establishment of new preparation method for solid dispersion formulation of tacrolimus Int. J. Pharmaceutics 2003, 267 (1-2) 79-91
8. Erlich, L.; Yu, D.; Pallister, D. A.; Levinson, R. S.; Gole, D. G.; Wilkinson, P. A.; Erlich, R. E.; Reeve, L. E.; Viegas, T. X. Relative bioavailability of danazol in dogs from liquid-filled hard gelatin capsules Int. J. Pharmaceutics 1999, 179 (1) 49-53
9. Gao, P.; Guyton, M. E.; Huang, T.; Bauer, J. M.; Stefanski, K. J.; Lu, Q. Enhanced Oral Bioavailability of a Poorly Water Soluble Drug PNU-91325 by Supersaturatable Formulations Drug Dev. Ind. Pharm. 2004, 30 (2) 221-229
10. Gao, P.; Morozowich, W. Development of supersaturatable self-emulsifying drug delivery system formulations for improving the oral absorption of poorly soluble drugs Expert Opin. Drug Delivery 2006, 3 (1) 97-110
11. Gao, P.; Akrami, A.; Alvarez, F.; Hu, J.; Li, L.; Ma, C.; Surapaneni, S. Characterization and optimization of AMG 517 supersaturatable self-emulsifying drug delivery system (S-SEDDS) for improved oral absorption J. Pharm. Sci. 2009, 98 (2) 516-528
12. Ilevbare, G. A.; Liu, H.; Edgar, K. J.; Taylor, L. S. Understanding Polymer Properties Important for Crystal Growth Inhibition-Impact of Chemically Diverse Polymers on Solution Crystal Growth of Ritonavir Cryst. Growth Des. 2012, 12 (6) 3133-3143
13. Warren, D. B.; Benameur, H.; Porter, C. J. H.; Pouton, C. W. Using polymeric precipitation inhibitors to improve the absorption of poorly water-soluble drugs: A mechanistic basis for utility J. Drug Target. 2010, 18 (10) 704-731
14. DiNunzio, J. C.; Miller, D. A.; Yang, W.; McGinity, J. W.; Williams, R. O. Amorphous Compositions Using Concentration Enhancing Polymers for Improved Bioavailability of Itraconazole Mol. Pharmaceutics 2008, 5 (6) 968-980
15. Ziller, K. H.; Rupprecht, H. Control of Crystal Growth in Drug Suspensions: 1) Design of a Control Unit and Application to Acetaminophen Suspensions) Drug Dev. Ind. Pharm. 1988, 14 (15) 2341-2370
16. Brewster, M. E.; Vandecruys, R.; Peeters, J.; Neeskens, P.; Verreck, G.; Loftsson, T. Comparative interaction of 2-hydroxypropyl-beta-cyclodextrin and sulfobutylether-beta-cyclodextrin with itraconazole: Phase-solubility behavior and stabilization of supersaturated drug solutions Eur. J. Pharm. Sci. 2008, 34 (2-3) 94-103
17. Vandecruys, R.; Peeters, J.; Verreck, G.; Brewster, M. E. Use of a screening method to determine excipients which optimize the extent and stability of supersaturated drug solutions and application of this system to solid formulation design Int. J. Pharmaceutics 2007, 342 (1-2) 168-175
18. Curatolo, W.; Nightingale, J.; Herbig, S. Utility of Hydroxypropylmethylcellulose Acetate Succinate (HPMCAS) for Initiation and Maintenance of Drug Supersaturation in the GI Milieu Pharm. Res. 2009, 26 (6) 1419-1431
19. Lindfors, L.; Forssen, S.; Westergren, J.; Olsson, U. Nucleation and crystal growth in supersaturated solutions of a model drug J. Colloid Interface Sci. 2008, 325 (2) 404-413
20. Matteucci, M. E.; Brettmann, B. K.; Rogers, T. L.; Elder, E. J.; Williams, R. O.; Johnston, K. P. Design of potent amorphous drug nanoparticles for rapid generation of highly supersaturated media Mol. Pharmaceutics 2007, 4 (5) 782-793
21. Kossena, G. A.; Charman, W. N.; Boyd, B. J.; Dunstan, D. E.; Porter, C. J. H. Probing drug solubilization patterns in the gastrointestinal tract after administration of lipid-based delivery systems: A phase diagram approach J. Pharm. Sci. 2004, 93 (2) 332-348
22. Bevernage, J.; Hens, B.; Brouwers, J.; Tack, J.; Annaert, P.; Augustijns, P. Supersaturation in human gastric fluids Eur. J. Pharm. Biopharm. 2012, 81 (1) 184-189
23. Abdi, H.; Williams, L. J. Principal component analysis Wiley Interdisc. Rev.: Comput. Stat. 2010, 2 (4) 433-459
24. Kleinbaum, D. G.; Kupper, L. L.; Muller, K. E. Applied regression analysis and other multivariable methods, 2 nd ed.; PWS-Kent Pub. Co.: Boston, MA, 1988; p xviii.
25. Wold, S.; Esbensen, K.; Geladi, P. Principal component analysis Chemometrics Intelligent Lab. Syst. 1987, 2 (1-3) 37-52
26. Jackson, J. E. Frontmatter. In A User's Guide to Principal Components; John Wiley & Sons, Inc.: New York, 2004; pp i-3.
27. Murphy, D.; Rodríguez-Cintrón, F.; Langevin, B.; Kelly, R. C.; Rodríguez-Hornedo, N. Solution-mediated phase transformation of anhydrous to dihydrate carbamazepine and the effect of lattice disorder Int. J. Pharmaceutics 2002, 246 (1-2) 121-134
28. Corporation, S. R. Physical/Chemical Property Database (PHYSPROP); SRC Environmental Science Center: Syracuse, NY, 2012.
29. El-Kattan, A. F.; Asbill, C. S.; Kim, N.; Michniak, B. B. The effects of terpene enhancers on the percutaneous permeation of drugs with different lipophilicities Int. J. Pharmaceutics 2001, 215 (1-2) 229-240
30. Queiroz, R. H. C.; Bertucci, C.; Malfará, W. R.; Dreossi, S. A. C.; Chaves, A. R.; Valério, D. A. R.; Queiroz, M. E. C. Quantification of carbamazepine, carbamazepine-10,11-epoxide, phenytoin and phenobarbital in plasma samples by stir bar-sorptive extraction and liquid chromatography J. Pharm. Biomed. Anal. 2008, 48 (2) 428-434
31. Good, D. J.; Rodríguez-Hornedo, N. R. Solubility Advantage of Pharmaceutical Cocrystals Cryst. Growth Des. 2009, 9 (5) 2252-2264
32. Alsenz, J.; Meister, E.; Haenel, E. Development of a partially automated solubility screening (PASS) assay for early drug development J. Pharm. Sci. 2007, 96 (7) 1748-1762
33. Bergström, C. A. S.; Wassvik, C. M.; Johansson, K.; Hubatsch, I. Poorly Soluble Marketed Drugs Display Solvation Limited Solubility J. Med. Chem. 2007, 50 (23) 5858-5862
34. Clarysse, S.; Psachoulias, D.; Brouwers, J.; Tack, J.; Annaert, P.; Duchateau, G.; Reppas, C.; Augustijns, P. Postprandial Changes in Solubilizing Capacity of Human Intestinal Fluids for BCS Class II Drugs Pharm. Res. 2009, 26 (6) 1456-1466
35. Bakatselou, V.; Oppenheim, R. C.; Dressman, J. B. Solubilization and Wetting Effects of Bile Salts on the Dissolution of Steroids Pharm. Res. 1991, 8 (12) 1461-1469
36. Riisager, L. L. The influence of complex formation on the degradation of γ-cyclodextrin by α-amylase. Masters Thesis, Aalborg University, Aalborg, Denmark, 2010.
37. Hurwitz, A. R.; Liu, S. T. Determination of aqueous solubility and pKa values of estrogens J. Pharm. Sci. 1977, 66 (5) 624-627
38. Kokubo, T.; Sugibayashi, K.; Morimoto, Y. Mathematical-Models Describing the Drug Release Kinetics from Pressure Sensitive Adhesive Matrix J. Controlled Release 1992, 20 (1) 3-12
39. Choudhary, M. I.; Musharraf, S. G.; Ali, R. A.; Atif, M.; Atta-ur-Rahman Microbial transformation of antifertility agents, norethisterone and 17α-ethynylestradiol Z. Naturforsch., B: Chem. Sci. 2004, 59 (3) 319-323
40. Bonati, M.; Gaspari, F.; Daranno, V.; Benfenati, E.; Neyroz, P.; Galletti, F.; Tognoni, G. Physicochemical and Analytical Characteristics of Amiodarone J. Pharm. Sci. 1984, 73 (6) 829-831
41. Benedini, L.; Messina, P. V.; Manzo, R. H.; Allemandi, D. A.; Palma, S. D.; Schulz, E. P.; Frechero, M. A.; Schulz, P. C. Colloidal properties of amiodarone in water at low concentration J. Colloid Interface Sci. 2010, 342 (2) 407-414
42. Riekes, M. K.; Tagliari, M. P.; Granada, A.; Kuminek, G.; Silva, M. A. S.; Stulzer, H. K. Enhanced solubility and dissolution rate of amiodarone by complexation with β-cyclodextrin through different methods Mater. Sci. Eng.: C 2010, 30 (7) 1008-1013
43. Kaukonen, A.; Boyd, B.; Charman, W.; Porter, C. Drug Solubilization Behavior During in Vitro Digestion of Suspension Formulations of Poorly Water-Soluble Drugs in Triglyceride Lipids Pharm. Res. 2004, 21 (2) 254-260
44. Babalola, C. P.; Adegoke, A. O.; Ogunjinmi, M. A.; Osimosu, M. O. Determination of physicochemical properties of halofantrine Afr. J. Med. Med. Sci. 2003, 32 (4) 357-9
45. Taillardat-Bertschinger, A.; Perry, C. S.; Galland, A.; Prankerd, R. J.; Charman, W. N. Partitioning of halofantrine hydrochloride between water, micellar solutions, and soybean oil: Effects on its apparent ionization constant J. Pharm. Sci. 2003, 92 (11) 2217-2228
46. Janssens, S.; de Armas, H. N.; Remon, J. P.; Van den Mooter, G. The use of a new hydrophilic polymer, Kollicoat IR (R), in the formulation of solid dispersions of Itraconazole Eur. J. Pharm. Sci. 2007, 30 (3-4) 288-294
47. Van Speybroeck, M.; Mols, R.; Mellaerts, R.; Thi, T. D.; Martens, J. A.; Humbeeck, J. V.; Annaert, P.; Mooter, G. V. D.; Augustijns, P. Combined use of ordered mesoporous silica and precipitation inhibitors for improved oral absorption of the poorly soluble weak base itraconazole Eur. J. Pharm. Biopharm. 2010, 75 (3) 354-365
48. Domańska, 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
49. Cheng, T.; Zhao, Y.; Li, X.; Lin, F.; Xu, Y.; Zhang, X.; Li, Y.; Wang, R.; Lai, L. Computation of Octanol-Water Partition Coefficients by Guiding an Additive Model with Knowledge J. Chem. Inf. Model. 2007, 47 (6) 2140-2148
50. McEvoy, G. K. Essentials 2004-2005: AHFS drug information; American Society of Health-System Pharmacists: Bethesda, MD, 2004; p xvi.
51. LlinaÌs, 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
52. Fábián, L. S.; Hamill, N.; Eccles, K. S.; Moynihan, H. A.; Maguire, A. R.; McCausland, L.; Lawrence, S. E. Cocrystals of Fenamic Acids with Nicotinamide Cryst. Growth Des. 2011, 11 (8) 3522-3528
53. TenHoor, C. N.; Bakatselou, V.; Dressman, J. Solubility of Mefenamic Acid Under Simulated Fed- and Fasted-State Conditions Pharm. Res. 1991, 8 (9) 1203-1205
54. Barbato, F.; La Rotonda, M. I.; Quaglia, F. Interactions of nonsteroidal antiinflammatory drugs with phospholipids: Comparison between octanol/buffer partition coefficients and chromatographic indexes on immobilized artificial membranes J. Pharm. Sci. 1997, 86 (2) 225-229
55. Zommer-Urbańska, S.; Bojarowicz, H. Spectrophotometric investigations on protolytic equilibria of mefenamic acid and determination by means of Fe(III) in methanol-aqueous media J. Pharm. Biomed. Anal. 1986, 4 (4) 475-481
56. Cafaggi, S.; Russo, E.; Caviglioli, G.; Parodi, B.; Stefani, R.; Sillo, G.; Leardi, R.; Bignardi, G. Poloxamer 407 as a solubilising agent for tolfenamic acid and as a base for a gel formulation Eur. J. Pharm. Sci. 2008, 35 (1-2) 19-29
57. Pentikäinen, P.; Penttilä, A.; Neuvonen, P.; Khalifah, R.; Hignite, C. Human metabolism of tolfenamic acid. I. Isolation, preliminary characterization and pharmacokinetics of tolfenamic acid and its metabolites Eur. J. Drug Metab. Pharmacokinet. 1982, 7 (4) 259-267
58. Chandran, S.; Gesenberg, C.; Levons, J.; Hubert, M.; Raghavan, K. A high-throughput spectrophotometric approach for evaluation of precipitation resistance J. Pharm. Biomed. Anal. 2011, 56 (4) 698-704
59. Megrab, N. A.; Williams, A. C.; Barry, B. W. Estradiol Permeation through Human Skin and Silastic Membrane-Effects of Propylene-Glycol and Supersaturation J. Controlled Release 1995, 36 (3) 277-294
60. Bevernage, J.; Forier, T.; Brouwers, J.; Tack, J.; Annaert, P.; Augustijns, P. Excipient-Mediated Supersaturation Stabilization in Human Intestinal Fluids Mol. Pharmaceutics 2011, 8 (2) 564-570
61. Kumar, A. C.; Erothu, H.; Bohidar, H. B.; Mishra, A. K. Bile-Salt-Induced Aggregation of Poly(N-isopropylacrylamide) and Lowering of the Lower Critical Solution Temperature in Aqueous Solutions J. Phys. Chem. B 2010, 115 (3) 433-439
62. Van Eerdenbrugh, B.; Taylor, L. S. Small Scale Screening To Determine the Ability of Different Polymers To Inhibit Drug Crystallization upon Rapid Solvent Evaporation Mol. Pharmaceutics 2010, 7 (4) 1328-1337
63. Plaizier-Vercammen, J. A. Interaction of povidone with aromatic compounds IV: Effects of macromolecule molecular weight, solvent dielectric constant, and ligand solubility on complex formation J. Pharm. Sci. 1983, 72 (9) 1042-1044
64. Miller, D. A.; DiNunzio, J. C.; Yang, W.; McGinity, J. W.; Williams, R. O. Enhanced In Vivo Absorption of Itraconazole via Stabilization of Supersaturation Following Acidic-to-Neutral pH Transition Drug Dev. Ind. Pharm. 2008, 34 (8) 890-902
65. Fedors, R. F. A method for estimating both the solubility parameters and molar volumes of liquids Polym. Eng. Sci. 1974, 14 (2) 147-154
66. Yin, X.; Yang, W.; Tang, Y.; Liu, Y.; Wang, J. The synergistic effect of orthophosphate and polymer on the precipitation of calcium carbonate Desalination 2010, 255 (1-3) 143-147