Microenvironmental pH-modification to improve dissolution behavior and oral absorption for drugs with pH-dependent solubility

Expert Opinion on Drug Delivery

Volumn 11, Issue 4, 2014, Pages 505-516

  Taniguchi, Chika ^a,b   Kawabata, Yohei ^b   Wada, Koichi ^b   Yamada, Shizuo ^a   Onoue, Satomi ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

^b NIPPON BOEHRINGER INGELHEIM CO LTD   (Japan)

Author keywords

Bioavailability; Dissolution; PH modification; Solid dosage forms

Indexed keywords

8 PRENYLNARINGENIN; ACECLOFENAC; BROMHEXINE; CALCIUM PHOSPHATE; CELECOXIB; CITRIC ACID; CYCLODEXTRIN; DILTIAZEM; DIPYRIDAMOLE; DRUG; EXCIPIENT; FUMARIC ACID; FUROSEMIDE; ISRADIPINE; MAGNESIUM OXIDE; MEGLUMINE; NANOCRYSTAL; NAPROXEN; NOSCAPINE; PELANSERIN; PROPIVERINE; QUINOLINE DERIVED ANTIINFECTIVE AGENT; SIBUTRAMINE; SODIUM CARBONATE; SUCCINIC ACID; TARTARIC ACID; TELMISARTAN; UNINDEXED DRUG; VERAPAMIL; VINPOCETINE;

CRYSTALLIZATION; DISPERSION; DRUG ABSORPTION; DRUG DESIGN; DRUG DOSAGE FORM; DRUG FORMULATION; DRUG PELLET; DRUG RELEASE; DRUG SOLUBILITY; HUMAN; MATRIX TABLET; MICROENVIRONMENTAL PH; NONHUMAN; PH; PH MEASUREMENT; REVIEW; SOLID;

ADMINISTRATION, ORAL; ANIMALS; BIOLOGICAL AVAILABILITY; CELLULAR MICROENVIRONMENT; CHEMISTRY, PHARMACEUTICAL; DRUG CARRIERS; EXCIPIENTS; GASTROINTESTINAL TRACT; HUMANS; HYDROGEN-ION CONCENTRATION; INTESTINAL ABSORPTION; SOLUBILITY;

EID: 84897855778     PISSN: 17425247     EISSN: 17447593     Source Type: Journal    
DOI: 10.1517/17425247.2014.881798     Document Type: Review

References (67)

1. Horter D, Dressman JB. Influence of physicochemical properties on dissolution of drugs in the gastrointestinal tract. Adv Drug Deliv Rev 2001;46:75-87
2. Yu LX, Amidon GL, Polli JE, et al. Biopharmaceutics classification system: the scientific basis for biowaiver extensions. Pharm Res 2002;19:921-5
3. Bassi P, Kaur G. pH modulation: a mechanism to obtain pH-independent drug release. Expert Opin Drug Deliv 2010;7:845-57
4. Rose EF. Factors influencing gastric emptying. J Forensic Sci 1979;24:200-6
5. Kulmatycki KM, Jamali F. Drug disease interactions: role of inflammatory mediators in pain and variability in analgesic drug response. J Pharm Pharm Sci 2007;10:554-66
6. Champagne ET. Low gastric hydrochloric acid secretion and mineral bioavailability. Adv Exp Med Biol 1989;249:173-84
7. Russell TL, Berardi RR, Barnett JL, et al. pH-related changes in the absorption of dipyridamole in the elderly. Pharm Res 1994;11:136-43
8. Lahner E, Annibale B, Delle Fave G. Systematic review: helicobacter pylori infection and impaired drug absorption. Aliment Pharmacol Ther 2009;29:379-86
9. Shelton MJ, Adams JM, Hewitt RG, et al. Effects of spontaneous gastric hypoacidity on the pharmacokinetics of zidovudine and didanosine. Pharmacotherapy 1997;17:438-44
10. Kawabata Y, Wada K, Nakatani M, et al. Formulation design for poorly watersoluble drugs based on biopharmaceutics classification system: basic approaches and practical applications. Int J Pharm 2011;420:1-10
11. Serajuddin AT, Jarowski CI. Effect of diffusion layer pH and solubility on the dissolution rate of pharmaceutical acids and their sodium salts. II: salicylic acid, theophylline, and benzoic acid. J Pharm Sci 1985;74:148-54
12. Serajuddin AT, Jarowski CI. Effect of diffusion layer pH and solubility on the dissolution rate of pharmaceutical bases and their hydrochloride salts. I: phenazopyridine. J Pharm Sci 1985;74:142-7
13. Tran PH, Tran TT, Lee KH, et al. Dissolution-modulating mechanism of pH modifiers in solid dispersion containing weakly acidic or basic drugs with poor water solubility. Expert Opin Drug Deliv 2010;7:647-61
14. Siepe S, Herrmann W, Borchert HH, et al. Microenvironmental pH and microviscosity inside pH-controlled matrix tablets: an EPR imaging study. J Control Release 2006;112:72-8
15. Dokoumetzidis A, Macheras P. A century of dissolution research: from Noyes and Whitney to the biopharmaceutics classification system. Int J Pharm 2006;321:1-11
16. Bergstrom CAS, Luthman K, Artursson P. Accuracy of calculated pHdependent aqueous drug solubility. Eur J Pharm Sci 2004;22:387-98
17. Avdeef A. Solubility of sparingly-soluble ionizable drugs. Adv Drug Deliv Rev 2007;59:568-90
18. Brouwers J, Brewster ME, Augustijns P. Supersaturating drug delivery systems: the answer to solubility-limited oral bioavailability? J Pharm Sci 2009;98:2549-72
19. Badawy SI, Hussain MA. Microenvironmental pH modulation in solid dosage forms. J Pharm Sci 2007;96:948-59
20. Bi M, Kyad A, Alvarez-Nunez F, et al. Enhancing and sustaining AMG 009 dissolution from a bilayer oral solid dosage form via microenvironmental pH modulation and supersaturation. AAPS Pharm Sci Tech 2011;12:1401-6
21. Bi M, Kyad A, Kiang YH, et al. Enhancing and sustaining AMG 009 dissolution from a matrix tablet via microenvironmental pH modulation and supersaturation. AAPS Pharm Sci Tech 2011;12:1157-62
22. Gutsche S, Krause M, Kranz H. Strategies to overcome pH-dependent solubility of weakly basic drugs by using different types of alginates. Drug Dev Ind Pharm 2008;34:1277-84
23. Pygall SR, Kujawinski S, Timmins P, et al. Mechanisms of drug release in citrate buffered HPMC matrices. Int J Pharm 2009;370:110-20
24. Doherty C, York P. Microenvironmental pH control of drug dissolution. Int J Pharm 1989;50:223-32
25. Fu K, Pack DW, Klibanov AM, et al. Visual evidence of acidic environment within degrading poly(lactic-co-glycolic acid) (PLGA) microspheres. Pharm Res 2000;17:100-6
26. Cope SJ, Hibberd S, Whetstone J, et al. Measurement and mapping of pH in hydrating pharmaceutical pellets using confocal laser scanning microscopy. Pharm Res 2002;19:1554-63
27. Pudipeddi M, Zannou EA, Vasanthavada M, et al. Measurement of surface pH of pharmaceutical solids: a critical evaluation of indicator dye-sorption method and its comparison with slurry pH method. J Pharm Sci 2008;97:1831-42
28. Siepe S, Lueckel B, Kramer A, et al. Strategies for the design of hydrophilic matrix tablets with controlled microenvironmental pH. Int J Pharm 2006;316:14-20
29. Badawy SI, Badawy S, Williams RC, et al. Effect of different acids on solidstate stability of an ester prodrug of a IIb/IIIa glycoprotein receptor Antagonist. Pharm Dev Technol 1999;4:325-31
30. Streubel A, Siepmann J, Dashevsky A, et al. pH-independent release of a weakly basic drug from water-insoluble and - soluble matrix tablets. J Control Release 2000;67:101-10
31. Kranz H, Guthmann C, Wagner T, et al. Development of a single unit extended release formulation for ZK 811 752, a weakly basic drug. Eur J Pharm Sci 2005;26:47-53
32. Ploen J, Andersch J, Heschel M, et al. Citric acid as a pH-modifying additive in an extended release pellet formulation containing a weakly basic drug. Drug Dev Ind Pharm 2009;35:1210-18
33. Thoma K, Ziegler I. Simultaneous quantification of released succinic acid and a weakly basic drug compound in dissolution media. Eur J Pharm Biopharm 1998;46:183-90
34. Siepe S, Lueckel B, Kramer A, et al. Assessment of tailor-made HPMC-based matrix minitablets comprising a weakly basic drug compound. Drug Dev Ind Pharm 2008;34:46-52
35. Lui CY, Amidon GL, Berardi RR, et al. Comparison of gastrointestinal pH in dogs and humans: implications on the use of the beagle dog as a model for oral absorption in humans. J Pharm Sci 1986;75:271-4
36. Morihara M, Aoyagi N, Kaniwa N, et al. Assessment of gastric acidity of Japanese subjects over the last 15 years. Biol Pharm Bull 2001;24:313-15
37. Mitra A, Kesisoglou F, Beauchamp M, et al. Using absorption simulation and gastric pH modulated dog model for formulation development to overcome achlorhydria effect. Mol Pharm 2011;8:2216-23
38. Taniguchi C, Inoue R, Kawabata Y, et al. Novel formulations of dipyridamole with microenvironmental pH-modifiers for improved dissolution and bioavailability under hypochlorhydria. Int J Pharm 2012;434:148-54
39. Wienen W, Entzeroth M, van Meel JCA, et al. A review on telmisartan: a novel, long-acting angiotensin II-Receptor antagonist. Cardiovasc Drug Rev 2000;18:127-54
40. Onoue S, Inoue R, Taniguchi C, et al. Improved dissolution and pharmacokinetic behavior of dipyridamole formulation with microenvironmental pH-modifier under hypochlorhydria. Int J Pharm 2012;426:61-6
41. Schilling SU, Bruce CD, Shah NH, et al. Citric acid monohydrate as a release-modifying agent in melt extruded matrix tablets. Int J Pharm 2008;361:158-68
42. Xu L, Luo Y, Feng J, et al. Preparation and in vitro-in vivo evaluation of none gastric resident dipyridamole (DIP) sustained-release pellets with enhanced bioavailability. Int J Pharm 2012;422:9-16
43. Espinoza R, Hong E, Villafuerte L. Influence of admixed citric acid on the release profile of pelanserin hydrochloride from HPMC matrix tablets. Int J Pharm 2000;201:165-73
44. Li DX, Jang K-Y, Kang W, et al. Enhanced solubility and bioavailability of sibutramine base by solid dispersion system with aqueous medium. Biol Pharm Bull 2010;33:279-84
45. Nie S, Pan W, Li X, et al. The effect of citric acid added to hydroxypropyl methylcellulose (HPMC) matrix tablets on the release profile of vinpocetine. Drug Dev Ind Pharm 2004;30:627-35
46. Guthmann C, Lipp R, Wagner T, et al. Development of a multiple unit pellet formulation for a weakly basic drug. Drug Dev Ind Pharm 2007;33:341-9
47. Kranz H, Wagner T. Effects of formulation and process variables on the release of a weakly basic drug from single unit extended release formulations. Eur J Pharm Biopharm 2006;62:70-6
48. Thoma K, Zimmer T. Retardation of weakly basic drugs with diffusion tablets. Int J Pharm 1990;58:197-202
49. Chakrabarti S, Southard MZ. Control of poorly soluble drug dissolution in conditions simulating the gastrointestinal tract flow. 2. Cocompression of drugs with buffers. J Pharm Sci 1997;86:465-9
50. Riis T, Bauer-Brandl A, Wagner T, et al. pH-independent drug release of an extremely poorly soluble weakly acidic drug from multiparticulate extended release formulations. Eur J Pharm Biopharm 2007;65:78-84
51. Gupta P, Bansal AK. Spray drying for generation of a ternary amorphous system of celecoxib, PVP, and meglumine. Pharm Dev Technol 2005;10:273-81
52. Kyorin Pharmaceutical Co., Ltd. Matrix-type sustained release preparation containing basic additive. WO2010110436A1; 2010
53. Novartis Pharma GmbH. Pharmaceutical compositions comprising a pH-dependent drug, a pH modifier and a retarding agent. WO2007022956A2; 2006
54. Boehringer Ingelheim International GmbH. Sustained release matrix systems for highly soluble drugs. WO2001022940A1;2000
55. Mutual Pharmaceutical Co., Inc. Controlled-release formulations, method of manufacture, and use thereof. US7794750B2;2008
56. Actavis Group Ptc Ehf. Modified release dosage form of sulfonylurea compound. WO2009004654A2;2008
57. Zeneca Ltd. Pharmaceutical compositions using thiazepine. US5948437A; 1997
58. Bayer AG. Sustained-release preparations of quinolone antibiotics and method for preparation thereof. WO2002000219A1; 2001
59. Dr. Karl Thomae Gmbh. Bromhexine delayed-release pharmaceutical form. US4438091A; 1982
60. Boehringer Ingelheim Gmbh. Dipyricamole sustained release forms comprising lacquer-coated particles and the preparation thereof. US4367217A; 1980
61. Takeda Pharmaceutical Co. Ltd. Method for improving absorbability of preparation, and preparation having improved absorbability. WO2010026993A1; 2009
62. Nipro Corp. Basis particles, method for manufacturing the same, and orallydisintegrating tablet. US20080311195A1; 2008
63. Chien WY. Potential development and new approaches in oral controlled-release drug delivery systems. Drug Dev Ind Pharm 1983;9:1291-330
64. Timmins P, Delargy AM, Howard JR. Optimization and characterization of a pH-independent extended-release hydrophuic matrix tablet. Pharm Dev Technol 1997;2:25-31
65. Janssens S, Van den Mooter G. Review: physical chemistry of solid dispersions. J Pharm Pharmacol 2009;61:1571-86
66. Dhirendra K, Lewis S, Udupa N, et al. Solid dispersions: a review. Pak J Pharm Sci 2009;22:234-46
67. Badawy SI, Gray DB, Zhao F, et al. Formulation of solid dosage forms to overcome gastric pH interaction of the factor Xa inhibitor, BMS-561389. Pharm Res 2006;23:989-96