2,205
Views
105
CrossRef citations to date
0
Altmetric
Reviews

Drug delivery strategies for poorly water-soluble drugs: the industrial perspective

, PhD, , PhD & , PhD
Pages 1481-1500 | Published online: 06 Sep 2011

Bibliography

  • Fahr A, van Hoogevest P, May S, Transfer of lipophilic drugs between liposomal membranes and biological interfaces: consequences for drug delivery. Eur J Pharm Sci 2005;26:251-65
  • Commissioner of Food and Drugs. Nanotechnology Task Force Report, FDA Rockville MD 20857, 2007
  • Final Report from the EMEA/CHMP-Think-Tank Group on Innovative Drug Development; 2007
  • Reflection Paper on Nanotechnology-based Medicinal Products for Human Use; 2006
  • Strickland CH. Nano-based drug and medical devices: FDA track record. Nanotechnol Law Bus 2007;4:179-88
  • Guidance for Industry: Liposome Drug Products: Chemistry, Manufacturing, and Controls; Human Pharmacokinetics and Bioavailability; and Labeling Documentation. In: (CDER) USDoHaHSCfDEaR; 2002
  • Draft Guidance on Doxorubicin HCl; 2010
  • Fahr A, Liu X. Drug delivery strategies for poorly water-soluble drugs. Expert Opin Drug Deliv 2007;4:403-16
  • Balbach S, Korn C. Pharmaceutical evaluation of early development candidates "the 100 mg-approach". Int J Pharm 2004;275:1-12
  • Gopinathan S, Noraldeen A, Wilson AGE. Development and application of a high throughput screening for oral administration in drug discovery. Future Med Chem 2010;2:1392-8
  • Ahuja G, Pathak K. Porous carriers for controlled/modulated drug delivery. Indian J Pharm Sci 2009;71:599-607
  • Leigh S, Leigh MLS, Van Hoogevest P, inventors; Phares Pharm Res NV assignee. Composition comprising low water soluble compounds within porous carriers. The Netherlands: 2004
  • Prendergast WF, Schafer HN. Nanocrystalline pharmaceutical patent litigation: the first case. Nanotechnol Law Bus 2008;5:157-61
  • Varma RK, Kaushal R, Junnarkar AY, Polysorbate 80: a pharmacological study. Arzneimittelforschung 1985;35:804-8
  • Masini E, Planchenault J, Pezziardi F, Histamine-releasing properties of Polysorbate 80 in vitro and in vivo: correlation with its hypotensive action in the dog. Agents Actions 1985;16:470-7
  • Bowers VD, Locker S, Ames S, The hemodynamic effects of Cremophor-EL. Transplantation 1991;51:847-50
  • Eschalier A, Lavarenne J, Burtin C, Study of histamine release induced by acute administration of antitumor agents in dogs. Cancer Chemother Pharmacol 1988;21:246-50
  • Eschalier A, Lavarenne J, Burtin C, Acute hemodynamic effects of an antitumoral agent: elliptinium. Involvement of histamine release. Agents Actions 1986;17:441-8
  • Ennis M, Lorenz W, Gerland W. Modulation of histamine release from rat peritoneal mast cells by non-cytotoxic concentrations of the detergents Cremophor El (oxethylated castor oil) and Triton X100. A possible explanation for unexpected adverse drug reactions? Agents Actions 1986;18:235-8
  • Ennis M, Lorenz W, Kapp B, Comparison of the histamine-releasing activity of cremophor E1 and some of its derivatives in two experimental models: the in vivo anaesthetized dog and in vitro rat peritoneal mast cells. Agents Actions 1985;16:265-8
  • Lorenz W, Reimann HJ, Schmal A, Histamine release in dogs by Cremophor E1 and its derivatives: oxethylated oleic acid is the most effective constituent. Agents Actions 1977;7:63-7
  • Lorenz W, Schmal A, Schult H, Histamine release and hypotensive reactions in dogs by solubilizing agents and fatty acids: analysis of various components in cremophor El and development of a compound with reduced toxicity. Agents Actions 1982;12:64-80
  • Thaysen G. Applications of Solutol HS 15 In: ExAct B; 1999. p. 7
  • Teelmann K, Schlappi B, Schupbach M, Preclinical safety evaluation of intravenously administered mixed micelles. Arzneimittelforschung 1984;34:1517-23
  • Strickley RG. Solubilizing excipients in oral and injectable formulations. Pharm Res 2004;21:201-30
  • Fahr A, van Hoogevest P, Kuntsche J, Lipophilic drug transfer between liposomal and biological membranes: what does it mean for parenteral and oral drug delivery? J Liposome Res 2006;16:281-301
  • Dai WG, Pollock-Dove C, Dong LC, Advanced screening assays to rapidly identify solubility-enhancing formulations: high-throughput, miniaturization and automation. Adv Drug Deliv Rev 2008;60:657-72
  • Dai WG, Dong LC, Li S, Parallel screening approach to identify solubility-enhancing formulations for improved bioavailability of a poorly water-soluble compound using milligram quantities of material. Int J Pharm 2007;336:1-11
  • Mansky P, Dai WG, Li S, Screening method to identify preclinical liquid and semi-solid formulations for low solubility compounds: miniaturization and automation of solvent casting and dissolution testing. J Pharm Sci 2007;96:1548-63
  • Lee YC, Zocharski PD, Samas B. An intravenous formulation decision tree for discovery compound formulation development. Int J Pharm 2003;253:111-19
  • Neervannan S. Preclinical formulations for discovery and toxicology: physicochemical challenges. Expert Opin Drug MetabToxicol 2006;2:715-31
  • Li P, Zhao L. Developing early formulations: practice and perspective. Int J Pharm 2007;341:1-19
  • Van Hoogevest P, Rogue V, Brumec M, Instant solubilization of poorly water-soluble drugs by in-situ loading of aqueous phospholipid dispersions suitable for parenteral administration. PDA J Pharm Sci Technol 2006;60:366-77
  • Van Hoogevest P, Liu X, Fahr A, Role of phospholipids in the oral and parenteral delivery of poorly water soluble drugs. J Drug Deliv Sci Technol 2011;21:5-16
  • Shah T, Patel D, Hirani J, Nanosuspensions as a drug delivery system: a comprehensive review. Drug Delivery Technol 2007;7:42-53
  • Niwa T, Miura S, Danjo K. Universal wet-milling technique to prepare oral nanosuspensions focused on discovery and pre-clinical animal studies. Development of particle design method. Int J Pharm 2011;405:218-27
  • Bittner B, Mountfield RJ. Intravenous administration of poorly soluble new drug entities in early drug discovery: the potential impact of formulation on pharmacokinetic parameters. Curr Opin Drug Discov Devel 2002;5:59-71
  • Amidon GL, Lennernas H, Shah VP, A theoretical basis for a biopharmaceutic drug classification: the correlation of in vitro drug product dissolution and in vivo bioavailability. Pharm Res 1995;12:413-20
  • Butler JM, Dressman JB. The developability classification system: application of biopharmaceutics concepts to formulation development. J Pharm Sci 2010;99:4940-54
  • Dressman J, Butler J, Hempenstall J, The BCS: where do we go from here ? Pharm Technol 2001;25:68-76
  • Corrigan OI. The biopharmaceutics drug classification and drugs administered in extended release (ER) formulations. Adv Exp Med Biol 1997;423:111-28
  • Dressman JB, Amidon GL, Reppas C, Dissolution testing as a prognostic tool for oral drug absorption: immediate release dosage forms. Pharm Res 1998;15:11-22
  • Nicolaides E, Galia E, Efthymiopoulos C, Forecasting the in vivo performance of four low solubility drugs from their in vitro dissolution data. Pharm Res 1999;16:1876-82
  • Lobenberg R, Kramer J, Shah VP, Dissolution testing as a prognostic tool for oral drug absorption: dissolution behavior of glibenclamide. Pharm Res 2000;17:439-44
  • Dressman JB, Reppas C. In vitro-in vivo correlations for lipophilic, poorly water-soluble drugs. Eur J Pharm Sci 2000;11(Suppl 2):S73-80
  • Kloefer B, Van Hoogevest P, Moloney R, Study of a standardized taurocholate-lecithin powder for preparing the biorelevant media FeSSIF and FaSSIF dissolution technologies. Dissol Technol 2010;17:6-13
  • Merisko-Liversidge E, Liversidge GG. Nanosizing for oral and parenteral drug delivery: a perspective on formulating poorly-water soluble compounds using wet media milling technology. Adv Drug Deliv Rev 2011;63:427-40
  • Juenemann D, Jantratid E, Wagner C, Biorelevant in vitro dissolution testing of products containing micronized or nanosized fenofibrate with a view to predicting plasma profiles. Eur J Pharm Biopharm 2011;77:257-64
  • Liversidge GG, Conzentino P. Drug particle size reduction for decreasing gastric irritancy and enhancing absorption of naproxen in rats. Int J Pharm 1995;125:309-13
  • Shono Y, Jantratid E, Kesisoglou F, Forecasting in vivo oral absorption and food effect of micronized and nanosized aprepitant formulations in humans. Eur J Pharm Biopharm 2010;76:95-104
  • Grunkemeyer JL, Mirejovsky D, Lenaz L, Significant improvement of oral bioavailability of a poorly soluble compound. AAPS; Nashville, TN, USA: 2005
  • Guzman HR, Tawa M, Zhang Z, Combined use of crystalline salt forms and precipitation inhibitors to improve oral absorption of celecoxib from solid oral formulations. J Pharm Sci 2007;96:2686-702
  • Hecq J, Deleers M, Fanara D, Preparation and in vitro/in vivo evaluation of nano-sized crystals for dissolution rate enhancement of ucb-35440-3, a highly dosed poorly water-soluble weak base. Eur J Pharm Biopharm 2006;64:360-8
  • Tong WT. Salt screening and selection: new challenges and considerations in the modern pharmaceutical research and development paradigm In: Qiu Y, Chen Y, Zhang GGZ, Liu L, Porter WR. editors. Developing Oral Dosage Forms: pharmaceutical theory and practice. Academic Press; Burlington, London, San Diego, New York; 2009. p. 75-85
  • Kojima T, Tsutsumi S, Yamamoto K, High-throughput cocrystal slurry screening by use of in situ Raman microscopy and multi-well plate. Int J Pharm 2010;399:52-9
  • Zimmerman J. inventor, Ciba-Geigy AG, assignee. Pyrimidin derivatives and process for their preparation. 1993
  • Buchdunger E, Zimmermann J, Mett H, Inhibition of the Abl protein-tyrosine kinase in vitro and in vivo by a 2-phenylaminopyrimidine derivative. Cancer Res 1996;56:100-4
  • Peng B, Dutreix C, Mehring G, Absolute bioavailability of imatinib (Glivec) orally versus intravenous infusion. J Clin Pharmacol 2004;44:158-62
  • Emend Injection Drug Description. Available from: http://www.rxlist.com/emend-injection-drug.htm
  • Webb MS, Rebstein P, Lamson W, Liposomal drug delivery: recent patents and emerging opportunities. Recent Patents Drug Deliv Formulation 2007;I:185-94
  • Bhavna, Ali M, Baboota S, Ali J. Patents on nanoparticulate drug delivery -a review. Recent Patents Drug Deliv Formulation 2008;2:83-9
  • Fu Q, Sun J, Zhang W, Nanoparticle Albumin-Bound (NAB) technology is a promising method for anti-cancer drug delivery. Recent Patents Anticancer Drug Discov 2009;4:262-72
  • Liversidge GG, Cundy KC, Bishop JF, inventors; Sterling Drug, Inc., assignee. Surface modified drug nanoparticles. US 5,145,684: 1992
  • Czekai DA, Seaman LP. inventors; Eastman Kodak, assignee. Continuous method of grinding pharmaceutical substances. US 5,718,388: 1998
  • Juhnke M, Berghausen J, Timpe C. Accelerated formulation development for nanomilled active pharmaceutical ingredients using a screening approach chemical engineering & technology. Chem Eng Technol 2010;33:1412-18
  • Lakshmi P, Kumar GH. Nano-suspension technology: a review. Int J Pharm Pharm 2010;2:35-40
  • Brewster ME, Loftsson T. Cyclodextrins as pharmaceutical solubilizers. Adv Drug Deliv Rev 2007;59:645-66
  • Cydex Pharmaceuticals, Inc.: Marketed products. Available from: http://cydexpharma.com/approvedproducts.html
  • Muller BW, Brauns U. inventors; Janssen Pharmaceutica N.V., assignee. Pharmaceutical compositions containing drugs which are instable or sparingly soluble in water and methods for their preparation. US 6,407,079: 2002
  • Stella V, Rajewski R. inventors; University of Kansas assignee. Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof. US 5134127: 1992
  • Pipkin JD, Mosher GL, Hecker DB. inventors; CyDex Pharmaceuticals, Inc., assignee. Sulfoalkyl ether cyclodextrin compositions and methods of preparation thereof. US 7629331: 2009
  • Antle V. inventor, CyDex Pharmaceuticals, Inc., assignee. Sulfoalkyl ether cyclodextrin compositions. US 7,635,773: 2009
  • Leigh S, Leigh MLS, Van Hoogevest P. inventors; Phares Pharmaceutical Research N.V., assignee. Crystal forms of astaxanthin. US 7,563,935: 2009
  • Gellie B. Intellectual properties and crystalline forms: how to get an European Patent on crystalline forms? 5th Bologna convention on crystal form Bologna; 2010
  • Fricker G, Kromp T, Wendel A, Phospholipids and lipid-based formulations in oral drug delivery. Pharm Res 2010;27:1469-86
  • Mullertz A, Ogbonna A, Ren S, New perspectives on lipid and surfactant based drug delivery systems for oral delivery of poorly soluble drugs. J Pharm Pharmacol 2010; In press
  • Kuentz M. Oral self-emulsifyng drug delivery sytems, from biopharmaceutical to technical formulation aspects. J Drug Deliv Sci Technol 2011;21:17-20
  • Mistry RB, Sheth NS. A review : self emulsifying drug delivery system. Int J Pharm Pharm Sci 2011;3:23-8
  • Davis ME, Brewster ME. Cyclodextrin-based pharmaceutics: past, present and future. Nat Rev Drug Discov 2004;3:1023-35
  • Gould S, Scott RC. 2-Hydroxypropyl-beta-cyclodextrin (HP-beta-CD): a toxicology review. Food Chem Toxicol 2005;43:1451-9
  • Breitenbach J, Magerlein M. Melt-Extruded Molecular Dispersions. In: Ghebre Sellassie I, Martin C. editors. Pharmaceutical extrusion technology. Marcel Dekker; New York, 2003. p. 245-60
  • Chiou WL, Riegelman S. Pharmaceutical applications of solid dispersion systems. J Pharm Sci 1971;60:1281-302
  • Prodduturi S, Urman KL, Otaigbe JU, Stabilization of hot-melt extrusion formulations containing solid solutions using polymer blends. AAPS PharmSciTech 2007;8:E1-10
  • Janssens S, Van den Mooter G. Review: physical chemistry of solid dispersions. J Pharm Pharmacol 2009;61:1571-86
  • Sporanox product. Available from: http://www.rxlist.com/sporanox-drug.htm
  • Intelence product. Available from: http://www.rxlist.com/intelence-drug.htm
  • Prograf product. Available from: http://www.rxlist.com/prograf-drug.htm
  • Crestor product. Available from: http://www.rxlist.com/crestor-drug.htm
  • Gris-PEG product. Available from: http://www.rxlist.com/gris-peg-drug.htm
  • Aoyagi N, Ogata H, Kaniwa N, Effect of food on the bioavailability of griseofulvin from microsize and PEG ultramicrosize (GRIS-PEG) plain tablets. J Pharmacobiodyn 1982;5:120-4
  • Kaletra product. Available from: http://www.rxlist.com/kaletra-tablets-drug.htm
  • Rapamune product. Available from: http://www.rxlist.com/rapamune-drug.htm
  • Emend oral product. Available from: http://www.rxlist.com/emend-drug.htm
  • Wu Y, Loper A, Landis E, The role of biopharmaceutics in the development of a clinical nanoparticle formulation of MK-0869: a Beagle dog model predicts improved bioavailability and diminished food effect on absorption in human. Int J Pharm 2004;285:135-46
  • Megace ES product. Available from: http://www.rxlist.com/megace-es-drug.htm
  • Megace ES product UK. Available from: http://www.medicines.org.uk/EMC/medicine/346/SPC/Megace+160+mg+Tablets/
  • Deschamps B, Musaji N, Gillespie JA. Food effect on the bioavailability of two distinct formulations of megestrol acetate oral suspension. Int J Nanomedicine 2009;4:185-92
  • Miele E, Spinelli GP, Tomao F, Albumin-bound formulation of paclitaxel (Abraxane ABI-007) in the treatment of breast cancer. Int J Nanomedicine 2009;4:99-105
  • Micha JP, Goldstein BH, Birk CL, Case report: Abraxane in the treatment of ovarian cancer: the absence of hypersensitivity reactions. Gynecol Oncol 2006;100:437-43
  • Abraxane product. Available from: http://www.rxlist.com/abraxane-drug.htm
  • Albumin product. Available from: http://www.orgyn.com/resources/genrx/D000114.asp
  • Invega sustenna product. Available from: http://www.rxlist.com/invega-sustenna-drug.htm
  • Ambisome product. Available from: www.ambisome.com
  • Veerareddy PR, Vobalaboina V. Lipid-based formulations of amphotericin B. Drugs Today (Barc) 2004;40:133-45
  • EMA 2008
  • Van Hoogevest P, Fankhauser P. An industrial liposomal dosage form for muramyl-tripeptide-phosphatidyl ethanolamine (MTP-PE). In: Fidler IJ, Lopez-Berestein G. editors. Liposomes in the therapy of infectious diseases and cancer. Alan R. Liss, Inc; New York 1989. p. 453
  • Schwartz RS, Tanaka Y, Fidler IJ, Increased adherence of sickled and phosphatidylserine-enriched human erythrocytes to cultured human peripheral blood monocytes. J Clin Invest 1985;75:1965-72
  • Schumann G, van Hoogevest P, Fankhauser P, Comparison of free and liposomal MTP-PE. Pharmacological and toxicological aspects. In: Fidler IJ, Lopez-Berestein G. editors. Liposomes in the therapy of infectious diseases and cancer. Alan R. Liss, Inc; New York; 1989. p. 191
  • Braun DG, van Hoogevest P, Schumann G. Adjuvants: theory and practical applications: muramyltripeptide-phosphatidylethanolamine MTP-PE - A Muramyldipeptide derivative with lipophilic properties. Oxford Butterworth-Heinemann; 1994
  • Visudyne product. Available from: www.visudyne.com
  • Desai NR, Agha BJ, Kale KM. inventors; QLT Phototherapeutics, Inc., assignee. Liposome compositions of porphyrin photosensitizers. Canada: 2000
  • Chowdhary RK, Shariff I, Dolphin D. Drug release characteristics of lipid based benzoporphyrin derivative. J Pharm Pharm Sci 2003;6:13-19
  • Richter AM, Cerruti-Sola S, Sternberg ED, Biodistribution of tritiated benzoporphyrin derivative (3H-BPD-MA), a new potent photosensitizer, in normal and tumor-bearing mice. J Photochem Photobiol B 1990;5:231-44
  • Visudyne European Public Assessment Report EMA; 2006
  • Definity product. Available from: http://www.rxlist.com/definity-drug.htm
  • Luigetti R. Reflection paper on the pharmaceutical development of intravenous medicinal products containing active substances solubilised in micellar systems (non-polymeric surfactants) DRAFT. 2010
  • Reflection paper on nanotechnology-based medicinal products for human use In: (CHMP) CFMPFHU; 2006
  • Pena C. A FDA perspective on nanomedicine: current initiatives in the US. In: Commisioner Oot; 2010
  • Manual of policies and procedures MAPP5015.9. Reporting format in nanotechnology information in CMC review 6/3/2010. In: Science CodearOop; 2010
  • Messner M, Kurkov SV, Flavia-Piera R, Self-assembly of cyclodextrins: the effect of the guest molecule. Int J Pharm 2011;408:235-47
  • Messner M, Kurkov SV, Brewster ME, Self-assembly of cyclodextrin complexes: aggregation of hydrocortisone/cyclodextrin complexes. Int J Pharm 2011;407:174-83
  • Van 't Klooster G, Hoeben E, Borghys H, Pharmacokinetics and disposition of rilpivirine (TMC278) nanosuspension as a long-acting injectable antiretroviral formulation. Antimicrob Agents Chemother 2010;54:2042-50
  • Teagarden DL, Baker DS. Practical aspects of lyophilization using non-aqueous co-solvent systems. Eur J Pharm Sci 2002;15:115-33

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.