Solid form changes during drug development: good, bad, and ugly case studies
Tóm tắt
Từ khóa
Tài liệu tham khảo
European medicines Agency, Assessment Report for Zypadhera, Doc Ref: 608654/2008. p 31. ( http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/000890/WC500054428.pdf . Accessed 23 Feb 2016)
Aungst BJ, Nguyen H, Taylor NJ, Bindra DS (2002) Formulation and food effects on the oral absorption of a poorly water soluble, highly permeable antiretroviral. J Pharm Sci 91:1390–1395
Briggs CA, Jennings RA, Wade R, Harasawa K, Ichikawa S, Minohara K, Nakagawa S (1999) Crystalline [R-(R*,R*]-2-(4-difluorophenyl)-β,δ-dihydroxy-5-(1-methylehtyl)-3-phenyl-4-[phenylamino)carbonyl]-1H-pyrrole-1-heptanoic acid hemi calcium salt (atorvastatin). US Patent 5,969,156, 19 Oct 1999
Byrn SR, Coates DA, Gushurst KS, Krzyzaniak JF, Li ZJ, Morrison HG, Park A, Vlahova PI (2003) Crystalline Forms of [R-(R*,R*]-2-(4-difluorophenyl)-β,δ-dihydroxy-5-(1-methylehtyl)-3-phenyl-4-[phenylamino)carbonyl]-1H-pyrrole-1-heptanoic acid hemi calcium salt (2:1). US Patent 6,605,729, 12 Aug 2003
Campeta AM, Chekal BP, Abramov YA, Meenan PL, Henson MJ, Shi B, Singer RA, Horspool KR (2010) Development of a targeted polymorph screening approach for a complex polymorphic and highly solvating API. J Pharm Sci 99:3874–3886
Crixivan Package Insert. (available at http://www.merck.com/product/usa/pi_circulars/c/crixivan/crixivan_pi.pdf . Accessed 23 Feb 2016)
Desikan S, Parsons RL, Davis WP, Ward JE, Marshall WJ, Toma PH (2005) Process development challenges to accommodate a late-appearing stable polymorph: a case study on the polymorphism and crystallization of a fast-track drug development compound. Org Proc Res Dev 9:933–942
Di Lorenzo R, Brogli A (2010) Profile of olanzapine long-acting injection for the maintenance treatment of adult patients with schizophrenia. Neuropsychiatr Dis Treat 6:573–581
Fish DN, North DS (2001) Gatifloxacin, an advanced 8-methoxy fluoroquinolone. Pharmacotherapy 21:35–39
Fukuda H, Hori S, Hiramatsu K (1998) Antibacterial activity of gatifloxacin (AM-1155, CG5501, BMS-206584), a newly developed fluoroquinolone, against sequentially acquired quinolone-resistant mutants and the norA transformant of Staphylococcus aureus. Antimicrob Agents Chemother 42:1917–1922
Gamble T, Sand P (2008) Patient perspectives in the management of overactive bladder, focus on transdermal oxybutynin. Patient Prefer Adherence 2:349–356
FDA approves over-the-counter Oxytrol for Women to treat overactive bladder. http://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm336815.htm . Accessed 23 Feb 2016
Lie JJ (2009) Triumph of the Heart. The Story of Statins. Oxford University Press, New York
Lin JH (1999) Role of pharmacokinetics in the discovery and development of indinavir. Adv Drug Deliv Rev 39:33–49
Lin JH, Ostovic D, Vacca JP (1998) Chapter 11. The integration of medicinal chemistry, drug metabolism, and pharmaceutical research and development in drug discovery and development. The story of Crxivan®, an HIV protease inhibitor. In: Borchardt RT, Freidinger RM, Sawyer TK, Smith PL (eds) Integration of Pharmaceutical Discovery and Development: Case Studies. Plenum Press, New York
Lui CY, Ostovic D, Katdare AV,Stemach C (2003) Dry granulation formulation for an HIV protease inhibitor. US Patent 6,645,961, 11 Nov 2003
Masuzawa K, Suzue S, Hirai K, Ishizaki T (1991) 8-Alkoxyquinolonecarboxylic acid and salts thereof. US patent 5,043,450, 27 Aug 1991
Matsumoto T, Hara M, Miyashita K, Kato Y (1999) 8-Alkoxyquinolonecarboxylic acid hydrate with excellet stability and process for producing the same. US patent 5,880, 283, 9 Mar 1999
Newman AW, Byrn SR (2003) Solid-state analysis of the active pharmaceutical ingredient in drug products. Drug Deliv Today 8:898–905
Oxytrol Package Insert. (available at http://pi.watson.com/data_stream.asp?product_group=1295&p=pi&language=E . Accessed 23 Feb 2016)
Paulekuhn GS, Dressman JB, Saal C (2007) Trends in active pharmaceutical ingredient salt selection based on analysis of the orange book database. J Med Chem 50:6665–6672
Pfizer Citizen Petition. Docket no 2005P-0452. 2005. (available at http://www.fda.gov/ohrms/dockets/dockets/05p0452/05p-0452-cp00001-01-vol1.pdf . Accessed 23 Feb 2016)
Raghaven KS, Ranadive SA, Gougoutas JZ, DiMarco JD, Parker WL, Davidovich M, Newman A (2002) Gatifloxacin pentahydrate. US patent 6,413, 969, 2 Jul 2002
Reutzel-Edens SM, Bush JK, Magee PA, Stephenson GA, Byrn SR (2003) Anhydrates and hydrates of olanzapine: crystallization, solid-state characterization, and structural relationships. Cryst Growth Des 3:897–907
Sathyan G, Chancellor MB, Gupta SK (2001) Effect of OROS® controlled-release delivery on the pharmacokinetics and pharmacodynamics of oxybutynin chloride. Br J Clin Phrmacol 52:409–417
Staszewski S, Morales-Ramirez J, Tashima KT, Rachlis A, Skiest D, Stanford J, Stryker R, Johnson P, Labriola DF, Farina D, Manion DJ, Ruiz NM (1999) Efavirenz plus zidovudine and lamivudine, efavirenz plus indinavir and indinavir plus zidovudine and lamivudine in the treatment of HIV-1 in adults. New Engl J Med 341:1865–1873
Tesslor L, Aronhime J, Lifshitz-Liron R, Maidan-Hanoch D, Hasson N (2003) Crystal forms of atorvastatin hemi-calcium and processes for their preparation as well as novel processes for preparing other forms. US Patent 7,256,212, 14 Aug 2007
Tully W (2003) Factory scale process for producing crystalline atorvastatin trihydrate hemi calcium salt. US patent 6,600,051 B2, 29 Jul 2003
Van Der Schaaf PA, Blatter F, Szelagiewicz M, Schoning K-U (2009) Crystalline Forms of Atorvastatin. US Patent 7,538,136, 26 May 2009
Wu C-Y, Benet LZ (2005) Predicting drug disposition via application of BCS: transport/absorption/elimination interplay and development of a biopharmaceutics drug disposition classification system. Pharm Res 22:11–23
Yeh KC, Deutsch PJ, Haddix H, Hesney M, Hoagland V, Ju WD, Justice SJ, Osborne B, Sterrett AT, Stone JA, Woolf E, Waldman S (1998) Single-dose pharmacokinetics of indinavir and the effect of food. Antimicrob Agents Chemother 42:332–338
Zyprexa Relprevv Package Insert December 2014. (available at http://pi.lilly.com/us/zyprexa_relprevv.pdf . Accessed 23 Feb 2016)
