Formulation and process design for a solid dosage form containing a spray-dried amorphous dispersion of ibipinabant

Pharmaceutical Development and Technology

Volumn 18, Issue 2, 2013, Pages 359-366

  Leane, Michael M ^a   Sinclair, Wayne ^a   Qian, Feng ^a   Haddadin, Raja ^a   Brown, Alan ^b   Tobyn, Mike ^a   Dennis, Andrew B ^a  

^a BRISTOL MYERS SQUIBB   (United States)

^b CERAM Research Ltd   (United Kingdom)

Author keywords

Amorphous; Coating; Crystallinity; Direct compression; Excipients; Lactose; Mannitol; Microcrystalline cellulose; Physical stability; Roller compaction; Spray dried dispersion; Tablet

Indexed keywords

IBIPINABANT; MANNITOL; MICROCRYSTALLINE CELLULOSE;

ARTICLE; CHEMICAL COMPOSITION; CRYSTALLIZATION; DISPERSION; DRUG DOSAGE FORM; DRUG FORMULATION; DRUG SOLUBILITY; DRUG STABILITY; PRIORITY JOURNAL; SPRAY DRYING; TABLET COMPRESSION; TABLET FORMULATION;

AMIDINES; CELLULOSE; CHEMISTRY, PHARMACEUTICAL; DRUG STABILITY; EXCIPIENTS; POLYMERS; PYRAZOLES; SOLUBILITY; TABLETS;

EID: 84872443900     PISSN: 10837450     EISSN: 10979867     Source Type: Journal    
DOI: 10.3109/10837450.2011.619544     Document Type: Article

References (45)

1. Hancock BC, Parks M. What is the true solubility advantage for amorphous pharmaceuticals? Pharm Res 2000;17:397-404 (Pubitemid 30395293)
2. Bhugra C, Pikal MJ. Role of thermodynamic, molecular, and kinetic factors in crystallization from the amorphous state. J Pharm Sci 2008;97:1329-1349
3. Leuner C, Dressman J. Improving drug solubility for oral delivery using solid dispersions. Eur J Pharm Biopharm 2000;50:47-60 (Pubitemid 30326688)
4. Surana R, Pyne A, Suryanarayanan R. Effect of preparation method on physical properties of amorphous trehalose. Pharm Res 2004;21:1167-1176 (Pubitemid 38960768)
5. Moore MD, Wildfong PLD. Aqueous solubility enhancement through engineering of binary solid composites: Pharmaceutical applications. J Pharm Innovat 2009;4:36-49
6. Friesen DT, Shanker R, Crew M, Smithey DT, Curatolo WJ, Nightingale JA. Hydroxypropyl methylcellulose acetate succinatebased spray-dried dispersions: An overview. Mol Pharm 2008;5: 1003-1019
7. Marsac PJ, Li T, Taylor LS. Estimation of drug-polymer miscibility and solubility in amorphous solid dispersions using experimentally determined interaction parameters. Pharm Res 2009;26:139-151
8. Marsac PJ, Rumondor AC, Nivens DE, Kestur US, Stanciu L, Taylor LS. Effect of temperature and moisture on the miscibility of amorphous dispersions of felodipine and poly(vinyl pyrrolidone J Pharm Sci 2010;99:169-185
9. Chan HK, Grant DJW. Influence of compaction on the intrinsic dissolution rate of modified acetaminophen and adipic acid crystals. Int J Pharm 1989;57:117-124 (Pubitemid 20011834)
10. Morris KR, Griesser UJ, Eckhardt CJ, Stowell JG. Theoretical approaches to physical transformations of active pharmaceutical ingredients during manufacturing processes. Adv Drug Deliv Rev 2001;48:91-114 (Pubitemid 32452293)
11. Ranzani LS, J. F, Galimany F, Santanach A, Gomez-Gomar AM, G. C, Galimany F, Gryczke A. Enhanced in vivo absorption of CB-1 antagonist in rats via solid solutions prepared by hot-melt extrusion. Drug Dev Ind Pharm 2011:DOI: 10.3109/03639045.036
12. .03535822
13. Thybo P, Pedersen BL, Hovgaard L, Holm R, Mullertz A. Characterization and physical stability of spray dried solid dispersions of probucol and PVP-K30. Pharm Dev Technol 2008; 13:375-386
14. Shah J, Vasanti S, Anroop B, Vyas H. Enhancement of dissolution rate of valdecoxib by solid dispersions technique with PVP K 30 & PEG 4000: Preparation and in vitro evaluation. J Incl Phenom Macro 2009;63:69-75
15. Fini A, Cavallari C, Ospitali F. Raman and thermal analysis of indomethacin/PVP solid dispersion enteric microparticles. Eur J Pharm Biopharm 2008;70:409-420
16. Thybo P, Kristensen J, Hovgaard L. Characterization and physical stability of tolfenamic acid-PVP K30 solid dispersions. Pharm Dev Technol 2007;12:43-53 (Pubitemid 46902610)
17. Damian F, Blaton N, Desseyn H, Clou K, Augustijns P, Naesens L et al.Solid state properties of pure UC-781 and solid dispersions with polyvinylpyrrolidone (PVP K30). J Pharm Pharmacol 2001; 53:1109-1116 (Pubitemid 32754941)
18. Tantishaiyakul V, Kaewnopparat N, Ingkatawornwong S. Properties of solid dispersions of piroxicam in polyvinylpyrrolidone. Int J Pharm 1999;181:143-151 (Pubitemid 29229801)
19. Taylor LS, Zografi G. Spectroscopic characterization of interactions between PVP and indomethacin in amorphous molecular dispersions. Pharm Res 1997;14:1691-1698 (Pubitemid 28062912)
20. Tantishaiyakul V, Kaewnopparat N, Ingkatawornwong S. Properties of solid dispersions of piroxicam in polyvinylpyrrolidone K-30. Int J Pharm 1996;143:59-66 (Pubitemid 26396399)
21. Kaushal AM, Gupta P, Bansal AK. Amorphous drug delivery systems: Molecular aspects, design, and performance. Crit Rev Ther Drug Carrier Syst 2004;21:133-193 (Pubitemid 41647581)
22. Ghebremeskel AN, Vemavarapu C, Lodaya M. Use of surfactants as plasticizers in preparing solid dispersions of poorly soluble API: Stability testing of selected solid dispersions. Pharm Res 2006;23:1928-1936 (Pubitemid 44200557)
23. Ghebremeskel AN, Vemavarapu C, Lodaya M. Use of surfactants as plasticizers in preparing solid dispersions of poorly soluble API: Selection of polymer-surfactant combinations using solubility parameters and testing the processability. Int J Pharm 2007; 328:119-129 (Pubitemid 44895482)
24. de Waard H, Hinrichs WL, Visser MR, Bologna C, Frijlink HW. Unexpected differences in dissolution behavior of tablets prepared from solid dispersions with a surfactant physically mixed or incorporated. Int J Pharm 2008;349:66-73 (Pubitemid 350299690)
25. Sinclair W, Leane M, Clarke G, Dennis A, Tobyn M, Timmins P 2011 Physical Stability and Recrystallization Kinetics of Amorphous Ibipinabant Drug Product by FT-Raman Spectroscopy. J Pharm Sci:In Press. DOI: 10.1002/jps.22658
26. Lange JH, Coolen HK, van Stuivenberg HH, Dijksman JA, Herremans AH, Ronken E et al. Synthesis, biological properties, and molecular modeling investigations of novel 3,4-diarylpyrazolines as potent and selective CB(1) cannabinoid receptor antagonists. J Med Chem 2004;47:627-643 (Pubitemid 38129720)
27. Fakes MG, Vakkalagadda BJ, Qian F, Desikan S, Gandhi RB, Lai C et al. Enhancement of oral bioavailability of an HIV-attachment inhibitor by nanosizing and amorphous formulation approaches. Int J Pharm 2009;370:167-174
28. Tobyn M, Brown J, Dennis AB, Fakes M, Gao Q, Gamble J et al. Amorphous drug-PVP dispersions: Application of theoretical, thermal and spectroscopic analytical techniques to the study of a molecule with intermolecular bonds in both the crystalline and pure amorphous state. J Pharm Sci 2009;98:3456-3468
29. Jordan MP. 1999. Moisture barrier film coating composition, method, and coated form. In Office USP, editor, ed., US: BPSI Holdings, Inc. US Patent No 5, 885, 617
30. Fowler CE, Gracia L, Edwards MI, Brown A, Rees GD. Fluoride penetration from toothpastes into incipient enamel erosive lesions investigated using dynamic secondary ion mass spectrometry. J Clin Dent 2009;20:186-191
31. Hancock BC, Zografi G. The relationship between the glass transition temperature and the water content of amorphous pharmaceutical solids. Pharm Res 1994;11:471-477 (Pubitemid 24144434)
32. Xie Y, Tao W, Morrison H, Chiu R, Jona J, Fang J et al. Quantitative determination of solid-state forms of a pharmaceutical development compound in drug substance and tablets. Int J Pharm 2008;362:29-36
33. Weuts I, Kempen D, Verreck G, Decorte A, Heymans K, Peeters J et al. Study of the physicochemical properties and stability of solid dispersions of loperamide and PEG6000 prepared by spray drying. Eur J Pharm Biopharm 2005;59:119-126 (Pubitemid 39573443)
34. Rumondor AC, Stanford LA, Taylor LS. Effects of polymer type and storage relative humidity on the kinetics of felodipine crystallization from amorphous solid dispersions. Pharm Res 2009;26:2599-2606
35. Airaksinen S, Karjalainen M, Kivikero N, Westermarck S, Shevchenko A, Rantanen J. Excipient selection can significantly affect solid-state phase transformation in formula wet granulation. AAPS PharmSciTech 2005; 6:E311-322
36. Airaksinen S, Luukkonen P, Jørgensen A, Karjalainen M, Rantanen J, Yliruusi J. Effects of excipients on hydrate formation in wet masses containing theophylline. J Pharm Sci 2003;92: 516-528 (Pubitemid 36258966)
37. Ku MS, Dulin W. A biopharmaceutical classification-based Right-First-Time formulation approach to reduce human pharmacokinetic variability and project cycle time from First-In-Human to clinical Proof-Of-Concept. Pharm Dev Technol 2010; 1-18. DOI: 10.3109/10837450.2010.535826
38. Hulse WL, Forbes RT, Bonner MC, Getrost M. The characterization and comparison of spray-dried mannitol samples. Drug Dev Ind Pharm 2009;35:712-718
39. Balani PN, Ng WK, Tan RB, Chan SY. Influence of excipients in comilling on mitigating milling-induced amorphization or structural disorder of crystalline pharmaceutical actives. J Pharm Sci 2010;99:2462-2474
40. Schmidt AG, Wartewig S, Picker KM. Potential of carrageenans to protect drugs from polymorphic transformation. Eur J Pharm Biopharm 2003;56:101-110 (Pubitemid 36802053)
41. Dhumal RS, Shimpi SL, Paradkar AR. Development of spraydried co-precipitate of amorphous celecoxib containing storage and compression stabilizers. Acta Pharm 2007;57:287-300 (Pubitemid 47429183)
42. Colombo I, Grassi G, Grassi M. Drug mechanochemical activation. J Pharm Sci 2009;98:3961-3986
43. Descamps M, Willart JF, Dudognon E, Caron V. Transformation of pharmaceutical compounds upon milling and comilling: The role of T(g). J Pharm Sci 2007;96:1398-1407 (Pubitemid 46797497)
44. Randolph Sanders J, Mason PJ, Whiteman M. Digital Fabrication 2005 - Final Program and Proceedings, Baltimore, MD, 2005, pp. 148-152
45. Lin KH, Lin SY, Li MJ. Compression forces and amount of outer coating layer affecting the time-controlled disintegration of the compression-coated tablets prepared by direct compression with micronized ethylcellulose. J Pharm Sci 2001;90: 2005-2009