Production and characterization of carbamazepine nanocrystals by electrospraying for continuous pharmaceutical manufacturing

Journal of Pharmaceutical Sciences

Volumn 101, Issue 3, 2012, Pages 1178-1188

  Wang, Mao ^a   Rutledge, Gregory C ^a   Myerson, Allan S ^a   Trout, Bernhardt L ^a  

^a Massachusetts Institute of Technology Cambridge   (United States)

Author keywords

Continuous pharmaceutical manufacturing; Controlled release; Crystallization; Electrospray; Nanocrystal; Nanoparticles; Nanotechnology; Polymorphism

Indexed keywords

CARBAMAZEPINE; METHANOL; NANOCRYSTAL; NANOPARTICLE;

ARTICLE; CONDUCTANCE; CRYSTALLIZATION; DISPERSION; DRUG BIOAVAILABILITY; DRUG MANUFACTURE; DRUG SOLUBILITY; ELECTRIC CURRENT; ELECTROSPRAY; FLOW RATE; HIGH TEMPERATURE; MORPHOLOGY; NEBULIZATION; PARTICLE SIZE; THERMODYNAMICS; VISCOSITY; X RAY DIFFRACTION;

EID: 84855910260     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.23024     Document Type: Article

References (56)

1. Kossik J. 2002. Think small: Pharmaceutical facility could boost capacity and slash costs by trading in certain batch operations for continuous versions. Pharmamag.com, article ID/DDAS-SEX 52B/. Accessed at: http://www.pharmamanufacturing.com, 2010.
2. Patricia A, Arnum V. 2008. Continuous processing: Moving with or against the manufacturing flow. Pharm Technol 9:52-58.
3. Valo H, Peltonen L, Vehvilainen S, Karjalainen M, Kostiainen R, Laaksonen T, Hirvonen J. 2009. Electrospray encapsulation of hydrophilic and hydrophobic drugs in poly(l-lactic acid) nanoparticles. Small 5(15):1791-1798.
4. Hogan CJ Jr, Yun KMa, Chen DR, Lenggoro W, Biswas P, Okuyama K. 2007. Controlled size polymer particle production via electrohydrodynamic atomization. Colloids Surf A Physicochem Eng Asp 311:67-76.
5. Cloupeau M, Foch BP. 1994. Electrohydrodynamic spraying functioning mode: A critical review. J Aerosol Sci 25(6):1021-1036.
6. Hartman RPA, Brunner DJ, Camelot DMA, Marijnissen JCM, Scarlett B. 2000. Jet break-up in electrohydrodynamic atomization in the cone-jet mode. J Aerosol Sci 3(1):65-95.
7. Wilhelm O, Madler L, Pratsinis SE. 2003. Electrosprayevaporation and deposition. Aerosol Sci 34:815-836.
8. Hong Y, Li Y, Yin Y, Li D, Zou G. 2008. Electrohydrodynamic atomization of quasi-monodisperse drug-loaded spherical/wrinkled microparticles. J Aerosol Sci 39:525-536.
9. Gomez A, Tangb K. 1994. Charge and fission of droplets in electrostatic sprays. Phys Fluids 6(1):404-414.
10. Gao L, Zhang D, Chen M. 2008. Drug nanocrystals for the formulation of poorly soluble drugs and its application as a potential drug delivery system. J Nanopart Res 10:845-862.
11. Jinno J, Kamada N, Miyake M, Yamada K, Mukai T, Odomi M, Toguchi H, Liversidge GG, Higaki K, Kimura T. 2006. Effect of particle size reduction on dissolution and oral absorption of a poorly water-soluble drug, cilostazol, in beagle dogs. J Control Release 111:56-64.
12. Merisko-Liversidge E, Liversidge GG, Cooper ER. 2003. Nanosizing: A formulation approach for poorly-water-soluble compounds. Eur J Pharm Sci 18:113-120.
13. Coppola D. 2003. Nanocrystal technology targets poorly water-soluble drugs. Pharm Technol 11:20.
14. Kawashima Y. 2001. Nanoparticulate systems for improved drug delivery. Adv Drug Deliv Rev 47:1-2.
15. Kim K, Lee IS, Centrone A, Hatton TA, Myerson AS. 2009. Formation of nanosized organic molecular crystals on engineered surfaces. J Am Chem Soc 131:18212-18213.
16. Lee AY, Lee IS, Dette SS, Boerner J, Myerson AS. 2005. Crystallization on confined engineered surfaces: A method to control crystal size and generate different polymorphs. J Am Chem Soc 127(43):14982-14983.
17. Brittain HG. 1999. Polymorphism in pharmaceutical solids. New York: Marcel Dekker.
18. Brittain HG. 2009. Polymorphism and solvatomorphism 2008. J Pharm Sci 8:1-22.
19. Shekunov BY, York P. 2000. Crystallization processes in pharmaceutical technology and drug delivery design. J Crystal Growth 211:122-136.
20. Rodríguez-Spong B, Price CP, Jayasankar A, Matzger AJ, Rodriguez-Hornedo N. 2003. General principles of pharmaceutical solid polymorphism: A supramolecular perspective. Adv Drug Deliv Rev 56:241-274.
21. Ha JM, Wolf JH, Hillmyer MA, Ward MD. 2004. Polymorph selectivity under nanoscopic confinement. J Am Chem Soc 126:3382-3383.
22. Beiner M, Rengarajan GT, Pankaj S, Enke D, Steinhart M. 2007. Manipulating the crystalline state of pharmaceuticals by nanoconfinement. Nano Lett 7(5):1381-1385.
23. Blagden N, Davey RJ. 2003. Polymorph selection: Challenges for the future? Crystal Growth Des 3(6):873-885.
24. Singhal D, Curatolo W. 2004. Drug polymorphism and dosage form design: A practical perspective. Adv Drug Deliv Rev 56:335-347.
25. Kelly RC, Rodriguez-Hornedo N. 2009. Solvent effects on the crystallization and preferential nucleation of carbamazepine anhydrous polymorphs: A molecular recognition perspective. Org Process Res Dev 13:1291-1300.
26. Grzesiak AL, Lang M, Kim K, Matzger AJ. Comparison of the four anhydrous polymorphs of carbamazepine and the crystal structure of form I. J Pharm Sci 92(11):2260-2271.
27. Yu JH, Fridrikh SV, Brenner MP, Rutledge GC. 2003. Controlling the fiber diameter during electrospinning. Phys Rev Lett 90(14):44502.
28. Sahoo NG, Kakran M, Shaal A, Li L, Muller RH, Pal M, Tan LP. 2011. Preparation and characterization of quercetinnanocrystals. J Pharm Sci 100(5):1-6.
29. Ganan-Calvo AM, Davila J, Barrero A. 1997. Current and droplet size in the electrospraying of liquids. Scaling laws. J Aerosol Sci 28(2):249-275.
30. Ganan-Calvo AM. 1997. Cone-jet analytical extension of Taylor's electrostatic solution and the asymptotic universal scaling laws in electrospraying. Phys Rev Lett 79(2):217-220.
31. Hartman RPA, Borra1 J-P, Brunner DJ, Marijnissen JCM, Scarlett B. 1999. The evolution of electrohydrodynamic sprays produced in the cone-jet mode, a physical model. J Electrostat 47:143-170.
32. Battacharjee PK, Scheider TM, Brenner MP, McKinley GH, Rutledge GC. 2010. On the measured current in electrospinning. J Appl Phys 107:044306.
33. Yao J, Lim K, Xie J, Hua J, Wang CH. 2008. Characterization of electrospraying process for polymeric particle fabrication. J Aerosol Sci 39:987-1002.
34. Almeria B, Deng W, Fahmy TM, Gomez A. 2010. Controlling the morphology of electrospray-generated PLGA microparticles for drug delivery. J Colloid Interface Sci 343:125-133.
35. Sloth J, Jorgensen K, Bach P, Jensen AD, Kiil S, Dam-Johansen K. 2009. Spray drying of suspensions for pharma and bio products: Drying kinetics and morphology. Ind Eng Chem Res 48:3657-3664.
36. Farid M. 2003. A new approach to modeling of single droplet drying. Chem Eng Sci 58:2985-2993.
37. Nesic S, Vodnik J. 1991. Kinetics of droplet evaporation. 46(2):527-537.
38. Vehring R, Ross WR, Lechuga-Ballesteros D. 2007. Particle formation in spray drying. Aerosol Sci 38:728-746.
39. Bird RB, Stewart WE, Lightfoot EN, 2001. Transport phenomena, chapter 17. 2nd ed. John Wiley & Sons, Inc.
40. Smith JN, Flagan RC, Beauchamp JL. 2002. Droplet evaporation and discharge dynamics in electrospray ionization. J Phys Chem A 106:9957-9967.
41. Charlesworth DH, Marshall WR. 1960. Evaporation from drops containing dissolved solids. AIChE J 6(1):9-23.
42. Wang L, Pai CL, Boyce MC, Rutledge GC. 2009. Wrinkled surface topographies of electrospun polymer fibers. Appl Phys Lett 94:151916.
43. Pai CL, Boyce MC, Rutledge GC. 2009. Morphology of porous and wrinkled fibers of polystyrene electrospun from dimethylformamide. 42:2102-2114.
44. Pauchard L, Allain C. 2003. Buckling instability induced by polymer solution drying. Eur Phys Lett 62(6):897-903.
45. Feng X, Bogan MJ, Agnes GR. 2001. Coulomb fission event resolved progeny droplet production from isolated evaporating methanol droplets. Anal Chem 73:4499-4507.
46. Konermann L. 2009. A simple model for the disintegration of highly charged solvent droplets during electrospray ionization. J Am Soc Mass Spectrom 20:496-506.
47. Nghiem LD, Schäfer AI, Elimelech M. 2005. Pharmaceutical retention mechanisms by nanofiltration membranes. Environ Sci Technol 39(19):7698-7705.
48. Knezic D, Zaccaro J, Myerson AS. 2004. Nucleation induction time in levitated droplets. J Phys Chem B 108(30):10672-10677.
49. Yu L. 2001. Amorphous pharmaceutical solids: Preparation, characterization and stabilization. Adv Drug Deliv Rev 48:27-42.
50. Erdemir D, Lee AY, Myerson AS. 2009. Nucleation of crystals from solution: Classical and two-step models. Acc Chem Res 42(5):621-629.
51. Park K, Evans JMB, Myerson AS. 2003. Determination of solubility of polymorphs using differential scanning calorimetry. Crystal Growth Des 3(6):991-995.
52. Mahalaxmi R, Ravikumar, Pandey S, Shirwaikar A, Shirwakikar A. 2009. Effect of recrystallization on size, shape, polymorph and dissolution of carbamazepine. Int J Pharm Tech Res 1(3):725-732.
53. Javadzadeh Y, Mohammadi A, Khoei NS, Nokhodchi A. 2009. Improvement of physicomechanical properties of carbamazepine by recrystallization at different pH values. Acta Pharm 59:187-197.
54. Nokhodchia A, Bolourtchianc N, Dinarvand R. 2005. Dissolution and mechanical behaviors of recrystallized carbamazepine from alcohol solution in the presence of additives. J Crystal Growth 274: 573-584.
55. Behme RJ, Brooke D. 1991. Heat of fusion measurement of a low melting polymorph of carbamazepine that undergoes multiple-phase changes during differential scanning calorimetry analysis. J Pharm Sci 80(10):986-990.
56. Mihranyan A, Stromme M. 2007. Solubility of fractal nanoparticles. Surface Sci 601:315-319.