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Received December 8, 2010
Accepted December 14, 2010
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Solid forms of pharmaceuticals: Polymorphs, salts and cocrystals
1Department of Chemical Engineering, Massachusetts Institute of Technology, USA 2Novartis-MIT Center for Continuous Manufacturing, 77 Massachusetts Avenue, Building 66, Cambridge, MA 02139, USA
Korean Journal of Chemical Engineering, February 2011, 28(2), 315-322(8), 10.1007/s11814-010-0520-0
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Abstract
Control and selection of the properties of active pharmaceutical ingredients is a crucial part of the drug development process. One major part of this process is the selection of an appropriate solid form. This review will discuss three major types of crystalline solids, polymorphs, salts and cocrystals and processes used to develop and find these forms.
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Yu L, Stephenson GA, Mitchell CA, Bunnell CA, Snorek SV, Bowyer JJ, Borchardt TB, Stowell JG, Byrn SR, J. Am. Chem. Soc., 122(4), 585 (2000)
Caira MR, Design of Organic Solids., 198, 163 (1998)
Bauer J, Spanton S, Henry R, Quick J, Dziki W, Porter W, Morris J, Pharm. Res., 18(6), 859 (2001)
Kempf DJ, Marsh KC, Denissen JF, Mcdonald E, Vasavanonda S, Flentge CA, Green BE, Fino L, Park CH, Kong XP, Wideburg NE, Saldivar A, Ruiz L, Kati WM, Sham HL, Robins T, Stewart KD, Hsu A, Plattner JJ, Leonard JM, Norbeck DW, P. Natl. Acad. Sci., USA., 92(7), 2484 (1995)
Law D, Krill SL, Schmitt EA, Fort JJ, Qiu YH, Wang WL, Porter WR, J. Pharm. Sci., 90(8), 1015 (2001)
Bernstein J, Polymorphism in molecular crystals, Clarendon, Oxford (2002)
Byrn SR, Solid state chemistry of drugs, Academic, New York (1999)
Ostwald WZ, Phys. Chem., 22, 289 (1897)
Aaltonen J, Alleso M, Mirza S, Koradia V, Gordon KC, Rantanen J, Eur. J. Pharm. Biopharm., 71(1), 23 (2009)
Morissette SL, Almarsson O, Peterson ML, Remenar JF, Read MJ, Lemmo AV, Ellis S, Cima MJ, Gardner CR, Adv.Drug. Deliv. Rev., 56(3), 275 (2004)
Mirza S, Miroshnyk I, Heinamaki J, Christiansen L, Karjalainen M, Yliruusi J, Aaps. Pharm. Sci., 5(2), 39 (2003)
Miroshnyk I, Khriachtchev L, Mirza S, Rantanen J, Heinamaki J, Yliruusi J, Cryst. Growth Des., 6(2), 369 (2006)
Hollingsworth MD, Peterson ML, Pate KL, Dinkelmeyer BD, Brown ME, J. Am. Chem. Soc., 124(10), 2094 (2002)
Childs SL, Chyall LJ, Dunlap JT, Coates DA, Stahly BC, Stahly GP, Cryst. Growth Des., 4(3), 441 (2004)
Garetz BA, Matic J, Myerson AS, Phys. Rev. Lett., 89(17), 175501 (2002)
Ruecroft G, Hipkiss D, Ly T, Maxted N, Cains PW, Org. Proc.Res. Dev., 9(6), 923 (2005)
Lang MD, Kampf JW, Matzger AJ, J. Pharm. Sci., 91(4), 1186 (2002)
Lee AY, Lee IS, Dettet SS, Boerner J, Myerson AS, J. Am. Chem. Soc., 127(43), 14982 (2005)
Lee IS, Lee AY, Myerson AS, Pharm. Res., 25(4), 960 (2008)
Singh A, Lee IS, Myerson AS, Cryst. Growth Des., 9(2), 1182 (2009)
Berge SM, Bighley LM, Monkhouse DC, J. Pharm. Sci., 66, 1 (1977)
Stahl PH, Wermuth G, G. (Eds): Handbook of Pharmaceutical Salts; Properties, Selection and Use (International Union of Pure and Applied Chemistry), New York, Wiley-VCH (2002)
Aakeroy CB, Fasulo ME, Desper J, Mol. Pharma., 4(3), 317 (2007)
Bastin RJ, Bowker MJ, Slater BJ, Org. Proc. Res. Dev., 4, 427 (2000)
Anderson BD, Flora KP, in ‘The Practice of Medicinal Chemistry', Ed. Wermuth CG, Academic Press Ltd. London, Chapter 34 (1996)
Kramer SF, Flynn GL, J. Pharm. Sci., 61, 1896 (1972)
Serajuddin ATM, Sheen PC, Mufson D, Bernstein DF, Augustine MA, J. Pharm. Sci., 75, 492 (1986)
Li S, Doyle P, Metz S, Royce AE, Serajuddin ATM, J. Pharma. Sci., 94(10), 2224 (2005)
Gross TD, Schaab K, Ouellette M, Zook S, Reddy JP, Shurtleff A, Sacaan AI, Alebic-Kolbah T, Bozigian H, Org. Proc. Res.Dev., 11, 365 (2007)
Dressman JB, Bass P, Ritschel WA, Friend DR, Rubinstein A, Ziv E, J. Pharm. Sci., 82, 857 (1993)
Redenti E, Szente L, Szejtli J, J. Pharm. Sci., 90(8), 979 (2001)
Russel TL, Berardi RR, Barnett JL, O’Sullivan TL, Wagner JG, Dressman JB, Pharm. Res., 11, 136 (1994)
Gould PL, Int. J. Pharm., 33, 201 (1986)
Sun CC, Grant DJ, AAPS, Pharm. Sci. Suppl., S-174, 1 (1999)
Gazda M, Dansereau RJ, Crail DJ, Sakkab DH, Virgin MM, Pharm. Sci., 1, S403 (1998)
Hammond RB, Hashim RS, Ma C, Roberts KJ, J. Pharm.Sci., 95(11), 2361 (2006)
Black SN, Collier EA, Davey RJ, Roberts RJ, J. Pharm.Sci., 96(5), 1053 (2007)
Madivada LR, Anumala RR, Gilla G, Alla S, Charagondla K, Kagga M, Bhattacharya A, Bandichhor R, Org. Proc. Res. Dev., 13, 1190 (2009)
Sallmann A, Bottmingen, R. Pfister and B. Switzerland, US3558690 (1971)
Bucci R, Magri AD, Magri AL, Fresenius, J. Anal. Chem., 362, 577 (1998)
Bradshaw J, Price BJ, Clitherow JW, GB1565966 (1980)
Durant GJ, Emmett JC, Ganellin CR, US3950333 (1976)
Yasufumi H, Isao Y, Yoshio I, Shinichi T, Noriki I, Yasuo I, Masaaki T, US4283408 (1981)
Almarsson O, Zaworotko MJ, Chem. Commun., 17, 1889 (2004)
Miroshnyk I, Mirza S, Sandler N, Expt. Opin. Drug Deliv., 6, 333 (2009)
Etter MC, J. Phys. Chem., 95, 4601 (1991)
Seaton CC, Chadwick K, Sadiq G, Guo K, Davey RJ, Cryst. Growth Des., 10, 726 (2010)
Morissettea SL, Almarsson O, Peterson ML, Remenar JF, Read MJ, Lemmo AV, Ellis S, Cima MJ, Gardner CR, Adv.Drug Deliv. Rev., 56, 275 (2004)
Trask AV, Jones W, Top. Curr. Chem., 35, 3523 (2005)
Chadwick K, Davey R, Sadiq G, Cross W, Pritchard R, Cryst. Eng. Comm., 11, 412 (2009)
Nehm SJ, Rodriguez-Spong B, Rodriguez-Hornedo N, Cryst. Growth Des., 6, 592 (2006)
Remenar JF, Peterson ML, Stephens PW, Zhang Z, Zimenkov Y, Hickey MB, Mol. Pharma., 4(3), 386 (2007)
Trask AV, Motherwell WDS, Jones W, Cryst. Growth Des., 5(3), 1013 (2005)
Vishweshwar P, McMahon JA, Bis JA, Zaworotko MJ, J. Pharm. Sci., 95, 499 (2006)
Childs SL, Chyall LJ, Dunlap JT, Smolenskaya VN, Stahly BC, Stahly GP, J. Am. Chem. Soc., 126(41), 13335 (2004)
Bak A, Gore A, Yanez E, Stanton M, Tufekcic S, Syed R, Akrami A, Rose M, Surapaneni S, Bostick T, King A, Neervannan S, Ostovic D, Koparkar K, J. Pharm. Sci., 97(9), 3942 (2008)
Remenar JF, Morissette SL, Peterson ML, Moulton B, MacPhee JM, Guzman HR, Almarsson O, J. Am. Chem. Soc., 125(28), 8456 (2003)
Galcera J, Molins E, Cryst. Growth Des., 9(1), 327 (2009)
Shan N, Zaworotko MJ, Drug Discov. Today., 13(9-10), 440 (2008)
Schultheiss N, Newmanwill A, Cryst. Growth Des., 9(6), 2950 (2009)
