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Art of Synthesis of Desired Polymorphs: A Review
Corresponding Author(s) : Nitin Tandon
Asian Journal of Chemistry,
Vol. 30 No. 1 (2018): Vol 30 Issue 1
Abstract
Polymorphism plays an important role in drug solubility and availability. The study of the polymorphism of active pharmaceutical ingredients has become crucial for the synthesis of active pharmaceutical ingredients. This review provides observations, synthetic methods and characterization techniques for polymorphs using the latest analytical techniques. The desired polymorph can be obtained by choosing the proper nucleation mechanism.
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- A.C. Zettlemoyer and M. Dekker, Nucleation, Marcel Dekker, New York (1969).
- N. Rodriguez-Hornedo and D. Murphy, J. Pharm. Sci., 88, 651 (1998); https://doi.org/10.1021/js980490h.
- J.W. Mullin, Crystallization, Butterworth-Hienemann, Oxford (1992).
- A. Myerson, Handbook of Industrial Crystallization, ButterworthHeinemann, Boston (2002).
- L.J. Chyall, J.M. Tower, D.A. Coates, T.L. Houston and S.L. Childs, Cryst. Growth Des., 2, 505 (2002); https://doi.org/10.1021/cg0200311.
- L.S. Taylor and G. Zografi, Pharm. Res., 14, 1691 (1997); https://doi.org/10.1023/A:1012167410376.
- M.D. Ward, Chem. Rev., 101, 1697 (2001); https://doi.org/10.1021/cr000020j.
- M. Lang, A.L. Grzesiak and A.J. Matzger, J. Am. Chem. Soc., 124, 14834 (2002); https://doi.org/10.1021/ja0286526.
- N. Rodríguez-Hornedo and D. Murphy, J. Pharm. Sci., 93, 449 (2004); https://doi.org/10.1002/jps.10496.
- D. Murphy, F. Rodriguez-Cintron, B. Langevin, R.C. Kelly and N. Rodriguez-Hornedo, Int. J. Pharm., 246, 121 (2002); https://doi.org/10.1016/S0378-5173(02)00358-7.
- N. Rodríguez-Hornedo, D. Lechuga-Ballesteros and H.-J. Wu, Int. J. Pharm., 85, 149 (1992); https://doi.org/10.1016/0378-5173(92)90144-Q.
- B. Rodriguez-Spong, C.P. Price, A. Jayasankar, A.J. Matzger and N. Rodriguez-Hornedo, Adv. Drug Deliv. Rev., 56, 241 (2004); https://doi.org/10.1016/j.addr.2003.10.005.
- Y. Suzuki, Bull. Chem. Soc. Jpn., 47, 2549 (1974); https://doi.org/10.1246/bcsj.47.2549.
- R.J. Behme, T.T. Kensler and D.G. Mikolasek, Process for Buspirone Hydrochloride Polymorphic Crystalline form Conversion, US Patent 4810789 (1989).
- F. Kaneko, H. Sakashita, M. Kobayashi and M. Suzuki, J. Phys. Chem., 98, 3801 (1994); https://doi.org/10.1021/j100065a041.
- N. Garti, E. Wellner and S. Sarig, Kristall Tech., 15, 1303 (1980); https://doi.org/10.1002/crat.19800151112.
- M.C. Martínez-Ohárriz, C. Martín, M.M. Goñi, C. Rodríguez-Espinosa, M.C. Tros De Ilarduya-Apaolaza and M. Sánchez, J. Pharm. Sci., 83, 174 (1994); https://doi.org/10.1002/jps.2600830212.
- L.-S. Wu, G. Torosian, K. Sigvardson, C. Gerard and M.A. Hussain, J. Pharm. Sci., 83, 1404 (1994); https://doi.org/10.1002/jps.2600831008.
- M. Kitamura, H. Furukawa and M. Asaeda,J. Cryst. Growth, 141, 193 (1994); https://doi.org/10.1016/0022-0248(94)90112-0.
- L.C. Chang, M.R. Caira and J.K. Guillory, J. Pharm. Sci., 84, 1169 (1995); https://doi.org/10.1002/jps.2600841007.
- J. Caplette, T. Frigo, M. Jozwiakowski, H. Shea, M. Mirmehrabi and P. Müller, Int. J. Pharam., 527, 42 (2017); https://doi.org/10.1016/j.ijpharm.2017.05.031.
- Y. Kumar, R.K. Thaper and S.M. Dileep Kumar, Process for the Production of Amorphous Atorvastatin Calcium, US Patent 6528660 (2003).
- C.A. Briggs, K. Harasawa, S. Ichikawa, R.A. Jennings, K. Minohara, S. Nakagawa and R.A. Wade, Crystalline Forms of [R-(R*,R*)]-2-(4-fluorophenyl)-β,δ-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrole-1-heptanoic acid hemi calcium salt (Atorvastatin), EP0848705 (2001).
- M. Otsuka, M. Onoe and Y. Matsuda, Drug Dev. Ind. Pharm., 20, 1453 (1994); https://doi.org/10.3109/03639049409038382.
- N. Kaneniwa, M. Otsuka and T. Hayashi, Chem. Pharm. Bull. (Tokyo), 33, 3447 (1985); https://doi.org/10.1248/cpb.33.3447.
- A. Saleki-Gerhardt, J.G. Stoweell, S.R. Byrn and G. Zografi, J. Pharm. Sci., 84, 318 (1995); https://doi.org/10.1002/jps.2600840311.
- Y. Fukumori, T. Fukuda, Y. Yamamoto, Y. Shigitani, Y. Hanyu, Y. Takeuchi and N. Sato, Chem. Pharm. Bull. (Tokyo), 31, 4029 (1983); https://doi.org/10.1248/cpb.31.4029.
- Y. Kawashima, T. Niwa, H. Takeuchi, T. Hino, Y. Itoh and S. Furuyama, J. Pharm. Sci., 80, 472 (1991); https://doi.org/10.1002/jps.2600800515.
- H.G. Brittain, K.R. Morris, D.E. Bugay, A.B. Thakur and A.T. Serajuddin, J. Pharm. Biomed. Anal., 11, 1063 (1993); https://doi.org/10.1016/0731-7085(93)80083-D.
- M. Otsuka, K. Otsuka and N. Kaneniwa, Drug Dev. Ind. Pharm., 20, 1649 (1994); https://doi.org/10.3109/03639049409050205.
- J. Pirttimäki, E. Laine, J. Ketolainen and P. Paronen, Int. J. Pharm., 95, 93 (1993); https://doi.org/10.1016/0378-5173(93)90394-U.
- N. Chieng, T. Rades and D. Saville, Eur. J. Pharm. Biopharm., 68, 771 (2008); https://doi.org/10.1016/j.ejpb.2007.09.001.
- S.P. Duddu and K. Weller, J. Pharm. Sci., 85, 345 (1996); https://doi.org/10.1021/js950376o.
- O. Funk, L. Schwabe and K.-H. Froemming, Pharmazie, 48, 745 (1993).
- G. Bettinetti, A. Gazzaniga, P. Mura, F. Giordano and M. Setti, Drug Dev. Ind. Pharm., 18, 39 (1992); https://doi.org/10.3109/03639049209043682.
- S.Y. Tsai, S.C. Kuo and S.Y. Lin, J. Pharm. Sci., 82, 1250 (1993); https://doi.org/10.1002/jps.2600821213.
- J. Fokkens, J. Van Amelsfoort, C. De Blaey, C. De Kruif and J. Wilting, Int. J. Pharm., 14, 79 (1983); https://doi.org/10.1016/0378-5173(83)90116-3.
- M. Sakiyama and A. Imamura, Thermochim. Acta, 142, 365 (1989); https://doi.org/10.1016/0040-6031(89)85032-4.
- M. Yoshioka, B.C. Hancock and G. Zografi, J. Pharm. Sci., 83, 1700 (1994); https://doi.org/10.1002/jps.2600831211.
- J. Gómez-Morales, Á. Hernández-Hernández, G. Sazaki and J.M. García-Ruiz, Cryst. Growth Des., 10, 963 (2010); https://doi.org/10.1021/cg901279t.
- A.S. Rankell, H.A. Liebermann and R.F. Schiffman, in: H. Lieberman and L. Lachman (Eds.), The Theory and Practice of Industrial Pharmacy, Lea & Feabiger, Philadelphia, pp. 47 (1986).
- L.-E. Briggner, G. Buckton, K. Bystrom and P. Darcy, Int. J. Pharm., 105, 125 (1994); https://doi.org/10.1016/0378-5173(94)90458-8.
- N.E. Digoxin, B. Dolle and J.M. Bafort, Pharm. Ind., 44, 630 (1982).
- T. Sato, M. Ishiwata and S. Nemoto, Yakuzaigaku, 49, 93 (1989).
- M.J. Pikal, A.L. Lukes, J.E. Lang and K. Gaines, J. Pharm. Sci., 67, 767 (1978); https://doi.org/10.1002/jps.2600670609.
- Y. Matsuda, M. Otsuka, M. Onoe and E. Tatsumi, J. Pharm. Pharmacol., 44, 627 (1992); https://doi.org/10.1111/j.2042-7158.1992.tb05483.x.
- W.C. Stagner and J.K. Guillory, J. Pharm. Sci., 68, 1005 (1979); https://doi.org/10.1002/jps.2600680823.
- B.H. Kim and J.K. Kim, Arch. Pharm. Res., 7, 47 (1984); https://doi.org/10.1007/BF02856921.
- M.L. Peterson, S.L. Morissette, C. McNulty, A. Goldsweig, P. Shaw, M. LeQuesne, J. Monagle, N. Encina, J. Marchionna,A. Johnson, J. GonzalezZugasti, A.V. Lemmo, S.J. Ellis, M.J. Cima and Ö. Almarsson, J. Am. Chem. Soc., 124, 10958 (2002); https://doi.org/10.1021/ja020751w.
- J.H. Perepezko, Mater. Sci. Eng. A, 178, 105 (1994); https://doi.org/10.1016/0921-5093(94)90527-4.
- B.A. Garetz, J.E. Aber, N.L. Goddard, R.G. Young and A.S. Myerson, Phys. Rev. Lett., 77, 3475 (1996); https://doi.org/10.1103/PhysRevLett.77.3475.
- M.D. Lang, J.W. Kampf and A.J. Matzger, J. Pharm. Sci., 91, 1186 (2002); https://doi.org/10.1002/jps.10093.
- A.L. Grzesiak, M. Lang, K. Kim and A.J. Matzger, J. Pharm. Sci., 92, 2260 (2003); https://doi.org/10.1002/jps.10455.
- S. Aitipamula, R. Banerjee, A.K. Bansal, K. Biradha, M.L. Cheney, A.R. Choudhury, G.R. Desiraju, A.G. Dikundwar, R. Dubey, N. Duggirala, P.P. Ghogale, S. Ghosh, P.K. Goswami, N.R. Goud, R.R.K.R. Jetti, P. Karpinski, P. Kaushik, D. Kumar, V. Kumar, B. Moulton,A. Mukherjee, G. Mukherjee, A.S. Myerson, V. Puri, A. Ramanan, T. Rajamannar, C.M. Reddy, N. Rodriguez-Hornedo, R.D. Rogers, T.N.G. Row, P. Sanphui, N. Shan, G. Shete, A. Singh, C.C. Sun, J.A. Swift, R. Thaimattam, T.S. Thakur, R. Kumar Thaper, S.P. Thomas, S. Tothadi, V.R. Vangala, N. Variankaval, P. Vishweshwar, D.R. Weyna and M.J. Zaworotko, Cryst. Growth Des., 12, 2147 (2012); https://doi.org/10.1021/cg3002948.
- J.S. Evans, Minerals, 7, 62 (2017); https://doi.org/10.3390/min7040062.
- P.J. Haines and F.W. Wilburn, in:Thermal Analysis and Differential Scanning Calorimetry, Blackie Academic and Professional, New York, USA, pp. 63–89 (1995).
- L. Yu, S.M. Reutzel and G.A. Stephenson, Pharm. Sci. Technol. Today, 1, 118 (1998); https://doi.org/10.1016/S1461-5347(98)00031-5.
- E.V. Boldyreva, V.A. Drebushchak, I.E. Paukov, Y.A. Kovalevskaya and T.N. Drebushchak, J. Therm. Anal. Calorim., 77, 607 (2004); https://doi.org/10.1023/B:JTAN.0000038998.47606.27.
- P. Láng, E. Várkonyi, J. Ulrich, P. Szabó-Révésza and Z. Aigner, Analysis, 102, 229 (2015).
- M.L.P. Leitãomlleitao@ci.uc.pt, J. Canotilho, M.S.C. Cruz, J.C. Pereira, A.T. Sousa and J.S. Redinha, J. Therm. Anal. Calorim., 68, 397 (2002); https://doi.org/10.1023/A:1016023315613.
- P.J. Haines and F.W. Wilburn, in:Thermal Methods of Analysis Principles, Blackie Academic and Professional, New York, pp. 95 (1995).
- K.R. Morris, A.W. Newman, D.E. Bugay, S.A. Ranadive, A.K. Singh, M. Szyper, S.A. Varia, H.G. Brittain and A.T.M. Serajuddin,Int. J. Pharm., 108, 195 (1994); https://doi.org/10.1016/0378-5173(94)90128-7.
- P. Vishweshwar, J.A. McMahon, M. Oliveira, M.L. Peterson and M.J. Zaworotko, J. Am. Chem. Soc., 127, 16802 (2005); https://doi.org/10.1021/ja056455b.
- T.L. Threlfall, Analyst, 120, 2435 (1995); https://doi.org/10.1039/an9952002435.
- K. Matsuo and M. Matsuoka, Cryst. Growth Des., 7, 411 (2007); https://doi.org/10.1021/cg060299i.
- P. Láng, V. Kiss, R. Ambrus, G. Farkas, P. Szabó-Révész, Z. Aigner and E. Várkonyi, J. Pharm. Biomed. Anal., 84, 177 (2013); https://doi.org/10.1016/j.jpba.2013.06.002.
- G. Salvetti, E. Tognoni, E. Tombari and G. Johari, Thermochim. Acta, 285, 243 (1996); https://doi.org/10.1016/0040-6031(96)02915-2.
- A. Grunenberg and P. Bosche, Crystal Modification of CDCH a Process for its Preparation and Pharmaceutical Formulations Comprising this Modification, US Patent 5849752 (1998).
- T.G. Rochow and E.G. Rochow, An Introduction to Microscopy by Means of Light, Electrons, X-rays or Ultrasound, Plenum Press, New York (1978).
- A.S. Borisov, P. Hazendonk and P.G. Hayes, J. Inorg. Organomet. Polym. Mater., 20, 183 (2010); https://doi.org/10.1007/s10904-010-9358-5.
- J.R. Smith, W. Xu and D. Raftery, J. Phys. Chem. B, 110, 7766 (2006); https://doi.org/10.1021/jp056195k.
- J.W. Lubach and E.J. Munson, ed: W.R. Hilfiker, Polymorphism in the Pharmaceutical Industry, Wiley, Weinheim, pp. 81-93 (2006).
- T.J. Offerdahl, Pharm. Tech., 30, 24 (2006).
- L.R. Chen, B.E. Padden, S.R. Vippagunta, E.J. Munson and D.J. Grant, Pharm. Res., 17, 619 (2000); https://doi.org/10.1023/A:1007533419711.
- M. Szelagiewicz, C. Marcolli, S. Cianferani,A. Hard, A. Vit,A. Burkhard, M. Von Raumer, U. Hofmeier, A. Zilian, E. Francotte and R. Schenker, J. Therm. Anal. Calorim., 57, 23 (1999); https://doi.org/10.1023/A:1010184805966.
- S.R. Byrn, G. Gray, R.R. Pfeiffer and J. Frye, J. Pharm. Sci., 74, 565 (1985); https://doi.org/10.1002/jps.2600740516.
- D.A. Skoog, F.J. Holler and T.A. Nieman, Principles of Instrumental Analysis, Thomson Learnin, Mississippi (2001).
- F. Rouessac and A. Rouessac, in:Infrared Apectroscopy, John Wiley & Sons, London, pp. 170-173 (2001).
- B.R. Jasti, J. Du and R.C. Vasavada, Int. J. Pharm., 118, 161 (1995); https://doi.org/10.1016/0378-5173(94)00325-Y.
- T. Uchida, E. Yonemochi, T. Oguchi, K. Terada, K. Yamamoto and Y. Nakai, Chem. Pharm. Bull. (Tokyo), 41, 1632 (1993); https://doi.org/10.1248/cpb.41.1632.
- M.M. Lowes, M.R. Caira, A.P. Lotter and J.G. Van der Watt, J. Pharm. Sci., 76, 744 (1987); https://doi.org/10.1002/jps.2600760914.
- T.J. Cholerton, J.H. Hunt, G. Klinkert and M. Martin-Smith, J. Chem. Soc., Perkin Trans. 2, 1961 (1984); https://doi.org/10.1039/P29840001761.
- A. Kiss and J. Répási, Analyst, 118, 661 (1993); https://doi.org/10.1039/AN9931800661.
- S. Botha and D. Flanagan, Int. J. Pharm., 82, 195 (1992); https://doi.org/10.1016/0378-5173(92)90175-2.
- H.G. Brittain, D.E. Bugay, S.J. Bogdanowich and J. Devincentis, Drug Dev. Ind. Pharm., 14, 2029 (1988); https://doi.org/10.3109/03639048809152001.
- K. Sasaki, H. Suzuki and H. Nakagawa, Chem. Pharm. Bull. (Tokyo), 41, 325 (1993); https://doi.org/10.1248/cpb.41.325.
- J.G. Graselli, M.K. Snavely and B.J. Bulkin, Chemical Applications of Raman Spectroscopy, John Wiley, New York (1981).
- X.J. Gu and W. Jiang, J. Pharm. Sci., 84, 1438 (1995); https://doi.org/10.1002/jps.2600841210.
- A.R. Pallipurath, F. Civati, J. Sibik, C. Crowley, J.A. Zeitler, P. McArdle and A. Erxleben, Int. J. Pharm., 528, 312 (2017); https://doi.org/10.1016/j.ijpharm.2017.06.020.
- K. Higashi, K. Ueda and K. Moribe, Adv. Drug Deliv. Rev., 117, 71 (2016); https://doi.org/10.1016/j.addr.2016.12.001.
References
A.C. Zettlemoyer and M. Dekker, Nucleation, Marcel Dekker, New York (1969).
N. Rodriguez-Hornedo and D. Murphy, J. Pharm. Sci., 88, 651 (1998); https://doi.org/10.1021/js980490h.
J.W. Mullin, Crystallization, Butterworth-Hienemann, Oxford (1992).
A. Myerson, Handbook of Industrial Crystallization, ButterworthHeinemann, Boston (2002).
L.J. Chyall, J.M. Tower, D.A. Coates, T.L. Houston and S.L. Childs, Cryst. Growth Des., 2, 505 (2002); https://doi.org/10.1021/cg0200311.
L.S. Taylor and G. Zografi, Pharm. Res., 14, 1691 (1997); https://doi.org/10.1023/A:1012167410376.
M.D. Ward, Chem. Rev., 101, 1697 (2001); https://doi.org/10.1021/cr000020j.
M. Lang, A.L. Grzesiak and A.J. Matzger, J. Am. Chem. Soc., 124, 14834 (2002); https://doi.org/10.1021/ja0286526.
N. Rodríguez-Hornedo and D. Murphy, J. Pharm. Sci., 93, 449 (2004); https://doi.org/10.1002/jps.10496.
D. Murphy, F. Rodriguez-Cintron, B. Langevin, R.C. Kelly and N. Rodriguez-Hornedo, Int. J. Pharm., 246, 121 (2002); https://doi.org/10.1016/S0378-5173(02)00358-7.
N. Rodríguez-Hornedo, D. Lechuga-Ballesteros and H.-J. Wu, Int. J. Pharm., 85, 149 (1992); https://doi.org/10.1016/0378-5173(92)90144-Q.
B. Rodriguez-Spong, C.P. Price, A. Jayasankar, A.J. Matzger and N. Rodriguez-Hornedo, Adv. Drug Deliv. Rev., 56, 241 (2004); https://doi.org/10.1016/j.addr.2003.10.005.
Y. Suzuki, Bull. Chem. Soc. Jpn., 47, 2549 (1974); https://doi.org/10.1246/bcsj.47.2549.
R.J. Behme, T.T. Kensler and D.G. Mikolasek, Process for Buspirone Hydrochloride Polymorphic Crystalline form Conversion, US Patent 4810789 (1989).
F. Kaneko, H. Sakashita, M. Kobayashi and M. Suzuki, J. Phys. Chem., 98, 3801 (1994); https://doi.org/10.1021/j100065a041.
N. Garti, E. Wellner and S. Sarig, Kristall Tech., 15, 1303 (1980); https://doi.org/10.1002/crat.19800151112.
M.C. Martínez-Ohárriz, C. Martín, M.M. Goñi, C. Rodríguez-Espinosa, M.C. Tros De Ilarduya-Apaolaza and M. Sánchez, J. Pharm. Sci., 83, 174 (1994); https://doi.org/10.1002/jps.2600830212.
L.-S. Wu, G. Torosian, K. Sigvardson, C. Gerard and M.A. Hussain, J. Pharm. Sci., 83, 1404 (1994); https://doi.org/10.1002/jps.2600831008.
M. Kitamura, H. Furukawa and M. Asaeda,J. Cryst. Growth, 141, 193 (1994); https://doi.org/10.1016/0022-0248(94)90112-0.
L.C. Chang, M.R. Caira and J.K. Guillory, J. Pharm. Sci., 84, 1169 (1995); https://doi.org/10.1002/jps.2600841007.
J. Caplette, T. Frigo, M. Jozwiakowski, H. Shea, M. Mirmehrabi and P. Müller, Int. J. Pharam., 527, 42 (2017); https://doi.org/10.1016/j.ijpharm.2017.05.031.
Y. Kumar, R.K. Thaper and S.M. Dileep Kumar, Process for the Production of Amorphous Atorvastatin Calcium, US Patent 6528660 (2003).
C.A. Briggs, K. Harasawa, S. Ichikawa, R.A. Jennings, K. Minohara, S. Nakagawa and R.A. Wade, Crystalline Forms of [R-(R*,R*)]-2-(4-fluorophenyl)-β,δ-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrole-1-heptanoic acid hemi calcium salt (Atorvastatin), EP0848705 (2001).
M. Otsuka, M. Onoe and Y. Matsuda, Drug Dev. Ind. Pharm., 20, 1453 (1994); https://doi.org/10.3109/03639049409038382.
N. Kaneniwa, M. Otsuka and T. Hayashi, Chem. Pharm. Bull. (Tokyo), 33, 3447 (1985); https://doi.org/10.1248/cpb.33.3447.
A. Saleki-Gerhardt, J.G. Stoweell, S.R. Byrn and G. Zografi, J. Pharm. Sci., 84, 318 (1995); https://doi.org/10.1002/jps.2600840311.
Y. Fukumori, T. Fukuda, Y. Yamamoto, Y. Shigitani, Y. Hanyu, Y. Takeuchi and N. Sato, Chem. Pharm. Bull. (Tokyo), 31, 4029 (1983); https://doi.org/10.1248/cpb.31.4029.
Y. Kawashima, T. Niwa, H. Takeuchi, T. Hino, Y. Itoh and S. Furuyama, J. Pharm. Sci., 80, 472 (1991); https://doi.org/10.1002/jps.2600800515.
H.G. Brittain, K.R. Morris, D.E. Bugay, A.B. Thakur and A.T. Serajuddin, J. Pharm. Biomed. Anal., 11, 1063 (1993); https://doi.org/10.1016/0731-7085(93)80083-D.
M. Otsuka, K. Otsuka and N. Kaneniwa, Drug Dev. Ind. Pharm., 20, 1649 (1994); https://doi.org/10.3109/03639049409050205.
J. Pirttimäki, E. Laine, J. Ketolainen and P. Paronen, Int. J. Pharm., 95, 93 (1993); https://doi.org/10.1016/0378-5173(93)90394-U.
N. Chieng, T. Rades and D. Saville, Eur. J. Pharm. Biopharm., 68, 771 (2008); https://doi.org/10.1016/j.ejpb.2007.09.001.
S.P. Duddu and K. Weller, J. Pharm. Sci., 85, 345 (1996); https://doi.org/10.1021/js950376o.
O. Funk, L. Schwabe and K.-H. Froemming, Pharmazie, 48, 745 (1993).
G. Bettinetti, A. Gazzaniga, P. Mura, F. Giordano and M. Setti, Drug Dev. Ind. Pharm., 18, 39 (1992); https://doi.org/10.3109/03639049209043682.
S.Y. Tsai, S.C. Kuo and S.Y. Lin, J. Pharm. Sci., 82, 1250 (1993); https://doi.org/10.1002/jps.2600821213.
J. Fokkens, J. Van Amelsfoort, C. De Blaey, C. De Kruif and J. Wilting, Int. J. Pharm., 14, 79 (1983); https://doi.org/10.1016/0378-5173(83)90116-3.
M. Sakiyama and A. Imamura, Thermochim. Acta, 142, 365 (1989); https://doi.org/10.1016/0040-6031(89)85032-4.
M. Yoshioka, B.C. Hancock and G. Zografi, J. Pharm. Sci., 83, 1700 (1994); https://doi.org/10.1002/jps.2600831211.
J. Gómez-Morales, Á. Hernández-Hernández, G. Sazaki and J.M. García-Ruiz, Cryst. Growth Des., 10, 963 (2010); https://doi.org/10.1021/cg901279t.
A.S. Rankell, H.A. Liebermann and R.F. Schiffman, in: H. Lieberman and L. Lachman (Eds.), The Theory and Practice of Industrial Pharmacy, Lea & Feabiger, Philadelphia, pp. 47 (1986).
L.-E. Briggner, G. Buckton, K. Bystrom and P. Darcy, Int. J. Pharm., 105, 125 (1994); https://doi.org/10.1016/0378-5173(94)90458-8.
N.E. Digoxin, B. Dolle and J.M. Bafort, Pharm. Ind., 44, 630 (1982).
T. Sato, M. Ishiwata and S. Nemoto, Yakuzaigaku, 49, 93 (1989).
M.J. Pikal, A.L. Lukes, J.E. Lang and K. Gaines, J. Pharm. Sci., 67, 767 (1978); https://doi.org/10.1002/jps.2600670609.
Y. Matsuda, M. Otsuka, M. Onoe and E. Tatsumi, J. Pharm. Pharmacol., 44, 627 (1992); https://doi.org/10.1111/j.2042-7158.1992.tb05483.x.
W.C. Stagner and J.K. Guillory, J. Pharm. Sci., 68, 1005 (1979); https://doi.org/10.1002/jps.2600680823.
B.H. Kim and J.K. Kim, Arch. Pharm. Res., 7, 47 (1984); https://doi.org/10.1007/BF02856921.
M.L. Peterson, S.L. Morissette, C. McNulty, A. Goldsweig, P. Shaw, M. LeQuesne, J. Monagle, N. Encina, J. Marchionna,A. Johnson, J. GonzalezZugasti, A.V. Lemmo, S.J. Ellis, M.J. Cima and Ö. Almarsson, J. Am. Chem. Soc., 124, 10958 (2002); https://doi.org/10.1021/ja020751w.
J.H. Perepezko, Mater. Sci. Eng. A, 178, 105 (1994); https://doi.org/10.1016/0921-5093(94)90527-4.
B.A. Garetz, J.E. Aber, N.L. Goddard, R.G. Young and A.S. Myerson, Phys. Rev. Lett., 77, 3475 (1996); https://doi.org/10.1103/PhysRevLett.77.3475.
M.D. Lang, J.W. Kampf and A.J. Matzger, J. Pharm. Sci., 91, 1186 (2002); https://doi.org/10.1002/jps.10093.
A.L. Grzesiak, M. Lang, K. Kim and A.J. Matzger, J. Pharm. Sci., 92, 2260 (2003); https://doi.org/10.1002/jps.10455.
S. Aitipamula, R. Banerjee, A.K. Bansal, K. Biradha, M.L. Cheney, A.R. Choudhury, G.R. Desiraju, A.G. Dikundwar, R. Dubey, N. Duggirala, P.P. Ghogale, S. Ghosh, P.K. Goswami, N.R. Goud, R.R.K.R. Jetti, P. Karpinski, P. Kaushik, D. Kumar, V. Kumar, B. Moulton,A. Mukherjee, G. Mukherjee, A.S. Myerson, V. Puri, A. Ramanan, T. Rajamannar, C.M. Reddy, N. Rodriguez-Hornedo, R.D. Rogers, T.N.G. Row, P. Sanphui, N. Shan, G. Shete, A. Singh, C.C. Sun, J.A. Swift, R. Thaimattam, T.S. Thakur, R. Kumar Thaper, S.P. Thomas, S. Tothadi, V.R. Vangala, N. Variankaval, P. Vishweshwar, D.R. Weyna and M.J. Zaworotko, Cryst. Growth Des., 12, 2147 (2012); https://doi.org/10.1021/cg3002948.
J.S. Evans, Minerals, 7, 62 (2017); https://doi.org/10.3390/min7040062.
P.J. Haines and F.W. Wilburn, in:Thermal Analysis and Differential Scanning Calorimetry, Blackie Academic and Professional, New York, USA, pp. 63–89 (1995).
L. Yu, S.M. Reutzel and G.A. Stephenson, Pharm. Sci. Technol. Today, 1, 118 (1998); https://doi.org/10.1016/S1461-5347(98)00031-5.
E.V. Boldyreva, V.A. Drebushchak, I.E. Paukov, Y.A. Kovalevskaya and T.N. Drebushchak, J. Therm. Anal. Calorim., 77, 607 (2004); https://doi.org/10.1023/B:JTAN.0000038998.47606.27.
P. Láng, E. Várkonyi, J. Ulrich, P. Szabó-Révésza and Z. Aigner, Analysis, 102, 229 (2015).
M.L.P. Leitãomlleitao@ci.uc.pt, J. Canotilho, M.S.C. Cruz, J.C. Pereira, A.T. Sousa and J.S. Redinha, J. Therm. Anal. Calorim., 68, 397 (2002); https://doi.org/10.1023/A:1016023315613.
P.J. Haines and F.W. Wilburn, in:Thermal Methods of Analysis Principles, Blackie Academic and Professional, New York, pp. 95 (1995).
K.R. Morris, A.W. Newman, D.E. Bugay, S.A. Ranadive, A.K. Singh, M. Szyper, S.A. Varia, H.G. Brittain and A.T.M. Serajuddin,Int. J. Pharm., 108, 195 (1994); https://doi.org/10.1016/0378-5173(94)90128-7.
P. Vishweshwar, J.A. McMahon, M. Oliveira, M.L. Peterson and M.J. Zaworotko, J. Am. Chem. Soc., 127, 16802 (2005); https://doi.org/10.1021/ja056455b.
T.L. Threlfall, Analyst, 120, 2435 (1995); https://doi.org/10.1039/an9952002435.
K. Matsuo and M. Matsuoka, Cryst. Growth Des., 7, 411 (2007); https://doi.org/10.1021/cg060299i.
P. Láng, V. Kiss, R. Ambrus, G. Farkas, P. Szabó-Révész, Z. Aigner and E. Várkonyi, J. Pharm. Biomed. Anal., 84, 177 (2013); https://doi.org/10.1016/j.jpba.2013.06.002.
G. Salvetti, E. Tognoni, E. Tombari and G. Johari, Thermochim. Acta, 285, 243 (1996); https://doi.org/10.1016/0040-6031(96)02915-2.
A. Grunenberg and P. Bosche, Crystal Modification of CDCH a Process for its Preparation and Pharmaceutical Formulations Comprising this Modification, US Patent 5849752 (1998).
T.G. Rochow and E.G. Rochow, An Introduction to Microscopy by Means of Light, Electrons, X-rays or Ultrasound, Plenum Press, New York (1978).
A.S. Borisov, P. Hazendonk and P.G. Hayes, J. Inorg. Organomet. Polym. Mater., 20, 183 (2010); https://doi.org/10.1007/s10904-010-9358-5.
J.R. Smith, W. Xu and D. Raftery, J. Phys. Chem. B, 110, 7766 (2006); https://doi.org/10.1021/jp056195k.
J.W. Lubach and E.J. Munson, ed: W.R. Hilfiker, Polymorphism in the Pharmaceutical Industry, Wiley, Weinheim, pp. 81-93 (2006).
T.J. Offerdahl, Pharm. Tech., 30, 24 (2006).
L.R. Chen, B.E. Padden, S.R. Vippagunta, E.J. Munson and D.J. Grant, Pharm. Res., 17, 619 (2000); https://doi.org/10.1023/A:1007533419711.
M. Szelagiewicz, C. Marcolli, S. Cianferani,A. Hard, A. Vit,A. Burkhard, M. Von Raumer, U. Hofmeier, A. Zilian, E. Francotte and R. Schenker, J. Therm. Anal. Calorim., 57, 23 (1999); https://doi.org/10.1023/A:1010184805966.
S.R. Byrn, G. Gray, R.R. Pfeiffer and J. Frye, J. Pharm. Sci., 74, 565 (1985); https://doi.org/10.1002/jps.2600740516.
D.A. Skoog, F.J. Holler and T.A. Nieman, Principles of Instrumental Analysis, Thomson Learnin, Mississippi (2001).
F. Rouessac and A. Rouessac, in:Infrared Apectroscopy, John Wiley & Sons, London, pp. 170-173 (2001).
B.R. Jasti, J. Du and R.C. Vasavada, Int. J. Pharm., 118, 161 (1995); https://doi.org/10.1016/0378-5173(94)00325-Y.
T. Uchida, E. Yonemochi, T. Oguchi, K. Terada, K. Yamamoto and Y. Nakai, Chem. Pharm. Bull. (Tokyo), 41, 1632 (1993); https://doi.org/10.1248/cpb.41.1632.
M.M. Lowes, M.R. Caira, A.P. Lotter and J.G. Van der Watt, J. Pharm. Sci., 76, 744 (1987); https://doi.org/10.1002/jps.2600760914.
T.J. Cholerton, J.H. Hunt, G. Klinkert and M. Martin-Smith, J. Chem. Soc., Perkin Trans. 2, 1961 (1984); https://doi.org/10.1039/P29840001761.
A. Kiss and J. Répási, Analyst, 118, 661 (1993); https://doi.org/10.1039/AN9931800661.
S. Botha and D. Flanagan, Int. J. Pharm., 82, 195 (1992); https://doi.org/10.1016/0378-5173(92)90175-2.
H.G. Brittain, D.E. Bugay, S.J. Bogdanowich and J. Devincentis, Drug Dev. Ind. Pharm., 14, 2029 (1988); https://doi.org/10.3109/03639048809152001.
K. Sasaki, H. Suzuki and H. Nakagawa, Chem. Pharm. Bull. (Tokyo), 41, 325 (1993); https://doi.org/10.1248/cpb.41.325.
J.G. Graselli, M.K. Snavely and B.J. Bulkin, Chemical Applications of Raman Spectroscopy, John Wiley, New York (1981).
X.J. Gu and W. Jiang, J. Pharm. Sci., 84, 1438 (1995); https://doi.org/10.1002/jps.2600841210.
A.R. Pallipurath, F. Civati, J. Sibik, C. Crowley, J.A. Zeitler, P. McArdle and A. Erxleben, Int. J. Pharm., 528, 312 (2017); https://doi.org/10.1016/j.ijpharm.2017.06.020.
K. Higashi, K. Ueda and K. Moribe, Adv. Drug Deliv. Rev., 117, 71 (2016); https://doi.org/10.1016/j.addr.2016.12.001.