General principles of pharmaceutical solid polymorphism: A supramolecular perspective

Advanced Drug Delivery Reviews

Volumn 56, Issue 3, 2004, Pages 241-274

  Rodríguez Spong, Barbara ^a   Price, Christopher P ^a   Jayasankar, Adivaraha ^a   Matzger, Adam J ^a   Rodríguez Hornedo, Naír ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

Cocrystals; Crystal engineering; Crystallization; Molecular dispersions; Solvates; Supramolecular isomers; Supramolecular pharmaceutics

Indexed keywords

CRYSTALLIZATION; DRUG PRODUCTS; ENTHALPY; ENTROPY; FREE ENERGY; SELF ASSEMBLY; THERMODYNAMIC STABILITY;

CRYSTALLINE STATES; MOLECULAR RECOGNITION;

SUPRAMOLECULAR CHEMISTRY;

CARBAMAZEPINE; NABUMETONE; SULFAPYRIDINE;

CHEMICAL ANALYSIS; CRYSTALLIZATION; DENSITY; DIFFERENTIAL SCANNING CALORIMETRY; DRUG DESIGN; DRUG STABILITY; DRUG STRUCTURE; ELECTROCHEMISTRY; ENERGY; ENTHALPY; ENTROPY; HEAT; KINETICS; LASER; MICROSCOPY; MISCIBILITY; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHARMACEUTICAL ENGINEERING; PRIORITY JOURNAL; REVIEW; SOLID; SOLID STATE; SPECTROSCOPY; TEMPERATURE; THERMAL ANALYSIS; THERMODYNAMICS; THERMOGRAVIMETRY; VIBRATION; X RAY POWDER DIFFRACTION;

EID: 1042298891     PISSN: 0169409X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.addr.2003.10.005     Document Type: Article

References (196)

1. Brittain H.G. Polymorphism in Pharmaceutical Solids. 1999;Marcel Dekker, New York.
2. Byrn S.R., Pfeiffer R.R., Stephenson G., Grant D.J.W., Gleason W.B. Solid-State Chemistry of Drugs. 1999;SSCI, West Lafayette, IN.
3. Etter M.C., Macdonald J.C., Bernstein J. Graph-set analysis of hydrogen-bond patterns in organic crystals. Acta Crystallogr. Sect. B, Struct. Commun. 46:1990;256-262.
4. Etter M.C., Reutzel S.M. Hydrogen-bond directed cocrystallization and molecular recognition properties of acyclic imides. J. Am. Chem. Soc. 113:1991;2586-2598.
5. Desiraju G.R. Supramolecular synthons in crystal engineering - a new organic synthesis. Angew. Chem., Int. Ed. Engl. 34:1995;2311-2327.
6. Desiraju G.R. Crystal engineering: outlook and prospects. Curr. Sci. 81:2001;1038-1042.
7. Desiraju G.R. Chemistry beyond the molecule. Nature. 412:2001;397-400.
8. Moulton B., Zaworotko M.J. From molecules to crystal engineering: supramolecular isomerism and polymorphism in network solids. Chem. Rev. 101:2001;1629-1658.
9. Desiraju G.R. Hydrogen bridges in crystal engineering: interactions without borders. Accounts Chem. Res. 35:2002;565-573.
10. Fernandez-Lopez S., Kim H.S., Choi E.C., Delgado M., Granja J.R., Khasanov A., Kraehenbuehl K., Long G., Weinberger D.A., Wilcoxen K.M., Ghadiri M.R. Antibacterial agents based on the cyclic D,L-alpha-peptide architecture. Nature. 412:2001;452-455.
11. Brader M.L., Sukumar M., Pekar A.H., McClellan D.S., Chance R.E., Flora D.B., Cox A.L., Irwin L., Myers S.R. Hybrid insulin cocrystals for controlled release delivery. Nat. Biotechnol. 20:2002;800-804.
12. Walsh R.D.B., Bradner M.W., Fleischman S., Morales L.A., Moulton B., Rodríguez-Hornedo N., Zaworotko M.J. Crystal engineering of the composition of pharmaceutical phases. Chem. Commun. 2:2003;186-187.
13. S.G. Fleischman, S.S. Kuduva, J.A. McMahon, B. Moulton, R.D. Bailey Walsh, N. Rodríguez-Hornedo, M.J. Zaworotko, Crystal engineering of the composition of pharmaceutical phases: multiple-component crystalline solids involving carbamazepine, Cryst. Growth Des. (2003), (in press).
14. Dunitz J.D., Bernstein J. Disappearing polymorphs. Accounts Chem. Res. 28:1995;193-200.
15. Rodríguez-Hornedo N., Murphy D. Significance of controlling crystallization mechanisms and kinetics in pharmaceutical systems. J. Pharm. Sci. 88:1999;651-660.
16. Davey R.J., Allen K., Blagden N., Cross W.I., Lieberman H.F., Quayle M.J., Righini S., Seton L., Tiddy G.J.T. Crystal engineering - nucleation, the key step. Cryst. Eng. Commun. 4:2002;257-264.
17. Zhang G.G.Z., Gu C.H., Zell M.T., Burkhardt R.T., Munson E.J., Grant D.J.W. Crystallization and transitions of sulfamerazine polymorphs. J. Pharm. Sci. 91:2002;1089-1100.
18. N. Rodríguez-Hornedo, D. Murphy, Surfactant-facilitated crystallization of dihydrate carbamazepine during dissolution of anhydrous polymorph, J. Pharm. Sci. (2003), (in press).
19. Braga D., Desiraju G.R., Miller J.S., Orpen A.G., Price S.L. Innovation in crystal engineering. Cryst. Eng. Commun. 4:2002;500-509.
20. Desiraju G.R. Crystal Design: Structure and Function. 2003;Wiley, West Sussex.
21. Brittain H.G., Byrn S.R. Structural aspects of polymorphism. Brittain H.G. Polymorphism in Pharmaceutical Solids. 1999;73-124 Marcel Dekker, New York.
22. Braga D., Gerpioni F. Polymorphism, crystal transformations and gas-solid reactions. Desiraju G.R. Crystal Design: Structure and Function. 2003;325-373 Wiley, West Sussex.
23. Aakeroy C.B., Beatty A.M., Helfrich B.A., Nieuwenhuyzen M. Do polymorphic compounds make good cocrystallizing agents? A structural case study that demonstrates the importance of synthon flexibility. Cryst. Growth Des. 3:2003;159-165.
24. Taylor L.S., Zografi G. Spectroscopic characterization of interactions between PVP and indomethacin in amorphous molecular dispersions. Pharm. Res. 14:1997;1691-1698.
25. Tong P., Zografi G. A study of amorphous molecular dispersions of indomethacin and its sodium salt. J. Pharm. Sci. 90:2001;1991-2004.
26. Etter M.C. Hydrogen-bonds as design elements in organic chemistry. J. Phys. Chem. 95:1991;4601-4610.
27. Bernstein J., Davey R.J., Henck J.O. Concomitant polymorphs. Angew. Chem., Int. Ed. 38:1999;3441-3461.
28. Grant D.J.W. Theory and origin of polymorphism. Brittain H.G. Polymorphism in Pharmaceutical Solids. 1999;1-33 Marcel Dekker, New York.
29. Vippagunta S.R., Brittain H.G., Grant D.J.W. Crystalline solids. Adv. Drug Deliv. Rev. 48:2001;3-26.
30. Nangia A., Desiraju G.R. Pseudopolymorphism: occurrences of hydrogen bonding organic solvents in molecular crystals. Chem. Commun. 7:1999;605-606.
31. Hancock B.C., Parks M. What is the true solubility advantage for amorphous pharmaceuticals? Pharm. Res. 17:2000;397-404.
32. Nangia A. Database research in crystal engineering. Cryst. Eng. Commun. 4:2002;93-101.
33. Burger A., Ramberger R. Polymorphism of pharmaceuticals and other molecular crystals. I. Theory of thermodynamic rules. Mikrochim. Acta. 2:1979;259-271.
34. Yu L., Reutzel S.M., Stephenson G.A. Physical characterization of polymorphic drugs: an integrated characterization strategy. Pharm. Sci. Technol. Today. 1:1998;118-127.
35. Yu L. Inferring thermodynamic stability relationship of polymorphs from melting data. J. Pharm. Sci. 84:1995;966-974.
36. Hancock B.C., Zografi G. Characteristics and significance of the amorphous state in pharmaceutical systems. J. Pharm. Sci. 86:1997;1-12.
37. Shalaev E., Zografi G. The concept of 'structure' in amorphous solids from the perspective of the pharmaceutical sciences. Amorphous Food and Pharmaceutical Systems. vol. 281:2002;11-30 The Royal Society of Chemistry, Cambridge.
38. Brittain H.G., Grant D.J.W. Effects of polymorphism and solid-state solvation on solubility and dissolution rate. Brittain H.G. Polymorphism in Pharmaceutical Solids. 1999;279-330 Marcel Dekker, New York.
39. Shefter E., Higuchi T. Dissolution behavior of crystalline solvated and nonsolvated forms of some pharmaceuticals. J. Pharm. Sci. 52:1963;781-791.
40. Murphy D., Rodríguez-Cintrón F., Langevin B., Kelly R.C., Rodríguez-Hornedo N. Solution-mediated phase transformation of anhydrous to dihydrate carbamazepine and the effect of lattice disorder. Int. J. Pharm. 246:2002;121-134.
41. Behme R.J., Brooke D. Heat of fusion measurement of a low melting polymorph of carbamazepine that undergoes multiple-phase changes during differential scanning calorimetry analysis. J. Pharm. Sci. 80:1991;986-990.
42. Mehdizadeh M., Grant D.J.W. Solubility and complexation behavior of griseofulvin in fatty acid-isooctane mixtures. J. Pharm. Sci. 73:1984;1195-1203.
43. Rodríguez-Hornedo N., Sinclair B.D. Crystallization: significance in product development, processing, and performance. Encyclopedia of Pharmaceutical Technology. 2002;671-690 Marcel Dekker, New York.
44. Grzesiak A.L., Lang M., Kim K., Matzger A.J. Comparison of the four anhydrous polymorphs of carbamazepine and the crystal structure of form I. J. Pharm. Sci. 92:2003;2260-2271.
45. Exceptions to the rules have been noted: [46].
46. Burger A., Ramberger R. Polymorphism of pharmaceuticals and other molecular crystals. II. Applicability of thermodynamic rules. Mikrochim. Acta. 2:1979;273-316.
47. Grunenberg A., Henck J.O., Siesler H.W. Theoretical derivation and practical application of energy temperature diagrams as an instrument in preformulation studies of polymorphic drug substances. Int. J. Pharm. 129:1996;147-158.
48. Price C.P., Grzesiak A.L., Lang M., Matzger A.J. Polymorphism of nabumetone. Cryst. Growth Des. 2:2002;501-503.
49. Kitaigorodskii A.I. Molecular Crystals and Molecules. 1973;Academic Press, New York.
50. Although this rule is formulated for comparing densities at absolute zero, it is routinely applied to structures determined even at room temperature. However, comparing densities between polymorphs whose crystal structures have been determined at different temperatures must always be done with caution.
51. Chyall L.J., Tower J.M., Coates D.A., Houston T.L., Childs S.L. Polymorph generation in capillary spaces: the preparation and structural analysis of a metastable polymorph of nabumetone. Cryst. Growth Des. 2:2002;505-510.
52. Bauer J., Spanton S., Henry R., Quick J., Dziki W., Porter W., Morris J. Ritonavir: an extraordinary example of conformational polymorphism. Pharm. Res. 18:2001;859-866.
53. Frankenbach G.M., Etter M.C. Relationship between symmetry in hydrogen-bonded benzoic acids and the formation of acentric crystal structures. Chem. Mater. 4:1992;272-278.
54. Gu C.H., Grant D.J.W. Estimating the relative stability of polymorphs and hydrates from heats of solution and solubility data. J. Pharm. Sci. 90:2001;1277-1287.
55. Ostwald W. Studien über die bildung und umwandlung fester körper. Z. Phys. Chem. 22:1897;289-330.
56. Davey R.J., Blagden N., Potts G.D., Docherty R. Polymorphism in molecular crystals: stabilization of a metastable form by conformational mimicry. J. Am. Chem. Soc. 119:1997;1767-1772.
57. Threlfall T. Crystallisation of polymorphs: thermodynamic insight into the role of solvent. Org. Process Res. Dev. 4:2000;384-390.
58. Blagden N., Davey R.J., Rowe R., Roberts R. Disappearing polymorphs and the role of reaction by-products: the case of sulphathiazole. Int. J. Pharm. 172:1998;169-177.
59. Gu C.H., Young V., Grant D.J.W. Polymorph screening: influence of solvents on the rate of solvent-mediated polymorphic transformation. J. Pharm. Sci. 90:2001;1878-1890.
60. Weissbuch I., Popovitzbiro R., Lahav M., Leiserowitz L. Understanding and control of nucleation, growth, habit, dissolution and structure of 2-dimensional and 3-dimensional crystals using tailor-made auxiliaries. Acta Crystallogr. Sect. B, Struct. Commun. 51:1995;115-148.
61. Zettlemoyer A.C. Nucleation. 1969;Marcel Dekker, New York.
62. Mullin J.W. Crystallization. 1992;Butterworth-Heinemann, Oxford.
63. Söhnel O., Garside J. Precipitation: Basic Principles and Industrial Applications. 1992;Butterworth-Heinemann, Oxford.
64. Myerson A.S. Handbook of Industrial Crystallization. 2002;Butterworth- Heinemann, Boston.
65. Perepezko J.H. Nucleation reactions in undercooled liquids. Mater. Sci. Eng. A. 178:1994;105-111.
66. Perepezko J.H. Kinetic processes in undercooled melts. Mater. Sci. Eng. A. 226:1997;374-382.
67. Ward M.D. Bulk crystals to surfaces: combining X-ray diffraction and atomic force microscopy to probe the structure and formation of crystal interfaces. Chem. Rev. 101:2001;1697-1725.
68. Lang M.D., Grzesiak A.L., Matzger A.J. The use of polymer heteronuclei for crystalline polymorph selection. J. Am. Chem. Soc. 124:2002;14834-14835.
69. Rodríguez-Hornedo N., Lechuga-Ballesteros D., Wu H.J. Phase transition and heterogeneous/epitaxial nucleation of hydrated and anhydrous theophylline crystals. Int. J. Pharm. 85:1992;149-162.
70. Gibbs J.W. Collected Works. 1948;Yale University Press, New Haven.
71. Volmer M. Kinetic der Phasenbildung. 1939;Steinkopff, Leipzig.
72. Becker R., Döring W. The kinetic treatment of nuclear formation in supersaturated vapors. Ann. Phys. 24:1935;719-752.
73. Turnbull D., Fisher J.C. Rate of nucleation in condensed systems. J. Chem. Phys. 17:1949;71-73.
74. Mersmann A. Calculation of interfacial tensions. J. Cryst. Growth. 102:1990;841-847.
75. Davey R.J., Hilton A.M., Garside J. Crystallization from oil in water emulsions: particle synthesis and purification of molecular materials. Chem. Eng. Res. Des. 75:1997;245-251.
76. Davey R.J., Garside J., Hilton A.M., Mcewan D., Morrison J.W. Purification of molecular mixtures below the eutectic by emulsion crystallization. Nature. 375:1995;664-666.
77. Davey R.J., Garside J., Hilton A.M., McEwan D., Morrison J.W. Emulsion solidification of meta-chloronitrobenzene: purification and crystallisation. J. Cryst. Growth. 166:1996;971-975.
78. Carter P.W., Ward M.D. Topographically directed nucleation of organic crystals on molecular single crystal substrates. J. Am. Chem. Soc. 115:1993;11521-11535.
79. Carter P.W., Hillier A.C., Ward M.D. Nanoscale surface topography and growth of molecular crystals: the role of anisotropic intermolecular bonding. J. Am. Chem. Soc. 116:1994;944-953.
80. Bonafede S.J., Ward M.D. Selective nucleation and growth of an organic polymorph by ledge-directed epitaxy on a molecular-crystal substrate. J. Am. Chem. Soc. 117:1995;7853-7861.
81. Yu L. Nucleation of one polymorph by another. J. Am. Chem. Soc. 125:2003;6380-6381.
82. Ward M.D. Organic crystal surfaces: structure, properties and reactivity. Curr. Opin. Colloid Interf. Sci. 2:1997;51-64.
83. Chemburkar S.R., Bauer J., Deming K., Spiwek H., Patel K., Morris J., Henry R., Spanton S., Dziki W., Porter W., Quick J., Bauer P., Donaubauer J., Narayanan B.A., Soldani M., Riley D., McFarland K. Dealing with the impact of ritonavir polymorphs on the late stages of bulk drug process development. Org. Process Res. Dev. 4:2000;413-417.
84. De Smidt J.H., Fokkens J.G., Grijseels H., Crommelin D.J.A. Dissolution of theophylline monohydrate and anhydrous theophylline in buffer solutions. J. Pharm. Sci. 75:1986;497-501.
85. Luhtala S. Effect of sodium lauryl sulfate and polysorbate-80 on crystal growth and aqueous solubility of carbamazepine. Acta Pharm. Nordica. 4:1992;85-90.
86. Gu C.H., Chatterjee K., Young V., Grant D.J.W. Stabilization of a metastable polymorph of sulfamerazine by structurally related additives. J. Cryst. Growth. 235:2002;471-481.
87. Blagden N., Davey R.J., Lieberman H.F., Williams L., Payne R., Roberts R., Rowe R., Docherty R. Crystal chemistry and solvent effects in polymorphic systems - sulfathiazole. J. Chem. Soc., Faraday Trans. 94:1998;1035-1044.
88. R.C. Kelly, N. Rodríguez-Hornedo, Directed nucleation and solution-mediated phase transformation of carbamazepine in aqueous and organic solutions, New Orleans, LA, USA, IEC-055, 2003.
89. Tang X.L.C., Pikal M.J., Taylor L.S. A spectroscopic investigation of hydrogen bond patterns in crystalline and amorphous phases in dihydropyridine calcium channel blockers. Pharm. Res. 19:2002;477-483.
90. Hancock B.C. Disordered drug delivery: destiny, dynamics and the Deborah number. J. Pharm. Pharmacol. 54:2002;737-746.
91. Guillory J.K. Generation of polymorphs, hydrates, solvates, and amorphous solids. Brittain H.G. Polymorphism in Pharmaceutical Solids. 1999;183-226 Marcel Dekker, New York.
92. Saleki-Gerhardt A., Stowell J.G., Byrn S.R., Zografi G. Hydration and dehydration of crystalline and amorphous forms of raffinose. J. Pharm. Sci. 84:1995;318-323.
93. Pikal M.J., Lukes A.L., Lang J.E., Gaines K. Quantitative crystallinity determinations for beta-lactam antibiotics by solution calorimetry - correlations with stability. J. Pharm. Sci. 67:1978;767-772.
94. Tsukushi I., Yamamuro O., Suga H. Heat-capacities and glass transitions of ground amorphous solid and liquid-quenched glass of tri-O-methyl-beta- cyclodextrin. J. Non-Cryst. Solids. 175:1994;187-194.
95. Brittain H.G. Methods for the characterization of polymorphs and solvates. Brittain H.G. Polymorphism in Pharmaceutical Solids. 1999;227-278 Marcel Dekker, New York.
96. Andronis V., Zografi G. Crystal nucleation and growth of indomethacin polymorphs from the amorphous state. J. Non-Cryst. Solids. 271:2000;236-248.
97. Bernstein J., Hagler A.T. Conformational polymorphism - the influence of crystal structure on molecular conformation. J. Am. Chem. Soc. 100:1978;673-681.
98. Yu L., Reutzel-Edens S.M., Mitchell C.A. Crystallization and polymorphism of conformationally flexible molecules: problems, patterns, and strategies. Org. Process Res. Dev. 4:2000;396-402.
99. Bernstein J. Polymorphism in Molecular Crystals. 2002;Oxford University Press, New York.
100. Prabhakar C., Reddy G.B., Reddy C.M., Nageshwar D., Devi A.S., Babu J.M., Vyas K., Sarma M.R., Reddy G.O. Process research and structural studies on nabumetone. Org. Process Res. Dev. 3:1999;121-125.
101. Reboul J.P., Cristau B., Soyfer J.C., Astier J.P. 5H-5-Dibenzyl[b,f] azepinecarboxamide (carbamazepine). Acta Crystallogr. Sect. B, Struct. Commun. 37:1981;1844-1848.
102. Himes V.L., Mighell A.D., Decamp W.H. Structure of carbamazepine-5H- dibenz[b.f]azepine-5-carboxamide. Acta Crystallogr. Sect. B, Struct. Commun. 37:1981;2242-2245.
103. Lowes M.M.J., Caira M.R., Lotter A.P., Vanderwatt J.G. Physicochemical properties and X-ray structural studies of the trigonal polymorph of carbamazepine. J. Pharm. Sci. 76:1987;744-752.
104. Lang M.D., Kampf J.W., Matzger A.J. Form IV of carbamazepine. J. Pharm. Sci. 91:2002;1186-1190.
105. 2S. Acta Crystallogr. Sect. C, Cryst. Struct. Commun. 40:1984;1848-1851.
106. Bar I., Bernstein J. Conformational polymorphism. 6. The crystal and molecular-structures of form-II, form-III, and form-V of 4-amino-N-2- pyridinylbenzenesulfonamide (sulfapyridine). J. Pharm. Sci. 74:1985;255-263.
107. Bernstein J. Polymorph-IV of 4-amino-N-2-pyridinylbenzenesulfonamide (sulfapyridine). Acta Crystallogr. Sect. C, Cryst. Struct. Commun. 44:1988;900-902.
108. Castle R.N., Witt N.F. The polymorphism of sulfapyridine. J. Am. Chem. Soc. 68:1946;64-66.
109. Kuhnert-Brandstätter M. Thermomicroscopy in the Analysis of Pharmaceuticals. 1971;Pergamon Press, New York.
110. Etter M.C. Encoding and decoding hydrogen-bond patterns of organic compounds. Accounts Chem. Res. 23:1990;120-126.
111. Betageri G.V., Makarla K.R. Characterization of glyburide-polyethylene glycol solid dispersions. Drug Dev. Ind. Pharm. 22:1996;731-734.
112. Law D., Krill S.L., Schmitt E.A., Fort J.J., Qiu Y.H., Wang W.L., Porter W.R. Physicochemical considerations in the preparation of amorphous ritonavir-poly(ethylene glycol) 8000 solid dispersions. J. Pharm. Sci. 90:2001;1015-1025.
113. Imaizumi H., Nambu N., Nagai T. Pharmaceutical interactions in dosage forms and processing. 40. Stabilization of amorphous state of indomethacin by solid dispersion in polyvinylpolypyrrolidone. Chem. Pharm. Bull. 31:1983;2510-2512.
114. Sekizaki H., Danjo K., Eguchi H., Yonezawa Y., Sunada H., Otsuka A. Solid-state interaction of ibuprofen with polyvinylpyrrolidone. Chem. Pharm. Bull. 43:1995;988-993.
115. Shamblin S.L., Huang E.Y., Zografi G. The effects of co-lyophilized polymeric additives on the glass transition temperature and crystallization of amorphous sucrose. J. Therm. Anal. 47:1996;1567-1579.
116. Lu Q., Zografi G. Phase behavior of binary and ternary amorphous mixtures containing indomethacin, citric acid, and PVP. Pharm. Res. 15:1998;1202-1206.
117. Suzuki H., Sunada H. Influence of water-soluble polymers on the dissolution of nifedipine solid dispersions with combined carriers. Chem. Pharm. Bull. 46:1998;482-487.
118. Shamblin S.L., Zografi G. Enthalpy relaxation in binary amorphous mixtures containing sucrose. Pharm. Res. 15:1998;1828-1834.
119. Matsumoto T., Zografi G. Physical properties of solid molecular dispersions of indomethacin with poly(vinylpyrrolidone) and poly(vinylpyrrolidone-co-vinylacetate) in relation to indomethacin crystallization. Pharm. Res. 16:1999;1722-1728.
120. Kohri N., Yamayoshi Y., Xin H., Iseki K., Sato N., Todo S., Miyazaki K. Improving the oral bioavailability of albendazole in rabbits by the solid dispersion technique. J. Pharm. Pharmacol. 51:1999;159-164.
121. Verreck G., Six K., Van Den Mooter G., Baert L., Peeters J., Brewster M.E. Characterization of solid dispersions of itraconazole and hydroxypropylmethylcellulose prepared by melt extrusion - Part I. Int. J. Pharm. 251:2003;165-174.
122. Beten D.B., Gelbcke M., Diallo B., Moes A.J. Interaction between dipyridamole and eudragit-s. Int. J. Pharm. 88:1992;31-37.
123. Aceves J.M., Cruz R., Hernandez E. Preparation and characterization of furosemide-eudragit controlled release systems. Int. J. Pharm. 195:2000;45-53.
124. Morris K.R., Rodríguez-Hornedo N. Hydrates. Encyclopedia of Pharmaceutical Technology. 1993;393-440 Marcel Dekker, New York.
125. Khankari R.K., Grant D.J.W. Pharmaceutical hydrates. Thermochim. Acta. 248:1995;61-79.
126. Morris K.R. Structural aspects of hydrates and solvates. Brittain H.G. Polymorphism in Pharmaceutical Solids. 1999;125-181 Marcel Dekker, New York.
127. Bingham A.L., Hughes D.S., Hursthouse M.B., Lancaster R.W., Tavener S., Threlfall T.L. Over one hundred solvates of sulfathiazole. Chem. Commun. 7:2001;603-604.
128. Infantes L., Motherwell S. Water clusters in organic molecular crystals. Cryst. Eng. Commun. 4:2002;454-461.
129. A.L. Gillon, N. Feeder, R.J. Davey, R. Storey, Hydration in molecular crystals - a Cambridge Structural Database analysis, Cryst. Growth Des. (2003), (in press).
130. Caira M.R., Van Tonder E.C., De Villiers M.M., Lotter A.P. Diverse modes of solvent inclusion in crystalline pseudopolymorphs of the anthelmintic drug niclosamide. J. Incl. Phenom. Mol. Recogn. Chem. 31:1998;1-16.
131. Laine E., Tuominen V., Ilvessalo P., Kahela P. Formation of dihydrate from carbamazepine anhydrate in aqueous conditions. Int. J. Pharm. 20:1984;307-314.
132. Ando H., Ohwaki T., Ishii M., Watanabe S., Miyake Y. Crystallization of theophylline in tablets. Int. J. Pharm. 34:1986;153-156.
133. Zhu H.J., Grant D.J.W. Influence of water activity in organic solvent plus water mixtures on the nature of the crystallizing drug phase. 2. Ampicillin. Int. J. Pharm. 139:1996;33-43.
134. Zhu H.J., Yuen C.M., Grant D.J.W. Influence of water activity in organic solvent plus water mixtures on the nature of the crystallizing drug phase: 1. Theophylline. Int. J. Pharm. 135:1996;151-160.
135. Panunto T.W., Urbanczyklipkowska Z., Johnson R., Etter M.C. Hydrogen-bond formation in nitroanilines - the first step in designing acentric materials. J. Am. Chem. Soc. 109:1987;7786-7797.
136. Etter M.C., Urbanczyklipkowska Z., Ziaebrahimi M., Panunto T.W. Hydrogen-bond directed cocrystallization and molecular recognition properties of diarylureas. J. Am. Chem. Soc. 112:1990;8415-8426.
137. Etter M.C., Adsmond D.A. The use of cocrystallization as a method of studying hydrogen-bond preferences of 2-aminopyrimidine. J. Chem. Soc., Chem. Commun. 8:1990;589-591.
138. Rouhi A.M. Bacteria: Beware! Chem. Eng. News. 79:2001;41-43.
139. Oswald I.D.H., Allan D.R., McGregor P.A., Motherwell W.D.S., Parsons S., Pulham C.R. The formation of paracetamol (acetaminophen) adducts with hydrogen-bond acceptors. Acta Crystallogr. Sect. B, Struct. Commun. 58:2002;1057-1066.
140. Amai M., Endo T., Nagase H., Ueda H., Nakagaki M. 1:1 Complex of octadecanoic acid and 3-pyridinecarboxamide. Acta Crystallogr. Sect. C, Cryst. Struct. Commun. 54:1998;1367-1369.
141. Yokoyama S., Sunohara M., Fujie T. Hygroscopicities of 3-aminopyridine (3AP) and fatty acid complexes (FA-3AP), and the release of 3AP from FA-3AP. Chem. Pharm. Bull. 41:1993;1876-1878.
142. J.A. Hill, Halogenated lower-alkanal adducts with nicotinamide, US Patent Number 2755283, Olin Mathiesen Chemical Corp., Patent and Trademark Office, Washington, DC, 1956.
143. Azizov M.A., Gershtein K.M. Compounds of nicotinic acid amide with cobalt and nickel chlorides. Dokl. Akad. Nauk. USSR. 1:1954;33-35.
144. Berge S.M., Bighley L.D., Monkhouse D.C. Pharmaceutical salts. J. Pharm. Sci. 66:1977;1-19.
145. Neau S.H. Pharmaceutical salts. Liu R. Water-Insoluble Drug Formulation. 2000;405-425 Interpharm Press, Denver.
146. Stahl P.H., Wermuth C.G. Handbook of Pharmaceutical Salts: Properties, Selection, and Use. 2002;Wiley-VCH, Weinheim.
147. Kramer S.F., Flynn G.L. Solubility of organic hydrochlorides. J. Pharm. Sci. 61:1972;1896-1904.
148. Biradha K., Zaworotko M.J. Supramolecular isomerism and polymorphism in dianion salts of pyromellitic acid. Mater. Res. Bull. 1:1998;67-78.
149. Gilli P., Bertolasi V., Ferretti V., Gilli G. Covalent nature of the strong homonuclear hydrogen-bond - study of the O-HO system by crystal structure correlation methods. J. Am. Chem. Soc. 116:1994;909-915.
150. Stanley N., Sethuraman V., Muthiah P.T., Luger P., Weber M. Crystal engineering of organic salts: hydrogen-bonded supramolecular motifs in pyrimethamine hydrogen glutarate and pyrimethamine formate. Cryst. Growth Des. 2:2002;631-635.
151. Shekunov B.Y., York P. Crystallization processes in pharmaceutical technology and drug delivery design. J. Cryst. Growth. 211:2000;122-136.
152. Pedireddi V.R., Jones W., Chorlton A.P., Docherty R. Creation of crystalline supramolecular arrays: a comparison of co-crystal formation from solution and by solid state grinding. Chem. Commun. 8:1996;987-988.
153. Shan N., Toda F., Jones W. Mechanochemistry and co-crystal formation: effect of solvent on reaction kinetics. Chem. Commun. 20:2002;2372-2373.
154. Elamin A.A., Ahlneck C., Alderborn G., Nyström C. Increased metastable solubility of milled griseofulvin, depending on the formation of a disordered surface-structure. Int. J. Pharm. 111:1994;159-170.
155. Mosharraf M., Nyström C. The effect of dry mixing on the apparent solubility of hydrophobic, sparingly soluble drugs. Eur. J. Pharm. Sci. 9:1999;145-156.
156. Weissbuch I., Lahav M., Leiserowitz L. Toward stereochentical control, monitoring, and understanding of crystal nucleation. Cryst. Growth Des. 3:2003;125-150.
157. Mann S., Heywood B.R., Rajam S., Walker J.B.A. Crystal engineering of inorganic materials at organized organic surfaces. ACS Symp. Ser. 444:1991;28-41.
158. This term refers to the range of energetically feasible forms in the same sense that conformational space refers to energetically accessible conformations of a molecule.
159. Peterson M.L., Morissette S.L., McNulty C., Goldsweig A., Shaw P., Lequesne M., Monagle J., Encina N., Marchionna J., Johnson A., Gonzalez-Zugasti J., Lemmo A.V., Ellis S.J., Cima M.J., Almarsson O. Iterative high-throughput polymorphism studies on acetaminophen and an experimentally derived structure for form III. J. Am. Chem. Soc. 124:2002;10958-10959.
160. Haisa M., Kashino S., Maeda H. Orthorhombic form of para- hydroxyacetanilide. Acta Crystallogr. Sect. B, Struct. Commun. 30:1974;2510-2512.
161. Haisa M., Kashino S., Kawai R., Maeda H. Monoclinic form of para-hydroxyacetanilide. Acta Crystallogr. Sect. B, Struct. Commun. 32:1976;1283-1285.
162. Di Martino P., Conflant P., Drache M., Huvenne J.P., Guyothermann A.M. Preparation and physical characterization of forms II and III of paracetamol. J. Therm. Anal. 48:1997;447-458.
163. Nichols G., Frampton C.S. Physicochemical characterization of the orthorhombic polymorph of paracetamol crystallized from solution. J. Pharm. Sci. 87:1998;684-693.
164. This study was extended to melt crystallization, which led to the production of form III under conditions essentially identical to the literature procedure [162]. Powder X-ray diffraction on this phase provides the best structural model yet proposed for form III of acetaminophen.
165. Garetz B.A., Aber J.E., Goddard N.L., Young R.G., Myerson A.S. Nonphotochemical, polarization-dependent, laser-induced nucleation in supersaturated aqueous urea solutions. Phys. Rev. Lett. 77:1996;3475-3476.
166. Zaccaro J., Matic J., Myerson A.S., Garetz B.A. Nonphotochemical, laser-induced nucleation of supersaturated aqueous glycine produces unexpected gamma-polymorph. Cryst. Growth Des. 1:2001;5-8.
167. Hooks D.E., Fritz T., Ward M.D. Epitaxy and molecular organization on solid substrates. Adv. Mater. 13:2001;227-241.
168. Stephenson G.A., Borchardt T.B., Byrn S.R., Bowyer J., Bunnell C.A., Snorek S.V., Yu L. Conformational and color polymorphism of 5-methyl-2-[(2- nitrophenyl)amino]-3-thiophenecarbonitrile. J. Pharm. Sci. 84:1995;1385-1386.
169. Yu L., Stephenson G.A., Mitchell C.A., Bunnell C.A., Snorek S.V., Bowyer J.J., Borchardt T.B., Stowell J.G., Byrn S.R. Thermochemistry and conformational polymorphism of a hexamorphic crystal system. J. Am. Chem. Soc. 122:2000;585-591.
170. Mitchell C.A., Yu L., Ward M.D. Selective nucleation and discovery of organic polymorphs through epitaxy with single crystal substrates. J. Am. Chem. Soc. 123:2001;10830-10839.
171. Yu L. Color changes caused by conformational polymorphism: optical-crystallography, single-crystal spectroscopy, and computational chemistry. J. Phys. Chem. A. 106:2002;544-550.
172. Byrn S.R., Pfeiffer R.R., Stephenson G., Grant D.J.W., Gleason W.B. Solid-state pharmaceutical chemistry. Chem. Mater. 6:1994;1148-1158.
173. Byrn S., Pfeiffer R., Ganey M., Hoiberg C., Poochikian G. Pharmaceutical solids: a strategic approach to regulatory considerations. Pharm. Res. 12:1995;945-954.
174. Brittain H.G. Physical Characterization of Pharmaceutical Solids. 1995;Marcel Dekker, New York.
175. Brittain H.G. Spectral methods for the characterization of polymorphs and solvates. J. Pharm. Sci. 86:1997;405-412.
176. Byrn et al. have documented a strategy for choosing which analytical technique should be used in the characterization of solid-state drug forms, including pure polymorphs, hydrates/solvates, desolvated solvates, and amorphous forms [173].
177. In the ATR experiment, mechanical contact is usually made with the sample. DRIFT often gives rise to complex spectra that are a convolution of absorption and reflectance features.
178. Findlay W.P., Bugay D.E. Utilization of Fourier transform Raman spectroscopy for the study of pharmaceutical crystal forms. J. Pharm. Biomed. Anal. 16:1998;921-930.
179. Vankeirsbilck T., Vercauteren A., Baeyens W., Van Der Weken G., Verpoort F., Vergote G., Remon J.P. Applications of Raman spectroscopy in pharmaceutical analysis. Trac-Trends Anal. Chem. 21:2002;869-877.
180. Szelagiewicz M., Marcolli C., Cianferani S., Hard A.P., Vit A., Burkhard A., Von Raumer M., Hofmeier U.C., Zilian A., Francotte E., Schenker R. In situ characterization of polymorphic forms the potential of Raman techniques. J. Therm. Anal. 57:1999;23-43.
181. Anquetil P.A., Brenan C.J.H., Marcolli C., Hunter I.W. Laser Raman spectroscopic analysis of polymorphic forms in microliter fluid volumes. J. Pharm. Sci. 92:2003;149-160.
182. H.G. Brittain, X-ray powder diffraction of pharmaceutical materials, Am. Pharm. Rev. 5 (2002) 74-76, 78, 80.
183. Neumann M.A., Leusen F.J.J., Engel G.E., Wilke S., Conesa-Moratilla C. Recent advances in structure solution from powder diffraction data. Int. J. Mod. Phys. B. 16:2002;407-414.
184. K.D.M. Harris, New opportunities for structure determination of molecular materials directly from powder diffraction data (2003) (in press).
185. The problem of obtaining accurate intensities in PXRD is important for more than SDPD. Preferred orientation of samples can cause dramatic intensity changes and even result in some peaks disappearing entirely. The literature on crystal polymorphism contains a number of examples of "new" polymorphs that are merely previously known forms exhibiting different preferred orientation.
186. Some progress has been made in making this process more rapid: [187].
187. D.M. Giaquinta, E.D. Carlson, High throughput crystallographic screening of materials, US Patent Number 2003068829, Symyx Technologies, Inc., Patent and Trademark Office, Washington, DC, 2003.
188. Blagden N., Davey R., Song M., Quayle M., Clark S., Taylor D., Nield A. A novel batch cooling crystallizer for in situ monitoring of solution crystallization using energy dispersive X-ray diffraction. Cryst. Growth Des. 3:2003;197-201.
189. For an extensive review of thermal methods and their uses in polymorph characterization: [190-193].
190. Giron D. Thermal-analysis and calorimetric methods in the characterization of polymorphs and solvates. Thermochim. Acta. 248:1995;1-59.
191. Giron D. Thermal analysis, microcalorimetry and combined techniques for the study of pharmaceuticals. J. Therm. Anal. 56:1999;1285-1304.
192. Giron D. Investigations of polymorphism and pseudo-polymorphism in pharmaceuticals by combined thermoanalytical techniques. J. Therm. Anal. 64:2001;37-60.
193. Giron D. Applications of thermal analysis and coupled techniques in pharmaceutical industry. J. Therm. Anal. 68:2002;335-357.
194. McCrone W.C. Jr. Fusion Methods in Chemical Microscopy. 1957;Interscience Publishers, New York.
195. Bugay D.E. Solid-state nuclear magnetic resonance spectroscopy: theory and pharmaceutical applications. Pharm. Res. 10:1993;317-327.
196. Tishmack P.A., Bugay D.E., Byrn S.R. Solid-state nuclear magnetic resonance spectroscopy - pharmaceutical applications. J. Pharm. Sci. 92:2003;441-474.