Cocrystallization for successful drug delivery

Expert Opinion on Drug Delivery

Volumn 10, Issue 2, 2013, Pages 201-213

  Sun, Changquan Calvin ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

Cocrystal; Crystal engineering; Crystallization; Drug delivery; Performance; Pharmaceutical property; Polymorph; Solid state; Solubility; Stability

Indexed keywords

CRYSTAL STRUCTURE; CRYSTALLIZATION; DRUG BIOAVAILABILITY; DRUG DELIVERY SYSTEM; DRUG RESEARCH; DRUG SOLUBILITY; HIGH THROUGHPUT SCREENING; PHARMACEUTICAL ENGINEERING; PHYSICAL CHEMISTRY; REVIEW; THERMODYNAMICS;

ANIMALS; CHEMISTRY, PHARMACEUTICAL; CRYSTALLIZATION; DRUG DELIVERY SYSTEMS; HUMANS; PHARMACEUTICAL PREPARATIONS; PROTEIN ENGINEERING; SOLUBILITY; THERMODYNAMICS;

EID: 84872730070     PISSN: 17425247     EISSN: 17447593     Source Type: Journal    
DOI: 10.1517/17425247.2013.747508     Document Type: Review

References (104)

1. Blagden N, de Matas M, Gavan P, York P. Crystal engineering of active pharmaceutical ingredients to improve solubility and dissolution rates. Adv Drug Del Rev 2007;59:617-30 (Pubitemid 47285407)
2. Guidance for industry: regulatory classification of pharmaceutical co-crystals. Food and Drug Administration; Silver Spring, MD; 2011
3. Almarsson O, Zaworotko MJ. Crystal engineering of the composition of pharmaceutical phases. Do pharmaceutical co-crystals represent a new path to improved medicines? Chem Comm 2004(17):1889-96 (Pubitemid 39335992)
4. Friscić T, Jones W. Benefits of cocrystallisation in pharmaceutical materials science: an update. J Pharm Pharmacol 2010;62:1547-59
5. Schultheiss N, Newman A. Pharmaceutical cocrystals and their physicochemical properties. Cryst Growth Des 2009;9:2950-67
6. Delori A, Friscić T, Jones W. The role of mechanochemistry and supramolecular design in the development of pharmaceutical materials. CrystEngComm 2012;14:2350-62
7. Vishweshwar P, McMahon JA, Bis JA, Zaworotko MJ. Pharmaceutical co-crystals. J Pharm Sci 2006;95(3):499-516
8. Variankaval N, Wenslow R, Murry J, et al. Preparation and solid-state characterization of nonstoichiometric cocrystals of a phosphodiesterase-IV inhibitor and L-tartaric acid. Cryst Growth Des 2006;6:690-700 (Pubitemid 43475360)
9. Friscić T, Fábián L, Burley JC, et al. Exploring cocrystal-cocrystal reactivity via liquid-assisted grinding: the assembling of racemic and dismantling of enantiomeric cocrystals. Chem Comm 2006(48):5009-11 (Pubitemid 44866517)
10. Caner H, Groner E, Levy L, Agranat I. Trends in the development of chiral drugs. Drug Discov Today 2004;9:105-10 (Pubitemid 38198306)
11. Smith SW. Chiral toxicology: it's the same thing. . only different. Toxicol Sci 2009;110(1):4-30
12. Toda F, Tanaka K, Miyamoto H, et al. Formation of racemic compound crystals by mixing of two enantiomeric crystals in the solid state. Liquid transport of molecules from crystal to crystal. J Chem Soc, Perkin Trans 1997;2:1877-85 (Pubitemid 127441833)
13. Jacques J, Collet A, Wilen SH. Enantiomers, racemates, and resolutions. Krieger Publishing Co; Malabar FL: 1991
14. Li ZJ, Abramov Y, Bordner J, et al. Solid-state acid-base interactions in complexes of heterocyclic bases with dicarboxylic acids: crystallography, hydrogen bond analysis, and 15N NMR spectroscopy. J Am Chem Soc 2006;128:8199-210 (Pubitemid 43967764)
15. Steiner T, Majerz I, Wilson CC. First O-H-N hydrogen bond with a centered proton obtained by thermally induced proton migration. Angew Chem Int Ed 2001;40:2651-4 (Pubitemid 32691704)
16. Childs SL, Stahly GP, Park A. The salt-cocrystal continuum: the influence of crystal structure on ionization state. Mol Pharm 2007;4:323-38 (Pubitemid 46983949)
17. Haynes DA, Jones W, Motherwell WD. Cocrystallisation of succinic and fumaric acids with lutidines: a systematic study. CrystEngComm 2006;8:830-40 (Pubitemid 44656854)
18. Childs SL, Hardcastle KI. Cocrystals of piroxicam with carboxylic acids. Cryst Growth Des 2007;7:1291-304
19. Perumalla SR, Sun CC. Confused HCl: hydrogen chloride or hydrochloric acid? Chem Eur J 2012;18:6462-6
20. Perumalla SR, Sun CC. Design and synthesis of solid state structures with conjugate acid-base pair interactions. CrystEngComm 2012;14:3851-3
21. Braga D, Grepioni F, Maini L, et al. From unexpected reactions to a new family of ionic co-crystals: the case of barbituric acid with alkali bromides and caesium iodide. Chem Comm 2010;46:7715-17
22. Nehm SJ, Rodriguez-Spong B, Rodriguez-Hornedo N. Phase solubility diagrams of cocrystals are explained by solubility product and solution complexation. Cryst Growth Des 2006;6:592-600 (Pubitemid 43242126)
23. Bethune SJ, Huang N, Jayasanka A, Rodríguez-Hornedo N. Understanding and predicting the effect of cocrystal components and pH on cocrystal solubility. Cryst Growth Des 2009;9:3976-88
24. Aitipamula S, Banerjee R, Bansal AK, et al. Polymorphs, salts, and cocrystals: what's in a name? Cryst Growth Des 2012;12:2147-52
25. Sun CC. Materials science tetrahedron-a useful tool for pharmaceutical research and development. J Pharm Sci 2009;98:1671-87
26. Chow SF, Chen M, Shi L, et al. Simultaneously improving the mechanical properties, dissolution performance, and hygroscopicity of ibuprofen and flurbiprofen by cocrystallization with nicotinamide. Pharm Res 2012;29:1854-65
27. Good DJ, Rodriguez-Hornedo N. Solubility advantage of pharmaceutical cocrystals. Cryst Growth Des 2009;9:2252-64
28. Aakeroy CB, Forbes S, Desper J. Using cocrystals to systematically modulate aqueous solubility and melting behavior of an anticancer drug. J Am Chem Soc 2009;131:17048-9
29. Cheney ML, Shan N, Healey ER, et al. Effects of crystal form on solubility and pharmacokinetics: a crystal engineering case study of lamotrigine. Cryst Growth Des 2010;10:394-405
30. Gao Y, Zu H, Zhang J. Enhanced dissolution and stability of adefovir dipivoxil by cocrystal formation. J Pharm Pharmacol 2011;63:483-90
31. Shiraki K, Takata N, Takano R, et al. Dissolution improvement and the mechanism of the improvement from cocrystallization of poorly water-soluble compounds. Pharm Res 2008;25:2581-92
32. Childs SL, Chyall LJ, Dunlap JT, et al. Crystal engineering approach to forming cocrystals of amine hydrochlorides with organic acids. molecular complexes of fluoxetine hydrochloride with benzoic, succinic, and fumaric acids. J Am Chem Soc 2004;126:13335-42 (Pubitemid 39382761)
33. Puschner B, Poppenga RH, Lowenstine LJ, et al. Assessment of melamine and cyanuric acid toxicity in cats. J Vet Diagn Invest 2007;19:616-24 (Pubitemid 351202170)
34. McNamara DP, Childs SL, Giordano J, et al. Use of a glutaric acid cocrystal to improve oral bioavailability of a low solubility API. Pharm Res 2006;23:1888-97 (Pubitemid 44200553)
35. Trask AV, Motherwell WDS, Jones W. Pharmaceutical cocrystallization: engineering a remedy for caffeine hydration. Cryst Growth Des 2005;5:1013-21 (Pubitemid 40755572)
36. Trask AV, Motherwell WDS, Jones W. Physical stability enhancement of theophylline via cocrystallization. Int J Pharm 2006;320:114-23 (Pubitemid 44128714)
37. Ghosh S, Bag PP, Reddy CM. Co-crystals of sulfamethazine with some carboxylic acids and amides: co-former assisted tautomerism in an active pharmaceutical ingredient and hydrogen bond competition study. CrystEngComm 2011;11:3489-503
38. Vangala VR, Chow PS, Tan RBH. Characterization, physicochemical and photo-stability of a co-crystal involving an antibiotic drug, nitrofurantoin, and 4-hydroxybenzoic acid. CrystEngComm 2011;13:759-62
39. Braga D, Grepioni F. Reactions between or within molecular crystals. Angew Chem Int Ed 2004;43:4002-11 (Pubitemid 39257445)
40. MacGillivray LR, Papaefstathiou GS, Friscić T, et al. Supramolecular control of reactivity in the solid state: from templates to ladderanes to metal-organic frameworks. Acc Chem Res 2008;41:280-91
41. Duncan-Hewitt WC, Weatherly GC. Modeling the uniaxial compaction of pharmaceutical powders using the mechanical properties of single crystals. II: brittle materials. J Pharm Sci 1990;79:273-8 (Pubitemid 20146497)
42. Duncan-Hewitt WC, Weatherly GC. Modeling the uniaxial compaction of pharmaceutical powders using the mechanical properties of single crystals. I: Ductile materials. J Pharm Sci 1990;79:147-52 (Pubitemid 20148535)
43. Meier M, John E, Wieckhusen D, et al. Influence of mechanical properties on impact fracture: prediction of the milling behaviour of pharmaceutical powders by nanoindentation. Powder Technol 2009;188:301-13
44. Sun CC. Decoding powder tabletability-roles of particle adhesion and plasticity. J Adhes Sci Technol 2011;25(4):483-99
45. Sun CC, Hou H. Improving mechanical properties of caffeine and methyl gallate crystals by cocrystallization. Cryst Growth Des 2008;8(5):1575-9
46. Karki S, Friscić T, Fábián L, et al. Improving mechanical properties of crystalline solids by cocrystal formation: new compressible forms of paracetamol. Adv Mater 2009;21:3905-9
47. Chattoraj S, Shi L, Sun CC. Understanding the relationship between crystal structure, plasticity and compaction behavior of theophylline, methyl gallate, and their 1:1 cocrystal. CrystEngComm 2010;12:2466-72
48. Perumalla SR, Shi L, Sun CC. Improved mechanical properties of an ionized form of acetaminophen. CrystEngComm 2012;14:2389-90
49. Sun CC, Grant DJW. Influence of crystal structure on the tableting properties of sulfamerazine polymorphs. Pharm Res 2001;18(3):274-80 (Pubitemid 32595813)
50. Bag PP, Chen M, Sun CC, Reddy CM. Direct correlation among crystal structure, mechanical behaviour and tabletability in a trimorphic molecular compound. CrystEngComm 2012;14:3865-7
51. Lundblad RL, Macdonald FM. Handbook of biochemistry and molecular biology. 4th edition. CRC Press; New York: 2010. p. 537-945
52. Banerjee R, Bhatt PM, Ravindra NV, Desiraju GR. Saccharin salts of active pharmaceutical ingredients, their crystal structures, and increased water solubilities. Cryst Growth Des 2005;5:2299-309 (Pubitemid 41619324)
53. Porter WW III, Elie SC, Matzger AJ. Polymorphism in carbamazepine cocrystals. Cryst Growth Des 2008;8:14-16
54. Aitipamula S, Chow PS, Tan RBH. Dimorphs of a 1:1 cocrystal of ethenzamide and saccharin: solid-state grinding methods result in metastable polymorph. CrystEngComm 2009;11:889-95
55. Basavoju S, Bostrom D, Velaga SP. Indomethacin-saccharin cocrystal: design, synthesis and preliminary pharmaceutical characterization. Pharm Res 2008;25:530-41 (Pubitemid 351357724)
56. Bhatt PM, Ravindra NV, Banerjeea R, Desiraju GR. Saccharin as a salt former. Enhanced solubilities of saccharinates of active pharmaceutical ingredients. Chem Commun 2005;1073-5 (Pubitemid 40363476)
57. Takata N, Takano R, Uekusa H, et al. A spironolactone-saccharin 1:1 cocrystal hemihydrate. Cryst Growth Des 2010;10:2116-22
58. Lu E, Rodríguez-Hornedo N, Suryanarayanan R. A rapid thermal method for cocrystal screening. CrystEngComm 2008;10:665-8
59. Jeanjean B, Alberola S, Terol A, Sabon F. Study of paracetamol- theophylline and paracetamol-caffeine associations. Ann Pharm Fr 1979;37:95-100
60. Aitipamula S, Chow PS, Tan RBH. Trimorphs of a pharmaceutical cocrystal involving two active pharmaceutical ingredients: potential relevance to combination drugs. CrystEngComm 2009;11:1823-7
61. Vishweshwar P, McMahon JA, Peterson ML, et al. Crystal engineering of pharmaceutical co-crystals from polymorphic active pharmaceutical ingredients. Chem Comm 2005;4601-3 (Pubitemid 41428459)
62. Sanphui P, Goud NR, Khandavilli UBR, Nangia A. Fast dissolving curcumin cocrystals. Cryst Growth Des 2011;11:4135-45
63. Schultheiss N, Bethune S, Henck J-O. Nutraceutical cocrystals: utilizing pterostilbene as a cocrystal former. CrystEngComm 2010;12:2436-42
64. Bethune SJ, Schultheiss N, Henck J-O. Improving the poor aqueous solubility of nutraceutical compound pterostilbene through cocrystal formation. Cryst Growth Des 2011;11:2817-23
65. Miller JM, Collman BM, Greene LR, et al. Identifying the stable polymorph early in the drug discovery-development process. Pharm Dev Technol 2005;10:291-7 (Pubitemid 40677449)
66. Zhang GGZ, Henry RF, Borchardt TB, Lou X. Efficient co-crystal screening using solution-mediated phase transformation. J Pharm Sci 2007;96:990-5 (Pubitemid 46797470)
67. Bag PP, Patni M, Reddy CM. A kinetically controlled crystallization process for identifying new co-crystal forms: fast evaporation of solvent from solutions to dryness. CrystEngComm 2011;13:5650-2
68. Padrela L, Rodrigues MA, Velaga SP, et al. Formation of indomethacin-saccharin cocrystals using supercritical fluid technology. Eur J Pharm Sci 2009;38:9-17
69. Jayasankar A, Somwangthanaroj A, Shao ZJ, Rodríguez-Hornedo N. Cocrystal formation during cogrinding and storage is mediated by amorphous phase. Pharm Res 2006;23:2381-92 (Pubitemid 44511518)
70. Chadwick K, Davey R, Cross W. How does grinding produce co-crystals? Insights from the case of benzophenone and diphenylamine. CrystEngComm 2007;9:732-4
71. Friscić T, Jones W. Recent advances in understanding the mechanism of cocrystal formation via grinding. Cryst Growth Des 2009;9:1621-37
72. Chattoraj S, Bhugra C, Telang C, et al. Origin of two modes of non-isothermal crystallization of glasses produced by milling. Pharm Res 2012;29:1020-32
73. Friscić T, Trask AV, Jones W, Motherwell WDS. Screening for inclusion compounds and systematic construction of three-component solids by liquid-assisted grinding. Angew Chem Int Ed 2006;118:7708-12
74. Weyna DR, Shattock T, Vishweshwar P, Zaworotko MJ. Synthesis and structural characterization of cocrystals and pharmaceutical cocrystals: mechanochemistry vs slow evaporation from solution. Cryst Growth Des 2009;9:1106-23
75. Berry DJ, Seaton CC, Clegg W, et al. Applying hot-stage microscopy to co-crystal screening: a study of nicotinamide with seven active pharmaceutical ingredients. Cryst Growth Des 2008;8:1697-712
76. Medina C, Daurio D, Nagapudi K, Alvarez-Nunez F. Manufacture of pharmaceutical co-crystals using twin screw extrusion: a solvent-less and scalable process. J Pharm Sci 2010;99:1693-6
77. Desiraju GR. Supramolecular synthons in crystal engineering-a new organic synthesis. Angew Chem Int Ed 2003;34:2311-27
78. Vishweshwar P, McMahon JA, Oliveira M, et al. The predictably elusive form II of aspirin. J Am Chem Soc 2005;127:16802-3 (Pubitemid 41772837)
79. Lemmerer A, Bernstein J, Griesser UJ, et al. A tale of two polymorphic pharmaceuticals: pyrithyldione and propyphenazone and their 1937 co-crystal patent. Chem Eur J 2011;17:13445-60
80. Ueto T, Takata N, Muroyama N, et al. Polymorphs and a hydrate of furosemidenicotinamide 1:1 cocrystal. Cryst Growth Des 2012;12:485-94
81. Gryl M, Krawczuk A, Stadnicka K. Polymorphism of urea-barbituric acid co-crystals. Acta Cryst Sect B-Struct Sci 2008;64:623-32
82. Braga D, Palladino G, Polito M, et al. Three polymorphic forms of the co-crystal 4, 4¢-bipyridine/pimelic acid and their structural, thermal, and spectroscopic characterization. Chem Euro J 2008;14:10149-59
83. Stahly GP. Diversity in single-and multiple-component crystals. The search for and prevalence of polymorphs and cocrystals. Cryst Growth Des 2007;7:1007-26
84. Aakeroy CB, Beatty AM, Helfrich BA. Total synthesis" supramolecular style: design and hydrogen-bond-directed assembly of ternary supermolecules. Angew Chem Int Ed 2001;40:3240-2 (Pubitemid 32845406)
85. Karki S, Friscić T, Jones W, Motherwell WDS. Screening for pharmaceutical cocrystal hydrates via neat and liquid-assisted grinding. Mol Pharm 2007;3:347-54 (Pubitemid 46983951)
86. Bhogala BR, Basavoju S, Nangia A. Three-component carboxylic acid-bipyridine lattice inclusion host. Supramolecular synthesis of ternary cocrystals. Cryst Growth Des 2005;5:1683-6 (Pubitemid 41362443)
87. Cheung EY, Kitchin SJ, Harris KDM, et al. Direct structure determination of a multicomponent molecular crystal prepared by a solid-state grinding procedure. J Am Chem Soc 2003;125:14658-9 (Pubitemid 37475529)
88. Aakeroy CB, Desper J, Smith MM. Constructing, deconstructing, and reconstructing ternary supermolecules. Chem Comm 2007;3936-8 (Pubitemid 351194494)
89. Tothadi S, Mukherjee A, Desiraju GR. Shape and size mimicry in the design of ternary molecular solids: towards a robust strategy for crystal engineering. Chem Comm 2011;47:12080-2
90. Sherman BC. Solid substances comprising valproic acid and sodium valproate. US6077542; 2000
91. Petrusevski G, Naumov P, Jovanovski G, et al. Solid-state forms of sodium valproate, active component of the anticonvulsant drug Epilim. ChemMedChem 2008;3:1377-86
92. Brittain HG. Vibrational spectroscopic studies of cocrystals and salts. 3. Cocrystal products formed by benzenecarboxylic acids and their sodium salts. Cryst Growth Des 2010;10:1990-2003
93. Brittain HG. Vibrational spectroscopic studies of cocrystals and salts. 4. Cocrystal products formed by benzylamine, alpha-methylbenzylamine, and their chloride salts. Cryst Growth Des 2011;11:2500-9
94. Pop M, Sieger P, Cains P. Tiotropium fumarate: an interesting pharmaceutical cocrystal. J Pharm Sci 2009;98:1820-34
95. Chen AM, Ellison ME, Peresypkin A, et al. Development of a pharmaceutical cocrystal of a monophosphate salt with phosphoric acid. Chem Comm 2007;419-21 (Pubitemid 46105535)
96. Harrison WTA, Yathirajan HS, Bindya S, et al. Escitalopram oxalate: co-existence of oxalate dianions and oxalic acid molecules in the same crystal. Acta Cryst 2007;C63:o129-31
97. Smaldone RA, Forgan RS, Furukawa H, et al. Metal-organic frameworks from edible natural products. Angew Chem Int Ed 2010;49:8630-4
98. Miller JS, Stevens KR, Yang MT, et al. Rapid casting of patterned vascular networks for perfusable engineered three-dimensional tissues. Nat Mater 2012;11:768-74
99. Bak A, Gore A, Yanez E, et al. The co-crystal approach to improve the exposure of a water-insoluble compound: AMG 517 sorbic acid co-crystal characterization and pharmacokinetics. J Pharm Sci 2008;97:3942-56
100. Arora KK, Tayade NG, Suryanarayanan R. Unintended water mediated cocrystal formation in carbamazepine and aspirin tablets. Mol Pharm 2011;8:982-9
101. Good D, Miranda C, Rodríguez-Hornedo N. Dependence of cocrystal formation and thermodynamic stability on moisture sorption by amorphous polymer. CrystEngComm 2011;13:1181-9
102. Zhang S-W, Guzei IA, de Villiers MM, et al. Formation enthalpies and polymorphs of nicotinamide-R-mandelic acid co-crystals. Cryst Growth Des 2012;12:4090-7
103. Karamertzanis PG, Kazantsev AV, Issa N, et al. Can the formation of pharmaceutical cocrystals be computationally predicted? 2. Crystal structure prediction. J Chem Theory Comput 2009;5:1432-48
104. Day GM, Cooper TG, Cruz-Cabeza AJ, et al. Significant progress in predicting the crystal structures of small organic molecules-a report on the fourth blind test. Acta Cryst 2009;B65:107-25