Pharmaceutical co-crystals - A review

Ars Pharmaceutica

Volumn 50, Issue 3, 2009, Pages 99-117

  Sekhon, B S ^a  

^a Punjab College of Technical Education   (India)

Author keywords

Co crystallization; Heterosynthon; Hydrogen bonding; Pharmaceutical co crystal; Polymorph

Indexed keywords

CAPROLACTAM; EXEMESTANE; LAMIVUDINE; MEGESTROL ACETATE; NANOCRYSTAL; RESORCINOL; SUCCINIC ACID; ZIDOVUDINE;

CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; CHIRALITY; CRYSTAL; CRYSTAL STRUCTURE; CRYSTALLIZATION; DRUG BIOAVAILABILITY; DRUG FORMULATION; DRUG MECHANISM; DRUG SCREENING; DRUG SOLUBILITY; DRUG STABILITY; DRUG SYNTHESIS; FORCE; GENETIC POLYMORPHISM; HUMAN; MOLECULAR INTERACTION; PATENT; REVIEW; STOICHIOMETRY; THERMODYNAMICS;

EID: 76149121856     PISSN: 00042927     EISSN: 00042927     Source Type: Journal    
DOI: None     Document Type: Review

References (111)

1. Shan N, Zaworotko MJ. The role of co-crystals in pharmaceutical science. Drug Discovery Today 2008; 13:440-446.
2. Trask AV, Motherwell WDS, Jones W. Physical stability enhancement of theophylline via co-crystallization. Int J Pharm 2006; 320:114-123.
3. Jones W, Motherwell WDS, Trask AV. Pharmaceutical co-crystals: An Emerging approach to physical property enhancement. MRS Bull 2006; 31:875-879.
4. Zaworotko M. Crystal engineering of co-crystals and their relevance to pharmaceuticals and solid-state chemistry. Acta Cryst 2008; A64: C11-C12.
5. Sun CC, Hou H. Improving mechanical properties of caffeine and methyl gallate crystals by Co-crystallization. Cryst Grow Des 2008; 8:1575-1570.
6. Rodríguez-Hornedo N, Nehm SJ, Jayasankar A, Cocrystals: design, properties and formation mechanisms, In Encyclopedia of Pharmaceutical Technology, 3rd ed, Taylor & Francis, London, 2007, 615-635.
7. Aakeröy CB, Fasulo ME, Desper J. Cocrystal or salt: Does it really matter? Mol Pharma 2007; 4:317-322.
8. Trask AV. An overview of pharmaceutical co-crystals as intellectual property. Mol Pharma 2007; 4:301-309.
9. Jayasankar A, Somwangthanaroj A, Shao ZJ, Rodriguez-Hornedo N. Co-crystal formation during cogrinding and storage is mediated by amorphous phase. Pharm Res 2006; 23: 2381-2392.
10. Aakeroy CB, Salmon DJ. Building co-crystals with molecular sense and supramolecular sensibility. Cryst Eng Comm 2005; 7:439-448.
11. Miroshnyk I, Mirza S, Sandler N. Pharmaceutical co-crystals-an opportunity for drug product enhancement.Expert Opin Drug Delivery 2009; 6:333-341.
12. McMahon JA. Crystal Engineering of Novel Pharmaceutical Forms . Master of Science Thesis, Department of Chemistry, University of South Florida, USA, 2006.
13. Walsh RDB, Bradner MW,Fleischman S, Morales LA, Moulton B, Rodriguez-Hornedo N, Zaworotko MJ. Crystal engineering of the composition of pharmaceutical phases. Chem Commun 2003;186-187.
14. Schultheiss N, Newman A. Pharmaceutical co-crystals and their physicochemical properties. Cryst Growth Des.2009; 9: 2950-2967.
15. Tiekink ERT, Vittal JJ (Editors). Frontiers in Crystal Engineering, John Wiley & Sons, Ltd, 2006, Chapter 2: Crystal Engineering of Pharmaceutical Co-crystals, pp 25-50.
16. Vishweshwar P, McMahon JA, Bis JA, Zaworotko MJ. Pharmaceutical co-crystals J Pharm Sci 2006; 95:499-516.
17. Remenar JF, Morissette SL, Peterson ML, Moulton B, MacPhee JM, Guzmán H, Almarsson O, Crystal engineering of novel co-crystals of a triazole drug with 1,4-dicarboxylic acids. J Am Chem Soc 2003; 125:8456-8457.
18. Almarsson Ö, Zaworotko MJ. Crystal engineering of the composition of pharmaceutical phases. Do pharmaceutical co-crystals represent a new path to improved medicines? Chem Commun 2004; 1889-1896.
19. Peterson ML, Hickey MB, Zaworotko MJ, Almarsson O. Expanding the scope of crystal form evaluation in pharmaceutical science. J Pharm Pharmaceut Sci 2006; 9(3):317-326.
20. Fleischman SG, Kuduva SS,McMahon JA,Moulton B,Walsh RB, Rodriguez-Hornedo N, Zaworotko MJ. Crystal engineering of the composition of pharmaceutical phases. 2. Multiple component crystalline solids involving carbamazepine. Cryst Growth Des 2003; 3; 909-919.
21. McNamara DP, Childs SL, Giordano J, Iarriccio A, Cassidy J, Shet MS, Mannion R, O'Donnell E, Park A.Use of a glutaric acid cocrystal to improve oral bioavailability of a low solubility API. Pharma Res 2006; 23: 1888-1897.
22. Vishweshwar P, McMahon JA, Peterson ML, Hickey MB,Shattock TR, Zaworotko MJ. Crystal engineering of pharmaceutical co-crystals from polymorphic active pharmaceutical ingredients. Chem Commun.2005; 4601-4603.
23. Babu NJ, Reddy LS, Aitipamula S, Nangia A. Polymorphs and olymorphic cocrystals of temozolomide. Chem Asian J 2008; 3:1122-1133.
24. Sarma B, Reddy LS, Nangia A. The role of π-stacking in the composition of phloroglucinol and phenazine cocrystals. Cryst Growth Des 2008; 8:4546-4552.
25. Vishweshwar P, Nangia A, Lynch VM. Molecular complexes of homologous alkanedicarboxylic acids with isonicotinamide: X-ray crystal structures, hydrogen bond synthons, and melting point alternation. Crystal Growth Design 2003; 3:783-790.
26. Stahly GP. Diversity in single-and multiple-component crystals. The search for and prevalence of polymorphs and co-crystals. Cryst Growth Des 2007; 7:1007-1026.
27. Childs SL, Stahly GP, Park A. Salts and co-crystals of theophylline. Mol Pharma 2007; 4:323-338.
28. Stahl PH, Wermuth CG, editors. Handbook of pharmaceutical salts: properties, selection, and use. New York: Wiley-VCH; 2002.p 374
29. Serajuddin ATM. Salt formation to improve drug solubility. Advanced Drug Delivery Rev 2007; 59: 603-616.
30. Etter MC. Resolution of chiral olefinic hydrocarbons and sulfoxides by high-performance liquid chromatography via diastereomeric platinum complexes. J Am Chem Soc 1982; 104:1095-1096.
31. Etter MC. Hydrogen bonds as design elements in organic chemistry. J Phys Chem 1991; 95:4601-4610.
32. Etter MC. Encoding and decoding hydrogen bonds patterns of organic compounds. Acc Chem Res 1990; 23:120-126.
33. Whitesides GM, Wong AP. The intersection of biology and materials science.MRS Bull 2006; 31:19-27.
34. Mohamed S, Tocher DA, Vickers M, Karamertzanis PG,Price SL.Salt or co-crystal? A new series of crystal structures formed from simple pyridines and carboxylic acids. Cryst Growth Des 2009; 9: 2881-2889.
35. Trask AV, Motherwell WDS, Jones W. Pharmaceutical co-crystallization: Engineering a remedy for caffeine hydration. Cryst Grow Des 2005; 5: 1013-1021.
36. Berry DJ, Seaton CC, Clegg W, Harrington RW, Coles SJ, Horton PN, Hursthouse MB, Storey R, Jones W, Friscic T, Blagden N. Applying hot-stage microscopy to co-crystal screening: A study of nicotinamide with seven active pharmaceutical ingredients. Cryst Grow Des 2008; 8: 1697-1712.
37. Trask AV, Jones W. Crystal engineering of organic co-crystals by the solid-state grinding approach. Top Curr Chem 2005; 254: 41-70.
38. Takata N, Shiraki K, Takano R, Hayashi Y, Terada Y. Co-crystal screening of stanolone and mestanolone using slurry crystallization. Cryst Growth Des 2008; 8: 3032-3037.
39. Shekunov BY, York P. Crystallization processes in pharmaceutical technology and drug delivery design. J Cryst Growth 2000; 211: 122-136.
40. Morissette SL, Almarsson O, Peterson ML, Remenar JF, Read MJ, Lemmo AV, Ellis S, Cima MJ, Gardner CR. High-throughput crystallization: polymorphs, salts, co-crystals and solvates of pharmaceutical solids. Adv Drug Deliver Rev 2004; 56:275-300.
41. Trask AV, Haynes DA, Motherwell WDS, Jones W. Screening for crystalline salts via mechanochemistry. Chem Commun 2006;51-53.
42. Trask AV, van de Streek J, Motherwell WDS, Jones W. Achieving polymorphic and stoichiometric diversity in co-crystal formation:importance of solid-state grinding, Powder X-ray structure determination and seeding. Cryst Growth Des 2005; 5: 2233-2241.
43. Friscis T, Jones W. Recent advances in understanding the mechanism of cocrystal Formation via grinding. Cryst Growth Des 2009; 9: 1621-1637.
44. Morissette SL, Almarsson Ö, Peterson ML, Remenar J F,Read MJ, Lemmo AV, Ellis S, Cima MJ, Gardner CR. High-Throughput crystallization: Polymorphs, salts, co-crystals and solvates of pharmaceutical solids. Adv Drug Delivery Rev 2004; 56:275-300.
45. Blagden N, de Matas M, Gavan PT, York P. Crystal engineering of active pharmaceutical ingredients to improve solubility and dissolution rates. Advanced Drug Delivery Rev 2007;59:617-630.
46. 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: 1106-1123.
47. Viertelhaus M, Hilfiker R, Blatter F. Piracetam co-crystals with OH-group functionalized carboxylic acids. Cryst Growth Des 2009; 9: 2220-2228.
48. Karki S, Friscic T, Jones W, Motherwell WDS.Screening for Pharmaceutical cocrystal Hydrates via neat and liquid-assisted grinding. Mol pharmaceutics 2007; 4: 347-354.
49. Mcmahon, Jennifer , Peterson, Matthew , Zaworotko, Michael J. ,Shattock, Tanise ,Bourghol Hickey, Magali .Pharmaceutical Co-Crystal Compositions and Related Methods of Use . Patent number: 20070299033, 11/629807, 12/27/2007]
50. Anderson KM, Probert MR, Whiteley CN, Rowland AM, Goeta AE, Steed JW. Designing co-Crystals of pharmaceutically relevant compounds that crystallize with Z' > 1. Cryst Growth Desn 2009;9:1082-1087.
51. Bu ar DK, Henry RF, Lou X, Borchardt TB, Zhang GGZ. A hidden co-crystal of caffeine and adipic acid. Chem Commun 2007; 525-527.
52. Jayasankar A, Reddy LS, Bethune SJ, Rodr guezHornedo N. Role of co-crystal and solution chemistry on the formation and stability of co-crystals with different stoichiometry. Cryst Growth Des 2009; 9:889-897.
53. Caira MR. Sulfa drugs as model co-crystal formers. Mol Pharmaceut 2007; 4:310-316.
54. Bhatt PM, Azim Y, Thakur TS, Desiraju GR. Co-Crystals of the anti-HIV drugs lamivudine and zidovudine. Cryst Growth Des 2009;9:951-957
55. Bis JA, McLaughlin OL, Vishweshwar P, Zaworotko MJ. Supramolecular heterocatemers and their role in cocrystal design. Cryst Growth Des 2006; 6:2648-2650.
56. Trask AV, Samuel Motherwell WD, Jones W. Pharmaceuticalco- crystallization: Engineering a remedy for caffeine hydration. Cryst Growth Des 2005; 5:1013-1021.
57. Karki S, Friscic T, Jones W. Control and interconversion of co-crystal stoichiometry in grinding: stepwise mechanism for the formation of a hydrogen-bonded cocrystal. CrystEngComm 2009; 11: 470-481.
58. Alexander R, Borden F, Spragg R, Using Raman Spectroscopy to Characterize Pharmaceutical Co-crystals. PerkinElmer LAS, Nizar Issa, Robert Lancaster, University College, London.
59. Friscic T, Childs SL, Rizvi SAA, Jonesurnal W: The role of solvent in mechanochemical and sonochemical co-crystal formation: a solubility-based approach for predicting co-crystallisation outcome. CrystEngComm 2009; 11: 418-426.
60. Childs SL, Hardcastle KI. Co-crystals of piroxicam with carboxylic acids. Cryst Growth Des 2007; 7:1291-1304.
61. McNamara DP, Childs SL, Giordano J, Iarriccio A, Cassidy J, Shet M S, Mannion R, O'Donnell E, Park A. Use of a glutaric acid cocrystal to improve oral bioavailability of a low solubility API. Pharma Resh 2006; 23: 1888-1897.
62. Childs SL, Hardcastle KI. Co-crystals of chlorzoxazone with carboxylic acids. CrystEngComm 2007; 9: 364-367.
63. Childs, SL. Co-crystallization methods. Application No.: 11/527395, Publication Date: 04/19/2007.
64. Newman AW, Childs SL, Cowans BA. Salt and co-crystal form selection, Chapter 14, In: Preclinical Development Handbook: ADME and Biopharmaceutical Properties, Gad SC(Editor), Wiley, 2008.
65. Padrela L, Rodrigues MA, Velaga SP, Matos HA, Azevedo EG. Formation of indomethacin-saccharin co-crystals using supercritical fluid technology. Eur J Pharm Sci 2009; online 27 May 2009
66. Ter Horst H, Deij MA, Cains PW. Discovering new co-crystals. Cryst Growth Des 2009; 9:1531-1537.
67. Karki S, Friscic T, Jones W, Motherwell WDS. Screening for pharmaceutical co-crystal hydrates via neat and liquid-assisted grinding. Mol pharmaceutics 2007; 4:347-354.
68. Friscic T, Childs SL, Rizvi SAA, Jones W. The role of solvent in mechanochemical and sonochemical cocrystal formation: a solubility-based approach for predicting co-crystallisation outcome. CrystEngComm 2009; 11; 418-426.
69. Chen AM, Ellison ME, Peresypkin A, Wenslow RM, Variankaval N, Savarin CG, Natishan TK, Mathre DJ,Dormer PG, Euler DH,Ball RG, Ye Z, Wang Y, Santos I. Development of a pharmaceutical co-crystal of a monophosphate salt with phosphoric acid. Chemical communications 2007; 419-421.
70. Velaga SP, Basavoju S, Boström D. Norfloxacin saccharinate-saccharin dihydrate cocrystal -A new pharmaceutical co-crystal with an organic counter ion . J Mol Struct 2008; 889:150-153.
71. Sarma B, Reddy LS, Nangia A. The Role of π-stacking in the composition of phloroglucinol and phenazine co-crystals. Cryst Growth Des 2008; 8:4546-4552.
72. Issa N, Karamertzanis PG, Welch GWA, Price SL. Can the formation of pharmaceutical co-crystals be computationally predicted? I. Comparison of lattice energies. Cryst Growth Des 2009; 9:442-453.
73. Karamertzanis PG, Kazantsev AV, Issa N, Welch GWA, Adjiman CS, Pantelides CC, Price SL. Can the formation of pharmaceutical cocrystals be computationally predicted? 2. Crystal structure prediction. J Chem Theory Comput 2009; 5: 1432-1448.
74. Friscic T, Fabian L, Burley JC, Jones W, Motherwell WDS. Exploring cocrystal-cocrystal reactivity via liquid-assisted grinding: assembling of racemic and dismantling of enantiomeric co-crystals . Chem commun 2006; 5009-5011.
75. Childs SL, Chyall LJ, Dunlap JT, Smolenskaya VN, Stahly BC, Stahly GP. 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; 13335-13342.
76. Jayasankar A, Somwangthanaroj A, Shao ZJ, Rodriguez-Hornedo N. Co-crystal formation during cogrinding and storage is mediated by amorphous phase. Pharma Res 2006; 23:2381-2392.
77. Jayasankar A, Good DJ, Rodríguez-Hornedo N. Mechanisms by which moisture generates co-crystals. Mol Pharm 2007; 4:360-372.
78. Rodríguez-Hornedo N, Nehm SJ, Seefeldt KF, Pagán-Torres Y, Falkiewicz CJ. Reaction crystallization of pharmaceutical molecular complexes Mol Pharm 2006; 3:362-367.
79. Cincić D, Friscić T, Jones W. A stepwise mechanism for the mechanochemical synthesis of halogen-bonded co-crystal architectures. J Am Chem Soc 2008; 130:7524-7525.
80. Shiraki K, Takata N, Takano R, Hayashi Y, Terada K. Dissolution improvement and the mechanism of the improvement from co-crystallization of poorly water-soluble compounds. Pharm Res 2008; 25:2581-2592.
81. Jayasankar A. Understanding the mechanisms, thermodynamics and kinetics of cocrystallization to control phase transformations. Doctor of Philosophy Dissertation (Pharmaceutical Sciences), University of Michigan, USA, 2008.
82. Callear SK. Preparation, characterization and structural analysis of salts and co-crystals of organic compounds. University of Southampton, School of Chemistry, PhD Thesis, 2008, 253pp. http://eprints.soton.ac.uk/51224/]
83. Wenger M, Bernstein J. An alternate crystal form of gabapentin: A cocrystal with oxalic acid. Cryst Growth Des 2008; 8: 1595-1598.
84. Basavoju S, Bostrom D, Velaga SP. Indomethacin-saccharin co-crystal: Design, synthesis and preliminary pharmaceutical characterization. Pharm Res 2008; 25: 530-541.
85. Lu J, Rohani S. Preparation and characterization of theophylline - nicotinamide cocrystal. Org Process Res Dev, Article ASAP DOI: 10.1021/op900047r Publication Date (Web): May 28, 2009.
86. Allesø M, Velaga S, Alhalaweh A, Cornett C, Rasmussen MA, van den Berg F, de Diego HL, Rantanen J. Near-Infrared Spectroscopy for cocrystal screening. A comparative study with Raman Spectroscopy. Anal Chem 2008; 80:7755-7764.
87. Lu E, Rodríguez-Hornedo N, Suryanarayanan R. A rapid thermal method for cocrystal screening. CrystEngComm 2008; 10; 665- 668.
88. Variankaval N, Wenslow R, Murry J, Hartman R, Helmy R, Kwong E, Clas SD, Dalton C, Santos I. Preparation and solid-state characterization of nonstoichiometric co-crystals of a phosphodiesterase-IV inhibitor and L-tartaric acid . Cryst Growth Des 2006; 6: 690-700.
89. Wang S, Chen J. Gossypol co-crystals and the use thereof. United States Patent 7432300.
90. Cooke CL, Davey RJ. On the solubility of saccharinate salts and co-crystals. Cryst Growth Des 2008; 8: 3483-3485.
91. Nehm SJ, Rodríguez-Spong B, Rodríguez-Hornedo N. Phase solubility diagrams of co-crystals are explained by solubility product and solution complexation. Cryst Growth Des 2006; 6: 592-600.
92. Good DJ, Rodriguez-Hornedo N. Solubility advantage of pharmaceutical co-crystals. Cryst Growth Des 2009;9:2252-2264.
93. Ainouz A, Authelin JR, Billot P, Lieberman H. Modeling and prediction of co-crystal phase diagrams. Int J Pharmaceut 2009; 374: 82-89.
94. Schartman RR. On the thermodynamics of co-crystal formation. Int J Pharmaceut 2009; 365:77-80.
95. Karamertzanis PG, Kazantsev AV, Issa N, Welch GWA, Adjiman CS, Pantelides CC, Price SL."Modeling and prediction of the crystal structure of pharmaceutical cocrystals," presented at AIChE Annual Meeting, Philadelphia, PA, November 2008, 557b
96. Pop M, Sieger P, Cains PW. Tiotropium fumarate: an interesting pharmaceutical co-crystal. J Pharm Sci 2009; 98:1820-1834.
97. Koshima H, Miyauchi M. Polymorphs of a cocrystal with achiral and chiral structures prepared by pseudoseeding: Tryptamine /hydrocinnamic acid. Cryst Growth Des 2001; 1:355-357.
98. Schultz DA. Crystal Engineering of Co-crystals of Curcumin. Sixth Annual Raymond N. Castle Student Research Conference. Department of Chemistry,University of South Florida, 2008.
99. Handler N, Jaeger W, Puschacher H, Leisser K, Erker T. Synthesis of novel curcumin analogues and their evaluation as selective cyclooxygenase-1 (COX-1)inhibitors. Chem Pharm Bull 2007;55: 64-71.
100. Fahlman, B. D. Materials Chemistry; Springer: Mount Pleasant, MI, 2007; Vol. 1, pp 282-283.
101. Müller RH, Keck CM. Second generation of drug nanocrystals for delivery of poorly soluble drugs: smart Crystal technology. European Journal of Pharmaceutical Sciences 2008; 34:S20- S21;19th Helsinki Drug Research 2008, June 9-11, 2008, Helsinki,Finland, Abstracts: 19th Helsinki Drug Research 2008.
102. Keck CM, Müller RH. Drug nanocrystals of poorly soluble drugs produced by high pressure homogenisation . Eur J Pharma Biopharmaceut 2006; 62:3-16.
103. Hideko K. Preparation of nanococrystals of aminonitropyridines. Nippon Kagakkai Koen Yokoshu 2004; 84: 644.
104. Al-Kaysi RO, Muller AM, Frisbee RJ, Bardeen CJ. Formation of co-crystal nanorods by solid-state reaction of tetracyanobenzene in 9-methylanthracene molecular crystal nanorods. Cryst Growth Des 2009;9:1780-1785.
105. Butar DK, MacGillivray LR. Preparation and reactivity of nanocrystalline co-crystals formed via sonocrystallization. J Am Chem Soc 2007; 129:32-33.
106. Sreekanth BR, Vishweshwar P, Vyas K. Supramolecular synthon polymorphism in 2 : 1 co-crystal of 4-hydroxybenzoic acid and 2,3,5,6 -tetramethylpyrazine. Chem commun 2007; 3375-3377.
107. Badu N. J.; Reddy S. L.; Aitipamula S.; Nangia A. Polymorphs and polymorphic cocrystals of temozolomide. Chem Asian J 2008; 3:1122-1133.
108. Porter WW, III, Elie SC, Matzger AJ. Polymorphism in carbamazepine co-crystals. Cryst Growth Des 2008;8:14-16.
109. Ter Horst JH, Cains PW. Co-Crystal polymorphs from a solvent-mediated transformation Cryst Growth Des 2008;8: 2537-2542.
110. Aitipamula S, Chow PS, Tan RBH. Dimorphs of a 1 : 1 co-crystal of ethenzamide and saccharin: solid-state grinding methods result in metastable polymorph. CrystEngComm 2009; 11: 889-895.
111. Hickey MB, Peterson ML, Scoppettuolo LA., Morrisette SL, Vetter A, Guzman H, Remenar JF, Zhang Z, Tawa MD, Haley S, Zaworotko MJ, Almarsson O. Performance comparison of a co-crystal of carbamazepine with marketed product. Eur J Pharmaceut Biopharmaceut 2007; 67: 112-119.