Cocrystal systems of pharmaceutical interest: 2010

Crystal Growth and Design

Volumn 12, Issue 2, 2012, Pages 1046-1054

  Brittain, Harry G ^a  

^a Center for Pharmaceutical Physics   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CO-CRYSTALS; COCRYSTALLIZATION; STATE OF THE ART; SUBJECT MATTERS;

EID: 84858010853     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg201510n     Document Type: Review

References (67)

1. Aakeröy, C. B.; Salmon, D. J. Building Cocrystals with Molecular Sense and Supramolecular Sensibility. CrystEngComm 2005, 7, 439-448. (Pubitemid 41396867)
2. Vishweshwar, P.; McMahon, J. A.; Bis, J. A.; Zaworotko, M. J. Pharmaceutical Cocrystals. J. Pharm. Sci. 2006, 95, 499-516.
3. Shan, N.; Zaworotko, M. J. The Role of Cocrystals in Pharmaceutical Science. Drug Discovery Today 2008, 13, 440-446.
4. Desiraju, G. R. Supramolecular Synthons in Crystal Engineering: A New Organic Synthesis. Angew. Chem., Int. Ed. 1995, 34, 2311-2327.
5. Stahly, G. P. A Survey of Cocrystals Reported Prior to 2000. Cryst. Growth Des. 2009, 9, 4212-4229.
6. Brittain, H. G. Cocrystal Systems of Pharmaceutical Interest: 2007-2008. Profiles of Drug Substances, Excipients, and Related Methodology; Brittain, H. G., Ed.; Elsevier Academic Press: Amsterdam, 2010; Vol. 35; pp 373-390.
7. Brittain, H. G. Cocrystal Systems of Pharmaceutical Interest: 2009. Profiles of Drug Substances, Excipients, and Related Methodology; Brittain, H. G., Ed.; Elsevier Academic Press: Amsterdam, 2010; Vol. 36; pp 361-381.
8. Friščić, T.; Jones, W. Benefits of Cocrystallization in Pharmaceutical Materials Science: An Update. J. Pharm. Pharmacol. 2010, 62, 1547-1559.
9. Merz, K.; Vasylyeva, V. Development and Boundaries in the Field of Supramolecular Synthons. CrystEngComm 2010, 12, 3989-4002.
10. Aakeröy, C. B.; Rajbanshi, A.; Li, Z. J.; Desper, J. Mapping out the Synthetic Landscape for Recrystallization, Cocrystallization, and Salt Formation. CrystEngComm 2010, 12, 4231-4239.
11. Seaton, C. G.; Chadwick, K.; Sadiq, G.; Guo, K.; Davey, R. J. Designing Acid/Acid Cocrystals through the Application of Hammett Substituent Constants. Cryst. Growth Des. 2010, 10, 726-733.
12. Hathwar, V. R.; Pal, R.; Row, T. N. G. Charge Density Analysis of Crystals of Nicotinamide with Salicylic Acid and Oxalic Acid: An Insight into the Salt to Cocrystal Continuum. Cryst. Growth Des. 2010, 10, 3306-3310.
13. Molčanov, K.; Kojić-Prodić, B. Salt and Cocrystals of Chloranilic Acid with Organic Bases: Is it Possible to Predict Salt Formation? CrystEngComm 2010, 12, 925-939.
14. Stevens, J. S.; Byard, S. J.; Schroeder, S. L. M. Characterization of Proton Transfer by X-Ray Photoelectron Spectroscopy. Cryst. Growth Des. 2010, 10, 1435-1442.
15. Stevens, J. S.; Byard, S. J.; Schroeder, S. L. M. Salt or Cocrystal? Determination of Protonation State by X-Ray Photoelectron Spectroscopy. J. Pharm. Sci. 2010, 99, 4453-4457.
16. Good, D. J.; Rodríguez-Hornedo, N. Cocrystal Eutectic Constants and Prediction of Solubility Behavior. Cryst. Growth Des. 2010, 10, 1028-1032.
17. Mohammad, M. A.; Alhalaweh, A.; Bashimam, M.; Al-Mardini, M. A.; Velaga, S. Utility of Hansen Solubility Parameters in the Cocrystal Screening. J. Pharm. Pharmacol. 2010, 62, 1360-1362.
18. Huang, N.; Rodríguez-Hornedo, N. Effect of Micellar Solubilization on Cocrystal Solubility and Stability. Cryst. Growth Des. 2010, 10, 2050-2053.
19. Lapidus, S. H.; Stephens, P. W.; Arora, K. K.; Shattock, T. R.; Zaworotko, M. J. A Comparison of Cocrystal Structure Solutions from Powder and Single Crystal Techniques. Cryst. Growth Des. 2010, 10, 4630-4637.
20. Clarke, H. D.; Arora, K. K.; Bass, H.; Kavusu, P.; Ong, T. T.; Pujari, T.; Wojtas, L.; Zaworotko, M. J. Structure-Stability Relationships in Cocrystal Hydrates: Does the Promiscuity of Water make Crystalline Hydrates the Nemesis of Crystal Engineerinǧ Cryst. Growth Des. 2010, 10, 2152-2167.
21. Brittain, H. G. 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.
22. Elbagerma, M. A.; Edwards, H. G. M.; Munshi, T.; Hargreaves, M. D.; Matousek, P.; Scowen, I. J. Characterization of New Cocrystals by Raman Spectroscopy, Powder X-ray Diffraction, Differential Scanning Calorimetry, and Transmission Raman Spectroscopy. Cryst. Growth Des. 2010, 10, 2360-2371.
23. Kojima, T.; Tsutsumi, S.; Yamamoto, K.; Ikeda, Y.; Moriwaki, T. High-Throughput Cocrystal Slurry Screening by use of in situ Raman Microscopy and Multi-Well Plate. Int. J. Pharm. 2010, 399, 52-59.
24. Urbanus, J.; Roelands, C. P. M.; Verdoes, D.; Jansens, P. J.; ter Horst, J. H. Cocrystallization as a Separation Technology: Controlling Product Concentrations by Cocrystals. Cryst. Growth Des. 2010, 10, 1171-1179.
25. Boyd, S.; Back, K.; Chadwick, K.; Davey, R. J.; Seaton, C. C. Solubility, Metastable Zone Width Measurement and Crystal Growth of the 1:1 Benzoic Acid/Isonicotinamide Cocrystal in Solutions of Variable Stoichiometry. J. Pharm. Sci. 2010, 99, 3779-3786.
26. Yu, Z. Q.; Chow, P. S.; Tan, R. B. H. Operating Regions in Cooling Cocrystallization of Caffeine and Glutaric Acid in Acetonitrile. Cryst. Growth Des. 2010, 10, 2382-2387.
27. Jayasankar, A.; Roy, L.; Rodríguez-Hornedo, N. Transformation Pathways of Cocrystal Hydrates when Coformer Modulates Water Activity. J. Pharm. Sci. 2010, 99, 3977-3985.
28. Rager, T.; Hilfiker, R. Cocrystal Formation from Solvent Mixtures. Cryst. Growth Des. 2010, 10, 3237-3241.
29. Braga, D.; Grepioni, F.; Maini, L.; Mazzeo, P. P.; Rubini, K. Solvent-Free Preparation of Cocrystals of Phenazine and Acridine with Vanillin. Thermochim. Acta 2010, 507-508, 1-8.
30. Aher, S.; Dhumal, R.; Mahadik, K.; Paradkar, A.; York, P. Ultrasound Assisted Cocrystallization from Solution (USSC) Containing a Non-Congruently Soluble Cocrystal Component Pair: Caffeine/Maleic Acid. Eur. J. Pharm. Sci. 2010, 41, 597-602.
31. Padrela, L.; Rodrigues, M. A.; Velaga, S. P.; Fernandes, A. C.; Matos, H. A.; de Azevedo, E. G. Screening for Pharmaceutical Cocrystals Using the Supercritical Fluid Enhanced Atomization Process. J. Supercrit. Fluids 2010, 53, 156-164.
32. Alhalaweh, A.; Velaga, S. P. Formation of Cocrystals from Stoichiometric Solutions of Incongruently Saturating Systems by Spray Drying. Cryst. Growth Des. 2010, 10, 3302-3305.
33. Alhalaweh, A; Velaga, S. P. Formation of Cocrystals by Spray Drying. J. Pharm. Pharmacol. 2010, 62, 1332-1333.
34. Medina, C.; Daurio, D.; Nagapudi, K.; Alvarez-Nunez, F. Manufacture of Pharmaceutical Cocrystals using Twin Screw Extrusion: A Solvent-Less and Scalable Process. J. Pharm. Sci. 2010, 99, 1693-1696.
35. Dhumal, R. S.; Kelly, A. L.; York, P.; Coates, P. D.; Paradkar, A. Cocrystallization and Simultaneous Agglomeration Using Hot Melt Extrusion. Pharm. Res. 2010, 27, 2725-2733.
36. Sander, J. R. G.; Bučar, D.-K.; Henry, R. F.; Baltrusaitis, J.; Zhang, G. G. Z.; MacGillivray, L. R. A Red Zwitterionic Cocrystal of Acetaminophen and 2,4-Pyridine-dicarboxylic Acid. J. Pharm. Sci. 2010, 99, 3676-3683.
37. Arenas-Garcia, J. I.; Herrera-Ruiz, D.; Mondragon-Vásquez, K.; Morales-Rojas, H.; Höpfl, H. Cocrystals of Active Pharmaceutical Ingredients-Acetazolamide. Cryst. Growth Des. 2010, 10, 3732-3742.
38. Varughese, S.; Azim, Y.; Desiraju, G. R. Molecular Complexes of Alprazolam with Carboxylic Acids, Boric Acid, Boronic Acids, and Phenols. Evaluation of Supramolecular Heterosynthons Mediated by a Triazole Ring. J. Pharm. Sci. 2010, 99, 3743-3753.
39. Karki, S.; Friščić, T.; Fábián, L.; Jones, W. New Solid Forms of Artemisinin Obtained Through Cocrystallization. CrystEngComm 2010, 12, 4038-4041.
40. Habgood, M.; Deij, M. A.; Mazurek, J.; Price, S. L.; ter Horst, J. H. Carbamazepine Cocrystallization with Pyridine Carboxamides: Rationalization by Complementary Phase Diagrams and Crystal Energy Landscapes. Cryst. Growth Des. 2010, 10, 903-912.
41. He, G.; Chow, P. S.; Tan, R. B. H. Investigating the Intermolecular Interactions in Concentration-Dependent Solution Cocrystallization of Caffeine and p-Hydroxybenzoic Acid. Cryst. Growth Des. 2010, 10, 3763-3769.
42. Sander, G. Jr.; Bucar, D.-K.; Henry, R. F.; Zhang, G. G. Z.; MacGillivray, L. R. Pharmaceutical Nano-Cocrystals: Sonochemical Synthesis by Solvent Selection and Use of a Surfactant. Angew. Chem., Int. Edn. 2010, 49, 7284-7288.
43. Bučar, D. K.; Henry, R. F.; Duerst, R. W.; Lou, X.; MacGillivray, L. R.; Zhang, G. G. Z. A 1:1 Cocrystal of Caffeine and 2-Hydroxy-1-Naphthoic Acid Obtained via a Slurry Screening Method. J. Chem. Cryst. 2010, 40, 933-939.
44. Guo, K.; Sadiq, G.; Seaton, C.; Davey, R. J.; Yin, Q. Cocrystallization in the Caffeine/Maleic Acid System: Lessons from Phase Equilibria. Cryst. Growth Des. 2010, 10, 268-273.
45. Habgood, M.; Price, S. L. Isomers, Conformers, and Cocrystal Stoichiometry: Insights from the Crystal Energy Landscapes of Caffeine with the Hydroxybenzoic Acids. Cryst. Growth Des. 2010, 10, 3263-3272.
46. Lee, T.; Wang, P. Y. Screening, Manufacturing, Photoluminescence, and Molecular Recognition of Co-Crystals: Cytosine with Dicarboxylic Acids. Cryst. Growth Des. 2010, 10, 1419-1434.
47. Mahapatra, S.; Thakur, T. S.; Joseph, S.; Varughese, S.; Desiraju, G. R. 2010. New Solid State Forms of the Anti-HIV Drug Efavirenz: Conformational Flexibility and High Z' Issues. Cryst. Growth Des. 2010 10, 3191-3202.
48. Aitipamula, S.; Chow, P. S.; Tan, R. B. H. Conformational and Enantiotropic Polymorphism of a 1:1 Cocrystal Involving Ethenzamide and Ethylmalonic Acid. CrystEngComm 2010, 12, 3691-3697.
49. Aitipamula, S.; Chow, P. S.; Tan, R. B. H. Polymorphs and Solvates of a Cocrystal Involving an Analgesic Drug, Ethenzamide, and 3,5-Dinitrobenzoic Acid. Cryst. Growth Des. 2010, 10, 2229-2238.
50. Kastelic, J.; Hodnik, Z.; Sket, P.; Plavec, J.; Lah, N.; Leban, I.; Pajk, M.; Planinsek, O.; Kikelj, D. Fluconazole Cocrystals with Dicarboxylic Acids. Cryst. Growth Des. 2010, 10, 4943-4953.
51. Chen, S.; Xi, H.; Henry, R. F.; Marsden, I.; Zhang, G. G. Z. Chiral Cocrystal Solid Solution: Structures, Melting Point Phase Diagram, and Chiral Enrichment of (ibuprofen)2(4,4-dipyridyl). CrystEngComm 2010, 12, 1485-1493.
52. Jung, M.-S.; Kim, J.-S.; Kim, M.-S.; Alhalaweh, A.; Cho, W.; Hwang, S.-J.; Velaga, S. P. Bioavailability of Indomethacin-Saccharin Cocrystals. J. Pharm. Pharmacol. 2010, 62, 1560-1568.
53. Lemmerer, A.; Bernstein, J.; Kahlenberg, V. One-Pot Covalent and Supramolecular Synthesis of Pharmaceutical Co-Crystals Using the API Isoniazid: A Potential Supramolecular Reagent. CrystEngComm 2010, 12, 2856-2864.
54. Cheney, M. L.; Shan, N.; Healey, E. R.; Hanna, M.; Wojtas, L.; Zaworotko, M. J.; Sava, V.; Song, S.; Sanchez-Ramos, J. R. Effects of Crystal Form on Solubility and Pharmacokinetics: A Crystal Engineering Case Study of Lamotrigine. Cryst. Growth Des. 2010, 10, 394-405.
55. Corvis, Y.; Negrier, P.; Lazerges, M.; Massip, S.; Leger, J.-M.; Espeau, P. Lidocaine/L-Menthol Binary System: Cocrystallization versus Solid-State Immiscibility. J. Phys. Chem. B 2010, 114, 5420-5426.
56. Yadav, A. V.; Dabke, A. P.; Shete, A. S. Crystal Engineering to Improve Physicochemical Properties of Mefloquine Hydrochloride. Drug Dev. Ind. Pharm. 2010, 36, 1036-1045.
57. Cheney, M. L.; Weyna, D. R.; Shan, N.; Hanna, M.; Wojtas, L.; Zaworotko, M. J. Supramolecular Architectures of Meloxicam Carboxylic Acid Cocrystals, A Crystal Engineering Case Study. Cryst. Growth Des. 2010, 10, 4401-4413.
58. Schultheiss, N.; Lorimer, K.; Wolfe, S.; Desper, J. Attempted Construction of Minoxidil: Carboxylic Acid Cocrystals; 7 Salts and 1 Cocrystal Resulted. CrystEngComm 2010, 12, 742-749.
59. Schultheiss, N.; Bethune, S.; Henck, J.-O. Nutraceutical cocrystals: Utilizing pterostilbene as a cocrystal former. CrystEngComm 2010, 12, 2436-2442.
60. Schultheiss, N.; Roe, M.; Smit, J. P. Nifedipine-Pyrazine (2/1). Acta Crystallogr. 2010, E66, o2297-o2298.
61. Liao, X.; Gautam, M.; Grill, A.; Zhu, H. J. Effect of Position Isomerism on the Formation and Physicochemical Properties of Pharmaceutical Cocrystals. J. Pharm. Sci. 2010, 99, 246-254.
62. Khan, M.; Enkelmann, V.; Brunklaus, G. Crystal Engineering of Pharmaceutical Co-crystals: Application of Methyl Paraben as Molecular Hook. J. Am. Chem. Soc. 2010, 132, 5254-5263.
63. Takata, N.; Takano, R.; Uekusa, H.; Hayashi, Y.; Terada, K. A Spironolactone-Saccharin 1:1 Cocrystal Hemihydrate. Cryst. Growth Des. 2010, 10, 2116-2122.
64. Elbagerma, M. A.; Edwards, H. G. M.; Munshi, T.; Scowen, I. J. Identification of a new cocrystal of salicylic acid and benzamide of pharmaceutical relevance. Anal. Bioanal. Chem. 2010, 397, 137-146.
65. Chattoraj, S.; Shi, L.; Sun, C. C. Understanding the Relationship between Crystal Structure, Plasticity and Compaction Behavior of Theophylline, Methyl Gallate, and their 1:1 Cocrystal. CrystEngComm 2010, 12, 2466-2472.
66. Lu, J.; Rohani, S. Synthesis and Preliminary Characterization of Sulfamethazine-Theophylline Cocrystal. J. Pharm. Sci. 2010, 99, 4042-4047.
67. Stevens, J. S.; Byard, S. J.; Muryn, C. A.; Schroeder, S. L. M. Identification of Protonation State by XPS, Solid-State NMR, and DFT: Characterization of the Nature of a New Theophylline Complex by Experimental and Computational Methods. J. Phys. Chem. B 2010, 114, 13961-13969.