journal article·2012-05-02

Polymorphs, Salts, and Cocrystals: What’s in a Name?

Srinivasulu Aitipamula, Rahul Banerjee, Arvind K. Bansal, Kumar Biradha, Miranda L. Cheney, Angshuman Roy Choudhury, Gautam R. Desiraju, Amol G. Dikundwar, Ritesh Dubey, Nagakiran Duggirala, Preetam P. Ghogale, Soumyajit Ghosh, Pramod Kumar Goswami, N. Rajesh Goud, Ram R. K. R. Jetti, Piotr Karpinski, Poonam Kaushik, Dinesh Kumar, Vineet Kumar, Brian Moulton, Arijit Mukherjee, Gargi Mukherjee, Allan S. Myerson, Vibha Puri, Arunachalam Ramanan, T. Rajamannar, C. Malla Reddy, Nair Rodriguez-Hornedo, Robin D. Rogers, T. N. Guru Row, Palash Sanphui, Ning Shan, Ganesh Shete, Amit Singh, Changquan C. Sun, Jennifer A. Swift, Ram Thaimattam, Tejender S. Thakur, Rajesh Kumar Thaper, Sajesh P. Thomas, Srinu Tothadi, Venu R. Vangala, Narayan Variankaval, Peddy Vishweshwar, David R. Weyna, Michael J. Zaworotko

Crystal Growth & Design· Volume 12· Issue 5
Publisher page

Abstract

High Resolution Image Download MS PowerPoint Slide The December 2011 release of a draft United States Food and Drug Administration (FDA) guidance concerning regulatory classification of pharmaceutical cocrystals of active pharmaceutical ingredients (APIs) addressed two matters of topical interest to the crystal engineering and pharmaceutical science communities: (1) a proposed definition of cocrystals; (2) a proposed classification of pharmaceutical cocrystals as dissociable “API-excipient” molecular complexes. The Indo–U.S. Bilateral Meeting sponsored by the Indo–U.S. Science and Technology Forum titled The Evolving Role of Solid State Chemistry in Pharmaceutical Science was held in Manesar near Delhi, India, from February 2–4, 2012. A session of the meeting was devoted to discussion of the FDA guidance draft. The debate generated strong consensus on the need to define cocrystals more broadly and to classify them like salts. It was also concluded that the diversity of API crystal forms makes it difficult to classify solid forms into three categories that are mutually exclusive. This perspective summarizes the discussion in the Indo–U.S. Bilateral Meeting and includes contributions from researchers who were not participants in the meeting.
Source: openalex_inverted_index · Quality: baseline

Research context

OpenAlex topics: Crystallography and molecular interactions · Crystallization and Solubility Studies · Chemical Thermodynamics and Molecular Structure

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

Crystallization & Particle Science, Institute of Chemical and Engineering Sciences, A*STAR (Agency for Science, Technology and Research), 1, Pesek Road, Jurong Island, Singapore 627 833

National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India

Department of Pharmaceutics, NIPER, Sector 67, SAS Nagar, Punjab 160062, India

Department of Chemistry, Indian Institute of Technology, Kharagpur 721302,W. B., India

Thar Pharmaceuticals Inc., 3802 Spectrum Boulevard, Suite 120, Tampa, Florida 33612, United States

Indian Institute of Science Education and Research, Mohali Sector 81, S. A. S. Nagar, Manauli PO, Mohali, Punjab. 140306. India

Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, India

Department of Chemistry, University of South Florida, CHE205, 4202 E. Fowler Avenue, Tampa, Florida 33620, United States

Pharmaceutical R&D, Piramal Healthcare Ltd., 1 Nirlon Complex, Off. Western Express Highway, Goregaon East, Mumbai-400063, India

Department of Chemical Sciences, Indian Institute of Science Education and Research, Kolkata 741252, West Bengal, India

Solid State & Materials Chemistry Group, Department of Chemistry, Indian Institute of Technology, Delhi, New Delhi 110016, India

School of Chemistry, University of Hyderabad, Prof. C.R Rao Road, Gachibowli, Hyderabad-500 046, India

Chemical Research Division, API-R&D, Mylan Laboratories Limited, Plot No. 34A, Anrich Industrial Estate, Bollaram Village, Jinnaram Mandal, Medak District, Pin No. 502 325, A.P., India

Novartis Pharmaceuticals Corporation, One Health Plaza, East Hanover, New Jersey 07936, United States

Ranbaxy Laboratories Ltd., Chemical Research, Plot-20, Sector-18, Udyog Vihar Industrial Area, Gurgaon -122015 (Haryana), India

Department of Chemical Engineering, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Building 66-568, Cambridge Massachusetts 02139, United States

404-A, GH-2, Sector-5, Mansa Devi Complex, Panchkula-134109, Haryana, India

Sun Pharma Advanced Research Company Ltd., Tandalja, Vadodara, 390 020, Gujarat, India

College of Pharmacy, University of Michigan, 428 Church Street, Ann Arbor, Michigan 48109, United States

Department of Chemistry/Box 870336, 3006D Shelby Hall, 250 Hackberry Lane, The University of Alabama, Tuscaloosa, Alabama 35487, United States

Department of Pharmaceutics, College of Pharmacy, 9-127B Weaver-Densford Hall, 308 Harvard Street S.E., University of Minnesota, Minneapolis, Minnesota 55455, United States

Georgetown University, Department of Chemistry, 647 Reiss, 37th and O Streets NW Washington, DC 20057-1227, United States

Molecular and Structural Biology Division, CSIR-Central Drug Research Institute, Chattar Manzil Palace, P.O. Box 173, Lucknow 226 001, India

Molecular and Materials Characterization Lead, Merck Research Laboratories, 556 Morris Avenue, Summit, New Jersey 07901-1330, United States

API Finishing Technologies, Integrated Product Development, Dr. Reddy’s Laboratories Ltd., Bachupally, Hyderabad, India

References (61)

Show source-provided references
1. Haleblian J. · J. Pharm. Sci. · 1969 · 58 · 91110.1002/jps.2600580802 ↗
2. Hancock B. C. · J. Pharm. Sci. · 1997 · 86 · 110.1021/js9601896 ↗
3. Yu L. · Adv. Drug Delivery Rev. · 2001 · 48 · 2710.1016/S0169-409X(01)00098-9 ↗
4. Berge S. M. · J. Pharm. Sci. · 1977 · 66 · 110.1002/jps.2600660104 ↗
5. Almarsson Ö. · Chem. Commun. · 2004 · 7 · 188910.1039/b402150a ↗
6. Vishweshwar P. · J. Pharm. Sci. · 2006 · 95 · 49910.1002/jps.20578 ↗
7. Shan N. · Drug. Discovery Today · 2008 · 13 · 44010.1016/j.drudis.2008.03.004 ↗
8. Aakeröy C. B. · CrystEngComm · 2005 · 7 · 43910.1039/b505883j ↗
9. Schultheiss N. · Cryst. Growth Des. · 2009 · 9 · 295010.1021/cg900129f ↗
10. Stahly G. P. · Cryst. Growth Des. · 2009 · 9 · 421210.1021/cg900873t ↗
11. Friščič T. · J. Pharm. Pharmacol. · 2010 · 62 · 154710.1111/j.2042-7158.2010.01133.x ↗
12. Upadhyay N. · Int. J. Pharm. Sci. Rev. Res. · 2011 · 8 · 144
13. Babu N. J. · Cryst. Growth Des. · 2011 · 11 · 266210.1021/cg200492w ↗
14. Brittain H. G. · Cryst. Growth Des. · 2012 · 12 · 104610.1021/cg201510n ↗
15. Peterson M. L. · J. Am. Chem. Soc. · 2002 · 124 · 1095810.1021/ja020751w ↗
16. Wöhler F. · Justus Liebigs Ann. Chem. · 1844 · 51 · 153
17. Etter M. C. · J. Phys. Chem. · 1991 · 95 · 460110.1021/j100165a007 ↗
18. Hickey M. B. · Eur. J. Pharm. Biopharm. · 2007 · 67 · 11210.1016/j.ejpb.2006.12.016 ↗
19. McNamara D. P. · Pharm. Res. · 2006 · 23 · 188810.1007/s11095-006-9032-3 ↗
20. Remenar J. F. · J. Am. Chem. Soc. · 2003 · 125 · 845610.1021/ja035776p ↗
21. Bak A. · J. Pharm. Sci. · 2008 · 97 · 394210.1002/jps.21280 ↗
22. Wuest J. D. · Nat. Chem. · 2012 · 4 · 7410.1038/nchem.1256 ↗
23. Sharma C. V. K. · J. Chem. Soc., Perkin Trans. 2 · 1993 · 220910.1039/P29930002209 ↗
24. Braga D. · Chem. Commun. · 2010 · 46 · 771510.1039/c0cc02701d ↗
25. Ong T. T. · J. Am. Chem. Soc. · 2011 · 133 · 922410.1021/ja203002w ↗
26. Guidance for Industry: Regulatory Classification of Pharmaceutical Co-crystals;Food and Drug Administration:Silver Spring, MD, December 2011.
27. Aakeröy C. B. · CrystEngComm · 2005 · 7 · 43910.1039/b505883j ↗
28. Jones W. · MRS Bull. · 2006 · 341 · 87510.1557/mrs2006.206 ↗
29. Stahly G. P. · Cryst. Growth Des. · 2007 · 7 · 100710.1021/cg060838j ↗
30. Childs S. L. · Cryst. Growth Des. · 2007 · 7 · 129110.1021/cg060742p ↗
31. Bond A. D. · CrystEngComm · 2007 · 9 · 83310.1039/b708112j ↗
32. Bhogala B. R. · New J. Chem. · 2008 · 32 · 80010.1039/b800293b ↗
33. Guidance for Industry, ANDAs: Pharmaceutical Solid Polymorphism;Food and Drug Adminstration:Silver Spring, 2007.
34. Childs S. L. · J. Am. Chem. Soc. · 2004 · 126 · 1333510.1021/ja048114o ↗
35. Kastelic J. · Cryst. Growth Des. · 2010 · 10 · 494310.1021/cg1010117 ↗
36. Harrison W. T. A. · Acta Crystallogr. · 2007 · 63 · o129
37. Desiraju G. R. · Angew. Chem., Int. Ed. Engl. · 1995 · 34 · 231110.1002/anie.199523111 ↗
38. Walsh R. D. B. · Chem. Commun. · 2003 · 18610.1039/b208574g ↗
39. Bis J. A. · Cryst. Growth Des. · 2005 · 5 · 116910.1021/cg049622c ↗
40. Desiraju G. R. · 201110.1142/8060 ↗
41. Childs S. L. · Mol. Pharmaceutics · 2007 · 4 · 32310.1021/mp0601345 ↗
42. Aakeröy. C. B. · Mol. Pharmaceutics · 2007 · 4 · 31710.1021/mp060126o ↗
43. Nehm S. J. · Cryst. Growth Des. · 2006 · 6 · 59210.1021/cg0503346 ↗
44. Karki S. · Mol. Pharmaceutics · 2007 · 4 · 34710.1021/mp0700054 ↗
45. Petruševski G. · Inorg. Chem. Commun. · 2008 · 11 · 8110.1016/j.inoche.2007.10.024 ↗
46. bSherman, B. C., U.S. Patent 6,077,542, 2000.
47. Porter W. W. · Cryst. Growth Des. · 2008 · 8 · 1410.1021/cg701022e ↗
48. Clarke H. D. · Cryst. Growth Des. · 2010 · 10 · 215210.1021/cg901345u ↗
49. Trask A. V. · Mol. Pharmaceutics · 2007 · 4 · 30110.1021/mp070001z ↗
50. bReuter, K.U.S. Patent 6,570,036, 2003.10.1088/1126-6708/2003/01/036 ↗
51. cRemenar, J. F.; MacPhee, M.; Peterson, M. L.; Morissette, S. L.; Almarsson, Ö.U.S. 7,078,526, 2006.
52. dGonzalez-Zugasti, J.; Kane, N.; Oliveira, M.; Peterson, M.U.S. 7,763,112, 2010.
53. eAlmarsson, Ö.; Hickey, M. B.; Peterson, M. L.; Zaworotko, M. J.; Moulton, B.; Rodríguez-HornedoU.S. 7,927,613, 2011.
54. fMcMahon, J.; Peterson, M.; Zaworotko, M. J.; Shattock, T.; Hickey, M. B.US 7, 803,786, 2010.
55. gMascitti, V.; Collman, M.U.S. 8,080,580, 2011.
56. hConnelly, P. R.; Collier, S.; Tauber, M.U.S. 8,039,475, 2011.
57. iSun, T.; Jonitis, D.; Parent, S. D.U.S. 8,003,700, 2011.
58. jBauer, V. J.; O’Neill, M. H.; Kidon, B. J.; Jansen, B.U.S. 8,058,437, 2011.
59. kBlazecka, P. G.; Che, D.; MePhail, C. L.; Rey, A. W.U.S. 7,935,817, 2011.
60. lImamura, M.; Nakanishi, K.; Shiraki, R.; Onda, K.; Sasuga, D.; Yuda, M.U.S. 8,097,592, 2012.
61. Tothadi S. · Chem. Asian J. · 2012 · 7 · 33010.1002/asia.201100638 ↗