Salt and Cocrystal Form Selection

Preclinical Development Handbook: ADME and Biopharmaceutical Properties

Volumn , Issue , 2008, Pages 455-481

  Newman, Ann W ^a   Childs, Scott L ^a   Cowans, Brett A ^a  

^a SSCI Incorporated   (United States)

Author keywords

Hydrogen bond donors and acceptors; Investigational New Drug (IND) application; X ray powder diffraction (XRPD)

Indexed keywords

EID: 84875193045     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470249031.ch14     Document Type: Chapter

References (94)

1. Byrn SR, Pfeiffer RR, Stowell JG. Solid-State Chemistry of Drugs, 2nd ed. West Lafayette, IN:SSCI Inc; 1999.
2. Clas SD. The importance of characterizing the crystal form of the drug substance during drug development. Curr Opin Drug Discov Dev 2003;6:550-560.
3. Curatolo W. Physical-chemical properties of oral drug candidates in the discovery and exploratory development settings. Pharm Sci Technol Today 1998;1:387-393.
4. Gardner CR, Walsh CT, Almarsson O. Drugs as materials:valuing physical form in drug discovery. Nat Rev Drug Discov 2004;3:926-934.
5. Venkatesh S, Lipper RA. Role of the development scientist in compound lead selection and optimization. J Pharm Sci 2000;89:145-154.
6. Fiese EF. General pharmaceutics-the new physical pharmacy. J Pharm Sci 2003;92(7):1331-1342.
7. Huang LF, Tong WQ. Impact of solid state properties on developability assessment of drug candidates. Adv Drug Deliv Rev 2004;56:321-334.
8. Kibbey CE, Poole SK, Robinson B, Jackson JD, Durham D. An integrated process for measuring the physicochemical properties of drug candidates in a preclinical discovery environment. J Pharm Sci 2001;90:1164-1175.
9. Wenlock MC, Austin RP, Barton P, Davis AM, Leeson PD. A comparison of physiochemical property profiles of development and marketed oral drugs. J Med Chem 2003;46:1250-1256.
10. Stahl PH, Wermuth CG, Eds. Handbook of Pharmaceutical Salts. Hoboken, NJ:Wiley-VCH; 2002.
11. Balbach S, Korn C. Pharmaceutical evaluation of early development candidates "the 100 mg-approach. "Int J Pharm 2004;275:1-12.
12. Bastin RJ, Bowker MJ, Slater BJ. Salt selection and optimisation procedures for pharmaceutical new chemical entities. Org Proc Res Dev 2000;4:427-435.
13. Morris KR, Fakes MG, Thakur AB, Newman AW, Singh AK, Venit JJ, Spagnuolo CJ, Serajuddin ATM. An integrated approach to the selection of optimal salt form for a new drug candidate. Int J Pharm 1994;105:209-217.
14. Giron D. Characterisation of salts of drug substances. J Thermal Anal Calorimetry 2003;73:441-457.
15. Newman AW, Stahly GP. Form selection of pharmaceutical compounds. In:Ohannessian L, Ed. Handbook of Pharmaceutical Analysis, Volume 117. New York:Marcel Dekker; 2001, pp 1-57.
16. Braga D, Brammer L, Champness NR. New trends in crystal engineering. Crystengcomm 2005;7:1-19.
17. Erk P, Hengelsberg H, Haddow MF, van Gelder R. The innovative momentum of crystal engineering. Crystengcomm 2004;6:474-483.
18. Hulliger J, Roth SW, Quintel A, Bebie H. Polarity of organic supramolecular materials:a tunable crystal property. J Solid State Chem 2000;152:49-56.
19. Iimura N, Ohashi Y, Hirata H. Complex formation of perfumes with cationic surfactants and the enhanced thermal stability. Bull Chem Soc Jpn 2000;73:1097-1103.
20. Wong MS, Pan F, Bosshard C, Guenter P. Supramolecular synthesis of molecular co-crystals with highly optimized chromophoric orientation for second-order nonlinear optics. Polym Mater Sci Eng 1996;75:132-133.
21. Wong MS, Pan F, Gramlich V, Bosshard C, Gunter P. Self-assembly of an acentric co-crystal of a highly hyperpolarizable merocyanine dye with optimized alignment for nonlinear optics. Adv Materials 1997;9:554-557.
22. CFR 314.108(a) and Draft Guidance Applications Covered by Section 505(b)(2), http://www.fda.gov/cder/guidance/2853dft.htm.
23. Gould PL. Salt selection of basic drugs. Int J Pharm 1986;33:201-217.
24. Miyazaki S, Oshiba M, Nadai T. Precaution on use of hydrochloride salts in pharmaceutical formulation. J Pharm Sci 1981;70(6):594-596.
25. Bruno IJ, Cole JC, Lommerse JPM, Rowland RS, Taylor R, Verdonk ML. IsoStar:a library of information about nonbonded interactions. J Comput Aided Mol Des 1997; 11(6):525-537.
26. Chisholm J, Pidcock E, Van De Streek J, Infantes L, Motherwell S, Allen FH. Knowledge-based approaches to crystal design. Crystengcomm 2006;8:11-28.
27. Gillon AL, Feeder N, Davey RJ, Storey R. Hydration in molecular crystals-a Cambridge Structural Database analysis. Crystal Growth Des 2003;3:663-673.
28. Steiner T. The hydrogen bond in the solid state. Angew Chem Int Ed 2002;41:48-76.
29. Aakeroy CB, Salmon DJ. Building co-crystals with molecular sense and supramolecular sensibility. Crystengcomm 2005;7:439-448.
30. Anthony A, Desiraju GR, Jetti RKR, Kuduva SS, Madhavi NNL, Nangia A, Thaimattam R, Thalladi VR. Crystal engineering:some further strategies. Mater Res Bull 1998;1-18.
31. Desiraju GR. Supramolecular synthons in crystal engineering-a new organic-synthesis. Angew Chem Int Ed Engl 1995;34:2311-2327.
32. 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.
33. Fleischman SG, Kuduva SS, McMahon JA, Moulton B, Walsh RDB, Rodriguez-Hornedo N, Zaworotko MJ. Crystal engineering of the composition of pharmaceutical phases:multiple-component crystalline solids involving carbamazepine. Crystal Growth Des 2003;3:909-919.
34. McMahon JA, Bis JA, Vishweshwar P, Shattock TR, McLaughlin OL, Oswald MJ, Allan DR, McGregor PA, Motherwell WDS, Parsons S, Pulham CR. The formation of paracetamol (acetaminophen) adducts with hydrogen-bond acceptors. Acta Crystallogr B Struct Sci 2002;58:1057-1066.
35. Remenar JF, Morissette SL, Peterson ML, Moulton B, MacPhee JM, Guzman HR, Almarsson O. Crystal engineering of novel cocrystals of a triazole drug with 1,4-dicarboxylic acids. J Am Chem Soc 2003;125:8456-8457.
36. Rodriguez-Spong B, Price CP, Jayasankar A, Matzger AJ, Rodriguez-Hornedo N. General principles of pharmaceutical solid polymorphism:a supramolecular perspective. Adv Drug Deliv Rev 2004;56:241-274.
37. Trask AV, Motherwell WDS, Jones W. Pharmaceutical cocrystallization:engineering a remedy for caffeine hydration. Crystal Growth Des 2005;5:1013-1021.
38. 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.
39. Aakeroy CB, Desper J, Helfrich BA. Heteromeric intermolecular interactions as synthetic tools for the formation of binary co-crystals. Crystengcomm 2004;6:19-24.
40. Etter MC. Hydrogen-bonds as design elements in organic-chemistry. J Phys Chem 1991;95:4601-4610.
41. Amos JG, Indelicato JM, Pasini CE, Reutzel SM. US patent 6,001,996. 1999.
42. Nehm SJ, Rodriguez-Spong B, Rodriguez-Hornedo N. Phase solubility diagrams of cocrystals are explained by solubility product and solution complexation. Crystal Growth Des 2006;6:592-600.
43. Monissette SL, Almarsson O, Peterson ML, Remenar JF, Read J, Lemmo AV, Ellis S, Cima MJ, Gardner CR. High-throughput crystallization:polymorphs, salts, co-crystals and solvates of pharmaceutical solids. Adv Drug Deliv Rev 2004;56:275-300.
44. Remenar JF, MacPhee JM, Larson BK, Tyagi VA, Ho JH, McIlroy DA, Hickey MB, Shaw PB, Almarsson O. Salt selection and simultaneous polymorphism assessment via high-throughput crystallization:the case of sertraline. Org Proc Res Dev 2003;7:990-996.
45. Ware EC, Lu DR. An automated approach to salt selection for new unique trazodone salts. Pharm Res 2004;21:177-184.
46. Stephenson GA. Applications of X-ray powder diffraction in the pharmaceutical industry. Rigaku J 2005;22(1):2-15.
47. Kondritzer AA, Ellin RI, Edberg LJ. Investigation of methyl pyridinium-2-aldoxime salts. J Pharm Sci 1961;50(2):109.
48. Koehler HM, Hefferren JJ. Mineral salts of lidocaine. J Pharm Sci 1964;53(9):1126.
49. Childs SL, Chyall LJ, Dunlap JT, Coates DA, Stahly BC, Stahly GP. A metastable polymorph of metformin hydrochloride:isolation and characterization using capillary crystallization and thermal microscopy techniques. Crystal Growth Des 2004;4:441-449.
50. Rai RN, Varma KBR. Phase diagram and dielectric studies of binary organic materials. Mater Lett 2000;44:284-293.
51. Zalac S, Khan MZI, Gabelica V, Tudja M, Mestrovic E, Romih M. Paracetamol-propyl phenazone interaction and formulation difficulties associated with eutectic formation in combination solid dosage forms. Chem Pharm Bull 1999;47:302-307.
52. Kuhnert-Brandstatter M, Geiler M, Wurian I. Sci Pharm 1983;51:34-41.
53. Kofler A, Kolsek J. Mikrochimi Acta 1969;2:408-435.
54. Pedireddi VR, Jones W, Chorlton AP, Docherty R. Creation of crystalline supramolecular arrays:a comparison of co-crystal formation from solution and by solid state grinding. Chem Commun 1996;987-988.
55. Shan N, Toda F, Jones W. Mechanochemistry and co-crystal formation:effect of solvent on reaction kinetics. Chem Commun 2002;2372-2373.
56. Trask AV, Haynes DA, Motherwell WDS, Jones W. Screening for crystalline salts via mechanochemistry. Chem Commun 2006;51-53.
57. Trask AV, van de Streek J, Motherwell WDS, Jones W. Achieving polymorphic and stoichiometric diversity in cocrystal formation:importance of solid-state grinding, powder X-ray structure determination, and seeding. Crystal Growth Des 2005;5:2233-2241.
58. Brittain HG, Ed. Physical Characterization of Pharmaceutical Solids. New York:Marcel Dekkar; 1995.
59. Brittain HG, Bogdanowich SJ, Bugay DE, DeVincentis J, Lewen G, Newman AW. Physical characterization of pharmaceutical solids. Pharm Res 1991;8(8):963-973.
60. Mehrens SM, Kale UJ, Qu XG. Statistical analysis of differences in the Raman spectra of polymorphs. J Pharm Sci 2005;94:1354-1367.
61. Tishmack PA, Bugay DE, Byrn SR. Solid-state nuclear magnetic resonance spectroscopy-pharmaceutical applications. J Pharm Sci 2003;92:441-474.
62. Stephenson GA, Forbes RA, Reutzel-Edens SM. Characterization of the solid state:quantitative issues. Adv Drug Deliv Rev 2001;48:67-90.
63. 13 C NMR spectroscopy and powder X-ray diffraction for analyzing mixtures of polymorphs of neotame. Anal Chem 1999;71(16):3325-3331.
64. Reutzel-Edens SM, Bush JK. Solid-state NMR spectroscopy of small molecules:from NMR crystallography to the characterization of solid oral dosage forms. Am Pharm Rev 2002;5/2:112-115.
65. Stahly GP, Bates S, Andres MC, Cowans BA. Discovery of a new polymorph of dehydroepiandrosterone (prasterone) and solution of its crystal structure from X-ray powder diffraction data. Crystal Growth Des 2006;6:925-932.
66. Reutzel-Edens SM, Newman AW. The physical characterization of hygroscopicity in pharmaceutical solids. In Hilfiker R, Ed. Polymorphism. Weinheim:Wiley-VCH; 2006, pp 235-258.
67. Giron D, Mutz M, Garnier S. Solid-state of pharmaceutical compounds-impact of the ICH Q6 guideline on industrial development. J Thermal Anal Calorimetry 2004;77:709-747.
68. Singhal D, Curatolo W.. Drug polymorphism and dosage form design:a practical perspective. Adv Drug Deliv Rev 2004;56:335-347.
69. Raw AS, Furness MS, Gill DS, Adams RC, Holcombe FO, Yu LX.. Regulatory considerations of pharmaceutical solid polymorphism in abbreviated new drug applications (ANDAs). Adv Drug Deliv Rev 2004;56:397-414.
70. Yu LX, Furness MS, Raw AS, Outlaw KPW, Nashed NE, Ramos E, Miller SPF, Adams RC, Fang F, Patel RM, Holcombe FO, Chiu YY, Hussain AS.. Scientific considerations of pharmaceutical solid polymorphism in abbreviated new drug applications. Pharm Res 2003;20:531-536.
71. Stahly GP. Polymorphism in crystals:fundamentals, predications and industrial practice. Presented at the American Chemical Society ProSpectives Meeting, Tampa, FL, 23-26 Feb 2003.
72. Q6A Specifications, Test procedures and acceptance criteria for new drug substances and new drug products:chemical substances. Fed Reg 1997;62:62889-62910.
73. Byrn SA, Pfeiffer R, Ganey M, Hoiberg C, Poochikian G. Pharm Res 1995;12:945-954.
74. Blagden N, Davey RJ. Polymorph selection:Challenges for the future? Crystal Growth Des. 2003;3:873-885.
75. Guillory JK. Generation of polymoprhs, hydrates, solvates, and amorphous solids. In Brittain HG, Ed. Polymorphism in Pharmaceutical Solids. New York:Marcel Dekker; 1999, Ch 5, pp 183-226.
76. Bernstein J. Polymorphism in Molecular Crystals. London:Oxford Science Publications; 2002.
77. Gracin S, Uusi-Penttila M, Rasmuson AC. Influence of ultrasound on the nucleation of polymorphs of p-aminobenzoic acid. Crystal Growth Des 2005;5:1787-1794.
78. Davey RJ, Allen K, Blagden N, Cross WI, Lieberman HF, Quayle MJ, Righini S, Seton L, Tiddy GJT. Crystal engineering-nucleation, the key step. Crystengcomm 2002;257-264.
79. Fabbiani FPA, Allan DR, David WIF, Moggach SA, Parsons S, Pulham CR. High-pressure recrystallisation-a route to new polymorphs and solvates. Crystengcomm 2004;6:505-512.
80. Morris KM, Rodriquez-Hornedo N. Hydrates. In Swarbrick J, Boylan JC, Eds. Encyclopedia of Pharmaceutical Technology, Volume 7. New York:Marcel Dekker; 1993, pp 393-440.
81. Burger A, Grießer UJ. The polymorphic drug substances of the European Pharmacopoeia. Part 7:Physical stability, hygroscopicity and solubility of succinylsulfathiazole crystal forms. Eur J Pharm Biopharm 1991;37:118-124.
82. Herbstein FH. Diversity amidst similarity:a multidisciplinary approach to phase relationships, solvates, and polymorphs. Crystal Growth Des 2004;4:1419-1429.
83. Morris KR, Griesser UJ, Eckhardt CJ, Stowell JG. Theoretical approaches to physical transformations of active pharmaceutical ingredients during manufacturing processes. Adv Drug Deliv Rev 2001;91-114.
84. Miller JM, Collman BM, Greene LR, Grant DJW, Blackburn AC. Identifying the stable polymorph early in the drug discovery-development process. Pharm Dev Technol 2005;10:291-297.
85. Grunenberg A, Henck J-O, Siesler HW. Theoretical derivation and practical application of energy/temperature diagrams as an instrument in preformulation studies of polymorphic drug substances. Int J Pharm 1996;129:147-158.
86. Burger A, Ramburger R. On the polymorphism of pharmaceuticals and other molecular crystals. I. Mikrochim Acta (Wien) II 1979;259-272.
87. Burger A, Ramburger R. On the polymorphism of pharmaceuticals and other molecular crystals. II. Mikrochim Acta (Wien) II 1979;273-316.
88. Behme RJ, 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 1991;80(10):986-990.
89. Behme RJ, Brooke D, Farney RF, Kensler TT. Characterization of polymorphism of gepirone hydrochloride. J Pharm Sci 1985;74(10):1041-1046.
90. Yu L, Stephenson GA, Mitchell CA, Bunnell CA, Snorek SV, Bowyer JJ, Borchardt TB, Stowell JG, Byrn SR. Thermochemistry and conformational polymorphism of a hexamorphic crystal system. J Am Chem Soc 2000;122(4):585-591.
91. Sanghvi T, Ni N, Yalkowsky SH. A simple modified absorption potential. Pharm Res 2001;18(12):1794-1796.
92. Anderson NG. Practical Process Research and Development. San Diego, CA:Academic Press; 2000.
93. International Conference on Harmonisation;Q2B validation of analytical procedures:methodology. Fed Reg 1997;62:27464.
94. Newman AW, Byrn SR. Solid-state analysis of the active pharmaceutical ingredient in drug products. Drug Discov Today 2003;8(9):898-905.