A thermodynamic-based approach to analyzing a highly solvating polymorphic system: The desolvation window method

Journal of Pharmaceutical Sciences

Volumn 100, Issue 1, 2011, Pages 186-194

  Samas, Brian ^a   Seadeek, Christopher ^a   Campeta, Anthony M ^a   Chekal, Brian P ^a  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

Crystallization; Desolvation; Hydrate; Hydrates solvates; Materials science; Polymorph; Polymorphism; Solid state; Solvate; Thermodynamics

Indexed keywords

AXITINIB; ZIPRASIDONE;

ANALYTIC METHOD; ARTICLE; CRYSTALLIZATION; DESOLVATION; DRUG FORMULATION; DRUG IMPURITY; SOLID STATE; SOLVATION; THERMODYNAMICS;

EID: 78650038479     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.22265     Document Type: Article

References (30)

1. Chemburkar SR, Bauer J, Deming K, Spiwek H, Patel K, Morris J, Henry R, Spanton S, Dziki W, Porter W, Quick J, Bauer P, Donaubauer J, Narayanan BA, Soldani M, Riley D, McFarland K. 2000. Dealing with the impact of ritonavir polymorphs on the late stages of bulk drug process development. Org Process Res Dev 4: 413-417.
2. Hilfker R. 2006. Polymorphism in the pharmaceutical industry. Weinheim, Germany: Wiley-VCH.
3. Petrova RI, Peresypkin A, Mortko CJ, Mckeown AE, Lee JL, Williams M. 2009. Rapid conversion of API hydrates to anhydrous forms in aqueous media. J Pharm Sci 98: 4111-4118.
4. Hu TC, Wang SL, Chen TF, Lin SY. 2002. Hydration-induced proton transfer in the solid state of norfloxacin. J Pharm Sci 91: 1351-1357.
5. Katdare AV, Bavitz JF. 1984. Hydrate related dissolution characteristics of norfloxacin. Drug Dev Ind Pharm 10: 789-807.
6. Wu LS, Gerard C, Koval C, Rowe S, Hussain MA. 1994. Crystallinity, hygroscopicity and dissolution of moricizine hydrochloride hemihydrate. J Pharm Biomed Anal 12: 1043-1046.
7. Shibata M, Kokubo H, Morimoto K, Morisaka K, Ishida T, Inoue M. 1983. X-ray structural studies and physicochemical properties of cimetidine polymorphism. J Pharm Sci 72: 1436-1442.
8. Reutzel-Edens SM, Kleemann RL, Lewellen PL, Borghese AL, Antoine LJ. 2003. Crystal forms of LY334370 HCl: Isolation, solid-state characterization, and physicochemical properties. J Pharm Sci 92: 1196-1205.
9. Allen PV, Rahn PD, Sarapu AC, Vanderwielen AJ. 1978. Physical characterization of erythromycin: Anhydrate, monohydrate, and dihydrate crystalline solids. J Pharm Sci 67: 1087-1093.
10. Zhu H, Khankari RK, Padden BE, Munson EJ, Gleason WB, Grant DJW. 1996. Physicochemical characterization of nedocromil bivalent metal salt hydrates. 1. Nedocromil magnesium. J Pharm Sci 85: 1026-1034.
11. Zhu H, Padden BE, Munson EJ, Grant DJW. 1997. Physicochemical characterization of nedocromil bivalent metal salt hydrates. 2. Nedocromil zinc. J Pharm Sci 86: 418-429.
12. Gardner GL. 1976. Kinetics of the dehydration of calcium oxalate trihydrate crystals in aqueous solution. J Colloid Interface Sci 54: 298-310.
13. Zhu H, Grant DJW. 1996. Influence of water activity in organic solvent+water mixtures on the nature of crystallizing drug phase. 2. Ampicillin. Int J Pharm 139: 33-43.
14. Khankari RK, Grant DJW. 1995. Pharmaceutical hydrates. Thermochim Acta 248: 61-79.
15. Byrn SR, Pfeiffer RR, Stowell JG. 1999. Solid-state chemistry of drugs. West Lafayette: SSCI, Inc.
16. Ibragimov B. 1999. A simple correlation between the structures of different crystal modifications of a given host-guest complex and their crystallization temperatures. J Incl Phenom 34: 345-353.
17. Black SN, Phillips A, Scott CI. 2009. Crystallisation design space: Avoiding a hydrate in water-based process. Org Process Res Dev 13: 78-83.
18. Gu C, Young V, Jr., Grant DJW. 2001. Polymorph screening: Influence of solvents on the rate of solvent-mediated polymorphic transformation. J Pharm Sci 90: 1878-1890.
19. Ostwald W. 1897. Studien uber die bildung und umwandlung fester korper. Z Phys Chem 22: 289-330.
20. Desikan S, Parsons RL, Davis WP, Ward JE, Marshall WJ, Toma PH. 2005. Process development challenges to accommodate a late-appearing stable polymorph: A case study on the polymorphism and crystallization of a fast-track drug development compound. Org Process Res Dev 9: 933.
21. Price CP, Glick GD, Matzger AJ. 2006. Dissecting the behavior of a promiscuous solvate former. Angew Chem Int Ed 45: 2062-2066.
22. Bingham AL, Hughes DS, Hursthouse MB, Lancaster RW, Tavener S, Threlfall TL. 2001. Over one hundred solvates of sulfathiazole. Chem Commun 7: 603-604.
23. Gdaniec M, Ibragimov BT, Talipov SA. 1996. Gossypol. In: Comprehensive supramolecular chemistry, Vol. 6. pp. 117-145.
24. Van de Streek J. 2007. All series of multiple solvates (including hydrates) from the Cambridge Structural Database. Cryst Eng Comm 9: 350-352.
25. Chekal BP, Campeta AM, Abramov YA, Feeder N, Glynn PP, McLaughlin RW, Meenan PA, Singer RA. 2009. The challenges of developing an API crystallization process for a complex polymorphic and highly solvating system: Part 1. Org Process Res Dev 13: 1327-1337.
26. Campeta AM, Chekal BP, Abramov YA, Meenan PA, Henson MJ, Shi B, Singer RA, Horspool K. 2010. Development of a targeted polymorph screening approach for a complex polymorphic and highly solvating API. J Pharm Sci (in press).
27. Miller JM, Collman BM, Greene LR, Grant DJW, Blackburn AC. 2005. Identifying the stable polymorph early in the drug discovery-development process. Pharm Dev Technol 10: 275-281.
28. Gong Y, Collman BM, Mehrens SM, Lu E, Miller JM, Blackburn AC, Grant DJW. 2007. Stable-form screening: Overcoming trace impurities that inhibit solution mediated phase transformation to the stable polymorph of sulfamerazine. J Pharm Sci 97: 2130-2144.
29. Threlfall T. 2000. Crystallisation of polymorphs: Thermodynamic insight into the role of solvent. Org Process Res Dev 4: 384-390.
30. Fabian L. 2009. Cambridge structural database analysis of molecular complementarily in cocrystals. Cryst Growth Des 9: 1436-1443.