Classification of the crystallization behavior of amorphous active pharmaceutical ingredients in aqueous environments

Pharmaceutical Research

Volumn 31, Issue 4, 2014, Pages 969-982

  Van Eerdenbrugh, Bernard ^a,b   Raina, Shweta ^a   Hsieh, Yi Ling ^a,c   Augustijns, Patrick ^b   Taylor, Lynne S ^a  

^a PURDUE UNIVERSITY   (United States)

^b DEPARTMENT OF PHARMACEUTICAL AND PHARMACOLOGICAL SCIENCES   (Belgium)

^c ALLERGAN INC   (United States)

Author keywords

active pharmaceutical ingredient; amorphous; crystallization; polarized light microscopy; synchrotron radiation

Indexed keywords

4 HYDROXYBIPHENYL; ACECLOFENAC; ANTHRANILIC ACID; BENZAMIDE; BENZOCAINE; BIFONAZOLE; CAFFEINE; CARVEDILOL; CHLORPROPAMIDE; CHLORZOXAZONE; CINCHOCAINE; CINNARIZINE; CLOTRIMAZOLE; DIMETHYL SULFOXIDE; DIPYRIDAMOLE; FELBINAC; FENOFIBRATE; FLUFENAMIC ACID; FLURBIPROFEN; HALOPERIDOL; INDOMETACIN; INDOPROFEN; KETOPROFEN; LIDOCAINE; LORATADINE; MICONAZOLE; PARACETAMOL; PROCAINE; TOLBUTAMIDE; UNINDEXED DRUG; DRUG; SOLUTION AND SOLUBILITY; WATER;

ANALYTICAL EQUIPMENT; AQUEOUS SOLUTION; ARTICLE; CONTROLLED STUDY; CRYSTALLIZATION; DRUG CLASSIFICATION; DRUG SOLUBILITY; PH; PHOTOCHEMICAL QUENCHING; POLARIZATION MICROSCOPE; POLARIZATION MICROSCOPY; PRECIPITATION; PRIORITY JOURNAL; RADIATION SCATTERING; SOLID STATE; SYNCHROTRON RADIATION; TURBIDITY; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION; CHEMISTRY; CLASSIFICATION; PROCEDURES; SOLUTION AND SOLUBILITY;

CRYSTALLIZATION; PHARMACEUTICAL PREPARATIONS; PHARMACEUTICAL SOLUTIONS; WATER; X-RAY DIFFRACTION;

EID: 84897097503     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-013-1216-z     Document Type: Article

References (41)

1. Lipinski CA. Drug-like properties and the causes of poor solubility and poor permeability. J Pharmacol Toxicol Methods. 2000;44(1):235-49.
2. Millard JW, Alvarez-Núňez FA, Yalkowsky SH. Solubilization by cosolvents - establishing useful constants for the log-linear model. Int J Pharm. 2002;245(1-2):153-66.
3. Brewster ME, Loftsson T. Cyclodextrins as pharmaceutical solubilizers. Adv Drug Deliv Rev. 2007;59(7):645-66.
4. Stella VJ, Nti-Addae KW. Prodrug strategies to overcome poor water solubility. Adv Drug Deliv Rev. 2007;59(7):677-94.
5. Van Eerdenbrugh B, Van den Mooter G, Augustijns P. Top-down production of drug nanocrystals: nanosuspension stabilization, miniaturization and transformation into solid products. Int J Pharm. 2008;364(1):64-75.
6. Leuner C, Dressman J. Improving drug solubility for oral delivery using solid dispersions. Eur J Pharm Biopharm. 2000;50(1):47-60.
7. Hancock BC, Parks M. What is the true solubility advantage for amorphous pharmaceuticals? Pharm Res. 2000;17(4):397-404.
8. Murdande SB, Pikal MJ, Shanker RM, Bogner RH. Solubility advantage of amorphous pharmaceuticals: I. A thermodynamic analysis. J Pharm Sci. 2010;99(3):1254-64.
9. Murdande SB, Pikal MJ, Shanker RM, Bogner RH. Solubility advantage of amorphous pharmaceuticals: II. Application of quantitative thermodynamic relationships for prediction of solubility enhancement in structurally diverse insoluble pharmaceuticals. Pharm Res. 2010;27(12):2704-14.
10. Murdande SB, Pikal MJ, Shanker RM, Bogner RH. Solubility advantage of amorphous pharmaceuticals, Part 3: Is maximum solubility advantage attainable and sustainable? J Pharm Sci. 2011;100(10):4349-56.
11. Hsieh YL, Ilevbare GA, Van Eerdenbrugh B, Box KJ, Sanchez-Felix MV, Taylor LS. pH-Induced precipitation behavior of weakly basic compounds: determination of extent and duration of supersaturation using potentiometric titration and correlation to solid state properties. Pharm Res. 2012;29(10):2738-53.
12. Ilevbare GA, Taylor LS. Liquid-liquid phase separation in highly supersaturated aqueous solutions of poorly-water soluble drugs - implications for solubility enhancing formulations. Cryst Growth Des. 2013;13(4):1497-509.
13. Zhou DL, Zhang GGZ, Law D, Grant DJW, Schmitt EA. Physical stability of amorphous pharmaceuticals: importance of configurational thermodynamic quantities and molecular mobility. J Pharm Sci. 2002;91(8):1863-72.
14. Graeser KA, Patterson JE, Zeitler JA, Gordon KC, Rades T. Correlating thermodynamic and kinetic parameters with amorphous stability. Eur J Pharm Sci. 2009;37(3-4):492-8.
15. Van Eerdenbrugh B, Taylor LS. Small scale screening to determine the ability of different polymers to inhibit drug crystallization upon rapid solvent evaporation. Mol Pharm. 2010;7(4):1328-37.
16. Van Eerdenbrugh B, Taylor LS. An ab initio polymer selection methodology to prevent crystallization in amorphous solid dispersions by application of crystal engineering principles. CrystEngComm. 2011;13(20):6171-8.
17. Baird JA, Van Eerdenbrugh B, Taylor LS. A classification system to assess the crystallization tendency of organic molecules from undercooled melts. J Pharm Sci. 2010;99(9):3787-806.
18. Van Eerdenbrugh B, Baird JA, Taylor LS. Crystallization tendency of active pharmaceutical ingredients following rapid solvent evaporation - classification and comparison with crystallization tendency from undercooled melts. J Pharm Sci. 2010;99(9):3826-38.
19. Miyajima M, Koshika A, Okada J, Ikeda M, Nishimura K. Effect of polymer crystallinity on papaverine release from poly (L-lactic acid) matrix. J Control Release. 1997;49(2-3):207-15.
20. Van Eerdenbrugh B, Stuyven B, Froyen L, Van Humbeeck J, Martens JA, Augustijns P, et al. Downscaling drug nanosuspension production: processing aspects and physicochemical characterization. AAPS PharmSciTech. 2009;10(1):44-53.
21. Van Eerdenbrugh B, Alonzo DE, Taylor LS. Influence of particle size on the ultraviolet spectrum of particulate-containing solutions: implications for in-situ concentration monitoring using UV/vis fiber-optic probes. Pharm Res. 2011;28(7):1643-52.
22. Vandecruys R, Peeters J, Verreck G, Brewster ME. Use of a screening method to determine excipients which optimize the extent and stability of supersaturated drug solutions and application of this system to solid formulation design. Int J Pharm. 2007;342(1-2):168-75.
23. Warren DB, Benameur H, Porter CJH, Pouton CW. Using polymeric precipitation inhibitors to improve the absorption of poorly water-soluble drugs: a mechanistic basis for utility. J Drug Target. 2010;18(10):704-31.
24. Bevernage J, Forier T, Brouwers J, Tack J, Annaert P, Augustijns P. Excipient-mediated supersaturation stabilization in human intestinal fluids. Mol Pharm. 2011;8(2):564-70.
25. Alonzo DE, Gao Y, Zhou DL, Mo HP, Zhang GGZ, Taylor LS. Dissolution and precipitation behavior of amorphous solid dispersions. J Pharm Sci. 2011;100(8):3316-31.
26. Brick MC, Palmer HJ, Whitesides TH. Formation of colloidal dispersions of organic materials in aqueous media by solvent shifting. Langmuir. 2003;19(16):6367-80.
27. McMahon LE, Timmins P, Williams AC, York P. Characterization of dihydrates prepared from carbamazepine polymorphs. J Pharm Sci. 1996;85(10):1064-9.
28. Krc J. Crystallographic properties of flufenamic acid. Microscope. 1977;25(1):31-45.
29. 2 flufenamic acid. Cryst Struct Commun. 1973;2:459-61.
30. Allen FH. The Cambridge structural database: a quarter of a million crystal structures and rising. Acta Crystallogr. 2002;B58:380-8.
31. Murthy HMK, Bhat TN, Vijayan M. Structural studies of analgesics and their interactions. 9. Structure of a new crystal form of 2-([3- (trifluoromethyl)phenyl]amino)benzoic acid (flufenamic acid). Acta Crystallogr. 1982;B38:315-7.
32. Chen XM, Li TL, Morris KR, Byrn SR. Crystal packing and chemical reactivity of two polymorphs of flufenamic acid with ammonia. Mol Cryst Liq Cryst. 2002;381:121-31.
33. Mullin JW. Crystallization. 4th ed. Oxford: Elsiever Butterworth- Heinemann; 2001.
34. Peeters J, Neeskens P, Tollenaere JP, Van Remoortere P, Brewster ME. Characterization of the interaction of 2-hydroxypropyl-β-cyclodextrin with itraconazole at pH 2, 4, and 7. J Pharm Sci. 2002;91(6):1414-22.
35. Yalkowsky SH, He Y. Handbook of aqueous solubility data. Boca Raton: CRC Press LLC; 2003.
36. Alonzo DE, Zhang GGZ, Zhou DL, Gao Y, Taylor LS. Understanding the behavior of amorphous pharmaceutical systems during dissolution. Pharm Res. 2010;27(4):608-18.
37. Greco K, Bogner R. Solution-mediated phase transformation: significance during dissolution and implications for bioavailability. J Pharm Sci. 2012;101(9):2996-3018.
38. Baird JA, Thomas LC, Aubuchon SR, Taylor LS. Evaluating the non-isothermal crystallization behavior of organic molecules from the undercooled melt state using rapid heat/cool calorimetry. CrystEngComm. 2013;15(1):111-9.
39. Mahlin D, Ponnambalam S, Hockerfelt MH, Bergstrom CAS. Toward in silico prediction of glass-forming ability from molecular structure alone: a screening tool in early drug development. Mol Pharm. 2011;8(2):498-506.
40. Yu L, Reutzel-Edens SM, Mitchell CA. Crystallization and polymorphism of conformationally flexible molecules: problems, patterns, and strategies. Org Process Res Dev. 2000;4(5):396-402.
41. Hursthouse MB, Huth LS, Threlfall TL. Why do organic compounds crystallise well or badly or ever so slowly? Why is crystallisation nevertheless such a good purification technique? Org Process Res Dev. 2009;13(6):1231-40.