Critical considerations for the qualitative and quantitative determination of process-induced disorder in crystalline solids

Journal of Pharmaceutical Sciences

Volumn 103, Issue 9, 2014, Pages 2595-2604

  Newman, Ann ^a   Zografi, George ^b  

^a Seventh Street Development Group   (United States)

^b UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

amorphous; crystal defects; crystal growth; physical characterization; physical stability

Indexed keywords

CALORIMETRY; CHEMICAL PHENOMENA; CRYSTAL STRUCTURE; CRYSTALLINE SOLID; CRYSTALLIZATION; DIFFERENTIAL SCANNING CALORIMETRY; FREEZE DRYING; GLASS TRANSITION TEMPERATURE; HUMIDITY; LIMIT OF DETECTION; LIMIT OF QUANTITATION; LIQUID CRYSTAL; MECHANICAL STRESS; MOISTURE; MOLECULE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PARTICLE SIZE; QUALITATIVE ANALYSIS; QUANTITATIVE ANALYSIS; RAMAN SPECTROMETRY; REVIEW; SIGNAL NOISE RATIO; SOLID STATE; SPRAY DRYING; STORAGE; WATER TRANSPORT; X RAY DIFFRACTION; CHEMISTRY; DRUG STABILITY; MEDICINAL CHEMISTRY; PHARMACEUTICS; PROCEDURES;

DRUG;

CHEMISTRY, PHARMACEUTICAL; CRYSTALLIZATION; DRUG STABILITY; PHARMACEUTICAL PREPARATIONS; TECHNOLOGY, PHARMACEUTICAL; X-RAY DIFFRACTION;

EID: 84906318741     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.23930     Document Type: Note

References (50)

1. Bates S, Zografi G, Engers D, Morris K, Crowley K, Newman A,. 2006. Analysis of amorphous and nanocrystalline solids from their X-ray diffraction patterns. Pharm Res 23: 2333-2349.
2. Wunderlich B,. 1999. A classification of molecules, phases and transitions as recognized by thermal analysis. Thermochim Acta 340-341: 37-52.
3. Stillinger FH, Weber TA,. 1984. Packing structures and transitions in liquids and solids. Science 225: 983-989.
4. Boldyrev VV,. 1975. Topochemical reactions: Particularities of their mechanism and outlook of their research, Part I. J Therm Anal 7: 685-694.
5. Sherwood JN,. 1969. Lattice defects in organic crystals. Mol Cryst 9: 37-57.
6. Burt HM, Mitchell AG,. 1981. Crystal defects and dissolution. Int J Pharm. 9: 137-152.
7. Hong Wen HL, Stowell JG, Morris KR, Byrn SR,. 2010. Crystal quality and physical reactivity in the case of flufenamic acid (FFA). J Pharm Sci 99: 3839-3848.
8. Foster MC, Ewing GE,. 2000. Adsorption of water on NaCl (001) surface II: An infrared study at ambient temperatures. J Chem Phys 112: 6817-6826.
9. Hancock BC, Shamblin SL,. 2001. Molecular mobility of amorphous pharmaceuticals using differential scanning calorimetry. Thermochim Acta 380: 95-107.
10. Billinge SJL, Thorpe MF,. 1998. Local structure from diffraction patterns. New York: Plenum.
11. Ediger MD, Angell CA, Nagel SR,. 1996. Supercooled liquids and glasses. J Phys Chem 100: 13200-13212.
12. Hancock BC, Zografi G,. 1997. Characteristics and significance of the amorphous state in pharmaceutical systems. J of Pharm Sci 86: 1-12.
13. Newman AW, Reutzel-Edens SM, Zografi G,. 2008. Characterization of the hygroscopic properties of active pharmaceutical ingredients. J Pharm Sci 97: 1047-1058.
14. Newman A, Knipp G, Zografi G,. 2012. Assessing the performance of amorphous solid dispersions. J Pharm Sci 101: 1356-1374.
15. Hill JJ, Shalaev EY, Zografi G,. 2005. Thermodynamic and dynamic factors involved in the stability of native protein structure in amorphous solids in relation to levels of hydration. J Pharm Sci 94: 1636-1667.
16. Saleki-Gerhardt A, Ahlneck C, Zografi G,. 1994. Assessment of disorder in crystalline solids. Int J Pharm 101: 237-247.
17. Ahlneck C, Zografi G,. 1990. The molecular basis of moisture effects on the physical and chemical stability of drugs in the solid state. Int J Pharm Sci 62: 87-95.
18. Tromans D, Meech JA,. 2001. Enhanced dissolution of minerals: Stored energy, amorphism,and mechanical activation. Miner Eng 14: 1359-1377.
19. Wildfong PLD, Hancock BC, Moore MD, Morris KR,. 2006. Towards an understanding of the structurally based potential for mechanically activated disordering of small organic crystals. J Pharm Sci 95: 2645-2656.
20. Crowley KJ, Zografi G,. 2002. Cryogenic grinding of indomethacin polymorphs and solvates: Assessment of amorphous phase formation and amorphous phase stability. J Pharm Sci 91: 492-507.
21. Dujardin N, Willart JF, Dudognon E, Descamps M,. 2013. Mechanism of solid state amorphization of glucose upon milling. J Phys Chem 117: 1437-1443.
22. Sheth AR, Bates S, Muller FX, Grant DJ,. 2005. Local structure in amorphous phases of piroxicam from powder X-ray diffractometery. Cryst Growth Des 5: 571-578.
23. Saleki-Gerhardt A, Stowell JG, Byrn SR, Zografi G,. 1995. Hydration and dehydration of crystalline and amorphous forms of raffinose. J Pharm Sci 84: 318-323.
24. Taylor LS, York P,. 1998. Characterization of the phase transitions of trehalose dihydrate on heating and subsequent dehydration. J Pharm Sci 87: 347-355.
25. g. J Pharm Sci 96: 1398-1407.
26. Bates S, Kelly RC, Ivanisevic I, Schields P, Zografi G, Newman A,. 2000. Assessment of defects and amorphous structure produced in raffinose pentahydrate upon dehydration. J Pharm Sci 89: 128-143.
27. Ward GH, Schultz RK,. 1995. Process-induced crystallinity changes in albuterol sulfate and its effects on powder physical stability. Pharm Res 12: 773-779.
28. Murphy D, Rodriguez-Antron F, Langevin B, Kelly RC, Rodriguez-Hornedo N,. 2002. Solution mediated phase transformation of anhydrous to dihydrate carbamazepine and the effect of lattice disorder. Int J Pharm 246: 121-134.
29. Zhixin Z, Qiu J, Tnamee R, Kirsch LE,. 2012. Kinetic model for solid-state degradation of gabapentin. J Pharm Sci 101: 2123-2133.
30. Hancock BC, Zografi G,. 1996. The effects of solid-state processing on water vapor sorption by aspirin. J Pharm Sci 85: 246-248.
31. Badway SIF, Williams RC, Gilbert DL,. 1999. Chemical stability of an ester prodrug of a glycoprotein iib/iiia receptor antagonist in solid dosage forms. J Pharm Sci 88: 428-433.
32. Zimper U, Aaltonen J, McGoverin CM, Gordon KC, Krauel-Goellner K, Rades T,. 2010. Quantification of process induced disorder in milled samples using different analytical techniques. Pharmaceutics 2: 30-40.
33. Lehto V-P, Tenho M, Vaha-Heikkila K, Harjunen P, Paallysaho M, Valisaari J, Ia PN, Jarvinen K,. 2006. The comparison of seven different methods to quantify the amorphous content of spray dried lactose. Powder Technol 167: 85-93.
34. Shah B, Kakumanu VK, Bansal AK,. 2006. Analytical techniques for quantification of amorphous/crystalline phases in pharmaceutical solids. J Pharm Sci 95: 1641-1665.
35. Bruce GR, Gill PS,. 1999. Estimates of precision in a standard additions analysis. J Chem Educ 76 (6): 805-807.
36. Vollenbroek j, Hebbink GA, Ziffels S, Steckel H,. 2010. Determination of low levels of amorphous content in inhalation grade lactose by moisture sorption isotherms. Int J Pharm 395: 62-70.
37. Bhugra C, Pikal MJ,. 2008. Role of thermodynamic, molecular, and kinetic factors in crystallization from the amorphous state. J Pharm Sci 97: 1329-1349.
38. Surana S, Pyne A, Suryanarayanan R,. 2004. Effect of aging on the physical properties of amorphous trehalose. Pharm Res 21: 867-874.
39. Bugay DE, Newman AW, Findlay WP,. 1996. Quantitation of cefepime.2HCl dihydrate in cefepime.2HCl monohydrate by diffuse reflectance IR and powder X-ray diffraction techniques. J Pharm Biomed Anal 15: 49-61.
40. Harjunen P, Lehto V-P, Valisaari J, Lankinen T, Paronen P, Jarvinen K,. 2001. Effects of ethanol to water ratio in feed solution on the crystallinity of spray-dried lactose. Drug Dev Ind Pharm 98: 949-955.
41. Newman AW, Byrn SR,. 2003. Solid-state analysis of the active pharmaceutical ingredient in drug products. Drug Discov Today 8: 898-905.
42. Braun DE, Maas SG, Zencirci N, Langes C, Urbanetz NA, Griesser UJ,. 2010. Simultaneous quantitative analysis of ternary mixtures of D-mannitol polymorphs by FT-Raman spectroscopy and multivariate calibration models. Int J Pharm 385: 29-36.
43. Hu Y, Macfhionnghaile P, Caron V, Tajber L, Healy AM, Erxleben A, McArdle P,. 2013. Formation, physical stability, and quantification of process-induced disorder in cryomilled samples of a model polymorphic drug. J Pharm Sci 102: 93-103.
44. International Conference on Harmonisation. 1997. Guideline on the v alidation of analytical procedures: Methodology. Federal Register 62 (96): 27464-27467. http://www.federalregister.gov/articles/1997/05/19/97-13063/ international-conference-on-harmonisation-guideline-on-the-validation-of- analytical-procedures
45. Clas S-D, Lalonde K, Khougaz K, Dalton CR, Bilbeisi R,. 2012. Detection of a minor amorphous phase in crystalline etoricoxib by dynamic mechanical analysis: Comparison with Raman spectroscopy and modulated differential scanning calorimetry. J Pharm Sci 101: 558-565.
46. Venkatesh GM, Barnett ME, Osusu-Fordjour C, Galop M,. 2001. Detection of low levels of the amorphous phase in crystalline pharmaceutical materials by thermally stimulated current spectrometry. Pharm Res 18: 98-103.
47. Young PM, Chlou H, Tee T, Traini D, Chan H-K,. 2007. The use of organic vapor sorption to determine low levels of amorphous content in processed pharmaceutical powders. Drug Dev Ind Pharm 33: 91-97.
48. Zhou Y, LoBello R, Cai C, Crane N, Poshni F, Porter III WW, Cain YT,. 2010. Measurement of an amorphous form in a pharmaceutical drug product using FT-Raman spectroscopy. Am Pharm Rev July-Aug: 34-41.
49. Woo XY, Tan RBH, Braatz RD,. 2006. Precise tailoring of the crystal size distribution by controlled growth and continuous seeding from impinging jet crystallizers. CrysEngComm 13: 2006-2014.
50. Tong P, Zografi G,. 2003. Effects of water vapor absorption on the physical and chemical stability of amorphous sodium indomethacin. AAPS PharmSciTech 5: 1-8.