Decoupling the effects of surface chemistry and humidity on solid-state hydrolysis of aspirin in the presence of dicalcium phosphate dihydrate

Journal of Pharmaceutical Sciences

Volumn 101, Issue 4, 2012, Pages 1496-1507

  Cassidy, Andrew M ^a   Gardner, Catherine E ^a   Auffret, Tony ^b   Aldous, Barry ^b   Jones, William ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

Atomic force microscopy; Chemical stability; Crystals; Degradation products; Drug interactions; Excipients; Materials science; Microscopy; Moisture sorption; Solid state stability; Surface chemistry

Indexed keywords

ACETYLSALICYLIC ACID; CALCIUM PHOSPHATE DIBASIC; EXCIPIENT;

ANISOTROPY; ARTICLE; ATOMIC FORCE MICROSCOPY; CRYSTAL; HUMIDITY; HYDROLYSIS; MOLECULAR INTERACTION; SCANNING ELECTRON MICROSCOPY; SOLID STATE HYDROLYSIS; SURFACE PROPERTY; TOPOGRAPHY;

EID: 84857504878     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.23038     Document Type: Article

References (36)

1. Gardner CR, Walsh CT, Almarsson O. 2004. Drugs as materials: Valuing physical form in drug discovery. Nat Rev Drug Discov 3:926-934.
2. Cui Y. 2007. A material science perspective of pharmaceutical solids. Int J Pharm 339:3-18.
3. Byrn SR, Xu W, Newman AW. 2001. Chemical reactivity in solid-state pharmaceuticals: Formulation implications. Adv Drug Deliv Rev 48:115-136.
4. Mroso PV, Po ALW, Irwin WJ. 1982. Solid-state stability of aspirin in the presence of excipients: Kinetic interpretation, modeling, and prediction. J Pharm Sci 71:1096-1101.
5. Garrett ER. 1957. The kinetics of solvolysis of acyl esters of salicyclic acid. J Am Chem Soc 79:3401-3408.
6. Leeson LJ, Mattocks AM. 1958. Decomposition of aspirin in the solid state. J Am Pharm Assoc 47:329-333.
7. Hasegawa J, Hanano M, Awazu S. 1975. Decomposition of acetylsalicyclic acid and its derivatives in solid state. Chem Pharm Bull 23:86-97.
8. Ball MC. 1994. Solid-state hydrolysis of aspirin. J Chem Soc Faraday Trans 90:997-1001.
9. Hancock BC, Zografi G. 1996. Effects of solid-state processing on water vapor sorption by aspirin. J Pharm Sci 85:246-248.
10. Harding L, Qi S, Hill G, Reading M, Craig D. 2008. The development of microthermal analysis and photothermal microspectroscopy as novel approaches to drug-excipient compatibility studies. Int J Pharm 354:149-157.
11. Campanella L, Micieli V, Tomassetti M, Vecchio S. 2001. Kinetic investigation and predictive model for the isothermal degradation time in two commercial acetylsalicylic acid-based pharmaceutical tablet formulations. Thermochim Acta 526:151-156.
12. Landin M, Casalderrey M, Martinez-Pacheco R, Gómez-Amoza JL, Souto C, Concheiro A, Rowe RC. 1995. Chemical stability of acetylsalicylic acid in tablets prepared with different particle size fractions of a commercial brand of dicalcium phosphate dihydrate. Int J Pharm 123:143-144.
13. Glombitza BW, Schmidt PC. 1995. Surface acidity of solid pharmaceutical excipients II. Effect of the surface acidity on the decomposition rate of acetylsalicylic acid. Eur J Pharm Biopharm 41:114-119.
14. Atsushi W, Yumikoa Y, Kozo T. 1982. Crystal habits and dissolution behavior of aspirin. Chem Pharm Bull 30:2958-2963.
15. Wheatley PJ. 1964. The crystal and molecular structure of aspirin. J Chem Soc 6036-6048.
16. Heng JY, Bismarck A, Lee AF, Wilson K, Williams DR. 2007. Anisotropic surface chemistry of aspirin crystals. J Pharm Sci 96:2134-2144.
17. Danesh A, Davies M, Hinder S, Roberts C, Tendler S, Williams P, Wilkins M. 2000. Surface characterization of aspirin crystal planes by dynamic chemical force microscopy. Anal Chem 72:3419-3422.
18. Danesh A, Connell SD, Davies MC, Roberts CJ, Tendler SJB, Williams PM, Wilkins MJ. 2001. An in situ dissolution study of aspirin crystal planes (100) and (001) by atomic force microscopy. Pharm Res 18:299-303.
19. Roberts CJ. 2005. What can we learn from atomic force microscopy adhesion measurements with single drug particles? Eur J Pharm Sci 24:153-157.
20. Adi H, Traini D, Chan HK, Young PM. 2007. The influence of drug morphology on aerosolisation efficiency of dry powder inhaler formulations. J Pharm Sci 97:2780-2788.
21. Ducker WA, Senden TJ, Pashley RM. 1992. Direct measurement of colloidal forces using an atomic force microscope. Nature 353:239-241.
22. Butt HJ, Cappella B, Kappl M. 2005. Force measurements with the atomic force microscope: Technique, interpretation and applications. Surf Sci Rep 59:1-152.
23. Sader JE, Chon JWM, Mulvaney P. 1999. Calibration of rectangular atomic force microscope cantilevers. Rev Sci Instrum 70:3967-3969.
24. Young PM, Price R, Tobyn MJ, Buttrum M, Dey F. 2003. Investigation into the effect of humidity on drug-drug interactions using the atomic force microscope. J Pharm Sci 92:815-822.
25. Hooton JC, German CS, Allen S, Davies MC, Roberts CJ, Tendler SJB, Williams PM. 2003. Characterization of particle-interactions by atomic force microscopy: Effect of contact area. Pharm Res 20:508-514.
26. Connors KA, Amidon GL, Stella VJ. 1986. Chemical stability of pharmaceuticals. Wiley-IEEE, Hoboken, New Jersey, USA 07030-5774, pp 220-230.
27. Cassidy AM. 2010. Probing pharmaceutical materials with atomic force microscopy. Ph.D. Thesis. University of Cambridge, Cambridge CB2 1TN, UK.
28. Paajanen M, Katainen J, Pakarinen OH, Foster AS, Lahtinen J. 2006. Experimental humidity dependency of small particle adhesion on silica and titania. J Colloid Interface Sci 304:518-523.
29. Brunauer S. 1943. The adsoprtion of gases and valors. Princeton University Press, Princeton, New Jersey, U S A 08540-5237.
30. Gady B, Schleef D, Reifenberger R, Rimai D, DeMejo LP. 1996. Identification of electrostatic and van der Waals interaction forces between a micrometer-size sphere and a flat substrate. Phys Rev B 53:8065-8070.
31. Eve JK, Patel N, Luk SY, Ebbens SJ, Roberts CJ. 2002. A study of single drug particle adhesion interactions using atomic force microscopy. Int J Pharm 238:17-27.
32. Bunker MJ, Davies MC, James MB, Roberts CJ. 2007. Direct observation of single particle electrostatic charging by atomic force microscopy. Pharm Res 24:1165-1169.
33. Young PM, Price R, Tobyn MJ, Buttrum M, Dey F. 2004. The influence of relative humidity on the cohesion properties of micronized drugs used in inhalation therapy. J Pharm Sci 93:753-761.
34. Jones R, Pollock HM, Cleaver JAS, Hodges CS. 2002. Adhesion forces between glass and silicon surfaces in air studied by AFM: Effects of relative humidity, particle size, roughness, and surface treatment. Langmuir 18:8045-8055.
35. Wen H, Li T, Morris KR, Park K. 2004. Dissolution study on aspirin and α-glycine crystals. J Phys Chem B 108:11219-11227.
36. Cassidy A, Gardner C, Jones W. 2009. Following the surface response of caffeine cocrystals to controlled humidity storage by atomic force microscopy. Int J Pharm 379:59-66.