Molecular dynamics simulation of amorphous indomethacin

Molecular Pharmaceutics

Volumn 10, Issue 1, 2013, Pages 102-114

  Xiang, Tian Xiang ^a   Anderson, Bradley D ^a  

^a University of Kentucky   (United States)

Author keywords

amorphous solids; diffusion; hydrogen bonding; indomethacin; mobility; molecular dynamics simulation; relaxation

Indexed keywords

AMIDE; DIMER; INDOMETACIN; WATER;

ANALYTIC METHOD; ARTICLE; CHEMICAL INTERACTION; CONFORMATION; COOLING; DENSITY; DIASTEREOISOMER; DIFFUSION COEFFICIENT; FORCE; GLASS TRANSITION TEMPERATURE; HYDROGEN BOND; MOLECULAR DIFFUSIVITY; MOLECULAR DYNAMICS; PREDICTION; PRIORITY JOURNAL; PROBABILITY; ROTATION; X RAY DIFFRACTION;

CRYSTALLIZATION; EYEGLASSES; HYDROGEN BONDING; INDOMETHACIN; MOLECULAR DYNAMICS SIMULATION; PHASE TRANSITION; TRANSITION TEMPERATURE; WATER; X-RAY DIFFRACTION;

EID: 84872166445     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp3000698     Document Type: Article

References (71)

1. Patel, D. D.; Joguparthi, V.; Wang, Z.; Anderson, B. D. Maintenance of supersaturation I: indomethacin crystal growth kinetic modeling using an online second-derivative ultraviolet spectroscopic method J. Pharm. Sci. 2011, 100, 2623-41
2. Hancock, B. C.; Zografi, G. Characteristics and significance of the amorphous state in pharmaceutical systems J. Pharm. Sci. 1997, 86, 1-12
3. Leuner, C.; Dressman, J. Improving drug solubility for oral delivery using solid dispersions Eur. J. Pharm. Biopharm. 2000, 50, 47-60
4. Serajuddin, A. T. Solid dispersion of poorly water-soluble drugs: early promises, subsequent problems, and recent breakthroughs J. Pharm. Sci. 1999, 88, 1058-66
5. Taylor, L. S.; Zografi, G. Spectroscopic characterization of interactions between PVP and indomethacin in amorphous molecular dispersions Pharm. Res. 1997, 14, 1691-8
6. Hancock, B. C.; Parks, M. What is the true solubility advantage for amorphous pharmaceuticals? Pharm. Res. 2000, 17, 397-404
7. Crowley, K. J.; Zografi, G. Cryogenic grinding of indomethacin polymorphs and solvates: assessment of amorphous phase formation and amorphous phase physical stability J. Pharm. Sci. 2002, 91, 492-507
8. Savolainen, M.; Heinz, A.; Strachan, C.; Gordon, K. C.; Yliruusi, J.; Rades, T.; Sandler, N. Screening for differences in the amorphous state of indomethacin using multivariate visualization Eur. J. Pharm. Sci. 2007, 30, 113-23
9. Swallen, S. F.; Kearns, K. L.; Mapes, M. K.; Kim, Y. S.; McMahon, R. J.; Ediger, M. D.; Wu, T.; Yu, L.; Satija, S. Organic glasses with exceptional thermodynamic and kinetic stability Science 2007, 315, 353-6
10. Karmwar, P.; Graeser, K.; Gordon, K. C.; Strachan, C. J.; Rades, T. Investigation of properties and recrystallisation behaviour of amorphous indomethacin samples prepared by different methods Int. J. Pharm. 2011, 417, 94-100
11. Hutchinson, J. M.; Montserrat, S. The application of modulated differential scanning calorimetry to the glass transition of polymers. I. A single-parameter theoretical model and its predictions Thermochim. Acta 1996, 286, 263-96
12. Tribone, J. J.; O'Reilly, J. M.; Greener, J. Analysis of enthalpy relaxation in poly(methyl methacrylate): effects of tacticity, deuteration, and thermal history Macromolecules 1986, 19, 1732-9
13. Rumondor, A. C. F.; Wikstroem, H.; Van Eerdenbrugh, B.; Taylor, L. S. Understanding the Tendency of Amorphous Solid Dispersions to Undergo Amorphous-Amorphous Phase Separation in the Presence of Absorbed Moisture AAPS PharmSciTech 2011, 12, 1209-19
14. Patterson, J. E.; James, M. B.; Forster, A. H.; Lancaster, R. W.; Butler, J. M.; Rades, T. The influence of thermal and mechanical preparative techniques on the amorphous state of four poorly soluble compounds J. Pharm. Sci. 2005, 94, 1998-2012
15. Andronis, V.; Zografi, G. The molecular mobility of supercooled amorphous indomethacin as a function of temperature and relative humidity Pharm. Res. 1998, 15, 835-42
16. Aso, Y.; Yoshioka, S.; Kojima, S. Relationship between the crystallization rates of amorphous nifedipine, phenobarbital, and flopropione, and their molecular mobility as measured by their enthalpy relaxation and (1)H NMR relaxation times J. Pharm. Sci. 2000, 89, 408-16
17. Aso, Y.; Yoshioka, S.; Kojima, S. Explanation of the crystallization rate of amorphous nifedipine and phenobarbital from their molecular mobility as measured by (13)C nuclear magnetic resonance relaxation time and the relaxation time obtained from the heating rate dependence of the glass transition temperature J. Pharm. Sci. 2001, 90, 798-806
18. Carpentier, L.; Decressain, R.; Desprez, S.; Descamps, M. Dynamics of the amorphous and crystalline alpha-, gamma-phases of indomethacin J. Phys. Chem. B 2006, 110, 457-64
19. Mapes, M. K. Dynamics in model supercooled liquids: Self-diffusion in o-terphenyl and indomethacin. Ph.D. Dissertation, University of Wisconsin, Madison, WI, 2006.
20. Donth, E. The Glass Transition: Relaxation Dynamics in Liquids and Disordered Materials; Springer-Verlag: Berlin, 2001.
21. Vyazovkin, S.; Dranca, I. Physical stability and relaxation of amorphous indomethacin J. Phys. Chem. B 2005, 109, 18637-44
22. Andronis, V.; Zografi, G. Crystal nucleation and growth of indomethacin polymorphs from the amorphous state J. Non-Cryst. Solids 2000, 271, 236-248
23. Chen, X.; Morris, K. R.; Griesser, U. J.; Byrn, S. R.; Stowell, J. G. Reactivity differences of indomethacin solid forms with ammonia gas J. Am. Chem. Soc. 2002, 124, 15012-9
24. Aubrey-Medendorp, C.; Swadley, M. J.; Li, T. The polymorphism of indomethacin: an analysis by density functional theory calculations Pharm. Res. 2008, 25, 953-9
25. Masuda, K.; Tabata, S.; Kono, H.; Sakata, Y.; Hayase, T.; Yonemochi, E.; Terada, K. Solid-state 13C NMR study of indomethacin polymorphism Int. J. Pharm. 2006, 318, 146-53
26. Yoshioka, M.; Hancock, B. C.; Zografi, G. Crystallization of indomethacin from the amorphous state below and above its glass transition temperature J. Pharm. Sci. 1994, 83, 1700-5
27. Hancock, B. C.; Shamblin, S. L.; Zografi, G. Molecular mobility of amorphous pharmaceutical solids below their glass transition temperatures Pharm. Res. 1995, 12, 799-806
28. Yu, L. Amorphous pharmaceutical solids: preparation, characterization and stabilization Adv. Drug Delivery Rev. 2001, 48, 27-42
29. De Angelis, M. G.; Sarti, G. C. Solubility of Gases and Liquids in Glassy Polymers Annu. Rev. Chem. Biomol. Eng. 2011, 2, 97-120
30. Paul, W.; Bedrov, D.; Smith, G. D. Glass transition in 1,4-polybutadiene: Mode-coupling theory analysis of molecular dynamics simulations using a chemically realistic model Phys. Rev. E: Stat., Nonlinear, Soft Matter Phys. 2006, 74, 021501
31. Abdel-Halim, H.; Traini, D.; Hibbs, D.; Gaisford, S.; Young, P. Modelling of molecular phase transitions in pharmaceutical inhalation compounds: an in silico approach Eur. J. Pharm. Biopharm. 2011, 78, 83-9
32. Gupta, J.; Nunes, C.; Vyas, S.; Jonnalagadda, S. Prediction of solubility parameters and miscibility of pharmaceutical compounds by molecular dynamics simulations J. Phys. Chem. B 2011, 115, 2014-23
33. Huynh, L.; Grant, J.; Leroux, J. C.; Delmas, P.; Allen, C. Predicting the solubility of the anti-cancer agent docetaxel in small molecule excipients using computational methods Pharm. Res. 2008, 25, 147-57
34. Yang, H.; Li, Z.-S.; Qian, H.-j.; Yang, Y.-b.; Zhang, X.-b.; Sun, C -c. Molecular dynamics simulation studies of binary blend miscibility of poly(3-hydroxybutyrate) and poly(ethylene oxide) Polymer 2004, 45, 453-7
35. Barrat, J.-L.; Baschnage, J.; Lyulin, A. Molecular dynamics simulations of glassy polymers Soft Matter 2010, 6, 3430-46
36. Xiang, T. X.; Anderson, B. D. A molecular dynamics simulation of reactant mobility in an amorphous formulation of a peptide in poly(vinylpyrrolidone) J. Pharm. Sci. 2004, 93, 855-76
37. Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Results obtained with the correlation energy density functionals of Becke and Lee, Yang and Parr Chem. Phys. Lett. 1989, 157, 200-6
38. Pomelli, C. S.; Tomasi, J.; Barone, V. An improved iterative solution to solve the electrostatic problem in the polarizable continuum model Theor. Chem. Acc. 2001, 105, 446-51
39. Duan, Y.; Wu, C.; Chowdhury, S.; Lee, M. C.; Xiong, G.; Zhang, W.; Yang, R.; Cieplak, P.; Luo, R.; Lee, T.; Caldwell, J.; Wang, J.; Kollman, P. A point-charge force field for molecular mechanics simulations of proteins based on condensed-phase quantum mechanical calculations J. Comput. Chem. 2003, 24, 1999-2012
40. Bayly, C. I.; Cieplak, P.; Cornell, W.; Kollman, P. A. A well-behaved electrostatic potential based method using charge restraints for deriving atomic charges: the RESP model J. Phys. Chem. 1993, 97, 10269-80
41. Cieplak, P.; Caldwell, J.; Kollman, P. Molecular mechanical models for organic and biological systems going beyond the atom centered two body additive approximation: aqueous solution free energies of methanol and N-methyl acetamide, nucleic acid base, and amide hydrogen bonding and chloroform/water partition coefficients of the nucleic acid bases J. Comput. Chem. 2001, 22, 1048-57
42. Verlet, L. Computer "experiments" on classical fluids. I. Thermodynamical properties of Lennard-Jones molecules Phys. Rev. 1967, 159, 98-103
43. Berendsen, H. J. C.; Postma, J. P. M.; Van Gunsteren, W. F.; DiNola, A.; Haak, J. R. Molecular dynamics with coupling to an external bath J. Chem. Phys. 1984, 81, 3684-90
44. Ewald, P. Die berechnung optischer und elektrostatischer gitterpotentiale Ann. Phys. 1921, 64, 253-87
45. Humphrey, W.; Dalke, A.; Schulten, K. VMD: visual molecular dynamics J. Mol. Graphics 1996, 14 (33-8) 27-8
46. Aceves-Hernandez, J. M.; Nicolas-Vazquez, I.; Aceves, F. J.; Hinojosa-Torres, J.; Paz, M.; Castano, V. M. Indomethacin polymorphs: Experimental and conformational analysis J. Pharm. Sci. 2009, 98, 2448-63
47. Jaidann, M.; Abou-Rachid, H.; Lafleur-Lambert, X.; Lussier, L.-S.; Gagnon, N.; Brisson, J. Modeling and measurement of glass transition temperatures of energetic and inert systems Polym. Eng. Sci. 2008, 1141-50
48. Lyulin, A. V.; Balabaev, N. K.; Michels, M. A. J. Molecular-weight and cooling-rate dependence of simulated Tg for amorphous polystyrene Macromolecules 2003, 36, 8574-5
49. Yu, K.-Q.; Li, Z.-S.; Sun, J. Polymer structures and glass transition: A molecular dynamics simulation study Macromol. Theory Simul. 2001, 10, 624-33
50. Marsac, P. J. Formation and stabilization of amorphous molecular level solid dispersions. Ph.D. Dissertation, Purdue University, West Lafayette, IN, 2007.
51. Marsac, P. J.; Li, T.; Taylor, L. S. Estimation of drug-polymer miscibility and solubility in amorphous solid dispersions using experimentally determined interaction parameters Pharm. Res. 2009, 26, 139-51
52. Tong, P.; Zografi, G. Solid-state characteristics of amorphous sodium indomethacin relative to its free acid Pharm. Res. 1999, 16, 1186-92
53. Götze, W. Complex Dynamics of Glass-Forming Liquids: A Mode-Coupling Theory; Oxford University Press: Oxford, 2009.
54. Marsac, P. J.; Rumondor, A. C.; Nivens, D. E.; Kestur, U. S.; Stanciu, L.; Taylor, L. S. Effect of temperature and moisture on the miscibility of amorphous dispersions of felodipine and poly(vinyl pyrrolidone) J. Pharm. Sci. 2010, 99, 169-85
55. Strachan, C. J.; Rades, T.; Gordon, K. C. A theoretical and spectroscopic study of gamma-crystalline and amorphous indomethacin J. Pharm. Pharmacol. 2007, 59, 261-9
56. Borne, R.; Levi, M.; Wilson, N. Nonsteroidal anti-inflammatory drugs. In Foye's Principles of Medicinal Chemistry; Lemke, T. L.; Williams, D. A.; Roche, V. F.; Zito, S. W., Eds.; Lippincott Williams and Wilkins: Philadelphia, PA, 2008; pp 954-1003.
57. 1H NMR and Molecular Modeling Study on the Inclusion Complex β-Cyclodextrin- Indomethacin J. Org. Chem. 1996, 61, 909-14
58. Swallen, S. F.; Traynor, K.; McMahon, R. J.; Ediger, M. D.; Mates, T. E. Self-diffusion of supercooled tris-naphthylbenzene J. Phys. Chem. B 2009, 113, 4600-8
59. Bernabei, M.; Moreno, A. J.; Zaccarelli, E.; Sciortino, F.; Colmenero, J. From caging to Rouse dynamics in polymer melts with intramolecular barriers: a critical test of the mode coupling theory J. Chem. Phys. 2011, 134, 024523
60. Colmenero, J.; Narros, A.; Alvarez, F.; Arbe, A.; Moreno, A. J. Atomic motions in the αβ-region of glass-forming polymers: molecular versus mode coupling theory approach J. Phys.: Condens. Matter 2007, 19, 205127/1-205127/11
61. Kucukpinar, E.; Doruker, P. Molecular simulations of small gas diffusion and solubility in copolymers of styrene Polymer 2003, 44, 3607-20
62. Muller-Plathe, F. Molecular dynamics simulation of gas transport in amorphous polypropylene J. Chem. Phys. 1992, 96, 3200-5
63. Smith, G. D.; Bedrov, D. Relationship between the α- and β-relaxation processes in amorphous polymers: insight from atomistic molecular dynamics simulations of 1,4-polybutadiene melts and blends J. Polym. Sci., Part B: Polym. Phys. 2007, 45, 627-43
64. Sidebottom, D. L.; Green, P. F.; Brow, R. K. Anomalous-diffusion model of ionic transport in oxide glasses Phys. Rev. B: Condens. Matter Mater. Phys. 1995, 51, 2770-6
65. Williams, G.; Watts, D. C. Non-symmetrical dielectric relaxation behavior arising from a simple empirical decay function Trans. Faraday Soc. 1970, 66, 80-5
66. Williams, G.; Watts, D. C.; Dev, S. B.; North, A. M. Further considerations of nonsymmetrical dielectric relaxation behavior arising from a simple empirical decay function Trans. Faraday Soc. 1971, 67, 1323-35
67. Kohlrausch, R. Theorie des elektrischen Rückstandes in der Leidner Flasche Ann. Phys. Chemie (Poggendorff) 1854, 91, 179-213
68. Andronis, V.; Zografi, G. Molecular mobility of supercooled amorphous indomethacin, determined by dynamic mechanical analysis Pharm. Res. 1997, 14, 410-4
69. He, R.; Craig, D. Q. An investigation into the thermal behaviour of an amorphous drug using low frequency dielectric spectroscopy and modulated temperature differential scanning calorimetry J. Pharm. Pharmacol. 2001, 53, 41-8
70. Dawson, K. J.; Kearns, K. L.; Ediger, M. D.; Sacchetti, M. J.; Zografi, G. D. Highly stable indomethacin glasses resist uptake of water vapor J. Phys. Chem. B 2009, 113, 2422-7
71. Swallen, S. F.; Ediger, M. D. Self-diffusion of the amorphous pharmaceutical indomethacin near Tg Soft Matter 2011, 7, 10339-44