Polymorph formation and nucleation mechanism of tolfenamic acid in solution: An investigation of pre-nucleation solute association

Pharmaceutical Research

Volumn 29, Issue 2, 2012, Pages 460-470

  Mattei, Alessandra ^a   Li, Tonglei ^a  

^a UNIVERSITY OF KENTUCKY   (United States)

Author keywords

Dimer; Nucleation; Polymorph; Self association; Supersaturation

Indexed keywords

ALCOHOL; DIMER; TOLFENAMIC ACID; ANALGESIC AGENT; ANTHRANILIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CONCENTRATION (PARAMETERS); CONFORMATION; CRYSTALLIZATION; DRUG STRUCTURE; HYDROGEN BOND; MOLECULAR INTERACTION; MOLECULAR STABILITY; NUCLEATION; POLYMORPHIC FORMATION; PRIORITY JOURNAL; QUANTUM MECHANICS; SOLID STATE; SUPERSATURATION; ULTRAVIOLET SPECTROSCOPY; CHEMICAL STRUCTURE; CHEMISTRY; DIMERIZATION; SOLUTION AND SOLUBILITY; X RAY CRYSTALLOGRAPHY;

ANALGESICS; ANTHRANILIC ACIDS; CRYSTALLIZATION; CRYSTALLOGRAPHY, X-RAY; DIMERIZATION; MODELS, MOLECULAR; MOLECULAR CONFORMATION; SOLUTIONS;

EID: 84860859560     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-011-0574-7     Document Type: Article

References (63)

1. Byrn SR, Pfeiffer RR, Stowell JG. Solid state chemistry of drugs. West Lafayette: SSCI, Inc.; 1999.
2. Hilfiker R. Polymorphism: in the pharmaceutical industry. Weinheim: Wiley-VCH; 2006.
3. Cote A, Zhou G, Stanik M. A novel crystallization methodology to ensure isolation of the most stable crystal form. Org Process Res Dev. 2009;13:1276-83.
4. Kee NCS, Tan RBH, Braatz RD. Selective crystallization of the metastable α-form of L-glutamic acid using concentration feedback control. Cryst Growth Des. 2009;9:3044-51.
5. Brittain HG. Polymorphism and solvatomorphism 2009. J Pharm Sci. 2011;100:1260-79.
6. Lahav M, Leiserowitz L. The effect of solvent on crystal growth and morphology. Chem Eng Sci. 2001;56:2245-53. (Pubitemid 33763446)
7. Long S, Parkin S, Siegler MA, Cammers A, Li T. Polymorphism and phase behaviors of 2-(phenylamino)nicotinic acid. Cryst Growth Des. 2008;8:4006-13.
8. Musumeci D, Hunter CA, McCabe JF. Solvent effects on acridine polymorphism. Cryst Growth Des. 2010;10:1661-4.
9. Jiang S, ter Horst JH, Jansens PJ. Concomitant polymorphism of o-aminobenzoic acid in antisolvent crystallization. Cryst Growth Des. 2008;8:37-43.
10. Kitamura M, Hironaka S. Effect of temperature on antisolvent crystallization and transformation behaviors of thiazole-derivative polymorphs. Cryst Growth Des. 2006;6:1214-8. (Pubitemid 43832856)
11. Lee EH, Byrn SR, Carvajal MT. Additive-induced metastable single crystal of mefenamic acid. Pharm Res. 2006;23:2375-80. (Pubitemid 44511517)
12. Lee EH, Boerrigter SXM, Rumondor ACF, Chamarthy SP, Byrn SR. Formation and solid-state characterization of a salt-induced metastable polymorph of flufenamic acid. Cryst Growth Des. 2008;8:91-7.
13. Kitamura M. Strategy for control of crystallization of polymorphs. CrystEngComm. 2009;11:949-64.
14. Etter MC. Hydrogen bonds as design elements in organic chemistry. J Phys Chem. 1991;95:4601-10.
15. Weissbuch I, Lahav M, Leiserowitz L. Toward stereochemical control, monitoring, and understanding of crystal nucleation. Cryst Growth Des. 2003;3:125-50.
16. Bernstein J, Etter MC, Leiserowitz L. In: Dunitz JD, Bürgi H-B, editors. Structure correlations. Weinheim: VCH; 1994. p. 431-507.
17. Chen J, Sarma B, Evans JMB, Myerson AS. Pharmaceutical crystallization. Cryst Growth Des. 2011;11:887-95.
18. Becker R, Döring W. Kinetische behandlung der keimbildung in übersättingten dämpfen. Ann Phys. 1935;24:719.
19. Volmer M. Kinetik der phasenbildung. Dresden: Steinkopf; 1939.
20. Kashchiev D, van Rosmalen GM. Review: nucleation in solutions revisited. Cryst Res Technol. 2003;38:555-74.
21. Myerson AS, Lo PY. Cluster formation and diffusion in supersaturated binary and ternary amino-acid solutions. J Cryst Growth. 1991;110:26-33.
22. Davey RJ, AllenK, Blagden N, CrossWI, LiebermanHF, Quayle MJ, et al. Crystal engineering-nucleation, the key step. CrystEngComm. 2002;4:257-64.
23. Ostwald W. Studien über die Bildung und Umwandlung fester Körper. Z Phys Chem. 1897;22:289-330.
24. Haisa M, Kashino S, Kawai R, Maeda H. Monoclinic form of para-hydroxyacetanilide. Acta Crystallogr. 1976;B32:1283-5.
25. Vekilov PG. Dense liquid precursor for the nucleation of ordered solid phases from solution. Cryst Growth Des. 2004;4:671-85. (Pubitemid 39091291)
26. Vekilov PG. Nucleation. Cryst Growth Des. 2010;10:5007-19.
27. Gavezzotti A. Molecular aggregation of acetic acid in a carbon tetrachloride solution: a molecular dynamics study with a view to crystal nucleation. Chem Eur J. 1999;5:567-76. (Pubitemid 129504166)
28. Shore JD, Perchak D, Shnidman Y. Simulations of the nucleation of AgBr from solution. J Chem Phys. 2000;113:6276-84.
29. Galkin O, Pan W, Filobelo L, Hirsch RE, Nagel RL, Vekilov PG. Two-step mechanism of homogeneous nucleation of sickle cell hemoglobin polymers. Biophys J. 2007;93:902-13. (Pubitemid 47219782)
30. Erdemir D, Lee AY, Myerson AS. Nucleation of crystals from solution: classical and two-step models. Acc Chem Res. 2009;42:621-9.
31. Asherie N, Lomakin A, Benedek GB. Phase diagram of colloidal solutions. Phys Rev Lett. 1996;77:4832-5. (Pubitemid 126627706)
32. Sommerdijk NAJM, de With G. Biomimetic CaCO3 mineralization using designer molecules and interfaces. Chem Rev. 2008;108:4499-550.
33. Pouget EM, Bomans PHH, Goos JACM, Frederik PM, de With G, Sommerdijk NAJM. The initial stages of templatecontrolled CaCO3 formation revealed by cryo-TEM. Science. 2009;323:1455-8.
34. Galkin O, Vekilov PG. Direct determination of the nucleation rates of protein crystals. J Phys Chem B. 1999;103:10965-71.
35. Davey RJ, Blagden N, Righini S, Alison H, Quayle MJ, Fuller S. Crystal polymorphism as a probe for molecular self-assembly during nucleation from solutions: the case of 2,6-dihydroxybenzoic acid. Cryst Growth Des. 2001;1:59-65. (Pubitemid 33717093)
36. Parveen S, Davey RJ, Dent G, Pritchard RG. Linking solution chemistry to crystal nucleation: the case of tetrolic acid. Chem Commun. 2005;12:1531-3. (Pubitemid 40543536)
37. Erdemir D, Chattopadhyay S, Guo L, Ilavsky J, Amenitsch H, Segre CU, et al. Relationship between self-association of glycine molecules in supersaturated solutions and solid state outcome. Phys Rev Lett. 2007;99:115702-4.
38. Yu L, Kingman NG. Glycine crystallization during spray drying: the pH effect on salt and polymorphic forms. J Pharm Sci. 2002;91:2367-75. (Pubitemid 35231199)
39. Gidalevitz D, Feidenhans'l R, Matlis S, Smilgies DM, Christensen MJ, Leiserowitz L. Monitoring in situ growth and dissolution of molecular crystals: towards determination of the growth units. Angew Chem Int Ed Engl. 1997;36:955-9.
40. Huang J, Stringfellow TC, Yu L. Glycine exists mainly as monomers, not dimers, in supersaturated aqueous solutions: implications for understanding its crystallization and polymorphism. J Am Chem Soc. 2008;130:13973-80.
41. Andersen KV, Larsen S, Alhede B, Gelting N, Buchardt O. Characterization of 2 polymorphic forms of tolfenamic acid, N-(2-methyl-3-chlorophenyl) anthranilic acid-their crystal structures and relative stabilities. J Chem Soc Perkin Trans 2. 1989;10:1443-7.
42. Lopez-Mejias V, Kampf JW, Matzger AJ. Polymer-induced heteronucleation of tolfenamic acid: structural investigation of a pentamorph. J Am Chem Soc. 2009;131:4554-5.
43. Morcillo J, Gallego E, Peral F. A critical study of the application of ultraviolet spectroscopy to the self-association of adenine, adenosine and 5′-AMP in aqueous solution. J Mol Struct. 1987;157:353-69.
44. Peral F, Gallego E. Self-association of pyrimidine and some of its methyl derivatives in aqueous solution. J Mol Struct. 1995;372:101-12.
45. Kelly SM, Jess TJ, Price NC. How to study proteins by circular dichroism. Biochim Biophys Acta Proteins Proteom. 2005;1751:119-39.
46. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, et al. Gaussian 03, Revision C.02. Wallingford: Gaussian Inc.; 2004.
47. Mammino L, Kabanda MM. A computational study of the interactions of the phloroglucinol molecule with water. J Mol Struct Theochem. 2008;852:36-45.
48. Boys SF, Bernardi F. Calculation of small molecular interactions by differences of separate total energies-some procedures with reduced errors. Mol Phys. 1970;19:553-66.
49. Feng S, Li T. Predicting lattice energy of organic crystals by density functional theory with empirically corrected dispersion energy. J Chem Theory Comput. 2006;2:149-56.
50. Li T, Feng S. Empirically augmented density functional theory for predicting lattice energies of aspirin, acetaminophen polymorphs, and ibuprofen homochiral and racemic crystals. Pharm Res. 2006;23:2326-32. (Pubitemid 44511513)
51. Kohn W, Meir Y, Makarov DE. Van der Waals energies in density functional theory. Phys Rev Lett. 1998;80:4153-6. (Pubitemid 128621870)
52. Dobson JF, McLennan K, Rubio A, Wang J, Gould T, Le HM, et al. Prediction of dispersion forces: is there a problem? Aust J Chem. 2001;54:513-27. (Pubitemid 33694005)
53. Dion M, Rydberg H, Schröder E, Langreth DC, Lundqvist BI. Van der Waals density functional for general geometries. Phys Rev Lett. 2004;92:246401-4.
54. Hepburn J, Scoles G, Penco R. A simple but reliable method for the prediction of intermolecular potentials. Chem Phys Lett. 1975;36:451-6.
55. Wu Q, Yang WT. Empirical correction to density functional theory for van der Waals interactions. J Chem Phys. 2002;116:515-24. (Pubitemid 34064586)
56. Dovesi R, Saunders VR, Roetti C, Orlando R, Zicovich-Wilson CM, Pascale F, et al. Crystal06 User's Manual. Torino: Universita'di Torino; 2006.
57. Cardew PT, Davey RJ. The kinetics of solvent-mediated phasetransformations. Proc R Soc London. 1985;A398:415-28.
58. Gu CH, Young V, Grant DJW. Polymorph screening: influence of solvents on the rate of solvent-mediated polymorphic transformation. J Pharm Sci. 2001;90:1878-90. (Pubitemid 33062608)
59. Zhang GGZ, Gu CH, Zell MT, Burkhardt RT, Munson EJ, Grant DJW. Crystallization and transitions of sulfamerazine polymorphs. J Pharm Sci. 2002;91:1089-100. (Pubitemid 34640934)
60. Rao CNR. Ultra-violet and visible spectroscopy. London: Butterworths; 1961.
61. Hughes CE, Hamad S, Harris KDM, Catlow CRA, Griffiths PC. A multi-technique approach for probing the evolution of structural properties during crystallization of organic materials from solution. Faraday Discuss. 2007;136:71-89.
62. Surov AO, Szterner P, Zielenkiewicz W, Perlovich GL. Thermodynamic and structural study of tolfenamic acid polymorphs. J Pharm Biom Anal. 2009;50:831-40. The sublimation enthalpies of TFA forms I and II were experimentally determined as 128.4 and 135.1 kJ/mol at 298 K, respectively. Note that the experimental value of sublimation enthalpy of form I was directly determined, but that of form II was estimated based on solution calorimetry data. Their claim of phase transition from form I to II in solution contradicts our observation.
63. Li T, Ayers PW, Liu SB, Swadley MJ, Aubrey-Medendorp C. Crystallization Force-a density functional theory concept for revealing intermolecular interactions and molecular packing in organic crystals. Chem Eur J. 2009;15:361-71.