Screening and characterization of cocrystal formation of metaxalone with short-chain dicarboxylic acids induced by solvent-assisted grinding approach

Thermochimica Acta

Volumn 575, Issue , 2014, Pages 313-321

  Lin, Hong Liang ^a   Wu, Tieh Kang ^a   Lin, Shan Yang ^a  

^a YUANPEI UNIVERSITY   (Taiwan)

Author keywords

Cocrystal, PXRD; Dicarboxylic acids; DSC FTIR; Metaxalone; Solvent assisted grinding

Indexed keywords

CO-CRYSTAL FORMATION; CO-CRYSTALS; DICARBOXYLIC ACID; DSC-FTIR; FOURIER TRANSFORM INFRARED MICROSPECTROSCOPY; METAXALONE; POWDER X-RAY DIFFRACTION (PXRD); SOLVENT EVAPORATION METHOD;

CHAINS; DIFFERENTIAL SCANNING CALORIMETRY; GRINDING (MACHINING); X RAY DIFFRACTION;

SOLVENTS;

EID: 84890259929     PISSN: 00406031     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tca.2013.10.029     Document Type: Article

References (43)

1. T. Friscic, and W. Jones Benefits of cocrystallization in pharmaceutical materials science: an update J. Pharm. Pharmacol. 62 2010 1547 1559
2. N. Qiao, M. Li, W. Schlindwein, N. Malek, A. Davies, and G. Trappitt Pharmaceutical cocrystals: an overview Int. J. Pharm. 419 2011 1 11
3. H.G. Brittain Pharmaceutical cocrystals: the coming wave of new drug substances J. Pharm. Sci. 102 2013 311 317
4. C.C. Sun Cocrystallization for successful drug delivery Expert Opin. Drug Deliv. 10 2013 201 213
5. I. Miroshnyk, S. Mirza, and N. Sandler Pharmaceutical co-crystals - an opportunity for drug product enhancement Expert Opin. Drug Deliv. 6 2009 333 341
6. B. Rodríguez-Spong, C.P. Price, A. Jayasankar, A.J. Matzger, and N. Rodríguez-Hornedo. General principles of pharmaceutical solid polymorphism: a supramolecular perspective Adv. Drug Deliv. Rev. 56 2004 241 274
7. A.V. Trask An overview of pharmaceutical cocrystals as intellectual property Mol. Pharm. 4 2007 301 309 (Pubitemid 46983946)
8. B.S. Sekhon Pharmaceutical co-crystals: a review Ars Pharm. 50 2009 99 117
9. S.R. Bysouth, J.A. Bis, and D. Igo Cocrystallization via planetary milling: enhancing throughput of solid-state screening methods Int. J. Pharm. 411 2011 169 171
10. G.C. Zhang, H.L. Lin, and S.Y. Lin Thermal analysis and FTIR spectral curve-fitting investigation of formation mechanism and stability of indomethacin-saccharin cocrystals via solid-state grinding process J. Pharm. Biomed. Anal. 66 2012 162 169
11. P.C. Hsu, H.L. Lin, S.L. Wang, and S.Y. Lin Solid-state thermal behavior and stability studies of theophylline-citric acid cocrystals prepared by neat cogrinding or thermal treatment J. Solid State Chem. 192 2012 238 245
12. T. Friscic, A.V. Trask, W. Jones, and W.D.S. Motherwell Screening for inclusion compounds and systematic construction of three-component solids by liquid-assisted grinding Angew. Chem. Int. Ed. 45 2006 7546 7550 (Pubitemid 44851678)
13. N. Shan, F. Toda, and W. Jones Mechanochemistry and co-crystal formation: effect of solvent on reaction kinetics Chem. Commun. 21 2002 2372 2373 (Pubitemid 35283628)
14. A.V. Trask, W.D.S. Motherwell, and W. Jones Solvent-drop grinding: green polymorph control of cocrystallisation Chem. Commun. 23 2004 890 891 (Pubitemid 38530287)
15. M.A. Pfeifer, D.R. Ross, J.P. Schrage, D.A. Gelber, M.P. Schumer, G.M. Crain, S.S. Markwell, and S. Jung A highly successful and novel model for the treatment of chronic painful diabetic neuropathy Diabetes Care 16 1993 1103 1115 (Pubitemid 23215398)
16. E.L. Spierings Chronic daily headache: a review Headache Quart. 11 2000 181 196 (Pubitemid 32128748)
17. P.P. Toth, and J. Urtis Commonly used muscle relaxant therapies for acute low back pain: a review of carisoprodol, cyclobenzaprine hydrochloride, and metaxalone Clin. Ther. 26 2004 1355 1367 (Pubitemid 39572151)
18. K. Kandasamy, V.S. Gowdra, H. Nammalvar, and A.K.S. Govindarajan Bioanalytical method development, validation and quantification of metaxalone in rat plasma by liquid chromatography tandem mass spectrometry J. Bioanal. Biomed. S6 2012 006 10.4172/1948-593X
19. J. Chattopadhyay, S. Sarkar, J.S. Mahanty, S. Hazra, M. Mitra, M.K. Singh, Metaxalone polymorphs. U.S. Patent 7750165, 2010.
20. K. Lorimer, K.W. Meyer, T. Sun, S. Watson, K.R. Nielsen, Amorphous metaxalone and amorphous dispersions thereof. WO2009085637, 2009.
21. J. Holland, C. Frampton, A. Chorlton, D. Gooding, Metaxalone cocrystals. WO2011077252, 2011.
22. R. Niederman, J. Zhang, and S. Kashket Short-chain carboxylic-acid- stimulated, PMN-mediated gingival inflammation Crit. Rev. Oral Biol. Med. 8 1997 269 290 (Pubitemid 27347331)
23. G.R. Desiraju Crystal Engineering: The Design of Organic Solids 1989 Elsevier Amsterdam, The Netherlands
24. C.C. Seaton Creating carboxylic acid co-crystals: the application of Hammett substitution constants CrystEngComm 13 2011 6583 6592
25. E.A. Losev, M.A. Mikhailenko, and E.V. Boldyreva Selective effect of carboxylic acids on glycine polymorphisms and cocrystal formation Doklady Phys. Chem. 439 2011 153 156
26. S.A. Myz, T.P. Shakhtshneider, K. Fucke, A.P. Fedotov, E.V. Boldyreva, V.V. Boldyrev, and N.I. Kuleshova Synthesis of co-crystals of meloxicam with carboxylic acids by grinding Mendeleev Commun. 19 2009 272 274
27. T.K. Wu, S.Y. Lin, H.L. Lin, and Y.T. Huang Simultaneous DSC-FTIR microspectroscopy used to screen and detect the co-crystal formation in real time Bioorg. Med. Chem. Lett. 21 2011 3148 3151
28. H.L. Lin, S.Y. Lin, C.C. Lin, C.H. Hsu, T.K. Wu, and Y.T. Huang Mechanical grinding effect on thermodynamics and inclusion efficiency of loratadine-cyclodextrin inclusion complex formation Carbohy. Polym. 87 2012 512 517
29. S.Y. Lin, and S.L. Wang Advances in simultaneous DSC-FTIR microspectroscopy for rapid solid-state chemical stability studies: some dipeptide drugs as examples Adv. Drug Deliv. Rev. 64 2012 461 478
30. S. Aitipamula, P.S. Chow, and R.B.H. Tan Conformational polymorphs of a muscle relaxant, metaxalone Cryst. Growth Des. 11 2011 4101 4109
31. E. Lu, N. Rodríguez-Hornedo, and R. Suryanarayanan A rapid thermal method for cocrystal screening CrystEngComm 10 2008 665 668
32. S.K. Callear, M.B. Hursthouse, and T.L. Threlfall Co-crystallisation of organic α,ω-dicarboxylic acids with the cyclic amides 2-pyrrolidinone and 2-imidazolidinone CrystEngComm 11 2009 1609 1614
33. M.R. Edwards, W. Jones, and W.D.S. Motherwell Influence of dicarboxylic acid structure on tape networks in co-crystals of 2-pyridone Cryst. Eng. 5 2002 25 36 (Pubitemid 34300767)
34. V.R. Pedireddi, S. Chatterjee, A. Ranganathan, and C.N.R. Rao A study of supramolecular hydrogen bonded complexes formed by aliphatic dicarboxylic acids with azaaromatic donors Tetrahedron 54 1998 9457 9474 (Pubitemid 28332718)
35. E. Batchelor, J. Klinowski, and W. Jones Crystal engineering using co-crystallisation of phenazine with dicarboxylic acids J. Mater. Chem. 10 2000 839 848
36. G. Smith, M.G. Coyne, and J.M. White Molecular cocrystals of aromatic carboxylic acids with 1,1-diethylurea: synthesis and the crystal structures of a series of nitro-substituted analogues Austral. J. Chem. 53 2000 203 208
37. M.A. Mohammad, A. Alhalaweh, and S.P. Velaga Hansen solubility parameter as a tool to predict cocrystal formation Int. J. Pharm. 407 2011 63 71
38. O.L. Evora, R.A.E. Castro, T.M.R. Maria, M.T.S. Rosado, M.R. Siliva, A.M. Beja, J. Canotilho, and M.E.S. Eusebio Pyrazinamide-diflunisal: a new dual-drug co-crystal Cryst. Growth Des. 11 2011 4780 4788
39. E. Zaini, Y.C. Sumirtapura, S.N. Soewandhi, A. Halim, H. Uekusa, and K. Fujii Cocrystalline phase transformation of binary mixture of trimethoprim and sulfamethoxazole by slurry technique Asian J. Pharm. Clin. Res. 3 2010 26 29
40. D. Giron Thermal analysis, microcalorimetry and combined techniques for the study of pharmaceuticals J. Therm. Anal. Calorimetry 56 1999 1285 1304
41. P. Mura, M. Cirri, M.T. Faucci, J.M. Ginès-Dorado, and G.P. Bettinetti Investigation of the effects of grinding and co-grinding on physicochemical properties of glisentide J. Pharm. Biomed. Anal. 30 2002 227 237 (Pubitemid 35013487)
42. H.L. Lin, P.C. Hsu, and S.Y. Lin Theophylline-citric acid co-crystals easily induced by DSC-FTIR microspectroscopy or different storage conditions Asian J. Pharm. Sci. 2013 (in press)
43. S. Krishnan, C.J. Raj, S.M. Navis Priya, R. Robert, S. Dinakaran, and S.J. Das Optical and dielectric studies on succinic acid single crystals Cryst. Res. Technol. 43 2008 845 850