Thermal analysis and FTIR spectral curve-fitting investigation of formation mechanism and stability of indomethacin-saccharin cocrystals via solid-state grinding process

Journal of Pharmaceutical and Biomedical Analysis

Volumn 66, Issue , 2012, Pages 162-169

  Zhang, Gang Chun ^a   Lin, Hong Liang ^a   Lin, Shan Yang ^a  

^a YUANPEI UNIVERSITY   (Taiwan)

Author keywords

Cocrystal; Cogrinding; Curve fitting; DSC; Formation mechanism; Indomethacin; Saccharin; Stability; Thermal effect

Indexed keywords

INDOMETACIN; SACCHARIN;

ARTICLE; CRYSTAL STRUCTURE; CURVE FITTING; DIFFERENTIAL SCANNING CALORIMETRY; DRUG STABILITY; DRUG STORAGE; DRUG STRUCTURE; EVAPORATION; FOURIER TRANSFORM INFRARED PHOTOACOUSTIC SPECTROSCOPY; GRINDING; HYDROGEN BOND; PRIORITY JOURNAL; SOLID STATE; THERMAL ANALYSIS;

CALORIMETRY, DIFFERENTIAL SCANNING; CRYSTALLIZATION; DRUG STABILITY; DRUG STORAGE; HYDROGEN BONDING; INDOMETHACIN; SACCHARIN; SOLVENTS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; TEMPERATURE; TIME FACTORS; TRANSITION TEMPERATURE;

EID: 84861221266     PISSN: 07317085     EISSN: 1873264X     Source Type: Journal    
DOI: 10.1016/j.jpba.2012.03.039     Document Type: Article

References (48)

1. Hauss D.J. Oral lipid-based formulations. Adv. Drug Deliv. Rev. 2007, 59:667-676.
2. Connors R.D., Elder E.J. Using a portfolio of particle growth technologies to enable delivery of drugs with poor water solubility. Drug Deliv. Technol. 2004, 4:78-83.
3. US FDA, The Biopharmaceutics Classification System (BCS) Guidance, 2009, http://www.fda.gov/AboutFDA/CentersOffices/CDER/ucm128219.htm.
4. Amidon G.L., Lennernäs H., Shah V.P., Crison J.R. A theoretical basis for a biopharmaceutics drug classification: the correlation of in vitro drug product dissolution and in vivo bioavailability. Pharm. Res. 1995, 12:413-420.
5. Emami J. In vitro-in vivo correlation: from theory to applications. J. Pharm. Pharm. Sci. 2006, 9:169-189.
6. Uppoor R.S. Regulatory considerations for in vitro/in vivo correlations. Am. Pharm. Rev. 2005, 8:42-45.
7. Loftsson T., Jarho P., Másson M., Järvinen T. Cyclodextrins in drug delivery. Expert Opin. Drug Deliv. 2005, 2:335-351.
8. Vemula V.R., Lagishetty V., Lingala S. Solubility enhancement techniques. Int. J. Pharm. Sci. Rev. Res. 2010, 5:41-51.
9. Wadke D.A., Serajuddin A.T.M., Jacobson H. Preformulation testing. Pharmaceutical Dosage Forms: Tablets 1989, vol. 1:1-73. Dekker, New York.
10. Serajuddin A.T.M. Solid dispersion of poorly water-soluble drugs: early promises, subsequent problems and recent breakthroughs. J. Pharm. Sci. 1998, 88:1058-1066.
11. Vishweshwar P., McMahon J.A., Bis J.A., Zaworotko M.J. Pharmaceutical co-crystals. J. Pharm. Sci. 2006, 95:499-516.
12. Schultheiss N., Newman A. Pharmaceutical cocrystals and their physicochemical properties. Cryst. Growth Des. 2009, 9:2950-2967.
13. Miroshnyk I., Mirza S., Sandler N. Pharmaceutical co-crystals-an opportunity for drug product enhancement. Expert Opin. Drug Deliv. 2009, 6:333-341.
14. Qiao N., Li M., Schlindwein W., Malek N., Davies A., Trappitt G. Pharmaceutical cocrystals: an overview. Int. J. Pharm. 2011, 419:1-11.
15. Davis R.E., Lorimer K.A., Wilkowski M.A., Rivers J.H. Studies of relationship in cocrystal systems. ACA Trans. 2004, 39:41-61.
16. Shiraki K., Takata N., Takano R., Hayashi Y., Terada K. Dissolution improvement and the mechanism of the improvement from cocrystallization of poorly water-soluble compounds. Pharm. Res. 2008, 25:2581-2592.
17. Trask A.V. An overview of pharmaceutical cocrystals as intellectual property. Mol. Pharm. 2007, 4:301-309.
18. Shan N., Zaworotko M.J. The role of cocrystals in pharmaceutical science. Drug Discov. Today 2008, 13:440-446.
19. Wu T.K., Lin S.Y., Lin H.L., Huang Y.T. Simultaneous DSC-FTIR microspectroscopy used to screen and detect the co-crystal formation in real time. Bioorg. Med. Chem. Lett. 2011, 21:3148-3151.
20. Trask A.V., Jones W. Crystal engineering of organic cocrystals by the solid-state grinding approach. Top. Curr. Chem. 2005, 254:41-70.
21. Friščić T., Jones W. Recent advances in understanding the mechanism of cocrystal formation via grinding. Cryst. Growth Des. 2009, 9:1621-1637.
22. Kaupp G. Mechanochemistry: the varied applications of mechanical bond-breaking. CrystEngComm 2009, 11:388-403.
23. Shan N., Toda F., Jones W. Mechanochemistry and co-crystal formation: effect of solvent on reaction kinetics. Chem. Commun. 2002, 2372-2373.
24. Karki S., Friscić T., Jones W., Motherwell W.D. Screening for pharmaceutical cocrystal hydrates via neat and liquid-assisted grinding. Mol. Pharm. 2007, 4:347-354.
25. Basavoju S., Boström D., Velaga S.P. Indomethacin-saccharin cocrystal: design, synthesis and preliminary pharmaceutical characterization. Pharm. Res. 2008, 25:530-541.
26. Padrela L., Rodrigues M.A., Velaga S.P., Matos H.A., de Azevedo E.G. Formation of indomethacin-saccharin cocrystals using supercritical fluid technology. Eur. J. Pharm. Sci. 2009, 38:9-17.
27. Allesø M., Velaga S., Alhalaweh A., Cornett C., Rasmussen M.A., van den Berg F., et al. Near-infrared spectroscopy for cocrystal screening. A comparative study with Raman spectroscopy. Anal. Chem. 2008, 80:7755-7764.
28. Jung M.S., Kim J.S., Kim M.S., Alhalaweh A., Cho W., Hwang S.J., et al. Bioavailability of indomethacin-saccharin cocrystals. J. Pharm. Pharmacol. 2010, 62:1560-1568.
29. Lin S.Y., Hsu C.H., Sheu M.T. Curve-fitting FTIR studies of loratadine/hydroxypropyl-beta-cyclodextrin inclusion complex induced by co-grinding process. J. Pharm. Biomed. Anal. 2010, 53:799-803.
30. Cheng W.T., Lin S.Y., Wang S.L. Differential scanning calorimetry with curvefitting program used to quantitatively analyze the polymorphic transformation of famotidine in the compressed compact. Drug Dev. Ind. Pharm. 2008, 34:1368-1375.
31. Mohammad M.A., Alhalaweh A., Velaga S.P. Hansen solubility parameter as a tool to predict cocrystal formation. Int. J. Pharm. 2011, 407:63-71.
32. Lu E., Rodriguez-Hornedo N., Suryanarayanan R. A rapid thermal method for cocrystal screening. CrystEngComm 2008, 10:665-668.
33. Évora O.L., Castro R.A.E., Maria T.M.R., Rosado M.T.S., Silva M.R., Beja A.M., et al. Pyrazinamide-diflunisal. A new dual-drug co-crystal. Cryst. Growth Des. 2011, 11:4780-4788.
34. Zaini E., Sumirtapura Y.C., Soewandhi S.N., Halim A., Uekusa H., Fujii K. Cocrystalline phase transformation of binary mixture of trimethoprim and sulfamethoxazole by slurry technique. Asian J. Pharm. Clin. Res. 2010, 3:26-29.
35. Mura P., Cirri M., Faucci M.T., Ginès-Dorado J.M., Bettinetti G.P. Investigation of the effects of grinding and co-grinding on physicochemical properties of glisentide. J. Pharm. Biomed. Anal. 2002, 30:227-237.
36. Giron D. Thermal analysis, microcalorimetry and combined techniques for the study of pharmaceuticals. J. Therm. Anal. Calorim. 1999, 56:1285-1304.
37. Umeda Y., Fukami T., Furuishi T., Suzuki T., Makimura M., Tomono K. Molecular complex consisting of two typical external medicines: intermolecular interaction between indomethacin and lidocaine. Chem. Pharm. Bull. (Tokyo) 2007, 55:832-836.
38. Wang F., Hui H., Barnes T.J., Barnett C., Prestidge C.A. Oxidized mesoporous silicon microparticles for improved oral delivery of poorly soluble drugs. Mol. Pharm. 2010, 7:227-236.
39. Del Arco M., Cebadera E., Gutiérrez S., Martín C., Montero M.J., Rives V., et al. Mg, Al layered double hydroxides with intercalated indomethacin: synthesis, characterization, and pharmacological study. J. Pharm. Sci. 2004, 93:1649-1658.
40. 2 stretching vibrations in some metal saccharinates: spectra-structure correlations. Spectrosc. Lett. 1995, 28:1095-1109.
41. Binev I.G., Stamboliyska B.A., Velcheva E.A. The infrared spectra and structure of o-sulfobenzimide (saccharin) and of its nitranion: an ab initio force field treatment. Spectrochim. Acta Part A 1996, 52:1135-1143.
42. Manning M.C. Use of infrared spectroscopy to monitor protein structure and stability. Expert Rev. Proteom. 2005, 2:731-743.
43. Sherman Hsu C.P. Infrared spectroscopy. Handbook of Instrumental Techniques for Analytical Chemistry 1998, 247-283. Prentice-Hall, Inc, New Jersey. F.A. Settle (Ed.).
44. Oberg K.A., Fink A.L. Methods for collecting and analyzing attenuated total reflectance FTIR spectra of proteins in solution. Tech. Protein Chem. 1995, 6:475-484.
45. Lórenz-Fonfría V.A., Padrós E. Curve-fitting of Fourier manipulated spectra comprising apodization, smoothing, derivation and deconvolution. Spectrochim. Acta. A: Mol. Biomol. Spectrosc. 2004, 60:2703-2710.
46. Dodd J.G., DeNoyer L.K. Curve-fitting: modeling spectra. Handbook of Vibrational Spectroscopy 2002, vol. 3:2215-2223. John Wiley & Sons Ltd, Chichester, UK. 2nd ed.
47. Kopp S. Stability testing of pharmaceutical products in a global environment. RAJ Pharm. 2006, 16:291-294.
48. Waterman K.C. The application of the Accelerated Stability Assessment Program (ASAP) to quality by design (QbD) for drug product stability. AAPS PharmSciTech 2011, 12:932-937.