Wettability and surface chemistry of crystalline and amorphous forms of a poorly water soluble drug

European Journal of Pharmaceutical Sciences

Volumn 40, Issue 2, 2010, Pages 84-93

  Puri, Vibha ^a   Dantuluri, Ajay K ^a   Kumar, Mahesh ^b   Karar, N ^b   Bansal, Arvind K ^a  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

^b NATIONAL PHYSICAL LABORATORY   (India)

Author keywords

Celecoxib; Surface chemistry; Surface free energy; Vapor sorption; Wettability

Indexed keywords

CELECOXIB; FLUORINE; OXYGEN;

ABSORPTION; ADSORPTION KINETICS; AQUEOUS SOLUTION; ARTICLE; CONCENTRATION (PARAMETERS); CONTACT ANGLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DIFFERENTIAL SCANNING CALORIMETRY; DRUG SOLUBILITY; DRUG STABILITY; DRUG STRUCTURE; HUMIDITY; HYDROGEN BOND; HYDROPHOBICITY; PARTICLE SIZE; PRIORITY JOURNAL; SURFACE PROPERTY; THERMODYNAMICS; WATER VAPOR; WETTABILITY; X RAY PHOTOELECTRON SPECTROSCOPY;

MICROSCOPY, ELECTRON, SCANNING; MOLECULAR STRUCTURE; PYRAZOLES; SULFONAMIDES; THERMODYNAMICS; WETTABILITY; X-RAY DIFFRACTION;

EID: 77952196842     PISSN: 09280987     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejps.2010.03.003     Document Type: Article

References (59)

1. Ahfat N.M., Buckton G., Burrows R., Ticehurst M.D. An exploration of inter-relationships between contact angle, inverse phase gas chromatography and triboelectric charging data. Eur. J. Pharm. Sci. 2000, 9:271-276.
2. Bérard V., Lesniewskab E., Andrèsa C., Pertuyc D., Larochec C., Pourcelota Y. Affinity scale between a carrier and a drug in DPI studied by atomic force microscopy. Int. J. Pharm. 2002, 247:127-137.
3. Bolis V., Fubini B., Coluccia S., Mostacci E. Surface hydration of crystalline and amorphous silicas. J. Thermal Anal. 1985, 30:1283-1292.
4. Buckton G. The assessment, and pharmaceutical importance, of the solid/liquid and the solid/vapor interface: a review with respect to powders. Int. J. Pharm. 1988, 44:1-8.
5. Buckton G. Surface characterization: understanding sources of variability in the production and use of pharmaceuticals. J. Pharm. Pharmacol. 1995, 47:265-275.
6. Buckton G. Interfacial Phenomena in Drug Delivery and Targeting 1995, Harwood Academic Publishers, Switzerland.
7. Buckton G., Beezer A.E. A microcalorimetric study of powder surface energetics. Int. J. Pharm. 1988, 41:139-145.
8. Buckton G., Darcy P. The use of gravimetric studies to assess the degree of crystallinity of predominantly crystalline powders. Int. J. Pharm. 1995, 123:265-271.
9. Buckton G., Gill H. The importance of surface energetics in powders for drug delivery and the establishment of inverse gas chromatography. Adv. Drug Delivery Rev. 2007, 59:1474-1479.
10. Carvajal M.T., Staniforth J.N. Interactions of water with the surfaces of crystal polymorphs. Int. J. Pharm. 2006, 307:216-224.
11. Chamarthy S.P., Pinal R., Carvajal M.T. Elucidating raw material variability - importance of surface properties and functionalities in pharmaceutical powders. AAPS PharmSciTech 2009, 10:780-788.
12. Cheema M.A., Siddiq M., Barbosa S., Taboada P., Mosquera V. Surface and bulk properties of two amphiphilic phenothiazine drugs in different aqueous media. J. Chem. Eng. Data 2008, 53:368-373.
13. Dev R.V., Rekha K.S., Vyas K., Mohanti S.B., Kumar P.R., Reddy G.O. Celecoxib, a COX-II inhibitor. Acta Crystallogr. 1999, C55:IUC9900161.
14. Dhumal R.S., Shimpi S.L., Paradkar A.R. Development of spray-dried co-precipitate of amorphous celecoxib containing storage and compression stabilizers. Acta Pharm. 2007, 57:287-300.
15. Dressman J.B., Amidon G.L., Reppas C., Shah V.P. Dissolution testing as a prognostic tool for oral drug absorption: immediate release dosage forms. Pharm. Res. 1998, 15:11-22.
16. Elamin A.A., Ahlneck C., Alderborn G., Nystrom C. Increased metstable solubility of milled griseofulvin depending on the formation of disordered surface structure. Int. J. Pharm. 1994, 111:159-170.
17. Forster S., Buckton G., Beezer A.E. The importance of chain length on the wettability and solubility of organic homologs. Int. J. Pharm. 1991, 72:29-34.
18. Galia E., Horton J., Dressman J.B. Albendazole generics-a comparative in vitro study. Pharm. Res. 1999, 16:1871-1875.
19. Girifalco L.A., Good R.J. A theory for the estimation of surface and interfacial energies. I. Derivation and application to interfacial tension. J. Phys. Chem. 1957, 61:904-909.
20. Gupta, P., 2004. Development of Amorphous System of Celecoxib: A Molecular Perspective. PhD Thesis. Department of Pharmaceutical Technology (Formulations), National Institute of Pharmaceutical Education and Research, SAS Nagar, India.
21. Gupta P., Bansal A.K. Devitrification of amorphous celecoxib. AAPS PharmSciTech 2005, 6:E223-E230.
22. Gupta P., Chawla G., Bansal A.K. Physical stability and solubility advantage from amorphous celecoxib: the role of thermodynamic quantities and molecular mobility. Mol. Pharm. 2004, 1:406-413.
23. Gupta P., Thilagavathi R., Chakraborti A.K., Bansal A.K. Differential molecular interactions between the crystalline and the amorphous phases of celecoxib. J. Pharm. Pharmacol. 2005, 57:1271-1278.
24. Hancock B.C., Shamblin S.L. Water vapour sorption by pharmaceutical sugars. PSTT 1998, 8:345-351.
25. Hancock B.C., Zografi G. The relationship between the glass transition temperature and the water content of amorphous pharmaceutical solids. Pharm. Res. 1994, 11:471-477.
26. He X., Barone M.R., Marsac P.J., Sperry D.C. Development of a rapidly dispersing tablet of a poorly wettable compound - formulation DOE and mechanistic study of effect of formulation excipients on wetting of celecoxib. Int. J. Pharm. 2008, 353:176-186.
27. Heng J.Y.Y., Bismarck A., Lee A.F., Wilson K., Williams D.R. Anisotropic surface energetics and wettability of macroscopic form I paracetamol crystals. Langmuir 2006, 22:2760-2769.
28. ICH (International Conference on Harmonization), 1997. Guidance for Industry Q3C Impurities: Residual Solvents.
29. Kaushal A., Chakraborti A.K., Bansal A.K. FTIR studies on differential intermolecular association in crystalline and amorphous states of structurally related non-steroidal anti-inflammatory drugs. Mol. Pharm. 2008, 5:937-945.
30. Kaushal A.M., Bansal A.K. Thermodynamic behavior of glassy state of structurally related compounds. Eur. J. Pharm. BioPharm. 2008, 69:1067-1076.
31. Lechuga-Ballesteros D., Bakri A., Miller D.P. Microcalorimetric measurement of the interactions between water vapor and amorphous pharmaceutical solids. Pharm. Res. 2003, 20:308-318.
32. Lemons J.E., Cooke F.W., Ratner B.D. Properties of materials. Biomaterials Science 2004, 23-66. Elsevier Academic Press, California. B.D. Ratner, A.S. Hoffman, F.J. Schoen, J.E. Lemons (Eds.).
33. Leonard, F., Patricia, M., 2001. Polymorphic crystalline forms of celecoxib. WO 01/42222 A1.
34. Lippold B.C., Ohm A. Correlation between wettability and dissolution rate of pharmaceutical powders. Int. J. Pharm. 1986, 28:67-74.
35. Löbenberg R., Amidon G.L. Modern bioavailability, bioequivalence, biopharmaceutics classification system. New scientific approaches to international regulatory standards. Eur. J. Pharm. Biopharm. 2000, 50:1-12.
36. Lu G.W., Hawley M., Smith M., Geiger B.M., Pfund W. Characterization of a novel polymorphic form of celecoxib. J. Pharm. Sci. 2006, 95:305-317.
37. Matteucci M.E., Miller M.A., Williams R.O., Johnston K.P. Highly supersaturated solutions of amorphous drugs approaching predictions from configurational thermodynamic properties. J. Phys. Chem. B 2008, 112:16675-16681.
38. Morris K.R., Griesser U.J., Eckhardt C.J., Stowell J.G. Theoretical approaches to phase transformations of active pharmaceutical ingredients during manufacturing processes. Adv. Drug Delivery Rev. 2001, 48:91-114.
39. Muster T.H., Prestige C.A. Application of time-dependent sessile drop contact angles on compacts to characterise the surface energetics of sulfathiazole crystals. Int. J. Pharm. 2002, 234:43-54.
40. Muster T.H., Prestige C.A. Face specific surface properties of pharmaceutical crystals. J. Pharm. Sci. 2002, 91:1432-1444.
41. Neumann A.W., Renzow D., Reumuth H., Richter I.E. Roughness influence on wetting. Fortschr. Kolloide Polym. 1971, 55:49-54.
42. Newell H.E., Buckton G., Butler D.A., Thielmann F., Williams D.R. The use of inverse gas chromatography to measure the surface energy of crystalline, amorphous, and recently milled lactose. Pharm. Res. 2001, 18:662-666.
43. Ohta M., Buckton G. Determination of the changes in surface energetics of cefditoren pivoxil as a consequence of processing induced disorder and equilibration to different relative humidities. Int. J. Pharm. 2004, 269:81-88.
44. Ohta M., Buckton G. A study of the differences between two amorphous spray-dried samples of cefditoren pivoxil which exhibited different physical stabilities. Int. J. Pharm. 2005, 289:31-38.
45. Paulson S., Vaughn M., Jessen S., Lawal Y., Gresk C., Yan B., et al. Pharmacokinetics of celecoxib after oral administration in dogs and humans: effect of food and site of absorption. J. Pharmacol. Exp. Ther. 2001, 297:638-645.
46. Smart B.E. Fluorine substituent effect. J. Fluorine Chem. 2001, 109:3-11.
47. Sun C.C., Kiang Y.H. On the identification of slip planes in organic crystals based on attachment energy calculation. J. Pharm. Sci. 2008, 97:3456-3461.
48. United States Pharmacopeia 31/National Formulary 26, 2008. Asian ed. United States Pharmacopeial Convention, Inc., Rockville, MD.
49. van Oss C.J., Giese R.F., Wu W. On the predominant donicity of polar surface. J. Adhesion 1997, 63:71-88.
50. van Oss C.J., Good R.J., Chaudhury M.K. Additive and nonadditive surface tension components and the interpretation of contact angles. Langmuir 1988, 4:884-891.
51. Woodward R.P. Prediction of adhesion and wetting from Lewis acid base measurements. Automotive 2000 2000.
52. Wu S. Calculation of interfacial tension in polymer system. J. Polym. Sci. Part C 1971, 34:19-30.
53. g. Pharm. Res. 2006, 23:2350-2355.
54. York P., Ticehurst M.D., Osborn J.C., Roberts R.J., Rowe R.C. Characterisation of the surface energetics of milled dl-propanolol hydrochloride using inverse gas chromatography and molecular modelling. Int. J. Pharm. 1998, 174:179-186.
55. Young S.A., Buckton G. Particle growth in aqueous suspensions: the influence of surface energy and polarity. Int. J. Pharm. 1990, 60:235-241.
56. Young T. An essay on the cohesion of fluids. Philos. Trans. R. Soc. 1805, 95:65-87.
57. Zhang D., Flory J.H., Panmai S., Batra U., Kaufman M.J. Wettability of pharmaceutical solids: its measurement and influence on wet granulation. Colloid Surf. A: Physicochem. Eng. Aspects 2002, 206:547-554.
58. Zhu L., Wong L., Yu L. Surface-enhanced crystallization of amorphous nifedipine. Mol. Pharm. 2006, 5:921-926.
59. Zografi G., Tam S.S. Wettability of pharmaceutical solids: estimates of solid surface polarity. J. Pharm. Sci. 1976, 65:1145-1149.