Solution-mediated phase transformation of anhydrous to dihydrate carbamazepine and the effect of lattice disorder

International Journal of Pharmaceutics

Volumn 246, Issue 1-2, 2002, Pages 121-134

  Murphy, D ^a,b   Rodriguez Cintron F ^a,c   Langevin, B ^a,d   Kelly, R C ^a   Rodriguez Hornedo N ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

^b BRISTOL MYERS SQUIBB PHARMACEUTICAL RESEARCH INSTITUTE   (United States)

^c UNIVERSITY OF PUERTO RICO   (Puerto Rico)

^d SANOFI   (France)

Author keywords

Amorphous solids; Crystallization; Grinding; Polymorphs; Solubility; Transformation rate

Indexed keywords

CARBAMAZEPINE; CRYSTALLIN;

ARTICLE; BIOLOGICAL MONITORING; CHEMICAL COMPOSITION; CONCENTRATION RESPONSE; CRYSTALLIZATION; DRUG SOLUBILITY; KINETICS; PRIORITY JOURNAL; SOLID; THERMAL ANALYSIS;

CALORIMETRY, DIFFERENTIAL SCANNING; CARBAMAZEPINE; CHEMISTRY, PHARMACEUTICAL; CRYSTALLIZATION; DRUG STABILITY; KINETICS; MICROSCOPY; PHARMACEUTICAL SOLUTIONS; POWDER DIFFRACTION; SOLUBILITY; SURFACE PROPERTIES; WATER;

EID: 0037057317     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0378-5173(02)00358-7     Document Type: Article

References (43)

1. Behme R.J., Brooke D. Heat of fusion measurement of a low melting polymorph of carbamazepine that undergoes multiple-phase changes during differential scanning calorimetry analysis. J. Pharm. Sci. 80:1991;986-990.
2. Bernstein J., Davey R.J., Henck J.O. Concomitant polymorphs. Angewandte Chemie - International Edition. 38:1999;3441-3461.
3. Boistelle R., Astier J.P. Crystallization mechanisms in solution. J. Cryst. Growth. 90:1988;14-30.
4. Byrn S., Pfeiffer R., Ganey M., Hoiberg C., Poochikian G. Pharmaceutical solids - a strategic approach to regulatory considerations. Pharm. Res. 12:1995;945-954.
5. Cardew, P.T., Davey, R.J., 1985. The kinetics of solvent-mediated phase-transformations. Proceedings of the Royal Society of London Series A - Mathematical Physical and Engineering Sciences, 398, 415-428.
6. Ceolin R., Toscani S., Gardette M.F., Agafonov V.N., Dzyabchenko A.V., Bachet B. X-Ray characterization of the triclinic polymorph of carbamazepine. J. Pharm. Sci. 86:1997;1062-1065.
7. Corrigan O.I., Holohan E.M., Sabra K. Amorphous forms of thiazide diuretics prepared by spray-drying. Int. J. Pharm. 18:1984;195-200.
8. Crison J.R., Weiner N.D., Amidon G.L. Dissolution media for in vitro testing of water-insoluble drugs: effect of surfactant purity and electrolyte on in vitro dissolution of carbamazepine in aqueous solutions of sodium lauryl sulfate. J. Pharm. Sci. 86:1997;384-388.
9. Davey R.J., Cardew P.T., Mcewan D., Sadler D.E. Rate-controlling processes in solvent-mediated phase- transformations. J. Cryst. Growth. 79:1986;648-653.
10. Edwards A.D., Shekunov B.Y., Forbes R.T., Grossmann J.G., York P. Time-resolved X-ray scattering using synchrotron radiation applied to the study of a polymorphic transition in carbamazepine. J. Pharm. Sci. 90:2001;1106-1114.
11. Elamin A.A., Ahlneck C., Alderborn G., Nystrom C. Increased metastable solubility of milled griseofulvin, depending on the formation of a disordered surface-structure. Int. J. Pharm. 111:1994;159-170.
12. Florence A.T., Salole E.G. Changes in crystallinity and solubility on comminution of digoxin and observations on spironolactone and oestradiol. J. Pharm. Pharmacol. 28:1976;637-642.
13. Gu C.H., Young V., Grant D.J.W. Polymorph screening: influence of solvents on the rate of solvent-mediated polymorphic transformation. J. Pharm. Sci. 90:2001;1878-1890.
14. Hancock B.C., Parks M. What is the true solubility advantage for amorphous pharmaceuticals? Pharm. Res. 17:2000;397-404.
15. Himes V.L., Mighell A.D., De Camp W.H. Structure of carbamazepine: 5H-dibenz[b, f]azepine-5-carboxamide. Acta Crystallographica. B37:1981;2242-2245.
16. Kahela P., Aaltonen R., Lewing E., Anttila M., Kristoffersson E. Pharmacokinetics and dissolution of 2 crystalline forms of carbamazepine. Int. J. Pharm. 14:1983;103-112.
17. Kaneniwa N., Ichikawa J.I., Yamaguchi T., Hayashi K., Watari N., Sumi M. Dissolution behavior of carbamazepine polymorphs. Yakugaku Zasshi - J. Pharm. Soc. Jpn. 107:1987;808-813.
18. Kaneniwa N., Yamaguchi T., Watari N., Otsuka M. Hygroscopicity of carbamazepine crystalline powders. Yakugaku Zasshi - J. Pharm. Soc. Jpn. 104:1984;184-190.
19. Kobayashi Y., Ito S., Itai S., Yamamoto K. Physicochemical properties and bioavailability of carbamazepine polymorphs and dihydrate. Int. J. Pharm. 193:2000;137-146.
20. Krahn F.U., Mielck J.B. Effect o F type and extent of crystalline disorder on chemical and physical stability of carbamazepine. Int. J. Pharm. 53:1989;25-34.
21. Laine E., Tuominen V., Ilvessalo P., Kahela P. Formation of dihydrate from carbamazepine anhydrate in aqueous conditions. Int. J. Pharm. 20:1984;307-314.
22. Lefebvre C., Guyothermann A.M., Draguetbrughmans M., Bouche R., Guyot J.C. Polymorphic transitions of carbamazepine during grinding and compression. Drug Dev. Ind. Pharm. 12:1986;1913-1927.
23. Li Y.H., Han J., Zhang G.G.Z., Grant D.J.W., Suryanarayanan R. In situ dehydration of carbamazepine dihydrate: a novel technique to prepare amorphous anhydrous carbamazepine. Pharm. Dev. Technol. 5:2000;257-266.
24. Lowes M.M.J., Caira M.R., Lotter A.P., Vanderwatt J.G. Physicochemical properties and X-ray structural studies of the trigonal polymorph of carbamazepine. J. Pharm. Sci. 76:1987;744-752.
25. Luhtala S., Kahela P., Kristofferson E. Effect of benzalkonium chloride on crystal growth and aqueous solubility of carbamazepine. Acta Pharmaceutica Fennica. 99:1990;59-68.
26. Meyer M.C., Straughn A.B., Jarvi E.J., Wood G.C., Pelsor F.R., Shah V.P. The bioequivalence of carbamazepine tablets with a history of clinical failures. Pharm. Res. 9:1992;1612-1616.
27. Mitchell C.A., Yu L., Ward M.D. Selective nucleation and discovery of organic polymorphs through epitaxy with single crystal substrates. J. Am. Chem. Soc. 123:2001;10830-10839.
28. Morris K.R., Griesser U.J., Eckhardt C.J., Stowell J.G. Theoretical approaches to physical transformations of active pharmaceutical ingredients during manufacturing processes. Advanced Drug Delivery Rev. 48:2001;91-114.
29. Mosharraf M., Nystrom C. The effect of dry mixing on the apparent solubility of hydrophobic, sparingly soluble drugs. Eur. J. Pharm. Sci. 9:1999;145-156.
30. Otsuka M., Matsumoto T., Kaneniwa N. Effect of environmental-temperature on polymorphic solid-state transformation of indomethacin during grinding. Chem. Pharm. Bull. 34:1986;1784-1793.
31. Otsuka M., Ofusa T., Matsuda Y. Effect of environmental humidity on the transformation pathway of carbamazepine polymorphic modifications during grinding. Coll. Sur. B - Biointerfaces. 13:1999;263-273.
32. 2O. Cryst. Res. Technol. 21:1986;1463-1468.
33. Rodríguez-Hornedo N., Lechuga-Ballesteros D., Wu H.J. Phase-transition and heterogeneous epitaxial nucleation of hydrated and anhydrous theophylline crystals. Int. J. Pharm. 85:1992;149-162.
34. Rodríguez-Hornedo N., Murphy D. Significance of controlling crystallization mechanisms and kinetics in pharmaceutical systems. J. Pharm. Sci. 88:1999;651-660.
35. Shefter E., Higuchi T. Dissolution behavior of crystalline solvated and non-solvated forms of some pharmaceuticals. J. Pharm. Sci. 52:1963;781-791.
36. Shekunov B.Y., York P. Crystallization processes in pharmaceutical technology and drug delivery design. J. Cryst. Growth. 211:2000;122-136.
37. Sunkersett M.R., Grimsey I.M., Doughty S.W., Osborn J.C., York P., Rowe R.C. The changes in surface energetics with relative humidity of carbamazepine and paracetamol as measured by inverse gas chromatography. Eur. J. Pharm. Sci. 13:2001;219-225.
38. Terrence C.F., Sax M., Fromm G.H., Chang C.-H., Yoo C.S. Effect of baclofen enantiomorphs on the spinal trigeminal nucleus and steric similarities of carbamazepine. Pharmacology. 27:1983;85-94.
39. Vippagunta S.R., Brittain H.G., Grant D.J.W. Crystalline solids. Advanced Drug Delivery Rev. 48:2001;3-26.
40. Wang J.T., Shiu G.K., Ting O.C., Viswanathan C.T., Skelly J.P. Effects of humidity and temperature on in-vitro dissolution of carbamazepine tablets. J. Pharm. Sci. 82:1993;1002-1005.
41. Yoshioka M., Hancock B.C., Zografi G. Crystallization of indomethacin from the amorphous state below and above its glass-transition temperature. J. Pharm. Sci. 83:1994;1700-1705.
42. Young W.W.L., Suryanarayanan R. Kinetics of transition of anhydrous carbamazepine to carbamazepine dihydrate in aqueous suspensions. J. Pharm. Sci. 80:1991;496-500.
43. Zhu H.J., Yuen C.M., Grant D.J.W. Influence of water activity in organic solvent plus water mixtures on the nature of the crystallizing drug phase.1. Theophylline. Int. J. Pharm. 135:1996;151-160.