Solid state characterization of the anti-HIV drug TMC114: Interconversion of amorphous TMC114, TMC114 ethanolate and hydrate

European Journal of Pharmaceutical Sciences

Volumn 38, Issue 5, 2009, Pages 489-497

  Van Gyseghem, Elke ^a   Stokbroekx, Sigrid ^b   de Armas, Hector Novoa ^b   Dickens, Jules ^b   Vanstockem, Marc ^c   Baert, Lieven ^c   Rosier, Jan ^c   Schueller, Laurent ^c   Van den Mooter, Guy ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

^b JANSSEN RESEARCH AND DEVELOPMENT   (Belgium)

^c Chem Pharm Development   (Belgium)

Author keywords

Amorphous form; Channel solvates; Solid state characterization; Solvate hydrate; TMC114 (Darunavir)

Indexed keywords

ALCOHOL; DARUNAVIR; DARUNAVIR ETHANOLATE; DARUNAVIR HYDRATE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG STABILITY; ENVIRONMENTAL TEMPERATURE; HEAT TREATMENT; HUMIDITY; HYDRATION; PHASE TRANSITION; PRIORITY JOURNAL; ROOM TEMPERATURE; SOLID STATE; SOLVATION; STORAGE TEMPERATURE; X RAY DIFFRACTION;

CALORIMETRY, DIFFERENTIAL SCANNING; CHEMISTRY, PHARMACEUTICAL; CRYSTALLIZATION; DRUG STABILITY; DRUG STORAGE; ETHANOL; HIV PROTEASE INHIBITORS; HUMIDITY; SPECTROPHOTOMETRY, INFRARED; STEREOISOMERISM; SULFONAMIDES; THERMOGRAVIMETRY; X-RAY DIFFRACTION;

EID: 70449732141     PISSN: 09280987     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejps.2009.09.013     Document Type: Article

References (28)

1. Altomare A., Cascarano G., Giacovazzo C., and Guagliardi A. Completion and refinement of crystal structures with SIR92. J. Appl. Cryst. 26 (1993) 343-350
2. Bandyopadhyay R., Erixon K., Young Jr. V.G., and Grant D.J.W. Effects of water activity on recrystallized l-lysine monohydrochloride. Proceedings of the World Congress on Particle Technology. The Brighton Center, Brighton (1998) 7-9
3. Bergerhoff, G., 2005. DIAMOND-Visual Crystal Structure Information System (Version 3). Prof. Dr. G. Bergerhoff, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany.
4. Byrn S.R. Solid-State Chemistry of Drugs (1982), Academic Press, New York
5. Brittain H.G., Bugay D.E., Bogdanowich S.J., and DeVincentis J. Spectral methods for determination of water. Drug Dev. Ind. Pharm. 14 (1988) 2029-2046
6. Cui Y. Historical perspectives-a material science perspective of pharmaceutical solids. Int. J. Pharm. 339 (2007) 3-18
7. Cox J.S.G., Woodard G.D., and McCrone W.C. Solid-state chemistry of cromolyn sodium (disodium cromoglycate). J. Pharm. Sci. 60 (1971) 1458-1465
8. D'Avolio A., Siccardi M., Sciandra M., Lorena B., Bonora S., Trentini L., and Di Perri G. HPLC-MS method for the simultaneous quantification of the new HIV protease inhibitor darunavir, and 11 other antiretroviral agents in plasma of HIV-infected patients. J. Chromatogr. B 859 (2007) 234-240
9. Ghosh A.K., Dawson Z.L., and Mitsuya H. Darunavir, a conceptually new HIV-1 protease inhibitor for the treatment of drug-resistant HIV. Bioorg. Med. Chem. 15 (2007) 7576-7580
10. Grant D.J.W. Theory and origin of polymorphism. In: Brittain H.G. (Ed). Drugs and the Pharmaceutical Sciences-Polymorphism in Pharmaceutical Solids vol. 95 (1999), Marcel Dekker, New York 1-2 Chapter 1
11. Haleblian J., and McCrone W. Pharmaceutical applications of polymorphism. J. Pharm. Sci. 58 (1969) 911-929
12. Haleblian J.K. Characterization of habits and crystalline modification of solids and their pharmaceutical applications. J. Pharm. Sci. 64 (1975) 1269-1288
13. Hammer S.M., Saag M.S., Schechter M., Montaner J.S.G., Schooley R.T., Jacobsen D.M., Thompson M.A., Carpenter C.C.J., Fischl M.A., Gazzard B.G., Gatell J.M., Hirsch M.S., Katzenstein D.A., Richman D.D., Vella S., Yeni P.G., and Volberding P.A. Special communication: treatment for adult HIV infection-2006 recommendations of the International AIDS Society-USA panel. JAMA 296 (2006) 827-843
14. Ivashkiv E. Ampicillin. In: Florey K. (Ed). Analytical Profiles of Drug Substances vol. 2 (1973), Academic Press, New York 1-62
15. Kaneniwa N., Yamaguchi T., Watari N., and Otsuka M. Hygroscopicity of carbamazepine crystalline powders. Yakugaku Zasshi 104 (1984) 184-190
16. Kovalevsky A.Y., Liu F., Leshchenko S., Ghosh A.K., Louis J.M., Harrison R.W., and Weber I.T. Ultra-high resolution crystal structure of HIV-1 protease mutant reveals two binding sites for clinical inhibitor TMC114. J. Mol. Biol. 363 (2006) 161-173
17. Martinez-Cajas J.L., and Wainberg M.A. Protease inhibitor resistance in HIV-infected patients: molecular and clinical perspectives. Antivir. Res. 76 (2007) 203-221
18. McCoy C. Darunavir: a nonpeptidic antiretroviral protease inhibitor. Clin. Therap. 29 (2007) 1559-1576
19. Morris K.R. Structural aspects of hydrates and solvates. In: Brittain H.G. (Ed). Drugs and the Pharmaceutical Sciences-Polymorphism in Pharmaceutical Solids vol. 95 (1999), Marcel Dekker, New York 125-181 Chapter 4
20. North A.C.T., Phillips D.C., and Mathews F.S. A semi-empirical method of absorption correction. Acta Cryst. A24 (1968) 351-359
21. Pauwels R. Mini-review: aspects of successful drug discovery and development. Antivir. Res. 71 (2006) 77-89
22. Sheldrick G.M. SHELXL97. Program For Crystal Structure Refinement (1997), University of Göttingen, Germany
23. Spek A.L. Single crystal structure validation with the program PLATON. J. Appl. Cryst. 36 (2003) 7-13
24. Stuart M. Transform, J&J, topiramate: new life, old products. In Vivo: The Business Med. Rep. 22 (2004) 71-72
25. Threlfall T.L. Analysis of organic polymorphs. A review. Analyst 120 (1995) 2435-2460
26. US Patent, 2002. 6350870. Process for preparing pure crystalline lorazepam. Patentstorm, http://www.patentstorm.us/patents/6350870/claims.html.
27. X-ray Single Crystal Analysis System, Version 2.2, 1996. Siemens Analytical X-ray Instruments Inc., Madison, WI, USA.
28. Yeni P. Update on HAART in HIV. J. Hepatol. 44 (2006) S100-S103