Persistency of a two-fold embrace in crystalline phases of bupropion hydrohalides: A thorough ab initio x-ray powder diffraction study

Crystal Growth and Design

Volumn 14, Issue 7, 2014, Pages 3603-3611

  Vladiskovic, Chiara ^a,b   Masciocchi, Norberto ^b  

^a Dipharma Francis srl   (Italy)

^b UNIVERSITY OF INSUBRIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN BONDS; SALTS; SUPRAMOLECULAR CHEMISTRY; X RAY POWDER DIFFRACTION;

CRYSTAL PHASIS; CRYSTALLINE PHASIS; DRIVING FORCES; HYDROGEN BONDING MOTIFS; POWDER DIFFRACTION ANALYSIS; POWDER DIFFRACTION METHODS; STATE OF THE ART; SUPRAMOLECULAR SYNTHONS;

DIFFRACTION;

EID: 84903747328     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/cg5005374     Document Type: Article

References (26)

1. Byrn, S. R. Pfeiffer, R. R. Stowell, J. G. Solid-State Chemistry of Drugs, 2 nd ed.; SSCI: West Lafayette, IN, 1999; pp 3-43.
2. Brittain, H. G. Polymorphism in Pharmaceutical Solids; Informa Healthcare: New York, 2009; pp 1-23.
3. Hilfiker, R. Polymorphism in the Pharmaceutical Industry; Wiley-VCH: Weinheim, Germany, 2006; pp 385-401.
4. Serajuddin, A. T. M. Salt formation to improve drug solubility Adv. Drug Delivery Rev. 2007, 59, 603-616 (Pubitemid 47285406)
5. Elder, D. P.; Holm, R.; Lopez de Diego, H. Use of pharmaceutical salts and cocrystals to address the issue of poor solubility Int. J. Pharm. 2013, 453, 88-100
6. Metha, N. B. Meta chloro substituted-alpha-butylamino-propiophenones. U.S. Patent 3,819,706, 25 June 1974.
7. Kelley, J. L.; Musso, D. L.; Boswell, G. E.; Soroko, F. E.; Cooper, B. R. (2 S,3 S,5 R)-2-(3,5-Difluorophenyl)-3,5-dimethyl-2-morpholinol: A Novel Antidepressant Agent and Selective Inhibitor of Norepinephrine Uptake J. Med. Chem. 1996, 39, 347-349 (Pubitemid 26041448)
8. Fang, Q. K.; Han, Z.; Grover, P.; Kessler, D.; Senanayake, C. H.; Wald, S. A. Rapid access to enantiopure bupropion and its major metabolite by stereospecific nucleophilic substitution on an α-ketotriflate Tetrahedron: Asymmetry 2000, 11, 3659-3663
9. Metha, N. B.; Yeowell, D. A. Biologisch wirksame Ketone. German Patent Application DE 2059618, 7 October 1971.
10. Oberegger, W.; Zhou, Maes, F.;, P.; Turchetta, S.; Jackson, G.; Massardo, P. Modified-Release Formulations of a Bupropion Salt, WIPO Patent Application WO 2007/002597, 4 January 2007.
11. Amidon, G. L.; Lennernas, H.; Shah, V. P.; Crison, J. R. A Theoretical Basis for a Biopharmaceutic Drug Classification: The Correlation of in Vitro Drug Product Dissolution and in Vivo Bioavailability Pharm. Res. 1995, 12, 413-420
12. Yu, L. W.; Amidon, G. L.; Polli, J. E.; Zhao, H.; Mehta, M. U.; Conner, D. P.; Shah, V. P.; Lesko, L. J.; Chen, M. L.; Lee, V. H.; Hussain, A. S. Biopharmaceutics Classification System: The Scientific Basis for Biowaiver Extensions Pharm. Res. 2002, 19, 921-925 (Pubitemid 34804232)
13. Maccaroni, E.; Malpezzi, L.; Masciocchi, N. Structures from Powders: Bupropion hydrochloride J. Pharm. Biomed. Anal. 2009, 50, 257-261
14. Maccaroni, E.; Malpezzi, L.; Famulari, A.; Masciocchi, N. Structural and energetic aspects of a new bupropion hydrochloride polymorph J. Pharm. Biomed. Anal. 2012, 60, 65-70
15. Turchetta, S.; Zenoni, M. Bupropion Hydrobromide Polymorphs, WIPO Patent Application WO 2010/015692, 11 February 2010.
16. Hu, X.; Xiang, H.; Gu, J.; Zhang, Y.; Chen, L. Preparation and Crystal Structures of Two Polymorphic Forms of Bupropion Hydrobromide Chin. J. Struct. Chem. 2011, 30, 1591-1596
17. Froimovitz, M.; George, C. Conformational Analysis and a Crystal Structure of Bupropion, an Antidepressant with Dopamine Reuptake Blocking Activity J. Chem. Inf. Comput. Sci. 1998, 38, 506-510 (Pubitemid 128594466)
18. Coelho, A. A. TOPAS-R, v3.0. Bruker AXS, Karlsruhe, Germany, 2005.
19. 6 by X-Ray Powder diffraction Mater. Res. Bull. 1988, 23, 447-452 (Pubitemid 18588821)
20. Cheary, R. W.; Coelho, A. A fundamental parameters approach to X-ray line-profile fitting J. Appl. Crystallogr. 1992, 25, 109-121
21. Bernstein, J. Polymorphism in molecular crystals; Clarendon Press: Oxford, U.K., 2002; pp 55-65.
22. Musso, D. L.; Mehta, N. B.; Soroko, F. E.; Ferris, R. M.; Hollingsworth, E. B.; Kenney, B. T. Synthesis and evaluation of the antidepressant activity of the enantiomers of bupropion Chirality 1993, 5 (7) 495-500 (Pubitemid 23328440)
23. Ponder, J. W.. TINKER Software Tools for Molecular Design, Version 6.2, 2013.
24. Steed, J. W.; Fucke, K.; Qureshi, N.; Yufit, D. S.; Howard, J. A. K. Hydrogen Bonding is not Everything: Extensive Polymorphism in a System with Conserved Hydrogen Bonded Synthons Cryst. Growth Des. 2010, 10, 880-886
25. Zhang, D.; Liping, G.; Zhang, Z.; Wang, L.; Shao, M. Heating-Induced Phase Transition of Bupropion Hydrobromide Polymorphs J. Pharm. Sci. 2012, 101, 3091-3095
26. Giron, D. Thermal analysis and calorimetric methods in the characterization of polymorphs and solvates Thermochim. Acta 1995, 240, 1-59