Crystal structure and physicochemical properties of crystalline form of 2'-O-{3-[(7-chloro-4-quinolinyl)amino]propyl}-9-deoxo-9a-methyl-9a-aza-9a-homoerythromycin A

Journal of Pharmaceutical Sciences

Volumn 100, Issue 7, 2011, Pages 2586-2598

  Filić, Darko ^a   Starčević, Kristina ^a   Pešić, Dijana ^a   Jurmanović, Stella ^a   Meenan, Eugene ^a   Spezzaferri, Alberto ^b   Dilović, Ivica ^c   Prugovečki, Biserka ^c  

^a GLAXOSMITHKLINE   (United Kingdom)

^b GSK   (Italy)

^c UNIVERSITY OF ZAGREB   (Croatia)

Author keywords

Crystal structure; Crystallography; Gas chromatography; Karl Fischer analysis; Moisture adsorption; Physicochemical characterization; SEM; Solubility; Stability; Thermal analysis (DSC and TGA); X ray powder diffractometry

Indexed keywords

2' O[3 [(7 CHLORO 4 QUINOLINYL)AMINO]PROPYL] 9 DEOXO 9A METHYL 9A AZA 9A HOMOERYTHROMYCIN A; ACETONITRILE; ANTIMALARIAL AGENT; CRYSTALLIN; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CRYSTAL STRUCTURE; CRYSTALLIZATION; DIFFERENTIAL SCANNING CALORIMETRY; DRUG SOLUBILITY; GAS CHROMATOGRAPHY; INTESTINE FLUID; MICROSCOPY; PHYSICAL CHEMISTRY; SCANNING ELECTRON MICROSCOPY; SOLID STATE; STOMACH JUICE; THERMOGRAVIMETRY; X RAY POWDER DIFFRACTION;

EID: 79955631074     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.22511     Document Type: Article

References (26)

1. Schöenfeld W, Kirst HA, Eds. 2002. Macrolide antiobiotics. Basel: Birkhäuser Verlag.
2. Dunne MW, Singh N, Shukla M, Valecha N, Bhattacharyya PC, Dev V, Patel K, Mohapatra MK, Lakhani J, Benner R, Lele C, Patki K. 2005. A multicenter study of azithromycin, alone and in combination with chloroquine, for the treatment of acute uncomplicated Plasmodium falciparum malaria in India. J Infect Dis 191:1582-1588.
3. Alihodžić S, Perić M, Pešić D. 2009. Patent US20090036388A1. CAN150:168690.
4. Grant DJW. 1999. Polymorphism in pharmaceutical solids. New York, Basel: Marcel Dekker, Inc., pp 1-33.
5. Bernstein J. 2002. Polymorphism in molecular crystals. Oxford: Clarendon Press, pp 240-256.
6. Hilfiker R, Blatter F, Raumer M. 2006. Polymorphism in the pharmaceutical industry. Weinhaim: Willey-VCH Verlag, pp 1-19.
7. Oxford Diffraction, Xcalibur CCD system, CRYSALIS Software System, V1.171.32.24, 2008. Oxford Diffraction Ltd.
8. Sheldrick GM. 1997. SHELXS97, program for the solution of crystal structures. Göttingen: University of Göttingen.
9. Sheldrick GM. 1997. SHELXL-97, program for the refinement of crystal structures. Göttingen: University of Göttingen.
10. Farrugia LJ. 1999. WinGX suite for small-molecule single-crystal crystallography. J Appl Crystallogr 32:837-838.
11. Spek AL. 1990. PLATON, an integrated tool for the analysis of the results of a single crystal structure determination. Acta Crystallogr A 46(suppl): C34.
12. Spek AL. 2005. PLATON, a multipurpose crystallographic tool. Utrecht, the Netherlands: Utrecht University.
13. Spek AL. 2003. Single-crystal structure validation with the program PLATON. J Appl Crystallogr 36:7-13.
14. Nardelli M. 1983. PARST: A system of fortran routines for calculating molecular structure parameters from results of crystal structure analyses. Comput Chem 7:95-98.
15. Nardelli M. 1995. PARST 95-An update to PARST: A system of Fortran routines for calculating molecular structure parameters from the results of crystal structure analyses. J Appl Crystallogr 28:659.
16. Farrugia LJ. 1997. ORTEP-3 for Windows-A version of ORTEP-III with a Graphical User Interface (GUI). J Appl Crystallogr 30:565.
17. DeLano WL. The PyMOL Molecular Graphics System. San Carlos, CA: DeLano Scientific LLC. Accessed at: http://www.pymol.org. (19 July 2010).
18. Macrae CF, Edgington PR, McCabe P, Pidcock E, Shields GP, Taylor R, Towler M, Van de Streek J. 2006. Mercury: visualization and analysis of crystal structures. J Appl Crystallogr 39:453-457.
19. Košutić-Hulita N, Matak-Vinković D, Vinković M, Novak P, Kobrehel G, Lazarevski G. 2001. Conformational behaviour of 11-O-methylazithromycin in the solid and solution state. Croatica Chemica Acta 74:327-341.
20. Etter MC, MacDonald JC, Bernstein 1990. Graph-set analysis of hydrogen-bond patterns in organic crystals. J Acta Crystallogr B 46:256-262.
21. Kamenar B, Mrvoš-Sermek D, Banić Z, Nagl A, Kobrehel G. 1991. Crystal and molecular structure of 9-deoxo-9a-ethyl-9a-aza-9a-homoerythronolide A. Croatica Chemica Acta 64:153-160.
22. Kamenar B, Mrvoš-Sermek D, Banić Z, Nagl A. 1990. Structure of 10, 10-dihydro-10-deoxo-10a-methyl-10a-aza-10a-homoerythronolide A. Acta Crystallogr C 46:1964-1966.
23. Cambridge Structural Database, V5.29. 2008 Cambridge, England: Cambridge Crystallographic Data Centre.
24. LeMahieu RA, Carson M, Kierstead RW. 1974. Glycoside cleavage reactions on erythromycin A. Preparation of erythronolide A. J Med Chem 17:953-956.
25. Fiese EF, Steffen SH. 1990. Comparison of the acid stability of azithromycin and erythromycin. J Antimicrob Chemother 25:39-47.
26. Lode H, Borner K, Koeppe P, Scharberg T. 1996. Azithromycin-Review of key chemical, pharmacokinetic and microbiological features. J Antimicrob Chemother 37(suppl C):1-8.