Crystal chemistry of the antibiotic doripenem

Journal of Pharmaceutical Sciences

Volumn 103, Issue 11, 2014, Pages 3641-3647

  Colombo, Valentina ^a   Masciocchi, Norberto ^b   Palmisano, Giovanni ^b  

^a UNIVERSITY OF MILAN   (Italy)

^b UNIVERSITY OF INSUBRIA   (Italy)

Author keywords

Crystal structure; Hydrates; Pseudopolymorphism; Thermal analysis; X ray powder diffractometry

Indexed keywords

DORIPENEM; ANTIINFECTIVE AGENT; CARBAPENEM DERIVATIVE; WATER;

ARTICLE; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; DIFFERENTIAL SCANNING CALORIMETRY; DRUG STRUCTURE; DRUG SYNTHESIS; POWDER DIFFRACTION; PROCESS CONTROL; TEMPERATURE; THERMAL ANALYSIS; THERMOGRAVIMETRY; CHEMICAL STRUCTURE; CHEMISTRY; CRYSTALLIZATION; HYDROGEN BOND; MEDICINAL CHEMISTRY; PHARMACEUTICS; PROCEDURES; X RAY CRYSTALLOGRAPHY;

ANTI-BACTERIAL AGENTS; CALORIMETRY, DIFFERENTIAL SCANNING; CARBAPENEMS; CHEMISTRY, PHARMACEUTICAL; CRYSTALLIZATION; CRYSTALLOGRAPHY, X-RAY; HYDROGEN BONDING; MODELS, MOLECULAR; MOLECULAR STRUCTURE; POWDER DIFFRACTION; TECHNOLOGY, PHARMACEUTICAL; TEMPERATURE; THERMOGRAVIMETRY; WATER;

EID: 84908444669     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.24166     Document Type: Article

References (38)

1. Bernstein J. 2002. Polymorphism in molecular crystals. Oxford University Press, New York, USA.
2. Brittain H. 2009. Polymorphism in pharmaceutical solids. Informa Healthcare USA, New York, USA.
3. Heinz A, Strachan CJ, Gordon KC, Rades T. 2009. Analysis of solidstate transformations of pharmaceutical compounds using vibrational spectroscopy. J Pharm Pharmacol 61:971-988.
4. Hilfiker R, Blatter F, von Raumer M. 2006. Relevance of solid-state properties for pharmaceutical products in polymorphism in the pharmaceutical industry; R. Hilfiker, Ed. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, FRG
5. ChiengaN, Radesb T, Aaltonen J. 2011. An overview of recent studies on the analysis of pharmaceutical polymorphs. J Pharm Biomed Anal 55:618-644.
6. Malpezzi L, Grato AM, Masciocchi N, Sironi A. 2005. Single crystal and powder diffraction characterization of three polymorphic forms of Acitretin. J Pharm Sci 94:1067-1078.
7. Maccaroni E, Alberti E, Malpezzi L, Masciocchi N, Vladiskovic C. 2008. Polymorphism of linezolid: A combined single-crystal, powder diffraction and NMR study. Int J Pharm 351:144-151.
8. Maccaroni E, Malpezzi L, Masciocchi N. 2009. Structures from powders: Bupropion hydrochloride. J Pharm Biomed Anal 50:257-261.
9. Moreno-Calvo E, Muntó M, Wurst K, Ventosa N, Masciocchi N, Veciana J. 2011. Polymorphs and solvates of nicardipine hydrochloride. Selective stabilization of different diastereomeric racemates. Mol Pharm 8:395-404.
10. 2-expanded solvents. Cryst Growth Des 14:58-68.
11. Harris KDM. 2004. Modern applications of powder X-ray diffraction in pharmaceutical sciences. Am Pharm Rev 7:86-91.
12. Fujii K, Uekusa H, Itoda N, Hasegawa G, Yonemochi E, Terada K, Pan Z, Harris KDM. 2010. Physicochemical understanding of polymorphism and solid-state dehydration/rehydration processes for the pharmaceutical material acrinol, by Ab initio powder X-ray diffraction analysis and other techniques. J Phys Chem C 114:580-586.
13. Papp-Wallace KM, Endimiani A, Taracila MA, Bonomo RA. 2011. Carbapenems: Past, present, and future. Antimicrob Agents Chemother 55:4943-4960.
14. Greer ND. 2008. Doripenem (Doribax): The newest addition to the carbapenems. Proc Bayl Univ Med Cent 21:337-341.
15. Mendez ASL, Mantovani L, Barbosa F, Sayago CTM, Garcia CV, Paula FR, da Silva FEB, Denardin ELG. 2011. Characterization of the antibiotic doripenem using physicochemical methods- Chromatography, spectrophotometry, spectroscopy and thermal analysis. Quim Nova 34:1634.
16. Saitho I, Takahira M, Kawakita T, Yoshioka Y. 2013. Novel crystal form of pyrrolidylthiocarbapenem derivative. Patent US20130059831A1.
17. Hotter A, Bartsch S, Backes A. 2011. Doripenem crystallization process. Patent EP2275424 A1.
18. Inoue M, Fujikane K, Sugiyama K, Tai H, Matsubara F, Oda K, Oya T, Hamada Y. 1997. Crystal of pyrrolidylthiocarbapenem derivative, lyophilized preparation containing said crystal, and process for producing the same. Patent EP0758651 A1.
19. Shankar D, Pandya VP, Meeran HNPN, Singh SK, Prasad M, Arora SK. 2013. Process for the preparation of polymorphs of doripenem. Patent WO2013068910 A1.
20. European Medicines Agency. 2008. CHMP assessment report for doribax. EMEA/309032/2008. Procedure no. EMEA/H/C/000891. Accessed the 10th Sept. 2014, at: http://www.ema.europa.eu/docs/en-GB/document-library/EPAR---Public-assessment-report/human/000891/WC500037151.pdf.
21. Saitoh I, Takahira M, Kawakita T, Yoshioka Y. 2005. Novel crystal form of pyrrolidylthiocarbapenem derivative. Patent EP1270575B1.
22. Hotter A, Bartsch S, Backes A. 2011. Doripenem crystallization process. Patent EP2275424A1.
23. Altomare A, BurlaMC, Giacovazzo C, Guagliardi A,Moliterni AGG, Polidori G, Rizzi R. 2001. QUANTO: A Rietveld program for quantitative phase analysis of polycrystalline mixtures. J Appl Cryst 34:392-397.
24. Coelho AA. 2003. Indexing of powder diffraction patterns by iterative use of singular value decomposition. J Appl Cryst 36:86-95.
25. Smith GS, Snyder RL. 1979. FN: A criterion for rating powder diffraction patterns and evaluating the reliability of powder-pattern indexing. J Appl Cryst 12:60-65.
26. Cheary RW, Coelho A. 1992. A fundamental parameters approach to X-ray line-profile fitting. J Appl Cryst 25:109-121.
27. Yanagi K, Takeuchi Y, Sunagawa M. 1992. Structure of a novel carbapenem antibiotic, meropenem. Acta Cryst C 48:1737-1739.
28. Ohtake N, Okamoto O, Mitomo R, Kato Y, Yamamoto K, Haga Y, Fukatsu H, Nakagawa S. 1997. 1 beta-Methyl-2-(5-substituted pyrrolidin-3-ylthio)carbapenems. 3. Synthesis and antibacterial activity of BO-2727 and its related compounds. J Antibiot 50:598.
29. Nakanishi H, Shionogi & Co. 2006. Method for preparation of aqueous doripenem solution. Patent EP1886682A1.
30. Karjalainen M, Airaksinen S, Rantanen J, Aaltonen J, Yliruusi J. 2005. Characterization of polymorphic solid-state changes using variable temperature X-ray powder diffraction. J Pharm Biomed Anal 39:27-32.
31. Tremayne M. 2004. The impact of powder diffraction on the structural study of organic materials. Phil Trans A Math Phys Eng Sci 362:2691-2707.
32. Giannini C, Guagliardi A, Millini R. 2002. Quantitative phase analysis by combining the Rietveld and the whole-pattern decomposition methods. J Appl Cryst 35:481-490.
33. Scarlett NVY, Madsen IC. 2006. Quantification of phases with partial or no known crystal structure. Powder Diffr 21:278-284.
34. Madsen IC, Scarlett NVY, Kern A. 2011. Description and survey of methodologies for the determination of amorphous content via X-ray powder diffraction. Z Kristallogr 226:944-955.
35. De La Torre AG, Bruque S, Aranda MAG. 2001. Rietveld quantitative amorphous content analysis. J Appl Crystallogr 34:196-202.
36. Byrn SR, Bates S, Ivanisevic I. 2005. Regulatory aspects of X-ray powder diffraction, part 1. Am Pharm Rev 55-59.
37. CabriW, Ghetti P, Pozzi G, Alpegiani M. 2007. Polymorphisms and patent, market, and legal battles: Cefdinir case study. Org Process Res Dev 11:64-72.
38. Ivanisevic I, McClurg RB, Schields PJ. 2010. Uses of X-ray powder diffraction in the pharmaceutical industry; Gad Shayne C, Ed. Pharmaceutical Sciences Encyclopedia: Drug Discovery, Development and Manufacturing, pp 1-42.