Reviewing the Manifold Aspects of Ganciclovir Crystal Forms

Crystal Growth and Design

Volumn 16, Issue 7, 2016, Pages 4108-4118

  Fernandes, José A ^a   Galli, Simona ^a   Palmisano, Giovanni ^a   Volante, Paolo ^b   Mendes, Ricardo F ^c   Paz, Filipe A Almeida ^c   Masciocchi, Norberto ^a  

^a UNIVERSITY OF INSUBRIA   (Italy)

^b Trifarma SpA   (Italy)

^c UNIVERSITY OF AVEIRO   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRAL AGENTS; HYDRATION; SINGLE CRYSTALS; THERMOANALYSIS;

ACTIVE PHARMACEUTICAL INGREDIENTS; CRYSTAL AND MOLECULAR STRUCTURE; HYDROCHLORIDE SALTS; POWDER X-RAY DIFFRACTION (PXRD); QUALITATIVE AND QUANTITATIVE ANALYSIS; SINGLE-CRYSTAL X-RAY DIFFRACTION STUDIES; THERMAL BEHAVIORS; VARIABLE TEMPERATURE;

X RAY DIFFRACTION;

EID: 84978175187     PISSN: 15287483     EISSN: 15287505     Source Type: Journal    
DOI: 10.1021/acs.cgd.6b00617     Document Type: Article

References (49)

1. Faulds, D.; Heel, R. C. Drugs 1990, 39 (4) 597-638 10.2165/00003495-199039040-00008
2. Crumpacker, C. S. N. Engl. J. Med. 1996, 335 (10) 721-729 10.1056/NEJM199609053351007
3. Wilhelmus, K. R. Cochrane Database Syst. Rev. 2010, 12) CD002898
4. Bernstein, J. Cryst. Growth Des. 2011, 11 (3) 632-650 10.1021/cg1013335
5. Brittain, H. G. Polymorphism in Pharmaceutical Solids; Informa Healthcare: New York, 2009.
6. Bernstein, J. Polymorphism in Molecular Crystals; International Union of Crystallography: Oxford, 2007.
7. Polymorphism: in the Pharmaceutical Industry; Hilfiker, R., Ed.; Wiley-VCH: Weinheim, 2006.
8. Desiraju, G. R. J. Chem. Sci. 2010, 122 (5) 667-675 10.1007/s12039-010-0055-2
9. Cabri, W.; Ghetti, P.; Pozzi, G.; Alpegiani, M. Org. Process Res. Dev. 2007, 11 (1) 64-72 10.1021/op0601060
10. Bernstein, J. Polymorphism and Patents from a Chemist's Point of View [1], Polymorphism: in the Pharmaceutical Industry; Hilfiker, R., Ed.; Wiley-VCH: Weinhem, 2006, pp 365-384.
11. Cruz-Cabeza, A. J.; Reutzel-Edens, S. M.; Bernstein, J. Chem. Soc. Rev. 2015, 44 (23) 8619-8635 10.1039/C5CS00227C
12. Griesser, U. J. The Importance of Solvates, Polymorphism: in the Pharmaceutical Industry; Hilfiker, R., Ed.; Wiley-VCH: Weinheim, 2006; pp 211-233.
13. Verheyden, J. P.; Martin, J. C. 9-(1,3-Dihydroxy-2-propoxymethyl)guanine as antiviral agent. US4355032, 1982.
14. Sarbajna, R. M.; Preetam, A.; Devi, A. S.; Suryanarayana, M. V.; Sethi, M.; Dutta, D. Mol. Cryst. Liq. Cryst. 2011, 537, 141-154 10.1080/15421406.2011.556472
15. Chan, T. W.; Nguyen, H. T. Anhydrous crystalline 9-(1,3-dihydroxy-2-propoxymethyl)guanine. US4642346, 1987.
16. Flores, R. L. R.; ávila, S. G.; Oliveira, J. F.; Carvalho, F. M. S.; Araújo, G. L. B.; Matos, J. R. In Caracterizaçao Fisico-Quĺmica e Analĺtica do Ganciclovir; Abratec: Serra Negra, 2014.
17. Parthasaradhi, R. B.; Rathnakar, R. K.; Muralidhara, R. D.; Raji, R. R.; Vamsi, K. B.; Subash, C. R. K.; Venkata, R. R. I. Process for the isolation of ganciclovir intermediate. WO20111114336A1, 2011.
18. Kawamura, T.; Hirayama, N. X-Ray Struct. Anal. Online 2009, 25, 51-52 10.2116/xraystruct.25.51
19. Salari, A.; Young, R. E. Int. J. Pharm. 1998, 163, 157-166 10.1016/S0378-5173(97)00378-5
20. Mao, W.; Wu, P. Unhydrous crystal form of ganciclovir sodium and preparation method thereof. CN 103570716, 2013.
21. Mao, W.; Wu, P.; Zhang, Q.; Cui, J. Crystal type ganciclovir sodium hydrate and preparing method thereof. CN103524505, 2014.
22. Volante, P.; Michelini, P. Ganciclovir sodium salt in crystalline form. WO/111049 A1, 2003.
23. Fernandes, J. A.; Sardo, M.; Mafra, L.; Choquesillo-Lazarte, D.; Masciocchi, N. Cryst. Growth Des. 2015, 15 (8) 3674-3683 10.1021/acs.cgd.5b00279
24. Vladiskovic, C.; Masciocchi, N. J. Pharm. Biomed. Anal. 2015, 107, 394-402 10.1016/j.jpba.2015.01.028
25. Giacobbe, C.; Palmisano, G.; Giovenzana, G. B.; Giovannelli, L.; Negri, R.; Masciocchi, N. J. Pharm. Biomed. Anal. 2015, 102, 305-313 10.1016/j.jpba.2014.09.028
26. Vladiskovic, C.; Masciocchi, N. Cryst. Growth Des. 2014, 14 (7) 3603-3611 10.1021/cg5005374
27. Vladiskovic, C.; Masciocchi, N.; Cervellino, A. J. Pharm. Sci. 2012, 101 (12) 4481-4489 10.1002/jps.23310
28. Barrio, M.; Maccaroni, E.; Rietveld, I. B.; Malpezzi, L.; Masciocchi, N.; Céolin, R.; Tamarit, J. J. Pharm. Sci. 2012, 101 (3) 1073-1078 10.1002/jps.22821
29. Maccaroni, E.; Giovenzana, G. B.; Palmisano, G.; Botta, D.; Volante, P.; Masciocchi, N. Steroids 2009, 74 (1) 102-111 10.1016/j.steroids.2008.09.014
30. Moreno-Calvo, E.; Muntó, M.; Wurst, K.; Ventosa, N.; Masciocchi, N.; Veciana, J. Mol. Pharmaceutics 2011, 8 (2) 395-404 10.1021/mp100251s
31. Colombo, V.; Masciocchi, N.; Palmisano, G. J. Pharm. Sci. 2014, 103 (11) 3641-3647 10.1002/jps.24166
32. Kottke, T.; Stalke, D. J. Appl. Crystallogr. 1993, 26, 615-619 10.1107/S0021889893002018
33. APEX2. Data Collection Software, Version 21-RC13; Bruker AXS: Delft, 2006.
34. SAINT+. Data Integration Engine v 723a; Bruker AXS: Madison, Wisconsin, USA.
35. Sheldrick, G. M. SADABS v201, Bruker/Siemens Area Detector Absorption Correction Program; Bruker AXS: Madison, Wisconsin, USA, 1998.
36. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, 64, 112-122 10.1107/S0108767307043930
37. Sheldrick, G. M. Acta Crystallogr., Sect. C: Struct. Chem. 2015, 71 (1) 3-8 10.1107/S2053229614024218
38. Coelho, A. A. J. Appl. Crystallogr. 2003, 36 (1) 86-95 10.1107/S0021889802019878
39. TOPAS-R, version 3.0, Bruker, Karlsruhe, Germany 2005.
40. Kleywegt, G. J.; Jones, T. A. Acta Crystallogr., Sect. D: Biol. Crystallogr. 1998, 54 (6) 1119-1131 10.1107/S0907444998007100
41. Jang, Y. H.; Noyes, K. T.; Sowers, L. C.; Goddard, W. A., III; Hwang, S.; Chung, D. S. J. Phys. Chem. B 2003, 107, 344-357 10.1021/jp020774x
42. Cheary, R. W.; Coelho, A. J. Appl. Crystallogr. 1992, 25 (2) 109-121 10.1107/S0021889891010804
43. March, A. Z. Kristallogr.-Cryst. Mater. 1932, 81, 285-297 10.1524/zkri.1932.81.1.285
44. Dollase, W. A. J. Appl. Crystallogr. 1986, 19 (4) 267-272 10.1107/S0021889886089458
45. Morris, K. R. In Polymorphism in Pharmaceutical Solids; Brittain, H. G., Ed.; Marcel Dekker: New York, 1999; pp 125-181.
46. Grell, J.; Bernstein, J.; Tinhofer, G. Acta Crystallogr., Sect. B: Struct. Sci. 1999, 55 (6) 1030-1043 10.1107/S0108768199007120
47. Macrae, C. F.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Shields, G. P.; Taylor, M.; van de Streek, J.; Towler, M. J. Appl. Crystallogr. 2006, 39, 453-457 10.1107/S002188980600731X
48. Martin, J. C.; Tippie, M. A.; McGee, D. P.; Verheyden, J. P. J. Pharm. Sci. 1987, 76, 180-184 10.1002/jps.2600760221
49. Boryski, J.; Golankiewicz, B. Synthesis 1999, 625-628 10.1055/s-1999-6058