journal article·2009-02-04

Co-Crystals of the Anti-HIV Drugs Lamivudine and Zidovudine

Prashant M. Bhatt, Yasser Azim, Tejender S. Thakur, Gautam R. Desiraju

Crystal Growth & Design· Volume 9· Issue 2
Publisher page

Abstract

Co-crystal forming abilities of the two anti-HIV drugs lamivudine and zidovudine were studied. A study of five crystal structures was carried out to investigate the general applicability of the retrosynthetic approach in the design of new co-crystals. This analysis of co-crystals and salt structures showed a complete to partial success, and in one case, a total failure to obtain the predicted synthon. Both screening strategies and retrosynthetic methods may be appropriate for the discovery of new active pharmaceutical ingredients co-crystals.
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Research context

OpenAlex topics: Crystallography and molecular interactions · Crystallization and Solubility Studies · Crystal structures of chemical compounds

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

School of Chemistry, University of Hyderabad, Hyderabad 500 046, India

References (97)

Show source-provided references
1. Bond A. D. · CrystEngComm · 2007 · 9 · 83310.1039/b708112j ↗
2. We do not specifically discuss the nomenclature aspects of co-crystals in this paper, but it will suffice to state that this is a topic that has elicited some interest and comment. See, for example,
3. Desiraju G. R. · CrystEngComm · 2003 · 5 · 46610.1039/b313552g ↗
4. Dunitz J. D. · CrystEngComm · 2003 · 5 · 50610.1039/b315687g ↗
5. Zukerman-Schpector J. · Z. Kristallogr. · 2008 · 223 · 23310.1524/zkri.2008.0021 ↗
6. Lara-Ochoa F. · Cryst. Growth Des. · 2007 · 7 · 121310.1021/cg070037w ↗
7. Rodríguez-Hornedo N. · Mol. Pharmaceutics · 2007 · 4 · 29910.1021/mp070042v ↗
8. Almarsson Ö. · Chem. Commun. · 2004 · 188910.1039/b402150a ↗
9. Wöhler F. · Ann. · 1844 · 51 · 145
10. Pfeiffer P. · 1927
11. cFoster, R.Organic Charge-Transfer Complexes;Academic:London, 1969.
12. Herbstein F. H. · 2005 · 110.1093/acprof:oso/9780198526605.001.0001 ↗
13. Some attention has been paid to crystals that contain three distinct compounds. See for example:
14. Bernstein J. · Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. · 1980 · 36 · 117010.1107/S056774088000550X ↗
15. Lynch D. E. · Chem. Commun. · 1992 · 30010.1039/C39920000300 ↗
16. Smolka T. · Struct. Chem. · 1999 · 10 · 42910.1023/A:1022427122156 ↗
17. Aakeröy C. B. · Angew. Chem., Int. Ed. · 2001 · 40 · 324010.1002/1521-3773(20010903)40:17<3240::AID-ANIE3240>3.0.CO;2-X ↗
18. Bhogala B. R. · CrystEngComm · 2005 · 7 · 55110.1039/b509162d ↗
19. Bhogala B. R. · Cryst. Growth Des. · 2005 · 5 · 168310.1021/cg058012p ↗
20. Aakeröy C. B. · Z. Kristallogr. · 2005 · 220 · 32510.1524/zkri.220.4.325.61619 ↗
21. Aakeröy C. B. · Chem. Commun. · 2005 · 282010.1039/b503718b ↗
22. Aakeröy C. B. · CrystEngComm · 2005 · 7 · 43910.1039/b505883j ↗
23. Fričić T. · Angew. Chem., Int. Ed. · 2006 · 45 · 754610.1002/anie.200603235 ↗
24. Shan N. · Chem. Commun. · 2002 · 237210.1039/b207369m ↗
25. Fleischman S. G. · Cryst. Growth Des. · 2003 · 3 · 90910.1021/cg034035x ↗
26. Remenar J. F. · J. Am. Chem. Soc. · 2003 · 125 · 845610.1021/ja035776p ↗
27. Olenik B. · Cryst. Growth Des. · 2003 · 3 · 18310.1021/cg034003+ ↗
28. Aakeröy C. B. · Cryst. Growth Des. · 2003 · 3 · 15910.1021/cg025593z ↗
29. Walsh R. D. · Chem. Commun. · 2003 · 18610.1039/b208574g ↗
30. Bhogala B. R. · Cryst. Growth Des. · 2003 · 3 · 54710.1021/cg034047i ↗
31. Childs S. L. · J. Am. Chem. Soc. · 2004 · 126 · 1333510.1021/ja048114o ↗
32. Gao X. · Angew. Chem., Int. Ed. · 2004 · 43 · 23210.1002/anie.200352713 ↗
33. Ma B. Q. · Cryst. Growth Des. · 2004 · 4 · 21110.1021/cg0341914 ↗
34. Reddy L. S. · Cryst. Growth Des. · 2004 · 4 · 8910.1021/cg034106s ↗
35. Trask A. V. · Chem. Commun. · 2005 · 880
36. Trask A. V. · Top. Curr. Chem. · 2005 · 254 · 4110.1007/b100995 ↗
37. Vishweshwar P. · Chem. Commun. · 2005 · 460110.1039/b501304f ↗
38. Fričić T. · Chem. Commun. · 2006 · 500910.1039/B613073A ↗
39. Fričić T. · Angew. Chem., Int. Ed. · 2006 · 45 · 754610.1002/anie.200603235 ↗
40. Bis J. A. · Cryst. Growth Des. · 2006 · 6 · 264810.1021/cg060516f ↗
41. Childs S. L. · Cryst. Growth Des. · 2007 · 7 · 129110.1021/cg060742p ↗
42. Stahly G. P. · Cryst. Growth Des. · 2007 · 7 · 100710.1021/cg060838j ↗
43. Cheney M. L. · Cryst. Growth Des. · 2007 · 7 · 61610.1021/cg0701729 ↗
44. Dabros M. · Angew. Chem., Int. Ed. · 2007 · 46 · 413210.1002/anie.200604830 ↗
45. Porter III W. W. · Cryst. Growth Des. · 2008 · 8 · 1410.1021/cg701022e ↗
46. Trask A. V. · Mol. Pharmaceutics · 2007 · 4 · 30110.1021/mp070001z ↗
47. Jones W. · MRS Bull. · 2006 · 31 · 87510.1557/mrs2006.206 ↗
48. Sarma J. A. R. P. · J. Chem. Soc., Perkin Trans. 2 · 1985 · 190510.1039/P29850001905 ↗
49. Desiraju G. R. · Angew. Chem., Int. Ed. · 1995 · 34 · 231110.1002/anie.199523111 ↗
50. Desiraju G. R. · Angew. Chem., Int. Ed. · 2007 · 46 · 834210.1002/anie.200700534 ↗
51. It should be noted here that there is no fundamental reason why co-crystal formation should be restricted to those cases where the two molecular components are linked with hydrogen bonds. In principle, any significant interaction like van der Waals (Reddy, D. S.; Craig, D. C.; Desiraju, G. R.J. Chem. Soc., Chem. Commun,1994, 1457), charge-transfer (Foster, R.Organic Charge-Transfer Complexes; Academic: London, 1969), halogen bonding (Metrangolo, P.; Neukirch, H; Pilati, T.; Resnati, G.Acc. Chem. Res.2005,38, 386) or hydrogen bonding should be equally acceptable. Probably what is not acceptable as a co-crystal is a two component system consisting of a solid solution of variable composition of two compounds, isostructural or otherwise (Kitaigorodskii, A. I.Mixed Crystals; Springer-Verlag: Berlin, 1984). Many of these issues are matters of individual interpretation.
52. Fox Z. · Antiviral Ther. · 2006 · 11 · 76110.1177/135965350601100608 ↗
53. Mitsuya H. · Science · 1990 · 249 · 153310.1126/science.1699273 ↗
54. Meléndez R. E. · Top. Curr. Chem. · 1998 · 198 · 9710.1007/3-540-69178-2_3 ↗
55. Pranata J. · J. Am. Chem. Soc. · 1991 · 113 · 281010.1021/ja00008a002 ↗
56. 1998
57. 2001
58. Sheldrick G. M. · 1998
59. Allen F. H. · New J. Chem. · 1999 · 2510.1039/a807212d ↗
60. Seto C. T. · J. Am. Chem. Soc. · 1993 · 115 · 90510.1021/ja00056a014 ↗
61. Lehn J. M. · J. Chem. Soc., Chem. Commun. · 1990 · 47910.1039/c39900000479 ↗
62. Lehn J. M. · Prog. Polym. Sci. · 2005 · 30 · 81410.1016/j.progpolymsci.2005.06.002 ↗
63. Arduini M. · J. Org. Chem. · 2003 · 68 · 109710.1021/jo020610c ↗
64. Mateos-Timoneda M. A. · Chem. Soc. Rev. · 2004 · 33 · 36310.1039/b305550g ↗
65. McClenaghan N. D. · J. Am. Chem. Soc. · 2003 · 125 · 1300410.1021/ja0372098 ↗
66. Desiraju G. R. · J. Chem. Soc., Chem. Commun. · 1991 · 42610.1039/c39910000426 ↗
67. Nangia A. · Chem. Commun. · 1999 · 60510.1039/a809755k ↗
68. Infantes L. · CrystEngComm · 2002 · 4 · 45410.1039/b204934a ↗
69. Infantes L. · CrystEngComm · 2003 · 5 · 48010.1039/b312846f ↗
70. Zafar A. · Tetrahedron Lett. · 1996 · 37 · 232710.1016/0040-4039(96)00287-0 ↗
71. Weber E. · J. Am. Chem. Soc. · 1984 · 106 · 329710.1021/ja00323a039 ↗
72. Babu N. J. · Cryst. Growth Des. · 2006 · 6 · 175310.1021/cg060378u ↗
73. Das D. · CrystEngComm · 2006 · 8 · 67410.1039/b606054d ↗
74. Aparna V. · J. Chem. Inf. Model. · 2005 · 45 · 72510.1021/ci049676u ↗
75. Srikrishnan T. · Nature · 1976 · 264 · 37910.1038/264379a0 ↗
76. Maye, K, J.; Goodson, G. W.; Wood, A. W.U.S. Patent No. US6113920, (5-09- 2000) .
77. Garcia-Tellado F. · J. Am. Chem. Soc. · 1991 · 113 · 926510.1021/ja00024a036 ↗
78. Caira M. R. · J. Crystallogr. Spectrosc. Res. · 1992 · 22 · 19310.1007/BF01186256 ↗
79. Geib S. J. · Angew. Chem., Int. Ed. · 1993 · 32 · 11910.1002/anie.199301191 ↗
80. Lynch D. E. · Aust. J. Chem. · 1994 · 47 · 109710.1071/CH9941097 ↗
81. Smith G. · Aust. J. Chem. · 1995 · 48 · 115110.1071/CH9951151 ↗
82. Lynch D. E. · Cryst. Eng. · 2000 · 3 · 7110.1016/S1463-0184(00)00029-0 ↗
83. Bensemann I. · Org. Biomol. Chem. · 2003 · 1 · 142510.1039/b211675h ↗
84. Barooah N. · J. Mol. Struct. · 2006 · 791 · 12210.1016/j.molstruc.2006.01.025 ↗
85. Aakeröy C. B. · New J. Chem. · 2006 · 30 · 145210.1039/B608267J ↗
86. Thakur T. S. · Cryst. Growth Des. · 2008 · 8 · 403110.1021/cg800371j ↗
87. Smith G. · Aust. J. Chem. · 2000 · 53 · 53110.1071/CH00072 ↗
88. Prabakaran P. · Acta Crystallogr., Sect. E: Struct. Rep. Online · 2001 · 57 · o93310.1107/S1600536801014465 ↗
89. Stanley N. · Cryst. Growth Des. · 2002 · 2 · 63110.1021/cg020027p ↗
90. Smith G. · Aust. J. Chem. · 2003 · 56 · 70710.1071/CH02163 ↗
91. Perpetuo G. J. · Acta Crystallogr., Sect. C: Cryst. Struct. Commun. · 2006 · 62 · 37210.1107/S0108270106015873 ↗
92. Thanigaimani K. · Acta Crystallogr., Sect. C: Cryst. Struct. Commun. · 2007 · 63 · 29510.1107/S0108270107005677 ↗
93. Smith G. · Acta Crystallogr., Sect. E: Struct. Rep. Online. · 2005 · 61 · 74610.1107/S160053680500499X ↗
94. Refcodes for these 16 structures are ACITEM, CYTZNC, GITYEN, GOXCOL, KEVSAG, MCYTIM10, MECTSI, QOCTUX, RADKOX, RADKOX01, TAZWUN, TAZXAU, TAZXEY, WEWZAA, XAXPES, ZUKXOS.
95. Bhatt P. M. · CrystEngComm · 2008
96. Banerjee R. · Cryst. Growth Des. · 2005 · 5 · 229910.1021/cg050125l ↗
97. 4-Quinolinone was one among 23 compounds that were co-crystallised with lamivudine. These compounds were selected because they contain hydrogen bond donor and/or acceptor groups. Co-crystals were obtained only with 4-quinolinone. The list of 23 compounds is given in theSupporting Information.