Ionic liquids as active pharmaceutical ingredients

ChemMedChem

Volumn 6, Issue 6, 2011, Pages 975-985

  Ferraz, Ricardo ^a,b   Branco, Luís C ^b   Prudêncio, Cristina ^a,c   Noronha, João Paulo ^b   Petrovski, Željko ^b  

^a POLYTECHNIC INSTITUTE OF PORTO   (Portugal)

^b UNIVERSIDADE NOVA DE LISBOA   (Portugal)

^c University of Porto   (Portugal)

Author keywords

Drugs; Ionic liquids; Medicinal chemistry; Pharmaceutical activity

Indexed keywords

1 ALKYL 3 METHYLIMIDAZOLIUM CHLORIDE; 1 ALKYLQUINOLINIUM BROMIDE; 3 METHYL 1 TETRADECYL 1H IMIDAZOL 3 IUM CHLORIDE; AMLODIPINE BESYLATE; AMOXICILLIN PLUS CLAVULANIC ACID; AMPHETAMINE; ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; DIDECYLDIMETHYLAMMONIUM SACCHARINATE; EMOLLIENT AGENT; FEXOFENADINE; GABAPENTIN; IBUPROFEN; IONIC LIQUID; LAMOTRIGINE; LEVOTHYROXINE; LISINOPRIL; LOCAL ANESTHETIC AGENT; LUBRICATING AGENT; METOPROLOL SUCCINATE; NONSTEROID ANTIINFLAMMATORY AGENT; OMEPRAZOLE; PANTOPRAZOLE; PENICILLIN G; SOLVENT; SUMATRIPTAN; TETRABUTYLPHOSPHONIUM TRIFLUOROTRIS(PERFLUOROETHYL)PHOSPHATE; TETRAOCTYLAMMONIUM BIS[(TRIFLUOROMETHYL)SULFONYL]AMIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VALPROIC ACID;

ANIMAL CELL; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL COMPOSITION; CONDUCTANCE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DENSITY; DRUG ACTIVITY; DRUG CLASSIFICATION; DRUG DELIVERY SYSTEM; DRUG DESIGN; DRUG SOLUBILITY; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; THERMOSTABILITY; VISCOSITY;

ANIMALS; ANTI-INFECTIVE AGENTS; ANTINEOPLASTIC AGENTS; BACTERIAL INFECTIONS; HUMANS; IONIC LIQUIDS; MYCOSES; NEOPLASMS;

EID: 79957610788     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201100082     Document Type: Article

References (77)

1. S. Zhang, X. Lu, Q. Zhou, X. Li, X. Zang, S. Li, Ionic Liquids: Physicochemical Properties, Elsevier, Amsterdam, 2009.
2. S. Sowmiah, V. Srinivasadesikan, M.-C. Tseng, Y.-H. Chu, Molecules 2009, 14, 3780-3813.
3. D. R. MacFarlane, K. R. Seddon, Aust. J. Chem. 2007, 60, 3-5.
4. T. Torimoto, T. Tsuda, K. Okazaki, S. Kuwabata, Adv. Mater. 2010, 22, 1196-1221.
5. D. R. MacFarlane, J. M. Pringle, K. M. Johansson, S. A. Forsyth, M. Forsyth, Chem. Commun. 2006, 1905-1917.
6. R. D. Rogers, G. A. Voth, Acc. Chem. Res. 2007, 40, 1077-1078.
7. P. Wasserscheid, T. Welton, Ionic Liquids in Synthesis, Wiley-VCH, Weinheim, 2007.
8. M. Freemantle, Chem. Eng. News 1998, 76 (13), 32-37.
9. D. B. Zhao, M. Wu, Y. Kou, E. Min, Catal. Today 2002, 74, 157-189.
10. M. J. Earle, K. R. Seddon, Pure Appl. Chem. 2000, 72, 1391-1398.
11. M. Haumann, A. Riisager, Chem. Rev. 2008, 108, 1474-1497;
12. W. S. Miao, T. H. Chan, Acc. Chem. Res. 2006, 39, 897-908.
13. X. Han, D. W. Armstrong, Acc. Chem. Res. 2007, 40, 1079-1086;
14. J. G. Huddleston, H. D. Willauer, R. P. Swatloski, A. E. Visser, R. D. Rogers, Chem. Commun. 1998, 1765-1766.
15. P. Hapiot, C. Lagrost, Chem. Rev. 2008, 108, 2238-2264;
16. D. R. Macfarlane, M. Forsyth, P. C. Howlett, J. M. Pringle, J. Sun, G. Annat, W. Neil, E. I. Izgorodina, Acc. Chem. Res. 2007, 40, 1165-1173.
17. T. Ichikawa, M. Yoshio, A. Hamasaki, T. Mukai, H. Ohno, T. Kato, J. Am. Chem. Soc. 2007, 129, 10662-10663;
18. K. Biswas, C. N. R. Rao, Chem. Eur. J. 2007, 13, 6123-6129.
19. F. vanRantwijk, R. A. Sheldon, Chem. Rev. 2007, 107, 2757-2785.
20. T. L. Greaves, C. J. Drummond, Chem. Rev. 2008, 108, 206-237;
21. S. Schneider, T. Hawkins, M. Rosander, G. Vaghjiani, S. Chambreau, G. Drake, Energy Fuels 2008, 22, 2871-2872.
22. W. L. Hough, M. Smiglak, H. Rodriguez, R. P. Swatloski, S. K. Spear, D. T. Daly, J. Pernak, J. E. Grisel, R. D. Carliss, M. D. Soutullo, J. H. Davis, R. D. Rogers, New J. Chem. 2007, 31, 1429-1436.
23. M. Deetlefs, K. R. Seddon, M. Shara, Phys. Chem. Chem. Phys. 2006, 8, 642-649.
24. J. D. Holbrey, K. R. Seddon, Clean Technol. Environ. Policy 1999, 1, 223-236.
25. M. J. Earle, P. B. McCormac, K. R. Seddon, Green Chem. 2000, 2, 261-262.
26. E. B. Carter, S. L. Culver, P. A. Fox, R. D. Goode, I. Ntai, M. D. Tickell, R. K. Traylor, N. W. Hoffman, J. H. Davis, Chem. Commun. 2004, 630-631.
27. J. Pernak, K. Sobaszkiewicz, I. Mirska, Green Chem. 2003, 5, 52-56.
28. J. S. Wilkes, Green Chem. 2002, 4, 73-80.
29. F. H. Hurley, T. P. Wier, J. Electrochem. Soc. 1951, 98, 203-206;
30. F. H. Hurley, T. P. Wier, J. Electrochem. Soc. 1951, 98, 207-212.
31. R. J. Gale, B. Gilbert, R. A. Osteryoung, Inorg. Chem. 1978, 17, 2728-2729.
32. S. Christie, R. H. Dubois, R. D. Rogers, P. S. White, M. J. Zaworotko, J. Inclusion Phenom. Mol. Recognit. Chem. 1991, 11, 103-114;
33. J. M. Martell, M. J. Zaworotko, J. Chem. Soc. Dalton Trans. 1991, 1495-1498;
34. J. S. Wilkes, M. J. Zaworotko, J. Chem. Soc. Chem. Commun. 1992, 965-967.
35. J. Fuller, R. T. Carlin, J. Chem. Crystallogr. 1994, 24, 489-493;
36. J. Fuller, R. T. Carlin, H. C. Delong, D. Haworth, J. Chem. Soc. Chem. Commun. 1994, 299-300.
37. H. Mizuuchi, V. Jaitely, S. Murdan, A. T. Florence, Eur. J. Pharm. Sci. 2008, 33, 326-331.
38. V. Jaitely, A. Karatas, A. T. Florence, Int. J. Pharm. 2008, 354, 168-173;
39. M. Moniruzzaman, N. Kamiya, M. Goto, J. Colloid Interface Sci. 2010, 352, 136-142;
40. M. Moniruzzaman, M. Tamura, Y. Tahara, N. Kamiya, M. Goto, Int. J. Pharm. 2010, 400, 243-250;
41. L. Viau, C. Tourné-Péteilh, J.-M. Devoisselle, A. Vioux, Chem. Commun. 2010, 46, 228-230.
42. H. Rodriguez, K. Bica, R. D. Rogers, Trop. J. Pharm. Res. 2008, 7, 1011-1012.
43. S. N. Black, E. A. Collier, R. J. Davey, R. J. Roberts, J. Pharm. Sci. 2007, 96, 1053-1068.
44. B. D. Anderson, R. A. Conradi, J. Pharm. Sci. 1985, 74, 815-820.
45. M. L. Peterson, M. B. Hickey, M. J. Zaworotko, O. Almarsson, J. Pharm. Pharm. Sci. 2006, 9, 317-326.
46. S. L. Morissette, Ö. Almarsson, M. L. Peterson, J. F. Remenar, M. J. Read, A. V. Lemmo, S. Ellis, M. J. Cima, C. R. Gardner, Adv. Drug Delivery Rev. 2004, 56, 275-300;
47. D. Singhal, W. Curatolo, Adv. Drug Delivery Rev. 2004, 56, 335-347.
48. S. Datta, D. J. W. Grant, Nat. Rev. Drug Discovery 2004, 3, 42-57.
49. J. Bauer, S. Spanton, R. Henry, J. Quick, W. Dziki, W. Porter, J. Morris, Pharm. Res. 2001, 18, 859-866.
50. A. T. Hulme, S. L. Price, D. A. Tocher, J. Am. Chem. Soc. 2005, 127, 1116-1117.
51. A. Brodin, A. Nyqvistmayer, T. Wadsten, B. Forslund, F. Broberg, J. Pharm. Sci. 1984, 73, 481-484.
52. J. Stoimenovski, D. R. MacFarlane, K. Bica, R. D. Rogers, Pharm. Res. 2010, 27, 521-526.
53. W. M. Reichert, J. D. Holbrey, K. B. Vigour, T. D. Morgan, G. A. Broker, R. D. Rogers, Chem. Commun. 2006, 4767-4779.
54. D. R. MacFarlane, S. A. Forsyth, J. Golding, G. B. Deacon, Green Chem. 2002, 4, 444-448.
55. J. Ranke, S. Stolte, R. Stormann, J. Arning, B. Jastorff, Chem. Rev. 2007, 107, 2183-2206;
56. A. Cornellas, L. Perez, F. Comelles, I. Ribosa, A. Manresa, M. T. Garcia, J. Colloid Interface Sci. 2011, 355, 164-171;
57. S. M. Saadeh, Z. Yasseen, F. A. Sharif, H. M. Abu Shawish, Ecotoxicol. Environ. Saf. 2009, 72, 1805-1809.
58. W. L. Hough-Troutman, M. Smiglak, S. Griffin, W. M. Reichert, I. Mirska, J. Jodynis-Liebert, T. Adamska, J. Nawrot, M. Stasiewicz, R. D. Rogers, J. Pernak, New J. Chem. 2009, 33, 26-33.
59. D. Demberelnyamba, K. S. Kim, S. J. Choi, S. Y. Park, H. Lee, C. J. Kim, I. D. Yoo, Bioorg. Med. Chem. 2004, 12, 853-857.
60. L. Carson, P. K. W. Chau, M. J. Earle, M. A. Gilea, B. F. Gilmore, S. P. Gorman, M. T. McCann, K. R. Seddon, Green Chem. 2009, 11, 492-497.
61. V. Kumar, S. V. Malhotra, Bioorg. Med. Chem. Lett. 2009, 19, 4643-4646.
62. J. Pernak, J. Feder-Kubis, Chem. Eur. J. 2005, 11, 4441-4449.
63. R. D. Rogers, K. R. Seddon, Science 2003, 302, 792-793.
64. P. M. Dean, J. Turanjanin, M. Yoshizawa-Fujita, D. R. MacFarlane, J. L. Scott, Cryst. Growth Des. 2009, 9, 1137-1145.
65. V. Kumar, S. V. Malhotra in Ionic Liquid Applications: Pharmaceuticals, Therapeutics, and Biotechnology, American Chemical Society, WashingtonDC, 2010, pp.1-12.
66. Z. F. Fei, T. J. Geldbach, D. B. Zhao, P. J. Dyson, Chem. Eur. J. 2006, 12, 2122-2130.
67. R. H. Shoemaker, Nat. Rev. Cancer 2006, 6, 813-823.
68. M. E. Olson, H. Ceri, D. W. Morck, A. G. Buret, R. R. Read, Can. J. Vet. Res. 2002, 66, 86-92.
69. L. S. C. Wan, J. Pharm. Sci. 1968, 57, 1903-1906.
70. R. Rogers, D. T. Daly, R. P. Swatloski, W. L. Hough, J. H. Davis, M. Smiglak, J. Pernak, S. K. Spear, WO2007044693, 2007;
71. R. Rogers, D. T. Daly, G. Gurau, D. MacFarlane, J. Turanjanin, P. Dean, J. L. Scott, K. Bica, K. Seddon, WO2010078300 (A1), 2010;
72. K. Bica, C. Rijksen, M. Nieuwenhuyzen, R. D. Rogers, Phys. Chem. Chem. Phys. 2010, 12, 2011-2017.
73. R. Löbenberg, G. L. Amidon, Eur. J. Pharm. Biopharm. 2000, 50, 3-12.
74. G. L. Amidon, H. Lennernäs, V. P. Shah, J. R. Crison, Pharm. Res. 1995, 12, 413-420.
75. Drug Topics: http://drugtopics.modernmedicine.com/drugtopics/data/articlestandard//drugtopics/252010/674976/article.pdf (accessed April 7, 2011).
76. M. Hoffer, N. J. Nutley, US2541651, 1951.
77. W. L. Hough, R. D. Rogers, Bull. Chem. Soc. Jpn. 2007, 80, 2262-2269.