Stereoselectivity of drug action

Drug Discovery Today

Volumn 2, Issue 4, 1997, Pages 138-147

  Triggle, David J ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTICONVULSIVE AGENT; ANTIHISTAMINIC AGENT; CALCIUM ANTAGONIST; CHOLINERGIC RECEPTOR BLOCKING AGENT; CICLOPROFEN; CIMETIDINE; DILTIAZEM; DISOPYRAMIDE; DOBUTAMINE; ETIDOCAINE; FLECAINIDE; FLUOXETINE; GALLOPAMIL; IBUPROFEN; INDINAVIR; ION CHANNEL; KETOCONAZOLE; KETOPROFEN; LABETALOL; LIDOCAINE; NARCOTIC ANTAGONIST; NIFEDIPINE; NITRENDIPINE; PHENYTOIN; QUINIDINE; TERFENADINE; TERODILINE; THALIDOMIDE; UNINDEXED DRUG; VERAPAMIL; VINBLASTINE;

CHIRALITY; DRUG ACTIVITY; DRUG MECHANISM; ENANTIOMER; HUMAN; PHARMACODYNAMICS; PHARMACOKINETICS; REVIEW; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 0031126364     PISSN: 13596446     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1359-6446(97)01010-6     Document Type: Review

References (97)

1. 1 Armstrong, R.W. et al. (1989) J. Am. Chem. Soc. 111, 7525-7530
2. 2 Mason, S.F. (1983) Int. Rev. Phys. Chem. 3, 217-241
3. 3 Keszethelyi, L. (1995) Q. Rev. Biophys. 28, 473-507
4. 4 Groves, J.T. and McConnell, H.M. (1996) Biophys. J. 70, 1573-1574
5. 5 delMilton, R.C., Milton, S.C.F. and Kent, S.B.H. (1992) Science 256, 1445-1448
6. 6 Lipmann, F., Hotchkiss, R.D. and Dubois, R.J. (1941) J. Biol. Chem. 141, 163-169
7. 7 Gross, E. and Morell, J.L. (1971) J. Am. Chem. Soc. 93, 4634-4635
8. 8 Montecucchi, C. (1981) Int. J. Pept. Protein Res. 10, 316-321
9. 9 Kreil, G. (1994) J. Biol. Chem. 269, 10967-10970
10. 10 Heck, S.D. et al. (1994) Science 266, 1065-1068
11. 11 Kuwada, M. et al. (1994) Mol. Pharmacol. 46, 587-593
12. 12 Leal, W.S. (1996) Proc. Natl. Acad. Sci. U. S. A. 93, 12112-12115
13. 13 FDA (1992) Chirality 4, 338-340
14. 14 Gross, M. et al. (1993) Drug Inf. J. 27, 453-457
15. 15 Marzo, A. (1994) Arzneim.-Forsch. Drug Res. 44, 791-793
16. 16 Ariëns, E.J., Soudijn, W. and Timmermans, P.B.M.W.M., eds (1983) Stereochemistry and Biological Activity of Drugs, Blackwell Scientific
17. 17 Wainer, I.W. and Drayer, D.E., eds (1993) Drug Stereochemistry, Analytical Methods and Pharmacology (2nd edn), Marcel Dekker
18. 18 Ariëns, E.J. (1983) Trends Pharmacol. Sci. 14, 68-75
19. 19 Millership, J.S. and Fitzpatrick, A. (1993) Chirality 5, 573-576
20. 20 Stinson, S.C. (1993) Chem. Eng. News 27 September, 38-65
21. 21 Stinson, S.C. (1994) Chem. Eng. News 19 September, 38-71
22. 22 Stinson, S.C. (1995) Chem. Eng. News 9 October, 44-74
23. 23 Triggle, D.J. (1996) in The Practice of Medicinal Chemistry (Wermuth, C., ed.), pp. 547-570, Academic Press
24. 24 Tanouye, E. (1996) Wall Street Journal 5 November, A1
25. 25 Blaschke, G. et al. (1979) Arzneim.-Forsch. Drug Res. 29, 1640-1642
26. 26 Wnendt, S. et al. (1996) Chirality 8, 390-396
27. 27 Hutt, A.J. and Tan, S.C. (1996) Drugs 52 (Suppl. 5), 1-12
28. 28 Jamali, F., Mehvar, R. and Pasutto, F.M. (1988) J. Pharm. Sci. 78, 695-715
29. 29 Ruffolo, R.R. (1991) Tetrahedron 47, 4953-4980
30. 30 Patil, P.N., Miller, D.D. and Trendelenburg, U. (1974) Pharmacol. Rev. 26, 323-392
31. 31 Hauck, R.S., Nau, H. and Elmazar, M.M.A. (1991) Naturwissenschaften 78, 272-274
32. 32 Buch, H.P., Schneider-Affeld, F. and Rummel, W. (1973) Naunyn-Schmiedeberg's Arch. Pharmacol. 277, 191-198
33. 33 Zimmerman, D.M. and Gesellchen, P.D. (1982) Annu. Rep. Med. Chem. 17, 21-30
34. 34 Clark, J.A., Zimmerman, H-J. and Tanner, L.A. (1990) Ann. Intern. Med. 113, 210-213
35. 35 Tucker, G.T. and Lennard, M.S. (1990) Pharmacol. Ther. 45, 309-329
36. 36 Levy, R.H. and Boddy, A.V. (1991) Pharm. Res. 8, 551-556
37. 37 Giacomini, K.M. et al. (1982) J. Pharmacokinet. Biopharm. 10, 1-14
38. 38 Lima, J.J., Boudoulas, H. and Blanford, M. (1981) J. Pharmacol. Exp. Ther. 219, 741-747
39. 39 Giacomini, J.C., Cox, B.M. and Blashke, T.F. (1980) Life Sci. 27, 1191-1197
40. 40 Vanhoutte, F. et al. (1991) Naunyn-Schmiedeberg's Arch. Pharmacol. 344, 662-673
41. 41 Giacomini, K.M. et al. (1986) J. Pharmacokinet. Biopharm. 14, 335-356
42. 42 Testa, B. and Trager, W.F. (1990) Chirality 2, 129-133
43. 43 Hille, B. (1992) Ion Channels (2nd edn), Sinauer
44. 44 Godfraind, T. (1994) Pharmacol. Ther. 64, 37-75
45. 45 Roden, D.M. and George, A.L. (1994) Annu. Rev. Med. 47, 135-148
46. 46 Ezzel, C. (1995) J. Natl. Inst. Health Res. 7, 30-32
47. 47 Narahashi, T. (1996) Pharmacol. Toxicol. 78, 1-14
48. 48 Gilmore, J. et al. (1995) Annu. Rep. Med. Chem. 30, 51-60
49. 49 Hille, B. (1977) J. Gen. Physiol. 69, 497-515
50. 50 Hondeghem, L.M. and Katzung, B.G. (1984) Annu. Rev. Pharmacol. 24, 387-423
51. 51 Kwon, Y-W. and Triggle, D.J. (1991) Chirality 3, 393-404
52. 52 McLoud, A.A., Thorogood, S. and Barnett, S. (1991) Br. Med. J. 302, 1469
53. 53 Andersson, K.E., Ekstrom, B. and Mattiasson, A. (1988) Acta Pharmacol. Toxicol. 63, 390-395
54. 54 Hartigan-Go, K. et al. (1996) Clin. Pharmacol. Ther. 60, 89-98
55. 55 Davies, A.J. et al. (1989) Br. Med. J. 298, 325
56. 56 Rampe, D. et al. (1993) Mol. Pharmacol. 44, 1240-1245
57. 57 Eichelbaum, M. and Gross, A.S. (1996) Adv. Drug Res. 28, 2-64
58. 58 Gruber, A., Peterson, C. and Reizenstein, P. (1988) Int. J. Cancer 41, 224-226
59. 59 Miller, T.P. et al. (1991) J. Clin. Oncol. 9, 17-24
60. 60 Schumacher, K. et al. (1992) in Dexverapamil - Circumventor of Multidrug Resistance (Eichelbaum, M., Hirth, H.P., Schumacher, K. and Traugott, U., eds), pp. 57-63, Kluwer
61. 61 Hollt, V. et al. (1992) Biochem. Pharmacol. 43, 2601-2608
62. 62 Triggle, D.J. (1990) in Cardiovascular Pharmacology (Antonaccio, M., ed.), pp. 107-160, Raven Press
63. 63 Triggle, D.J. (1989) in Molecular and Cellular Mechanisms of Antiarrhythmic Agents (Hondeghem, L., ed.), pp. 269-291, Futura Publishing
64. 64 Bean, B.P., Cohen, C.J. and Tsien, R.W. (1983) J. Gen. Physiol. 81, 613-642
65. 65 Sanguinetti, M.C. and Kass, R.S. (1984) Circ. Res. 55, 336-348
66. 66 Ehara, T. and Kaufmann, R. (1978) J. Pharmacol. Exp. Ther. 207, 49-55
67. 67 Yeh, J.Z. (1980) in Molecular Mechanisms of Anesthesia (Fink, B.R., ed.), pp. 35-44, Raven Press
68. 68 Ragsdale, D.S. et al. (1994) Science 265, 1724-1728
69. 69 Lee-Son, S. et al. (1992) Anesthesiology 77, 324-335
70. 70 Qu, Y. et al. (1995) Proc. Natl. Acad. Sci. U. S. A. 92, 11839-11843
71. 71 Ragsdale, D.S. et al. (1996) Proc. Natl. Acad. Sci. U. S. A. 93, 9270-9275
72. 72 Schuster, A. et al. (1996) EMBO J. 15, 2365-2370
73. 73 Hockerman, G.H. et al. (1995) J. Biol. Chem. 270, 22119-22122
74. 74 Triggle, D.J., Langs, D.A. and Janis, R.A. (1989) Med. Res. Rev. 9, 123-180
75. 75 Goldmann, S. and Stoltefuss, J. (1991) Angew. Chem. Int. Ed. Engl. 30, 1555-1578
76. 76 Zheng, W. et al. (1992) Mol. Pharmacol. 41, 535-541
77. 77 Peterson, B.Z. and Catterall, W.A. (1995) J. Biol. Chem. 270, 18201-18204
78. 78 Kass, R.S. (1987) Circ. Res. 61 (Suppl. 1), 1-5
79. 79 Medical Economics Co. (1996) Physicians Drug Reference (50th edn)
80. 80 Van Amsterdam, F.T.M. and Zaagsma, J. (1988) Arch. Pharmacol. 337, 213-219
81. 81 Jim, K. et al. (1981) Eur. J. Pharmacol. 76, 67-72
82. 82 Van Amsterdam, F.T.M. et al. (1990) J. Cardiovasc. Pharmacol. 15, 198-204
83. 83 Eichelbaum, M. et al. (1980) Klin. Wochenschr. 58, 919-925
84. 84 McCallister, R.M. and Kirsten, E.B. (1982) Clin. Pharmacol. Ther. 31, 418-426
85. 85 Reiter, M., Shand, D.G. and Pritchett, E.L.C. (1982) Clin. Pharmacol. Ther. 32, 711-720
86. 86 Eichelbaum, M., Mikus, G. and Vogelgesang, B. (1984) Br. J. Clin. Pharmacol. 17, 453-458
87. 87 Vogelgesang, B. et al. (1984) Br. J. Clin. Pharmacol. 18, 733-740
88. 88 Echizen, H., Vogelgesang, B. and Eichelbaum, M. (1985) Clin. Pharmacol. Ther. 36, 71-76
89. 89 Gross, A.S., Heuer, B. and Eichelbaum, M. (1988) Biochem. Pharmacol. 37, 4623-4627
90. 90 Gross, A.S. et al. (1993) Chirality 5, 414-418
91. 91 Carr, R.A. et al. (1993) Chirality 5, 443-447
92. 92 Somogyi, A. and Muirhead, M. (1987) Clin. Pharmacokinet. 12, 321-366
93. 93 Mikus, G. et al. (1990) J. Pharmacol. Exp. Ther. 253, 1042-1048
94. 94 Welling, A. et al. (1993) Circ. Res. 73, 974-980
95. 95 Heydorn, W.E. (1995) Pharm. News 2, 19-21
96. 96 Ariëns, E.J. (1984) Eur. J. Clin. Pharmacol. 26, 663-668
97. 97 Gold, L.S. et al. (1992) Science 258, 261-265