Important fluorinated drugs in experimental and clinical use

Journal of Fluorine Chemistry

Volumn 118, Issue 1-2, 2002, Pages 27-33

  Ismail, Fyaz M D ^a  

^a LIVERPOOL JOHN MOORES UNIVERSITY   (United Kingdom)

Author keywords

18F positron emission tomography; Antibacterials; Anticancer; Antimalarials; Antiparasitic; Bisquinolines; Drug; Fluorine; Kinases; Phospodiesterase inhibitors

Indexed keywords

AMODIAQUINE; ANTIBIOTIC AGENT; ANTIINFECTIVE AGENT; ANTIMALARIAL AGENT; ANTINEOPLASTIC AGENT; ANTIPARASITIC AGENT; CERIVASTATIN; DRUG RECEPTOR; EZETIMIBE; FLUINDOSTATIN; FLUORINE 18; FLUORINE DERIVATIVE; FLUOROACETIC ACID; FLUOXETINE; HALOFANTRINE; HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE INHIBITOR; MEFLOQUINE; MEVINOLIN; PHOSPHODIESTERASE INHIBITOR; PICLAMILAST; PRIMAQUINE; PRIMAQUINE DERIVATIVE; PROTEIN KINASE INHIBITOR; PYRONARIDINE; QUINOLINE DERIVED ANTIINFECTIVE AGENT; ROFLUMILAST; ROSUVASTATIN; SEROTONIN UPTAKE INHIBITOR; TAFENOQUINE; UNINDEXED DRUG;

ATHEROSCLEROSIS; CARDIOTOXICITY; CONTROLLED STUDY; COVALENT BOND; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG CLASSIFICATION; DRUG DESIGN; DRUG EFFICACY; DRUG MECHANISM; DRUG METABOLISM; DRUG POTENTIATION; DRUG RECEPTOR BINDING; DRUG SAFETY; DRUG STRUCTURE; DRUG USE; EXPERIMENTATION; FLUORINATION; HUMAN; LIPOPHILICITY; MEMBRANE; MENTAL DISEASE; MODULATION; MOLECULAR PROBE; MUSCLE DISEASE; NEUROTOXICITY; NONHUMAN; PARASITOSIS; POSITRON EMISSION TOMOGRAPHY; REVIEW; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; TREATMENT INDICATION;

EID: 0036882589     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-1139(02)00201-4     Document Type: Review

References (55)

1. D. O'Hagan, D.B. Harper, Fluorine-containing natural products, J. Fluorine Chem. 100 (1999) 127-133.
2. A.J. Elliott, in: M. Hudlicky, A.E. Pavlath (Eds.), Chemistry of Organic Fluorine Compounds. II. A Critical Review, ACS Monograph 187, American Chemical Society, Washington, DC, 1995, pp. 1119-1125.
3. B.E. Smart, Fluorine substituent effects (on bioactivity), J. Fluorine Chem. 109 (2001) 3-11.
4. B.K. Park, N.R. Kitteringham, P.M. O'Neill, Metabolism of fluorine containing drugs, Ann. Rev. Pharmacol. Toxicol. 41 (2001) 443-470;
5. M. Crucianelli, Flustrates: an attractive challenge for organic chemists, Chim. Ind. (2001) 1-5.
6. D.B. Berkowitz, M. Bose, (Alpha-monofluoroalkyl)phosphonates: a class of isoacidic and "tunable" mimics of biological phosphates, J. Fluorine Chem. 112 (2001) 13-33 (Special issue).
7. G. Resnati, V.A. Soloshonok, Fluoroorganic chemistry: synthetic challenges and biomedical rewards, in: Proceedings of the Tetrahedron Symposia; Tetrahedron 58 (1996) 1-330.
8. J. Fried, E.F. Sabo, 9α-Fluoro derivatives of cortisone and hydrocortisone, J. Am. Chem. Soc. 76 (1954) 1455-1456.
9. D.S. Bundschuh, M. Eltze, J. Barsig, L. Wollin, A. Hatzelmann, R. Beume, In vivo efficacy in airway disease models of roflumilast, a novel orally active PDE4 inhibitor, J. Pharmacol. Exp. Ther. 297 (2001) 280-290.
10. R.J. Chambers, E.F. Kleinman, J.B. Cheng, A. Marfat, A.J. Duplantier, J.W. Watson, WO 9845268, 1998.
11. Anonymous, Nicotinamide derivatives as selective inhibitors of PDE4, Exp. Opinion. Ther. Patents 9 (1999) 481-485.
12. J.A. Farmer, Learning from the Cerivastatin experience, Lancet 358 (9291) (2001) 1383-1385.
13. T. Kosoglou, M. Seiberling, P. Statkevich, L. Reyderman, L. Anderson, S. Sun, S.E. Maxwell, M.B. Affrime, E.P. Veltri, Pharmacodynamic interaction between Cerivastatin and the selective cholesterol absorption inhibitor Ezetimibe, Eur. Heart J. 22 (Suppl. 5) (2001) 252.
14. J.R. Wetterau, R.E. Gregg, T.W. Harrity, C. Arbeeny, M. Cap, F. Connolly, C.H. Chu, R.J. George, D.A. Gordon, H. Jamil, K.G. Jolibois, L.K. Kunselman, S.J. Lan, T.J. Maccagnan, B. Ricci, M. Yan, D. Young, Y. Chen, O.M. Fryszman, J.V. Logan, C.L. Musial, M.A. Poss, J.A. Robl, L.M. Simpkins, S.A. Biller, An MTP inhibitor that normalizes atherogenic lipoprotein levels in WHHL rabbits, Science 282 (1998) (5389) 751-754.
15. R.E. Gregg, H.G. Pouleur, J.R. Wetterau, US Patent no. 5,883,109 (1999).
16. J.L. Gallup, J.D. Sachs, The economic burden of malaria, Am. J. Trop. Med. Hyg. 64 (2001) 85-96.
17. D.G. Heppne, V.R. Ballou, Malaria in 1998: advances in diagnosis, Curr. Opin. Infect. Dis. 11 (1998) 519-530.
18. B.M. Kotecka, G.B. Barlin, M.D. Edstein, K.H. Rieckmann, New quinoline di-Mannich base compounds with greater antimalarial activity than chloroquine, amodiaquine, or pyronaridine, Antimicrob. Agents Chemother. 41 (1997) 1369-1374.
19. F.M.D. Ismail, M.J. Dascombe, P. Carr, S.E. North, An exploration of the structure-activity relationships of 4-aminoquinolines: novel antimalarials with activity in vivo, J. Pharm. Pharmacol. 48 (1996) 841-850.
20. F.M.D. Ismail, M.J. Dascombe, P. Carr, S.A.M. Merette, Novel aryl-antimalarials with antimalarial activity in vivo, J. Pharm. Pharmacol. 50 (1998) 483-492;
21. L. Manzel, L. Strekowski, F.M.D. Ismail, J.C. Smith, D.E. Macfarlane, Antagonism of immunostimulatory CpG-oligodeoxynucleotides by 4-aminoquinolines and other weak bases: mechanistic studies, J. Pharmacol. Exp. Therap. 291 (1999) 1337-1347;
22. D.E. Macfarlane, L. Strekowski, F.M.D. Ismail, L. Manzel, G.B. Barlin, Antagonism of immunostimulatory Cpg-oligonucleotides by 4-aminoquinolines and other weak bases, US Patent no. WO2000US16723 20000616 (2000);
23. F.M.D. Ismail, M.J. Dascombe, S. Alizadeh-Shekalgorabi, 2002, unpublished.
24. Potasman, A. Beny, H. Seligmanm, Neuropsychiatric problems in 2500 long-term young travelers to the tropics, J. Travel Med. 7 (2000) 5-9.
25. D. Irons, J. Morrow, Sudden death in a traveller following halofantrine administration-Togo, 2000, J. Am. Med. Assoc. 285 (2001) 1836-1836 (Reprinted from MMWR 59 (2001) 169-179).
26. F. Chorki, F. Grellepois, B. Crousse, M. Ourevitch, D. Bonnet-Delpon, J.P. Begue, Fluoro artemisinins: difluoromethylene ketones, J. Org. Chem. 66 (2001) 7858-7863.
27. W. Peters, B.L. Robinson, The chemotherapy of rodent malaria. LVI. Studies on the development of resistance to natural and synthetic endoperoxides, Ann. Trop. Med. Parasitol. 93 (1999) 325-339.
28. M. Szpilman, E.E. Korshin, R. Hoos, G.H. Posner, M.D. Bachi, Iron(II)-induced degradation of antimalarial beta-sulfonyl endoperoxides: evidence for the generation of potentially cytotoxic carbocations, J. Org. Chem. 66 (2001) 6531-6540.
29. J. Alzeer, J. Chollet, I. Heinze-Krauss, C. Hubschwerlen, H. Matile, R.G. Ridley, Phenyl β-methoxyacrylates: a new antimalarial pharmacophore, J. Med. Chem. 43 (2000) 560-568.
30. M.G. Etchegorry, J.P. Helenport, B. Pecoul, J. Jannin, D. Legros, Availability and affordability of treatment for human african trypanosomiasis, Trop. Med. Int. Health 6 (2001) 957-959.
31. Y.M. Traub-Cseko, J.M. Ramalho-Ortigao, A.P. Dantas, S.L. de Castro, H.S. Barbosa, K.H. Downing, Dinitroaniline herbicides against protozoan parasites: the case of Trypanosoma cruzi, Trends Parasitol. 17 (2001) 136-141.
32. A. Liendo, K. Lazardi K, J.A. Urbina, In vitro antiproliferative effects and mechanism of action of the bis-triazole D0870 and its S(-) enantiomer against Trypanosoma cruzi, J. Antimicrob. Chemother. 41 (1998) 197-205.
33. J. Bridges, Chemical inhibitors of protein kinases, Chem. Rev. 101 (2001) 2541-2571.
34. J. Baselga, S.D. Averbuch, ZD1839 (Iressa) as an anticancer agent, Drugs 60 (Suppl. 1) (2000) 33-40.
35. J. Bridges, D. Driscoll, W.D. Klohs, PCT Int. Appl. (2000) WO0031048.
36. J. Torrance, P.E. Jackson, E. Montgomery, K.W. Kinzler, B. Vogelstein, A. Wissner, M. Nunes, P. Frost, C.M. Discafani, Combinatorial chemoprevention of intestinal neoplasia, Nat. Med. 6 (2000) 1024-1028.
37. S.R. Wedge, D.J. Ogilvie, M. Dukes, J. Kendrew, J.O. Curwen, L.F. Hennequin, A.P. Thomas, E.S.E. Stokes, B. Curry, G.H.P. Richmond, P.F. Wadsworth, ZD4190: an orally active inhibitor of vascular endothelial growth factor signaling with broad-spectrum antitumor efficacy, Cancer Res. 60 (2000) 970-975.
38. K. Garber, Tyrosine kinase inhibitor research presses on despite halted clinical trial, J. Natl. Cancer Inst. 92 (2000) 967-969.
39. D.S. VanVliet, Y. Tachibana, K.F. Bastow, E.S. Huang, and K.H. Lee, Design, synthesis, and biological testing of 4-anilino-2-fluoro-4′-demethylpodophyllotoxin analogues as cytotoxic and antiviral agents (antitumor agents 207), J. Med. Chem. 44 (2001) 1422-1428.
40. I. Ojima, T. Inoue, J.C. Slater, S.N. Lin, S.D. Kuduk, S. Chakravarty, J.J. Walsh, T. Cresteil, B. Monsarrat, P. Pera, R.J. Bernacki, Synthesis of enatiopure fluorine-containing taxoids and their use as anticancer agents as well as probes for biomedical problems, Asymm. Fluoroorg. Chem. ACS Symp. Ser. 746 (2000) 158-181.
41. I. Ojima, T. Inoue, S. Chakravarty, Enantiopure fluorine-containing taxoids: potent anticancer agents and versatile probes for biomedical problems, J. Fluorine Chem. 97 (1999) 3-10.
42. O. Lavergne, D. Demarquay, C. Bailly, C. Lanco, A. Rolland, M. Huchet, H. Coulomb, N. Muller, N. Baroggi, J. Camara, C. Le Breton, E. Manginot, J.B. Cazaux, D.C.H. Bigg, Topoisomerase I-mediated antiproliferative activity of enantiomerically pure fluorinated homocamptothecins, J. Med. Chem. 43 (2000) 2285-2289.
43. X.S. Fei, W.S. Tian, Q.Y. Chen, Synthesis of 4-trifluoromethylsteroids: a novel class of steroid 5-reductase inhibitors, Bioorg. Med. Chem. Lett. 7 (1997) 3113-3118.
44. I. Hutchinson, M.S. Chua, H.L. Browne, V. Trapani, T.D. Bradshaw, A.D. Westwell, M.F.G. Stevens, Synthesis and in vitro biological properties of fluorinated 2-(4-aminophenyl)benzothiazoles (antitumor benzothiazoles 14), J. Med. Chem. 44 (2001) 1446-1455.
45. G.E. Zurenko, Synthesis and antibacterial activity of U-100592 and U-100766, two oxazolidinone antibacterial agents for the potential treatment of multidrug-resistant Gram-positive bacterial infections, J. Med. Chem. 39 (1996) 673-679.
46. H.N. Bramson, J. Corona, S.T. Davis, S.H. Dickerson, M. Edelstein, S.V. Frye, R.T. Gampe Jr., P.A. Harris, A. Hassell, W.D. Holmes, R.N. Hunter, K.E. Lackey, B. Lovejoy, M.J. Luzzio, V. Montana, Oxindole-based inhibitors of cyclin-dependent kinase 2 (CDK2): design, synthesis, enzymatic activities, and X-ray crystallographic analysis, J. Med. Chem. 44 (2001) 4339-4358.
47. S.J. Antony, E. Diaz-Vasquez, C. Stratton, Clinical experience with linezolid in the treatment of resistant Gram-positive infections, J. Natl. Med. Assoc. 93 (2001) 386-391.
48. 18F for imaging tumours by positron emission tomography, J. Fluorine Chem. 109 (2001) 3-11.
49. R. Bhatnagar, R. Hustinx, A. Alavi, Nuclear imaging methods for noninvasive drug monitoring, Adv. Drug. Deliv. Rev. 41 (2000) 41-54.
50. 18F]fluorodeoxyglucose and positron emission tomography: review and 1999 EORTC recommendations, Eur. J. Cancer 35 (1999) 1773-1782.
51. 18F] fluoro-3-(2(S)-azetidinylmethoxy)pyridine, a high-affinity radioligand for central nicotinic acetylcholine receptors, J. Label. Comp. Radiopharm. 43 (2000) 413-423.
52. 18F] fluticasone propionate as a radiotracer for lung deposition studies with PET, J. Label. Comp. Radiopharm. 39 (1997) 567-584.
53. A.T. Shulgin, A. Shulgin, Pihkal: A Chemical Love Story, Transform Press, Berkeley, CA, 1991.
54. S.M. Rubenstein, V. Baichwal, H. Beckmann, D.L. Clark, W. Frankmoelle, D. Roche, E. Santha, S. Schwender, M. Thoolen, Q. Ye, J.C. Jaen, Hydrophilic, pro-drug analogues of T138067 are efficacious in controlling tumor growth in vivo and show a decreased ability to cross the blood brain barrier, J. Med. Chem. 44 (2001) 3599-3605.
55. D. O'Hagan, C. Schaffrath, S.L. Cobb, J.T.G. Hamilton, C.D. Murphy, Biosynthesis of an organofluorine molecule-a fluorinase enzyme has been discovered that catalyses carbon-fluorine bond formation, Nature 416 (2002) 279-279.