Selectivity of febuxostat, a novel non-purine inhibitor of xanthine oxidase/xanthine dehydrogenase

Life Sciences

Volumn 76, Issue 16, 2005, Pages 1835-1847

  Takano, Yasuhiro ^a   Hase Aoki, Kumiko ^a   Horiuchi, Hideki ^a   Zhao, Lin ^b   Kasahara, Yoshinori ^a   Kondo, Shiro ^a   Becker, Michael A ^c  

^a TEIJIN PHARMA LIMITED   (Japan)

^b TAP PHARMACEUTICAL PRODUCTS INC   (United States)

^c UNIVERSITY OF CHICAGO   (United States)

Author keywords

Febuxostat; Purine metabolism; Pyrimidine metabolism; Xanthine oxidase inhibitor

Indexed keywords

FEBUXOSTAT; GUANINE DEAMINASE; HYPOXANTHINE PHOSPHORIBOSYLTRANSFERASE; OROTATE PHOSPHORIBOSYLTRANSFERASE; OROTIDINE 5' PHOSPHATE DECARBOXYLASE; PURINE NUCLEOSIDE PHOSPHORYLASE; XANTHINE DEHYDROGENASE; XANTHINE OXIDASE; XANTHINE OXIDASE INHIBITOR;

ARTICLE; DRUG SELECTIVITY; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME PURIFICATION; GOUT; HYPERURICEMIA; INHIBITION KINETICS; PURINE METABOLISM; PYRIMIDINE METABOLISM; STATISTICAL SIGNIFICANCE; TREATMENT INDICATION;

BOVINAE;

EID: 13444257733     PISSN: 00243205     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.lfs.2004.10.031     Document Type: Article

References (45)

1. F. Arellano, and J.A. Sacristan Allopurinol hypersensitivity syndrome: a review The Annals of Pharmacotherapy 27 3 1993 337 343
2. A. Berken Allopurinol-induced suppressor T cell dysfunction: A hypothesis Journal of the American Academy of Dermatology 5 5 1981 607 608
3. G.K. Brown, and W.J. O'Sullivan Inhibition of human erythrocyte orotidylate decarboxylase Biochemical Pharmacology 26 20 1977 1947 1950
4. E.W. Campion, R.J. Glynn, and L.O. DeLabry Asymptomatic hyperuricemia. Risks and consequences in the Normative Aging Study The American Journal of Medicine 82 3 1987 421 426
5. D. Daniewska-Michalska, T. Motyl, R. Gellert, W. Kukulska, M. Podgurniak, E. Opechowska-Pacocha, and K. Ostrowski Efficiency of hemodialysis of pyrimidine compounds in patients with chronic renal failure Nephron 64 2 1993 193 197
6. G.B. Elion Enzymatic and metabolic studies with allopurinol Annals of The Rheumatic Diseases 25 6 1966 608 614
7. G.B. Elion, T.F. Yu, A.B. Gutman, and G.H. Hitchings Renal clearance of oxipurinol, the chief metabolite of allopurinol The American Journal of Medicine 45 1 1968 69 77
8. R.M. Fox, D. Royse-Smith, and W.J. O'Sullivan Orotidinuria induced by allopurinol Science 168 933 1970 861 862
9. J.A. Fyfe, R.L. Miller, and T.A. Krenitsky Kinetic properties and inhibition of orotidine 5′-phosphate decarboxylase. Effects of some allopurinol metabolites on the enzyme The Journal of Biological Chemistry 248 11 1973 3801 3809
10. A. Giacomello, and C. Salerno Human hypoxanthine-guanine phosphoribosyltransferase. Steady state kinetics of the forward and reverse reactions The Journal of Biological Chemistry 253 17 1978 6038 6044
11. E.R. Giblett, A.J. Ammann, D.W. Wara, R. Sandman, and L.K. Diamond Nucleoside-phosphorylase deficiency in a child with severely defective T-cell immunity and normal B-cell immunity Lancet 1 7914 1975 1010 1013
12. M.D. Glantz, and A.S. Lewis Guanine deaminase from rabbit liver Methods in Enzymology 51 1978 512 517
13. A.P. Hall, P.E. Barry, T.R. Dawber, and P.M. McNamara Epidemiology of gout and hyperuricemia. A long-term population study The American Journal of Medicine 42 1 1967 27 37
14. K.R. Hande, R.M. Noone, and W.J. Stone Severe allopurinol toxicity. Description and guidelines for prevention in patients with renal insufficiency The American Journal of Medicine 76 1 1984 47 56
15. M. Hasegawa A facile one-pot synthesis of 4-alkoxy-1,3- benzenecarbonitrile Heterocycles 47 1998 857 864
16. H. Horiuchi, M. Ota, M. Kobayashi, H. Kaneko, Y. Kasahara, S. Nishimura, S. Kondo, and K. Komoriya A comparative study on the hypouricemic activity and potency in renal xanthine calculus formation of two xanthine oxidase/xanthine dehydrogenase inhibitors: TEI-6720 and allopurinol in rats Research Communications in Molecular Pathology and Pharmacology 104 3 1999 307 319
17. S. Hoshide, S. Nishimura, S. Ishii, K. Matsuzawa, N. Saito, and T. Tanaka Identification of metabolites of TMX-67, a new pharmaceutical entity for the treatment of gout or hyperuricemia, and their pharmacokinetic profiles in human 10th North American ISSX Meeting, Indianapolis, United States, October 24-28, 2000 2000
18. N. Kamatani, S. Fujimori, T. Hada, T. Hosoya, R. Kato, Y. Matsuzawa, T. Ueda, and H. Yamanaka Phase II dose response clinical trial using febuxostat (TMX-67), a novel-type xanthine oxidase/xanthine dehydrogenase inhibitor, for gout and hyperuricemia American College of Rheumatology Annual Scientific Meeting, Orland, United States, October 23-28, 2003 2003
19. G.L. Kantor Toxic epidermal necrolysis, azotemia, and death after allopurinol therapy The Journal of The American Medical Association 212 3 1970 478 479
20. W.N. Kelley, and T.D. Beardmore Allopurinol: alteration in pyrimidine metabolism in man Science 169 943 1970 388 390
21. K. Komoriya, Y. Osada, M. Hasegawa, H. Horiuchi, S. Kondo, R.C. Couch, and T.B. Griffin Hypouricemic effect of allopurinol and the novel xanthine oxidase inhibitor TEI-6720 in chimpanzees European Journal of Pharmacology 250 3 1993 455 460
22. T.A. Krenitsky, G.B. Elion, A.M. Henderson, and G.H. Hitchings Inhibition of human purine nucleoside phosphorylase. Studies with intact erythrocytes and the purified enzyme The Journal of Biological Chemistry 243 11 1968 2876 2881
23. T.A. Krenitsky, G.B. Elion, R.A. Strelitz, and G.H. Hitchings Ribonucleosides of allopurinol and oxoallopurinol. Isolation from human urine, enzymatic synthesis, and characterization The Journal of Biological Chemistry 242 11 1967 2675 2682
24. A.S. Lewis, and M.D. Glantz Rabbit liver guanine deaminase. Chemical, physical, and kinetic properties The Journal of Biological Chemistry 249 12 1974 3862 3866
25. I. Lieberman, A. Kornberg, and E.S. Simms Enzymatic synthesis of pyrimidine nucleotides; orotidine-5′-phosphate and uridine-5′- phosphate The Journal of Biological Chemistry 215 1 1955 403 451
26. V. Massey, H. Komai, G. Palmer, and G.B. Elion On the mechanism of inactivation of xanthine oxidase by allopurinol and other pyrazolo[3,4-d] pyrimidines The Journal of Biological Chemistry 245 11 1970 2837 2844
27. D.J. Nelson, and G.B. Elion Metabolic studies of high doses of allopurinol in humans Advances in Experimental Medicine and Biology 165 Pt A 1984 167 170
28. Y. Nishida, N. Kamatani, K. Tanimoto, and I. Akaoka Inhibition of purine nucleoside phosphorylase activity and of T-cell function with allopurinol-riboside Agents and Actions 9 5-6 1979 549 552
29. K. Okamoto, B.T. Eger, T. Nishino, S. Kondo, and E.F. Pai An extremely potent inhibitor of xanthine oxidoreductase. Crystal structure of the enzyme-inhibitor complex and mechanism of inhibition The Journal of Biological Chemistry 278 3 2003 1848 1855
30. Y. Osada, M. Tsuchimoto, H. Fukushima, K. Takahashi, S. Kondo, M. Hasegawa, and K. Komoriya Hypouricemic effect of the novel xanthine oxidase inhibitor, TEI-6720, in rodents European Journal of Pharmacology 241 2-3 1993 183 188
31. W.J. O'Sullivan Metabolic side-effects of allopurinol Progress in Biochemical Pharmacology 9 1974 147 193
32. S. Reiter, W. Loffler, W. Grobner, and N. Zollner Urinary oxipurinol-1-riboside excretion and allopurinol-induced oroticaciduria Advances in Experimental Medicine and Biology 195 Pt A 1986 453 460
33. R.W. Rundles, J.B. Wyngaarden, G.H. Hitchings, G.B. Elion, and H.R. Silberman Effects of a xanthine oxidase inhibitor on thiopurine metabolism, hyperuricemia and gout Transactions of The Association of American Physicians 76 1963 126 140
34. C. Sauve, J.L. Pinquier, A. Boissonnad, D. Sicard, and B. Christoforov Systemic allopurinol toxicity European Journal of Internal Medicine 3 1992 78 81
35. H.R. Schumacher, R.L. Wortmann, D. Eustace, R. Khosravan, N. Joseph-Ridge, D. Mulford, and A. Shukla Phase II, dose response, safety and efficacy clinical trial of a new oral xanthine oxidase inhibitor TMX-67 (febuxostat) in subjects with gout American College of Rheumatology Annual Scientific Meeting, Atlanta, United States, October 24-29, 2002 2002
36. A. Shoji, H. Yamanaka, and N. Kamatani A retrospective study of the relationship between serum urate level and recurrent attacks of gouty arthritis: Evidence for reduction of recurrent gouty arthritis with antihyperuricemic therapy Arthritis and Rheumatism 51 3 2004 321 325
37. K. Shostak, R.I. Christopherson, and M.E. Jones Direct spectrophotometric assays for orotate phosphoribosyltransferase and orotidylate decarboxylase Analytical Biochemistry 191 2 1990 365 369
38. H.A. Simmonds, S. Reiter, P.M. Davies, and J.S. Cameron Orotidine accumulation in human erythrocytes during allopurinol therapy: association with high urinary oxypurinol-7-riboside concentrations in renal failure and in the Lesch-Nyhan syndrome Clinical Science (London, England: 1979) 80 3 1991 191 197
39. J.Z. Singer, and S.L. Wallace The allopurinol hypersensitivity syndrome. Unnecessary morbidity and mortality Arthritis and Rheumatism 29 1 1986 82 87
40. T. Spector, and D.G. Johns Stoichiometric inhibition of reduced xanthine oxidase by hydroxypyrazolo [3,4-d]pyrimidines The Journal of Biological Chemistry 245 19 1970 5079 5085
41. J.D. Stoeckler, and R.E. Parks Jr. Purine nucleoside phosphorylase: Measurement of activity and use of inhibitors D.M. Paton Methods in Pharmacology (Vol. 6: Methods used in adenosine research) 1985 Plemun Press New York 147 162
42. P.D. Utsinger, and W.J. Young Allopurinol hypersensitivity. Granular deposition of IgM at the dermal-epidermal junction The American Journal of Medicine 61 2 1976 287 294
43. T. Yamamoto, Y. Moriwaki, Y. Fujimura, S. Takahashi, Z. Tsutsumi, T. Tsutsui, K. Higashino, and T. Hada Effect of TEI-6720, a xanthine oxidase inhibitor, on the nucleoside transport in the lung cancer cell line A549 Pharmacology 60 1 2000 34 40
44. T. Yamamoto, Y. Moriwaki, S. Takahashi, Z. Tsutsumi, J. Yamakita, and K. Higashino Effect of allopurinol and benzbromarone on the concentration of uridine in plasma Metabolism: Clinical and Experimental 46 12 1997 1473 1476
45. R. Yoshimura Renal transport of allopurinol and oxypurinol in patients with impaired renal transport of uric acid Teikyo Medical Journal 17 1994 327 338