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Chemical Compound Review

AKOS005430103     2-hydroxy-3-(3-oxo-1-phenyl- butyl)chromen...

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Disease relevance of Coumadin

  • Randomized trials of warfarin for atrial fibrillation [1].
  • We assessed the efficacy of warfarin, low-dose aspirin, or both in the secondary prevention of thrombosis in patients with the syndrome [2].
  • Incidence of cancer after prophylaxis with warfarin against recurrent venous thromboembolism. Duration of Anticoagulation Trial [3].
  • Among the 1207 patients with interpretable venograms, 231 of 617 patients (37.4 percent) in the warfarin group and 185 of 590 patients (31.4 percent) in the low-molecular-weight-heparin group had deep-vein thrombosis (P = 0.03) [4].
  • The rates of major hemorrhage were low (2.22 per 100 patient-years in the warfarin group and 1.49 per 100 patient-years in the aspirin group) [5].
  • Further investigation, with more complete assessment of confounders and that addresses the effect of warfarin on mortality of prostate cancer, is warranted [6].
  • For many patients receiving long-term anticoagulation who need to undergo a minor outpatient intervention, a brief (< or =5 days) periprocedural interruption of warfarin therapy is associated with a low risk of thromboembolism [7].

Psychiatry related information on Coumadin


High impact information on Coumadin

  • BACKGROUND: The conventional treatment strategy for patients with atrial fibrillation who are to undergo electrical cardioversion is to prescribe warfarin for anticoagulation for three weeks before cardioversion [13].
  • Therefore, we investigated whether warfarin, which is effective and superior to aspirin in the prevention of cardiogenic embolism, would also prove superior in the prevention of recurrent ischemic stroke in patients with a prior noncardioembolic ischemic stroke [5].
  • CONCLUSIONS: As compared with aspirin alone and a combination of aspirin and warfarin, treatment with aspirin and ticlopidine resulted in a lower rate of stent thrombosis, although there were more hemorrhagic complications than with aspirin alone [14].
  • METHODS: Of 1965 patients who underwent coronary stenting at 50 centers, 1653 (84.1 percent) met angiographic criteria for successful placement of the stent and were randomly assigned to one of three regimens: aspirin alone (557 patients), aspirin and warfarin (550 patients), or aspirin and ticlopidine (546 patients) [14].
  • One patient with prenatally diagnosed homocystinuria who was also heterozygous for factor V Leiden has received warfarin therapy since birth and has not had thrombosis (age, 18 months) [15].

Chemical compound and disease context of Coumadin


Biological context of Coumadin

  • Patients with these genetic variants have been shown to require lower maintenance doses of warfarin, but a direct association between CYP2C9 genotype and anticoagulation status or bleeding risk has not been established [21].
  • These results suggest that warfarin may be useful in the treatment of SCCL and also support the hypothesis that the blood coagulation mechanism may be involved in the growth and spread of cancer in man [22].
  • After anticoagulant treatment lasting up to 5 days, cell growth was not inhibited by warfarin at low doses (10(-4) to 10(-5) M), but both cell growth and cellular adherence to culture plates were inhibited at high doses (10(-3) to 10(-2) M) [23].
  • The involvement of vitamin K metabolism and function in two well characterized birth defects, warfarin embryopathy and vitamin K epoxide reductase deficiency, suggests that developmental signals from K-dependent pathways may be required for normal embryogenesis [24].
  • Sulphinpyrazone and warfarin: a probable drug interaction [25].

Anatomical context of Coumadin


Associations of Coumadin with other chemical compounds


Gene context of Coumadin

  • The principal enzyme involved in warfarin metabolism is CYP2C9, and 2 relatively common variant forms with reduced activity have been identified, CYP2C9*2 and CYP2C9*3 [21].
  • In 147 patients followed from the start of anticoagulation with warfarin, we have investigated whether VKORC1 gene mutations have affected doses of drug prescribed to acquire the target anticoagulation intensity [34].
  • These results demonstrate that coumarins (a common type of phytochemical) or their derivatives can be potent inhibitors of aromatase and may be useful in suppressing aromataseand ER-positive breast tumors [35].
  • We then examined the role of Gas6 by treating STZ-rats with warfarin, and found that warfarin treatment inhibited the phosphorylation of these molecules as well as the hypertrophy [36].
  • Expression of the ARSE gene in COS cells resulted in a heat-labile arylsulfatase activity that was inhibited by warfarin [37].
  • Polymorphisms in the VKORC1 gene are associated with warfarin maintenance dose requirements among both African Americans and Caucasians [38].
  • Other polymorphisms in GGCX previously associated with warfarin dose were not confirmed in this study, suggesting that the effects of GGCX are potentially population/treatment-dependent and will not have broad utility for determining warfarin dosing [39].
  • The heterozygous CYP2C9 and VKORC1 genotypes influence warfarin dosing in an early phase as well as steady state of warfarin therapy in Korean patients with mechanical heart valve replacement [40].

Analytical, diagnostic and therapeutic context of Coumadin


  1. Randomized trials of warfarin for atrial fibrillation. Singer, D.E. N. Engl. J. Med. (1992) [Pubmed]
  2. The management of thrombosis in the antiphospholipid-antibody syndrome. Khamashta, M.A., Cuadrado, M.J., Mujic, F., Taub, N.A., Hunt, B.J., Hughes, G.R. N. Engl. J. Med. (1995) [Pubmed]
  3. Incidence of cancer after prophylaxis with warfarin against recurrent venous thromboembolism. Duration of Anticoagulation Trial. Schulman, S., Lindmarker, P. N. Engl. J. Med. (2000) [Pubmed]
  4. A comparison of subcutaneous low-molecular-weight heparin with warfarin sodium for prophylaxis against deep-vein thrombosis after hip or knee implantation. Hull, R., Raskob, G., Pineo, G., Rosenbloom, D., Evans, W., Mallory, T., Anquist, K., Smith, F., Hughes, G., Green, D. N. Engl. J. Med. (1993) [Pubmed]
  5. A comparison of warfarin and aspirin for the prevention of recurrent ischemic stroke. Mohr, J.P., Thompson, J.L., Lazar, R.M., Levin, B., Sacco, R.L., Furie, K.L., Kistler, J.P., Albers, G.W., Pettigrew, L.C., Adams, H.P., Jackson, C.M., Pullicino, P. N. Engl. J. Med. (2001) [Pubmed]
  6. Use of warfarin and risk of urogenital cancer: a population-based, nested case-control study. Tagalakis, V., Tamim, H., Blostein, M., Collet, J.P., Hanley, J.A., Kahn, S.R. Lancet Oncol. (2007) [Pubmed]
  7. Risk of thromboembolism with short-term interruption of warfarin therapy. Garcia, D.A., Regan, S., Henault, L.E., Upadhyay, A., Baker, J., Othman, M., Hylek, E.M. Arch. Intern. Med. (2008) [Pubmed]
  8. Warfarin in the prevention of stroke associated with nonrheumatic atrial fibrillation. Veterans Affairs Stroke Prevention in Nonrheumatic Atrial Fibrillation Investigators. Ezekowitz, M.D., Bridgers, S.L., James, K.E., Carliner, N.H., Colling, C.L., Gornick, C.C., Krause-Steinrauf, H., Kurtzke, J.F., Nazarian, S.M., Radford, M.J. N. Engl. J. Med. (1992) [Pubmed]
  9. Acetaminophen and other risk factors for excessive warfarin anticoagulation. Hylek, E.M., Heiman, H., Skates, S.J., Sheehan, M.A., Singer, D.E. JAMA (1998) [Pubmed]
  10. Decision analysis and guidelines for anticoagulant therapy to prevent stroke in patients with atrial fibrillation. Thomson, R., Parkin, D., Eccles, M., Sudlow, M., Robinson, A. Lancet (2000) [Pubmed]
  11. Long-term oral anticoagulant therapy in patients with unstable angina or suspected non-Q-wave myocardial infarction: organization to assess strategies for ischemic syndromes (OASIS) pilot study results. Anand, S.S., Yusuf, S., Pogue, J., Weitz, J.I., Flather, M. Circulation (1998) [Pubmed]
  12. Atrial fibrillation and stroke prevention with warfarin in the long-term care setting. Gurwitz, J.H., Monette, J., Rochon, P.A., Eckler, M.A., Avorn, J. Arch. Intern. Med. (1997) [Pubmed]
  13. Use of transesophageal echocardiography to guide cardioversion in patients with atrial fibrillation. Klein, A.L., Grimm, R.A., Murray, R.D., Apperson-Hansen, C., Asinger, R.W., Black, I.W., Davidoff, R., Erbel, R., Halperin, J.L., Orsinelli, D.A., Porter, T.R., Stoddard, M.F. N. Engl. J. Med. (2001) [Pubmed]
  14. A clinical trial comparing three antithrombotic-drug regimens after coronary-artery stenting. Stent Anticoagulation Restenosis Study Investigators. Leon, M.B., Baim, D.S., Popma, J.J., Gordon, P.C., Cutlip, D.E., Ho, K.K., Giambartolomei, A., Diver, D.J., Lasorda, D.M., Williams, D.O., Pocock, S.J., Kuntz, R.E. N. Engl. J. Med. (1998) [Pubmed]
  15. Coexistence of hereditary homocystinuria and factor V Leiden--effect on thrombosis. Mandel, H., Brenner, B., Berant, M., Rosenberg, N., Lanir, N., Jakobs, C., Fowler, B., Seligsohn, U. N. Engl. J. Med. (1996) [Pubmed]
  16. Heparin for 5 days as compared with 10 days in the initial treatment of proximal venous thrombosis. Hull, R.D., Raskob, G.E., Rosenbloom, D., Panju, A.A., Brill-Edwards, P., Ginsberg, J.S., Hirsh, J., Martin, G.J., Green, D. N. Engl. J. Med. (1990) [Pubmed]
  17. A cluster of sulfatase genes on Xp22.3: mutations in chondrodysplasia punctata (CDPX) and implications for warfarin embryopathy. Franco, B., Meroni, G., Parenti, G., Levilliers, J., Bernard, L., Gebbia, M., Cox, L., Maroteaux, P., Sheffield, L., Rappold, G.A. Cell (1995) [Pubmed]
  18. Influenza vaccination and warfarin or theophylline toxicity in nursing-home residents. Patriarca, P.A., Kendal, A.P., Stricof, R.L., Weber, J.A., Meissner, M.K., Dateno, B. N. Engl. J. Med. (1983) [Pubmed]
  19. Thrombus formation on atherosclerotic plaques: pathogenesis and clinical consequences. Rauch, U., Osende, J.I., Fuster, V., Badimon, J.J., Fayad, Z., Chesebro, J.H. Ann. Intern. Med. (2001) [Pubmed]
  20. Racemic warfarin and trimethoprim-sulfamethoxazole interaction in humans. O'Reilly, R.A., Motley, C.H. Ann. Intern. Med. (1979) [Pubmed]
  21. Association between CYP2C9 genetic variants and anticoagulation-related outcomes during warfarin therapy. Higashi, M.K., Veenstra, D.L., Kondo, L.M., Wittkowsky, A.K., Srinouanprachanh, S.L., Farin, F.M., Rettie, A.E. JAMA (2002) [Pubmed]
  22. Effect of warfarin on survival in small cell carcinoma of the lung. Veterans Administration Study No. 75. Zacharski, L.R., Henderson, W.G., Rickles, F.R., Forman, W.B., Cornell, C.J., Forcier, R.J., Edwards, R., Headley, E., Kim, S.H., O'Donnell, J.R., O'Dell, R., Tornyos, K., Kwaan, H.C. JAMA (1981) [Pubmed]
  23. Effects of sodium warfarin and sodium heparin plus anticancer agents on growth of rat C6 glioma cells. McNiel, N.O., Morgan, L.R. J. Natl. Cancer Inst. (1984) [Pubmed]
  24. A novel role for vitamin K1 in a tyrosine phosphorylation cascade during chick embryogenesis. Saxena, S.P., Fan, T., Li, M., Israels, E.D., Israels, L.G. J. Clin. Invest. (1997) [Pubmed]
  25. Sulphinpyrazone and warfarin: a probable drug interaction. Gallus, A., Birkett, D. Lancet (1980) [Pubmed]
  26. A comparison of aspirin with placebo in patients treated with warfarin after heart-valve replacement. Turpie, A.G., Gent, M., Laupacis, A., Latour, Y., Gunstensen, J., Basile, F., Klimek, M., Hirsh, J. N. Engl. J. Med. (1993) [Pubmed]
  27. Delayed hypersensitivity in man: effects of systemic anticoagulation. Edwards, R.L., Rickles, F.R. Science (1978) [Pubmed]
  28. Drug prophylaxis for arterial thromboembolism--1981. Wessler, S. JAMA (1981) [Pubmed]
  29. Two-step warfarin therapy. Prevention of postoperative venous thrombosis without excessive bleeding. Francis, C.W., Marder, V.J., Evarts, C.M., Yaukoolbodi, S. JAMA (1983) [Pubmed]
  30. Cardioversion from atrial fibrillation without prolonged anticoagulation with use of transesophageal echocardiography to exclude the presence of atrial thrombi. Manning, W.J., Silverman, D.I., Gordon, S.P., Krumholz, H.M., Douglas, P.S. N. Engl. J. Med. (1993) [Pubmed]
  31. Prolongation of prothrombin time and severe gastrointestinal bleeding associated with combined use of warfarin and ketoprofen. Flessner, M.F., Knight, H. JAMA (1988) [Pubmed]
  32. Vitamin K-dependent carboxylation and vitamin K metabolism in liver. Effects of warfarin. Wallin, R., Martin, L.F. J. Clin. Invest. (1985) [Pubmed]
  33. Novobiocin and related coumarins and depletion of heat shock protein 90-dependent signaling proteins. Marcu, M.G., Schulte, T.W., Neckers, L. J. Natl. Cancer Inst. (2000) [Pubmed]
  34. A polymorphism in the VKORC1 gene is associated with an interindividual variability in the dose-anticoagulant effect of warfarin. D'Andrea, G., D'Ambrosio, R.L., Di Perna, P., Chetta, M., Santacroce, R., Brancaccio, V., Grandone, E., Margaglione, M. Blood (2005) [Pubmed]
  35. Biochemical and biological characterization of a novel anti-aromatase coumarin derivative. Chen, S., Cho, M., Karlsberg, K., Zhou, D., Yuan, Y.C. J. Biol. Chem. (2004) [Pubmed]
  36. Gas6 induces Akt/mTOR-mediated mesangial hypertrophy in diabetic nephropathy. Nagai, K., Matsubara, T., Mima, A., Sumi, E., Kanamori, H., Iehara, N., Fukatsu, A., Yanagita, M., Nakano, T., Ishimoto, Y., Kita, T., Doi, T., Arai, H. Kidney Int. (2005) [Pubmed]
  37. Identification by shotgun sequencing, genomic organization, and functional analysis of a fourth arylsulfatase gene (ARSF) from the Xp22.3 region. Puca, A.A., Zollo, M., Repetto, M., Andolfi, G., Guffanti, A., Simon, G., Ballabio, A., Franco, B. Genomics (1997) [Pubmed]
  38. Warfarin response and vitamin K epoxide reductase complex 1 in African Americans and Caucasians. Schelleman, H., Chen, Z., Kealey, C., Whitehead, A.S., Christie, J., Price, M., Brensinger, C.M., Newcomb, C.W., Thorn, C.F., Samaha, F.F., Kimmel, S.E. Clin. Pharmacol. Ther. (2007) [Pubmed]
  39. Gamma-glutamyl carboxylase (GGCX) tagSNPs have limited utility for predicting warfarin maintenance dose. Rieder, M.J., Reiner, A.P., Rettie, A.E. J. Thromb. Haemost. (2007) [Pubmed]
  40. Effect of CYP2C9 and VKORC1 genotypes on early-phase and steady-state warfarin dosing in Korean patients with mechanical heart valve replacement. Kim, H.S., Lee, S.S., Oh, M., Jang, Y.J., Kim, E.Y., Han, I.Y., Cho, K.H., Shin, J.G. Pharmacogenet. Genomics (2009) [Pubmed]
  41. Drugs and surgery in the prevention of ischemic stroke. Barnett, H.J., Eliasziw, M., Meldrum, H.E. N. Engl. J. Med. (1995) [Pubmed]
  42. Predictors of rehospitalization for symptomatic venous thromboembolism after total hip arthroplasty. White, R.H., Gettner, S., Newman, J.M., Trauner, K.B., Romano, P.S. N. Engl. J. Med. (2000) [Pubmed]
  43. A comparison of three months of anticoagulation with extended anticoagulation for a first episode of idiopathic venous thromboembolism. Kearon, C., Gent, M., Hirsh, J., Weitz, J., Kovacs, M.J., Anderson, D.R., Turpie, A.G., Green, D., Ginsberg, J.S., Wells, P., MacKinnon, B., Julian, J.A. N. Engl. J. Med. (1999) [Pubmed]
  44. Low molecular weight heparin: a critical analysis of clinical trials. Green, D., Hirsh, J., Heit, J., Prins, M., Davidson, B., Lensing, A.W. Pharmacol. Rev. (1994) [Pubmed]
  45. Calcification inside artificial hearts: inhibition by warfarin-sodium. Pierce, W.S., Donachy, J.H., Rosenberg, G., Baier, R.E. Science (1980) [Pubmed]
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