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Chemical Compound Review

Agrastat     (2S)-2-(butylsulfonylamino)- 3-[4-[4-(4...

Synonyms: Aggrastat, tirofiban, tirofibanum, CHEMBL916, Agrastat (TN), ...
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Disease relevance of L-Tyrosine, N-(butylsulfonyl)-O-(4-(4-piperidinyl)butyl)-


Psychiatry related information on L-Tyrosine, N-(butylsulfonyl)-O-(4-(4-piperidinyl)butyl)-


High impact information on L-Tyrosine, N-(butylsulfonyl)-O-(4-(4-piperidinyl)butyl)-

  • The same effect was observed when normal platelets were pretreated with the commercially available anti-alpha IIb beta 3 drugs abciximab, eptifibatide, or tirofiban [7].
  • We studied 9 patients who developed severe thrombocytopenia (platelets less than 25 x 10(9)/L) within several hours of treatment with the GPIIb/IIIa inhibitors tirofiban (4 patients) and eptifibatide (5 patients) [8].
  • Only with high-dose tirofiban, mean periprocedural platelet aggregation inhibition exceeded 80% [9].
  • METHODS: Outcomes among 4,809 patients randomized to tirofiban or abciximab during PCI with stent placement were compared according to whether they received 300 mg of clopidogrel before PCI (93.1%) versus immediately after the procedure [10].
  • METHODS: Sixty patients undergoing coronary stenting were randomly assigned to abciximab (bolus 0.25 mg/kg body weight, infusion 10 microg per min for 12 h), tirofiban (bolus 10 microg/kg, infusion 0.15 microg/kg per min for 72 h) or eptifibatide (bolus 180 microg/kg, infusion 2 microg/kg per min for 72 h) [11].

Chemical compound and disease context of L-Tyrosine, N-(butylsulfonyl)-O-(4-(4-piperidinyl)butyl)-


Biological context of L-Tyrosine, N-(butylsulfonyl)-O-(4-(4-piperidinyl)butyl)-

  • FK419 and tirofiban similarly inhibited platelet aggregation in vitro (IC50 values: 0.43+/-0.076 and 0.41+/-0.053 micromol/L) and dispersed aggregated platelets (EC50 values: 2.3+/-0.88 and 2.0+/-0.81 micromol/L) [16].
  • Sedimentation equilibrium demonstrated that both echistatin ligands induced substantial alphaIIbbeta3 dimerization. van't Hoff analysis revealed a pattern of entropy/enthalpy compensation similar to tirofiban, a small RGD ligand-mimetic that binds tightly to alphaIIbbeta3, but yields smaller conformational perturbations than echistatin [17].
  • Tirofiban prolonged bleeding time both in period 1 and in period 2 [18].
  • Effect of fibrinogen concentration and platelet count on the inhibitory effect of abciximab and tirofiban [19].
  • This review updates what is known about the pharmacokinetics of tirofiban in humans, especially in comparison with the monoclonal antibody against the IIb/IIIa receptor, abciximab [20].

Anatomical context of L-Tyrosine, N-(butylsulfonyl)-O-(4-(4-piperidinyl)butyl)-


Associations of L-Tyrosine, N-(butylsulfonyl)-O-(4-(4-piperidinyl)butyl)- with other chemical compounds


Gene context of L-Tyrosine, N-(butylsulfonyl)-O-(4-(4-piperidinyl)butyl)-

  • Platelet function was assessed before, during, and after tirofiban infusion using a panel of agonists for ADP receptors, PAR1 and PAR4 thrombin receptors, and collagen receptors [28].
  • The aim of the present in-vitro-investigation was to elucidate the impact of ABO blood group dependent vWF concentrations on tirofiban mediated inhibition of GPIIb/IIIa function [29].
  • Eptifibatide and 7E3, but not tirofiban, inhibit alpha(v)beta(3) integrin-mediated binding of smooth muscle cells to thrombospondin and prothrombin [30].
  • Thus, the application of tirofiban together with hDAF improves the performance of pig hearts by reducing myocardial damage and intravascular thrombosis [31].
  • In vitro testing of the GPIIb/IIIa blocking by a nonpeptidic analogue tirofiban and abciximab revealed a good correlation between the CPA test and the routine aggregometry [32].

Analytical, diagnostic and therapeutic context of L-Tyrosine, N-(butylsulfonyl)-O-(4-(4-piperidinyl)butyl)-

  • CONCLUSIONS: Despite differences between women and men in baseline characteristics, the benefit of an early invasive strategy incorporating tirofiban and intracoronary stents was similar in women and men and was enhanced in women presenting with markers of increased risk [33].
  • The volume of the platelet thrombi, which was 3,352 +/- 1,045 microm(3) before starting the second perfusion, was reduced to 778 +/- 102 microm(3), 812 +/- 122 microm(3), and 856 +/- 144 microm(3) after 6-min perfusion of blood containing abciximab, eptifibatide, and tirofiban, respectively [34].
  • Patients with STEMI ineligible for reperfusion were randomized to enoxaparin, enoxaparin plus tirofiban, UFH, or UFH plus tirofiban [3].
  • BACKGROUND: The use of HDB tirofiban in the catheterization laboratory is controversial [35].
  • Flow cytometry revealed that the reduction in the monocyte-platelet interaction by abciximab, tirofiban and eptifibatide was not significantly different (20.0 +/- 21.9%, 23.8 +/- 18.2% and 21.0 +/- 19.8%, respectively; p = 0.87) [11].


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  2. Tirofiban in unstable coronary disease. Liron, M. N. Engl. J. Med. (1998) [Pubmed]
  3. The safety and efficacy of subcutaneous enoxaparin versus intravenous unfractionated heparin and tirofiban versus placebo in the treatment of acute ST-segment elevation myocardial infarction patients ineligible for reperfusion (TETAMI): a randomized trial. Cohen, M., Gensini, G.F., Maritz, F., Gurfinkel, E.P., Huber, K., Timerman, A., Krzeminska-Pakula, M., Danchin, N., White, H.D., Santopinto, J., Bigonzi, F., Hecquet, C., Vittori, L. J. Am. Coll. Cardiol. (2003) [Pubmed]
  4. Six-month angiographic and clinical follow-up of patients prospectively randomized to receive either tirofiban or placebo during angioplasty in the RESTORE trial. Randomized Efficacy Study of Tirofiban for Outcomes and Restenosis. Gibson, C.M., Goel, M., Cohen, D.J., Piana, R.N., Deckelbaum, L.I., Harris, K.E., King, S.B. J. Am. Coll. Cardiol. (1998) [Pubmed]
  5. Platelet glycoprotein IIb/IIIa receptor blockade in coronary artery disease. Lincoff, A.M., Califf, R.M., Topol, E.J. J. Am. Coll. Cardiol. (2000) [Pubmed]
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  7. Recombinant factor VIIa enhances deposition of platelets with congenital or acquired alpha IIb beta 3 deficiency to endothelial cell matrix and collagen under conditions of flow via tissue factor-independent thrombin generation. Lisman, T., Moschatsis, S., Adelmeijer, J., Nieuwenhuis, H.K., De Groot, P.G. Blood (2003) [Pubmed]
  8. Acute thrombocytopenia after treatment with tirofiban or eptifibatide is associated with antibodies specific for ligand-occupied GPIIb/IIIa. Bougie, D.W., Wilker, P.R., Wuitschick, E.D., Curtis, B.R., Malik, M., Levine, S., Lind, R.N., Pereira, J., Aster, R.H. Blood (2002) [Pubmed]
  9. Achieved platelet aggregation inhibition after different antiplatelet regimens during percutaneous coronary intervention for ST-segment elevation myocardial infarction. Ernst, N.M., Suryapranata, H., Miedema, K., Slingerland, R.J., Ottervanger, J.P., Hoorntje, J.C., Gosselink, A.T., Dambrink, J.H., de Boer, M.J., Zijlstra, F., van't Hof, A.W. J. Am. Coll. Cardiol. (2004) [Pubmed]
  10. Triple antiplatelet therapy during percutaneous coronary intervention is associated with improved outcomes including one-year survival: results from the Do Tirofiban and ReoProGive Similar Efficacy Outcome Trial (TARGET). Chan, A.W., Moliterno, D.J., Berger, P.B., Stone, G.W., DiBattiste, P.M., Yakubov, S.L., Sapp, S.K., Wolski, K., Bhatt, D.L., Topol, E.J. J. Am. Coll. Cardiol. (2003) [Pubmed]
  11. Antiplatelet effects of abciximab, tirofiban and eptifibatide in patients undergoing coronary stenting. Neumann, F.J., Hochholzer, W., Pogatsa-Murray, G., Schömig, A., Gawaz, M. J. Am. Coll. Cardiol. (2001) [Pubmed]
  12. An in-vitro model to study device-induced thrombosis and embolism: evaluation of the efficacy of tirofiban, aspirin, and dipyridamole. Sukavaneshvar, S., Solen, K.A., Mohammad, S.F. Thromb. Haemost. (2000) [Pubmed]
  13. Single high-dose bolus tirofiban with high-loading-dose clopidogrel in primary coronary angioplasty. Bilsel, T., Akbulut, T., Yesilcimen, K., Terzi, S., Sayar, N., Dayi, S.U., Akgoz, H., Ergelen, M., Ciloglu, F. Heart and vessels. (2006) [Pubmed]
  14. Timing of angiography and revascularization in acute coronary syndromes: an analysis of the TACTICS-TIMI-18 trial. McCullough, P.A., Gibson, C.M., Dibattiste, P.M., Demopoulos, L.A., Murphy, S.A., Weintraub, W.S., Neumann, F.J., Khanal, S., Cannon, C.P. Journal of interventional cardiology. (2004) [Pubmed]
  15. Images in Cardiovscular Medicine. Tirofiban for cocaine-induced coronary artery thrombosis: a novel therapeutic approach. Frangogiannis, N.G., Farmer, J.A., Lakkis, N.M. Circulation (1999) [Pubmed]
  16. FK419, a novel nonpeptide GPIIb/IIIa antagonist, restores microvascular patency and improves outcome in the guinea-pig middle cerebral artery thrombotic occlusion model: comparison with tirofiban. Moriguchi, A., Maeda, M., Mihara, K., Aoki, T., Matsuoka, N., Mutoh, S. J. Cereb. Blood Flow Metab. (2005) [Pubmed]
  17. The disintegrin echistatin stabilizes integrin alphaIIbbeta3's open conformation and promotes its oligomerization. Hantgan, R.R., Stahle, M.C., Connor, J.H., Lyles, D.S., Horita, D.A., Rocco, M., Nagaswami, C., Weisel, J.W., McLane, M.A. J. Mol. Biol. (2004) [Pubmed]
  18. Enhancement by ticlopidine of the inhibitory effect on in vitro platelet aggregation of the glycoprotein IIb/IIIa inhibitor tirofiban. Umemura, K., Kondo, K., Ikeda, Y., Nakashima, M. Thromb. Haemost. (1997) [Pubmed]
  19. Effect of fibrinogen concentration and platelet count on the inhibitory effect of abciximab and tirofiban. Renda, G., Rocca, B., Crocchiolo, R., Cristofaro, R.D., Landolfi, R. Thromb. Haemost. (2003) [Pubmed]
  20. Clinical pharmacokinetics of tirofiban, a nonpeptide glycoprotein IIb/IIIa receptor antagonist: comparison with the monoclonal antibody abciximab. Kondo, K., Umemura, K. Clinical pharmacokinetics. (2002) [Pubmed]
  21. Molecular mechanisms of platelet-mediated leukocyte recruitment during myocardial reperfusion. Kupatt, C., Wichels, R., Horstkotte, J., Krombach, F., Habazettl, H., Boekstegers, P. J. Leukoc. Biol. (2002) [Pubmed]
  22. Treatment of acute basilar artery thrombosis with a combination of systemic alteplase and tirofiban, a nonpeptide platelet glycoprotein IIb/IIIa inhibitor: report of four cases. Junghans, U., Seitz, R.J., Wittsack, H.J., Aulich, A., Siebler, M. Radiology. (2001) [Pubmed]
  23. Treatment of acute central retinal artery occlusionwith the platelet glycoprotein IIb/IIIa receptor inhibitor tirofiban. Hölschermann, H., Krombach, C., Jung, A., Jacobi, F., Tillmanns, H., Weinand, F. Thromb. Haemost. (2005) [Pubmed]
  24. Randomized, double-blind, placebo-controlled dose-ranging study of tirofiban (MK-383) platelet IIb/IIIa blockade in high risk patients undergoing coronary angioplasty. Kereiakes, D.J., Kleiman, N.S., Ambrose, J., Cohen, M., Rodriguez, S., Palabrica, T., Herrmann, H.C., Sutton, J.M., Weaver, W.D., McKee, D.B., Fitzpatrick, V., Sax, F.L. J. Am. Coll. Cardiol. (1996) [Pubmed]
  25. Ischemic brain tissue salvaged from infarction by the GP IIb/IIIa platelet antagonist tirofiban. Junghans, U., Seitz, R.J., Ritzl, A., Wittsack, H.J., Fink, G.R., Freund, H.J., Siebler, M. Neurology (2002) [Pubmed]
  26. An overview of the results of clinical trials with glycoprotein IIb/IIIa inhibitors. Adgey, A.A. Eur. Heart J. (1998) [Pubmed]
  27. Tirofiban provides "platelet anesthesia" during cardiopulmonary bypass in baboons. Hiramatsu, Y., Gikakis, N., Anderson, H.L., Gorman, J.H., Marcinkiewicz, C., Gould, R.J., Niewiarowski, S., Edmunds, L.H. J. Thorac. Cardiovasc. Surg. (1997) [Pubmed]
  28. Pharmacodynamics and pharmacokinetics of the platelet GPIIb/IIIa inhibitor tirofiban in patients undergoing percutaneous coronary intervention: implications for adjustment of tirofiban and clopidogrel dosage. Kimmelstiel, C., Badar, J., Covic, L., Waxman, S., Weintraub, A., Jacques, S., Kuliopulos, A. Thromb. Res. (2005) [Pubmed]
  29. Impact of ABO blood groups on tirofiban mediated inhibition of platelet function. Feuring, M., Harenberg, J., Peiter, A., Ganschow, A., Ruf, A., Losel, R., Wehling, M., Schultz, A. Platelets (2005) [Pubmed]
  30. Eptifibatide and 7E3, but not tirofiban, inhibit alpha(v)beta(3) integrin-mediated binding of smooth muscle cells to thrombospondin and prothrombin. Lele, M., Sajid, M., Wajih, N., Stouffer, G.A. Circulation (2001) [Pubmed]
  31. Combining the hDAF transgene with the GP IIb/IIIa inhibitor tirofiban improves heart performance and reduces myocardial damage following hyperacute rejection in an ex vivo perfusion model. Brandl, U., Erhardt, M., Joeckle, H., Michel, S., Brenner, P., Bittmann, I., Roessle, M., Mordstein, V., Hammer, C., Schmoeckel, M., Reichart, B. Transplant. Proc. (2005) [Pubmed]
  32. Cone and plate(let) analyzer: monitoring glycoprotein IIb/IIIa antagonists and von Willebrand disease replacement therapy by testing platelet deposition under flow conditions. Varon, D., Lashevski, I., Brenner, B., Beyar, R., Lanir, N., Tamarin, I., Savion, N. Am. Heart J. (1998) [Pubmed]
  33. Benefit of an early invasive management strategy in women with acute coronary syndromes. Glaser, R., Herrmann, H.C., Murphy, S.A., Demopoulos, L.A., DiBattiste, P.M., Cannon, C.P., Braunwald, E. JAMA (2002) [Pubmed]
  34. Ability of anti-glycoprotein IIb/IIIa agents to dissolve platelet thrombi formed on a collagen surface under blood flow conditions. Goto, S., Tamura, N., Ishida, H. J. Am. Coll. Cardiol. (2004) [Pubmed]
  35. The additive value of tirofiban administered with the high-dose bolus in the prevention of ischemic complications during high-risk coronary angioplasty: the ADVANCE Trial. Valgimigli, M., Percoco, G., Barbieri, D., Ferrari, F., Guardigli, G., Parrinello, G., Soukhomovskaia, O., Ferrari, R. J. Am. Coll. Cardiol. (2004) [Pubmed]
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