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Chemical Compound Review

AG-J-93028     (2R)-2-[4-(3-oxo-1H-isoindol- 2...

Synonyms: SureCN1649902, KST-1A7880, LS-48136, CTK5B9554, AR-1A2668, ...
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Disease relevance of K 3920


High impact information on K 3920

  • In vitro and ex vivo studies in healthy subjects demonstrated the capacity of indobufen to largely suppress monocyte PGHS-2 activity at therapeutic plasma concentrations [2].
  • The purpose of this randomized, double-blind study was to evaluate the efficacy of indobufen, a reversible inhibitor of platelet cyclooxygenase, in the prevention of embolic events of cardiac origin [1].
  • Adverse drug reactions, mostly gastrointestinal or hemostasis disorders, occurred in 9.2% of indobufen-treated patients [1].
  • METHODS: A total of 916 patients with NRAF and a recent (< or = 15 days) cerebral ischemic episode were admitted to this multicenter, randomized study, during which they were treated with either indobufen (100 or 200 mg BID) or warfarin (to obtain an international normalized ratio of 2.0 to 3.5) for 12 months [5].
  • RESULTS: Indobufen prevents TF expression and activity both in isolated and in whole blood monocytes [6].

Chemical compound and disease context of K 3920


Biological context of K 3920

  • Indobufen is an inhibitor of platelet aggregation which acts by reversibly inhibiting the platelet cyclo-oxygenase enzyme [4].
  • The d-enantiomer form of indobufen totally accounts for the anti-cyclooxygenase and antiplatelet activity ex vivo and for the increase in bleeding time by indobufen in man [12].
  • 74 patients were randomized to treatment with indobufen (200 mg b.i.d.) and 76 patients to acenocoumarol (controlled by thrombotest) [13].
  • Reduction of TxA2 synthesis, coupled with a lack of effect on PGE2 levels and prevention of ERK1/2 phosphorylation are highlighted as the mechanisms through which indobufen negatively affects TF [6].
  • The plasma pharmacokinetics and urinary elimination of the enantiomers of indobufen (2-[p-(1-oxo-2-isoindolinyl)-phenyl]butyric acid), a novel platelet aggregation inhibitor, have been studied in male healthy volunteers given either the racemic compound or the S-enantiomer (200 mg racemate, 100 mg S-enantiomer) [14].

Anatomical context of K 3920


Associations of K 3920 with other chemical compounds


Gene context of K 3920


Analytical, diagnostic and therapeutic context of K 3920

  • Indobufen is well tolerated following oral administration and has been associated with a low incidence of adverse effects rarely requiring withdrawal of treatment [4].
  • Enantiospecific analysis of indobufen in plasma and urine was achieved by HPLC of its L-leucinamide diastereoisomers [14].
  • The role of Indobufen in preventing the formation of microthrombi on hemodialysis membranes has been investigated in 18 patients in a placebo controlled randomized double-blind cross-over study [16].
  • In the secondary prevention of thromboembolic events indobufen 200 mg once or twice daily was significantly more effective than no treatment although not as effective as ticlopidine 250 mg once or twice daily, during 1-year nonblind clinical trials [26].
  • A rapid and selective liquid chromatography (LC) with solid phase extraction (SPE) to quantify indobufen (INDB) enantiomers is described [27].


  1. Indobufen in the prevention of thromboembolic complications in patients with heart disease. A randomized, placebo-controlled, double-blind study. Fornaro, G., Rossi, P., Mantica, P.G., Caccia, M.E., Aralda, D., Lavezzari, M., Pamparana, F., Milanesi, G. Circulation (1993) [Pubmed]
  2. Differential suppression of thromboxane biosynthesis by indobufen and aspirin in patients with unstable angina. Cipollone, F., Patrignani, P., Greco, A., Panara, M.R., Padovano, R., Cuccurullo, F., Patrono, C., Rebuzzi, A.G., Liuzzo, G., Quaranta, G., Maseri, A. Circulation (1997) [Pubmed]
  3. ADP plays a key role in thrombogenesis in rats. Maffrand, J.P., Bernat, A., Delebassée, D., Defreyn, G., Cazenave, J.P., Gordon, J.L. Thromb. Haemost. (1988) [Pubmed]
  4. Indobufen. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in cerebral, peripheral and coronary vascular disease. Wiseman, L.R., Fitton, A., Buckley, M.M. Drugs (1992) [Pubmed]
  5. Indobufen versus warfarin in the secondary prevention of major vascular events in nonrheumatic atrial fibrillation. SIFA (Studio Italiano Fibrillazione Atriale) Investigators. Morocutti, C., Amabile, G., Fattapposta, F., Nicolosi, A., Matteoli, S., Trappolini, M., Cataldo, G., Milanesi, G., Lavezzari, M., Pamparana, F., Coccheri, S. Stroke (1997) [Pubmed]
  6. Indobufen inhibits tissue factor in human monocytes through a thromboxane-mediated mechanism. Eligini, S., Violi, F., Banfi, C., Barbieri, S.S., Brambilla, M., Saliola, M., Tremoli, E., Colli, S. Cardiovasc. Res. (2006) [Pubmed]
  7. Pharmacoeconomic aspects of patients treated by hemodialysis. Gazdikova, K., Korecka, P., Springer, V., Gazdik, F. Bratislavské lekárske listy. (2003) [Pubmed]
  8. Systematic review of long term anticoagulation or antiplatelet treatment in patients with non-rheumatic atrial fibrillation. Taylor, F.C., Cohen, H., Ebrahim, S. BMJ (2001) [Pubmed]
  9. Inhibition of thromboxane biosynthesis and platelet function by indobufen in type II diabetes mellitus. Davì, G., Patrono, C., Catalano, I., Custro, N., Giammarresi, C., Ganci, A., Cosentino, F., Notarbartolo, A. Arterioscler. Thromb. (1993) [Pubmed]
  10. A comparative study between indobufen and acetylsalicylic acid on beta-thromboglobulin, platelet factor 4 and platelet aggregation in patients with transient ischemic attacks. Orefice, G., Carrieri, P., Indaco, A., Iorillo, L., Fioretti, A. Acta neurologica. (1984) [Pubmed]
  11. Effects of indobufen and pentoxifylline on walking capacity and hemostasis in patients with intermittent claudication: results of six months of treatment. Panchenko, E., Eshkeeva, A., Dobrovolsky, A., Titaeva, E., Podinovskaya, Y., Hussain, K.M., Karpov, Y. Angiology. (1997) [Pubmed]
  12. The d-enantiomer form of indobufen totally accounts for the anti-cyclooxygenase and antiplatelet activity ex vivo and for the increase in bleeding time by indobufen in man. De Caterina, R., Sicari, R., Yan, A., Bernini, W., Giannessi, D., Lazzerini, G., Efthymiopoulos, C., Strolin-Benedetti, M. Thromb. Haemost. (1992) [Pubmed]
  13. The incidence of deep venous thrombosis in patients with an acute myocardial infarction treated with acenocoumarol or indobufen. Peters, S.H., Jonker, J.J., de Boer, A.C., den Ottolander, G.J. Thromb. Haemost. (1982) [Pubmed]
  14. The dispositional enantioselectivity of indobufen in man. Strolm Benedetti, M., Frigerio, E., Tamassia, V., Noseda, G., Caldwell, J. Biochem. Pharmacol. (1992) [Pubmed]
  15. Effects of antiplatelet therapy with indobufen or aspirin-dipyridamole on graft patency one year after coronary artery bypass grafting. Rajah, S.M., Nair, U., Rees, M., Saunders, N., Walker, D., Williams, G., Critchley, A., Beton, D., Campbell, C., Lawson, R.A. J. Thorac. Cardiovasc. Surg. (1994) [Pubmed]
  16. Microthrombus formation on hemodialysis membranes: a placebo controlled randomized trail of two doses of Indobufen. Salter, M.C., Mayor, P., Crow, M.J., Rajah, S.M., Davison, A.M. Clin. Nephrol. (1985) [Pubmed]
  17. Reduction by indobufen of neutrophil activation in peripheral arterial occlusive disease. Chello, M., Mastroroberto, P., Celi, V., Romano, F., Marchese, A.R., Colonna, A. J. Cardiovasc. Pharmacol. (1996) [Pubmed]
  18. The (+)-enantiomer is responsible for the antiplatelet and anti-inflammatory activity of (+/-)-indobufen. Cerletti, C., Manarini, S., Colombo, M., Tavani, A. J. Pharm. Pharmacol. (1990) [Pubmed]
  19. In vitro and ex vivo effects of indobufen on red blood cell deformability. Grasselli, S., Guerciolini, R., Iadevaia, V., Parise, P., Gresele, P., Nenci, G.G. Eur. J. Clin. Pharmacol. (1987) [Pubmed]
  20. Antithrombotic drugs in the primary medical management of intermittent claudication: a meta-analysis. Girolami, B., Bernardi, E., Prins, M.H., ten Cate, J.W., Prandoni, P., Hettiarachchi, R., Marras, E., Stefani, P.M., Girolami, A., Büller, H.R. Thromb. Haemost. (1999) [Pubmed]
  21. Excretion balance and urinary metabolism of indobufen in rats and mice. Grubb, N., Caldwell, J., Strolin-Benedetti, M. Biochem. Pharmacol. (1993) [Pubmed]
  22. Effects of racemic, S- and R-indobufen on cyclooxygenase and lipoxygenase activities in human whole blood. Patrignani, P., Volpi, D., Ferrario, R., Romanzini, L., Di Somma, M., Patrono, C. Eur. J. Pharmacol. (1990) [Pubmed]
  23. Indobufen compared with aspirin and dipyridamole on graft patency after coronary artery bypass surgery: results of a combined analysis. Cataldo, G., Heiman, F., Lavezzari, M., Marubini, E. Coron. Artery Dis. (1998) [Pubmed]
  24. Beta-thromboglobulin and platelet factor 4 plasma levels during haemodialysis: effect of indobufen. Pogliani, E.M., Colombi, M., Cristoforetti, G., Valenti, G., Miradoli, R., Buccianti, G. Pharmatherapeutica. (1982) [Pubmed]
  25. Double-blind, controlled, multicenter study of indobufen versus placebo in patients with intermittent claudication. Tönnesen, K.H., Albuquerque, P., Baitsch, G., Gomez Alonso, A., Ibanez, F., Kester, R.C., Leveson, S., Poredos, P. International angiology : a journal of the International Union of Angiology. (1993) [Pubmed]
  26. Indobufen: an updated review of its use in the management of atherothrombosis. Bhana, N., McClellan, K.J. Drugs & aging. (2001) [Pubmed]
  27. LC procedure with SPE for quantification of indobufen enantiomers: pharmacokinetic studies. Główka, F.K. Journal of pharmaceutical and biomedical analysis. (2000) [Pubmed]
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