SR 90107A/Org 31540, a novel anti-factor Xa antithrombotic agent

Cardiovascular Drug Reviews

Volumn 15, Issue 1, 1997, Pages 1-26

  Herbert, J M ^a   Petitou, M ^a   Lormeau, J C ^a   Cariou, R ^a   Necciari, J ^a   Magnani, H N ^b   Zandberg, P ^b   Van Amsterdam, R G M ^b   Van Boeckel, C A A ^b   Meuleman, D G ^b  

^a SANOFI   (France)

^b NV ORGANON   (Netherlands)

Author keywords

Factor Xa; Pentasaccharide; SR 90107A Org 31540; Thrombosis

Indexed keywords

ANTICOAGULANT AGENT; ANTITHROMBIN III; BLOOD CLOTTING FACTOR 10A; FONDAPARINUX; HEPARIN; PENTASACCHARIDE; PROTHROMBIN; THROMBOPLASTIN; UNCLASSIFIED DRUG;

ANTICOAGULATION; AREA UNDER THE CURVE; BABOON; BINDING SITE; BLEEDING; CLINICAL TRIAL; DOSE RESPONSE; DRUG BINDING; DRUG BIOAVAILABILITY; DRUG ELIMINATION; DRUG HALF LIFE; DRUG POTENCY; DRUG SAFETY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TOLERABILITY; HUMAN; INTRAVENOUS DRUG ADMINISTRATION; NONHUMAN; PARTIAL THROMBOPLASTIN TIME; PRIORITY JOURNAL; PROTHROMBIN TIME; RABBIT; REVIEW; SUBCUTANEOUS DRUG ADMINISTRATION; THROMBOCYTE FUNCTION; THROMBOSIS;

EID: 8544252429     PISSN: 08975957     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1527-3466.1997.tb00321.x     Document Type: Review

References (45)

1. Amar J, Caranobe C, Sie P, Boneu B. Antithrombotic potencies of heparins in relation to their antifactor Xa and antithrombin activities: An experimental study in two models of thrombosis in the rabbit. Br J Haematol 1990;76:94-100.
2. Andersson LO, Barrowcliffe TW, Holmer E, Johnson EA, Sims GEC. Anticoagulant properties of heparin fractionated by affinity chromatography on matrix-bound antithrombin III and by gel filtration. Thromb Res 1976;9:575-583.
3. Beguin S, Choay J, Hemker HC. The action of a synthetic pentasaccharide on thrombin generation in whole plasma. Thromb Haemost 1989;61:397-401.
4. Bendetowicz AV, Bara L, Samama MM. The inhibition of intrinsic prothrombinase and its generation by heparin and four derivatives in prothrombin poor plasma. Thromb Res 1990;58:445-454.
5. Bernat A, Hoffmann P, Sainte-Marie M, Herbert JM. The synthetic pentasaccharide SR 90107A/Org 31540 enhances tissue-type plasminogen activator-induced thrombolysis in rabbits. Fibrinolysis 1996;10:191-197.
6. Boneu B, Necciari J, Cariou R, et al. Pharmacokinetics and tolerance of the natural pentasaccharide (SR 90107A/Org 31540) with high affinity to antithrombin III in man. Thromb Haemost 1995;74:1468-1473.
7. Cadroy Y, Hanson SR, Harker LA. Antithrombotic effects of synthetic pentasaccharide with high affinity for plasma antithrombin III in non-human primates. Thromb Haemost 1993;70:631-635.
8. Carrie D, Caranobe C, Saivin S, et al. Pharmacokinetic and antithrombotic properties of two pentasaccharides with high affinity to antithrombin III in the rabbit: Comparison with CY 216. Blood 1994;84:2571-2577.
9. Casu B, Oreste P, Torri G, et al. The structure of heparin oligosaccharide fragments with anti-factor Xa activity containing the minimal antithrombin III-binding sequence. Biochem J 1981;197:599-609.
10. Choay J, Lormeau JC, Petitou M, Sinaÿ P, Fareed J. Structural studies on a biologically active hexasaccharide obtained from heparin, Ann NY Acad Sci 1981;370:644-649.
11. Choay J, Petitou M, Lormeau JC, Sinaÿ P, Casu B, Gatti G. Structure-activity relationship in heparin: A synthetic pentasaccharide with high affinity for antithrombin III and eliciting high anti-factor Xa activity. Biochem Biophys Res Commun 1983;116:492-499.
12. Crépon B, Donat F, Bârzu T, Herault JP. Pharmacokinetic (PK) parameters of AT-III binding pentasaccharides in three animal species: Predictive value for humans. Thromb Haemost 1993;69:654.
13. Elalamy I, Lecrubier C, Potevin F, et al. Absence of in vitro cross-reaction of pentasaccharide with the plasma heparin dependent factor of twenty-five patients with heparin associated thrombocytopenia. Thromb Haemost 1995;74:1384-1385.
14. Ellis V, Scully MF, Kakkar VV. The relative molecular mass dependence of the anti-factor Xa properties of heparin. Biochem J 1986;238:329-333.
15. Hemker HC, Choay J, Beguin S. Free factor Xa is on the main pathway of thrombin generation in clotting plasma. Biochem Biophys Acta 1989;992:409-411.
16. Hobbelen PMJ, Van Dinther TG, Vogel GMT, Van Boeckel CAA, Moelker HCT, Meuleman DG. Pharmacological profile of the chemically synthetized antithrombin III binding fragment of heparin (pentasaccharide) in rats. Thromb Haemost 1990;63:266-270.
17. Höök M, Björk I, Hopwood J, Lindahl U. Anticoagulant activity of heparin: Separation of high-activity and low-activity heparin species by affinity chromatography on immobilized antithrombin. FEBS Lett, 1976;66:90-93.
18. Lam LH, Silbert JE, Rosenberg RD. The separation of active and inactive forms of heparin. Biochem Biophys Res Commun 1976;69:570-577.
19. Lormeau JC, Herault JP. Comparative inhibition of extrinsic and intrinsic thrombin generation by standard heparin, a low molecular weight heparin and the synthetic AT-III-binding pentasaccharide. Thromb Haemost 1993;69:152-156.
20. Lormeau JC, Herault JP. The effect of the synthetic pentasaccharide SR 90107/ORG 31540 on thrombin generation ex vivo is uniquely due to AT-III-mediated neutralization of factor Xa. Thromb Haemost 1995;75:1474-1477.
21. Messmore HL, Griffin B, Fareed J, Coyne E, Seghatchian J. In vitro studies of the interaction of heparin, low molecular weight heparin and heparinoids with platelets. Ann NY Acad Sci 1989;556:217-231.
22. Mille B, Watton J, Barrowcliffe T, Mani JC, Lane D. Role of N- and C-terminal aminoacids in antithrombin binding to pentasaccharide. J Biol Chem 1994;269:29435-29443.
23. Ofosu FA, Choay J, Anvari N, Smith LM, Blajchman MA. Inhibition of factor X and factor V activation by dermatan sulfate and a pentasaccharide with high affinity for antithrombin III in human plasma. Eur J Biochem 1990;193:485-493.
24. Olson ST, Björk I, Sheffer R, Craig PA, Shore JD, Choay J. Role of the antithrombin-binding pentasaccharide in heparin acceleration of antithrombin-proteinase reactions. J Biol Chem 1992;267:12528-12538.
25. Olson ST, Björk I. Regulation of thrombin activity by antithrombin and heparin. Semin Thromb Hemostasis 1994;20:373-409.
26. Petitou M, Duchaussoy P, Lederman I, et al. Synthesis of heparin fragments: A α-methyl pentaoside with high affinity for antithrombin III. Carbohydr Res 1987;167:67-75.
27. Petitou M, van Boeckel CAA. Chemical synthesis of heparin fragments and analogues. Prog Chem Org Nat Prod 1992;60:143-210.
28. Pieters J, Willems G, Hemker C, Lindhout T. Inhibition of factor IXa and factor Xa by antithrombin III/heparin during factor X activation. J Biol Chem 1988;263:15313-15318.
29. Pieters J, Lindhout T, Willems G. Heparin-stimulated inhibition of factor IXa generation and factor IXa neutralization in plasma. Blood 1990;76:549-554.
30. Schoen P, Lindhout T, Willems G, Hemker C. Antithrombin III-dependent anti-prothrombinase activity of heparin and heparin fragments. J Biol Chem 1989;264:10002-10007.
31. Schoen P, Lindhout T. Flow and the inhibition of prothrombinase by antithrombin III and heparin. Blood 1991;78:118-124.
32. Thomas DP, Merton RE, Gray E, Barrowcliffe TW. The relative antithrombotic effectiveness of heparin, a low molecular weight heparin, and a pentasaccharide fragment in an animal model. Thromb Haemost 1989;204:204-207.
33. Thunberg L, Bäckström G, Lindahl U. Further characterization of the antithrombin-binding sequence in heparin. Carbohydr Res 1982;100:393-410.
34. Tollefsen DM. Insight into the mechanism of action of heparin cofactor II. Thromb Haemost 1995;74: 1209-1214.
35. Van Amsterdam RGM, Vogel GMT, Visser A, Kop WJ, Buiting MT, Meuleman DG. Synthetic analogues of the antithrombin III binding sequence of heparin. Prediction of in vivo residence times. Arterioscler Thromb Vasc Biol 1995;15:495-503.
36. Van Boeckel CAA, Beetz T, Vos JN, et al. Synthesis of a pentasaccharide corresponding to the antithrombin III binding fragment of heparin. J Carbohydr Chem 1985;4:293-321.
37. Van Boeckel CAA, Petitou M. The unique antithrombin III binding domain of heparin: A lead to new synthetic antithrombotics. Angew Chem im Ed Engl 1993;32:1671-1818.
38. Verstraete M. Pharmacotherapeutic aspects of unfractionated and low molecular weight heparins. Drugs 1990;40:498-530.
39. Visser A, Meuleman DG. Inhibition of the early stages of the thrombin generation reaction by various glycosaminoglycans. Thromb Res 1990;58:469-474.
40. Vogel GMT, van Amsterdam RGM, Kop WJ, Meuleman DG. Pentasaccharide and Orgaran® arrest, whereas heparin delays thrombus formation in a rat arteriovenous shunt. Thromb Haemostas 1993;69:29-34.
41. Vogel GMT, van Amsterdam RGM, Zandberg P, et al. Two new closely related rat models with relevance to arterial thrombosis: Efficacies of different antithrombotic drugs (submitted).
42. Walenga JM, Petitou M, Lormeau JC, Samama M, Fareed J. Choay J. Antithrombotic activity of a synthetic heparin pentasaccharide in a rabbit stasis thrombosis model using different thrombogenic challenges. Thromb Res 1987;46:187-198.
43. Walenga JM, Fareed J. Relative contribution of factor Xa and factor IIa inhibition in the mediation of the antithrombotic actions of LMWHs and synthetic heparin pentasaccharides. Thromb Haemorr Dis 1991;3:53-59.
44. Zandberg P, Princen AWM, Peters JLM, Meuleman DG. Effect of the synthetic pentasaccharide SR 90107A/Org 31540 and heparin on thrombolysis and on reocclusion after successful lysis of a thrombus in the femoral artery of a rabbit (submitted).
45. Zitoun D, Bara L, Bloch MF, Samama MM. Plasma TFPI activity after intravenous injection of pentasaccharide (PS) and unfractionated heparin in rabbits. Thromb Res 1994;75:577-580.