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Chemical Compound Review

Clexane     6-[5-acetamido-4,6-dihydroxy- 2...

Synonyms: Normiflo, Lovenox, enoxaparin, LMWH, Lovenox HP, ...
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Disease relevance of heparin


Psychiatry related information on heparin


High impact information on heparin


Chemical compound and disease context of heparin


Biological context of heparin


Anatomical context of heparin

  • Serum samples from each of 27 patients who had this clinical diagnosis contained heparin-dependent platelet antibodies and deposited more than normal amounts of IgG, IgA, or IgM on endothelial cells, stimulating the production of tissue factor [16].
  • We have previously reported that inhaled heparin prevents allergic bronchoconstriction in sheep and inhibits the anti-IgE-mediated release of histamine from mast cells in vitro [18].
  • METHODS: Levels of C-reactive protein and fibrinogen at enrollment and the maximal level of troponin T during the first 24 hours after enrollment were analyzed in 917 patients included in a clinical trial of low-molecular-weight heparin in unstable coronary artery disease [23].
  • This non-anticoagulant action of heparin is more likely to be related to a modulation of mediator release than to a direct effect on smooth muscle [18].
  • Heparin bonding reduces thrombogenicity of pulmonary-artery catheters [24].

Associations of heparin with other chemical compounds

  • It is demonstrated that free heparin and heparan sulfate can reconstitute a low affinity receptor that is, in turn, required for the high affinity binding of bFGF [25].
  • To exclude the possibility that heparin had any direct effect on airway smooth muscle, bronchial provocation with histamine was induced in five subjects on two further days after pretreatment with either heparin or placebo [18].
  • On days 3 through 5 the subjects were pretreated with 4 ml of inhaled heparin (1000 U per kilogram), cromolyn sodium (20 mg), or placebo according to a single-blind, randomized, crossover design and underwent exercise challenge 45 minutes later [18].
  • Human tryptase, a mast-cell-specific serine proteinase that may be involved in causing asthma and other allergic and inflammatory disorders, is unique in two respects: it is enzymatically active only as a heparin-stabilized tetramer, and it is resistant to all known endogenous proteinase inhibitors [26].
  • A heparin binding mitogenic protein isolated from bovine uterus shares NH2-terminal amino acid sequence with a protein isolated from newborn rat brain [27].

Gene context of heparin

  • Here we report the crystal structure of the FGFR2 ectodomain in a dimeric form that is induced by simultaneous binding to FGF1 and a heparin decasaccharide [28].
  • MIP-1 beta was immobilized by binding to proteoglycan: a conjugate of heparin with bovine serum albumin and cellular proteoglycan CD44 were both effective [29].
  • VEGF is a heparin-binding growth factor specific for vascular endothelial cells that is able to induce angiogenesis in vivo [30].
  • We describe the crystal structure at 2.65 A resolution of diphtheria toxin (DT) complexed 1:1 with a fragment of its cell-surface receptor, the precursor of heparin-binding epidermal-growth-factor-like growth factor (HBEGF) [31].
  • This interaction with HGF is highly selective since the HSPGs did not bind the chemokine stromal cell-derived factor (SDF)-1 alpha, even though the affinities of HGF and SDF-1alpha for heparin are similar [32].

Analytical, diagnostic and therapeutic context of heparin


  1. Heparin-induced thrombocytopenia. Fung, K.C., Chandar, S., Brieger, D. N. Engl. J. Med. (2001) [Pubmed]
  2. Treatment of mobile left ventricular thrombus with low-molecular-weight heparin. Mallory, R., Balcezak, T. N. Engl. J. Med. (1999) [Pubmed]
  3. Treatment of venous thrombosis with subcutaneous heparin. Salzman, E.W. N. Engl. J. Med. (1982) [Pubmed]
  4. Fondaparinux compared with enoxaparin for the prevention of venous thromboembolism after hip-fracture surgery. Eriksson, B.I., Bauer, K.A., Lassen, M.R., Turpie, A.G. N. Engl. J. Med. (2001) [Pubmed]
  5. Reactivation of unstable angina after the discontinuation of heparin. Théroux, P., Waters, D., Lam, J., Juneau, M., McCans, J. N. Engl. J. Med. (1992) [Pubmed]
  6. Subcutaneous low-molecular-weight heparin compared with continuous intravenous heparin in the treatment of proximal-vein thrombosis. Hull, R.D., Raskob, G.E., Pineo, G.F., Green, D., Trowbridge, A.A., Elliott, C.G., Lerner, R.G., Hall, J., Sparling, T., Brettell, H.R. N. Engl. J. Med. (1992) [Pubmed]
  7. Occurrence of heparin in the invertebrate styela plicata (Tunicata) is restricted to cell layers facing the outside environment. An ancient role in defense? Cavalcante, M.C., Allodi, S., Valente, A.P., Straus, A.H., Takahashi, H.K., Mourão, P.A., Pavão, M.S. J. Biol. Chem. (2000) [Pubmed]
  8. Relation between procedural activated coagulation time and outcome after percutaneous transluminal coronary angioplasty. Ferguson, J.J., Dougherty, K.G., Gaos, C.M., Bush, H.S., Marsh, K.C., Leachman, D.R. J. Am. Coll. Cardiol. (1994) [Pubmed]
  9. Transient global amnesia associated with acute heparin-induced thrombocytopenia. Warkentin, T.E., Hirte, H.W., Anderson, D.R., Wilson, W.E., O'Connell, G.J., Lo, R.C. Am. J. Med. (1994) [Pubmed]
  10. Neurologic complications in immune-mediated heparin-induced thrombocytopenia. Pohl, C., Harbrecht, U., Greinacher, A., Theuerkauf, I., Biniek, R., Hanfland, P., Klockgether, T. Neurology (2000) [Pubmed]
  11. Properties of the novel proinflammatory supergene "intercrine" cytokine family. Oppenheim, J.J., Zachariae, C.O., Mukaida, N., Matsushima, K. Annu. Rev. Immunol. (1991) [Pubmed]
  12. The heparin-binding (fibroblast) growth factor family of proteins. Burgess, W.H., Maciag, T. Annu. Rev. Biochem. (1989) [Pubmed]
  13. Effects of a low-molecular-weight heparin on thrombus regression and recurrent thromboembolism in patients with deep-vein thrombosis. Breddin, H.K., Hach-Wunderle, V., Nakov, R., Kakkar, V.V. N. Engl. J. Med. (2001) [Pubmed]
  14. Low-molecular-weight heparin in patients with deep-vein thrombosis. Pechlaner, C., Gritsch, W. N. Engl. J. Med. (2001) [Pubmed]
  15. Crystal structure of a complement control protein that regulates both pathways of complement activation and binds heparan sulfate proteoglycans. Murthy, K.H., Smith, S.A., Ganesh, V.K., Judge, K.W., Mullin, N., Barlow, P.N., Ogata, C.M., Kotwal, G.J. Cell (2001) [Pubmed]
  16. Immune endothelial-cell injury in heparin-associated thrombocytopenia. Cines, D.B., Tomaski, A., Tannenbaum, S. N. Engl. J. Med. (1987) [Pubmed]
  17. Low-molecular-weight heparin vs. warfarin for prophylaxis against deep-vein thrombosis. Hirsh, J. N. Engl. J. Med. (1994) [Pubmed]
  18. Preventing bronchoconstriction in exercise-induced asthma with inhaled heparin. Ahmed, T., Garrigo, J., Danta, I. N. Engl. J. Med. (1993) [Pubmed]
  19. Letter: Aspirin, heparin and hemorrhage. Rubenstein, J.J. N. Engl. J. Med. (1976) [Pubmed]
  20. Angiogenesis inhibition and tumor regression caused by heparin or a heparin fragment in the presence of cortisone. Folkman, J., Langer, R., Linhardt, R.J., Haudenschild, C., Taylor, S. Science (1983) [Pubmed]
  21. Heparin-induced immune thrombocytopenia. Babcock, R.B., Dumper, C.W., Scharfman, W.B. N. Engl. J. Med. (1976) [Pubmed]
  22. Temporal aspects of heparin-induced thrombocytopenia. Warkentin, T.E., Kelton, J.G. N. Engl. J. Med. (2001) [Pubmed]
  23. Markers of myocardial damage and inflammation in relation to long-term mortality in unstable coronary artery disease. FRISC Study Group. Fragmin during Instability in Coronary Artery Disease. Lindahl, B., Toss, H., Siegbahn, A., Venge, P., Wallentin, L. N. Engl. J. Med. (2000) [Pubmed]
  24. Heparin bonding reduces thrombogenicity of pulmonary-artery catheters. Hoar, P.F., Wilson, R.M., Mangano, D.T., Avery, G.J., Szarnicki, R.J., Hill, J.D. N. Engl. J. Med. (1981) [Pubmed]
  25. Cell surface, heparin-like molecules are required for binding of basic fibroblast growth factor to its high affinity receptor. Yayon, A., Klagsbrun, M., Esko, J.D., Leder, P., Ornitz, D.M. Cell (1991) [Pubmed]
  26. Human beta-tryptase is a ring-like tetramer with active sites facing a central pore. Pereira, P.J., Bergner, A., Macedo-Ribeiro, S., Huber, R., Matschiner, G., Fritz, H., Sommerhoff, C.P., Bode, W. Nature (1998) [Pubmed]
  27. Cloning and expression of a developmentally regulated protein that induces mitogenic and neurite outgrowth activity. Li, Y.S., Milner, P.G., Chauhan, A.K., Watson, M.A., Hoffman, R.M., Kodner, C.M., Milbrandt, J., Deuel, T.F. Science (1990) [Pubmed]
  28. Crystal structure of fibroblast growth factor receptor ectodomain bound to ligand and heparin. Pellegrini, L., Burke, D.F., von Delft, F., Mulloy, B., Blundell, T.L. Nature (2000) [Pubmed]
  29. T-cell adhesion induced by proteoglycan-immobilized cytokine MIP-1 beta. Tanaka, Y., Adams, D.H., Hubscher, S., Hirano, H., Siebenlist, U., Shaw, S. Nature (1993) [Pubmed]
  30. Vascular endothelial growth factor is a secreted angiogenic mitogen. Leung, D.W., Cachianes, G., Kuang, W.J., Goeddel, D.V., Ferrara, N. Science (1989) [Pubmed]
  31. Crystal structure of the complex of diphtheria toxin with an extracellular fragment of its receptor. Louie, G.V., Yang, W., Bowman, M.E., Choe, S. Mol. Cell (1997) [Pubmed]
  32. Regulation of cytokine signaling by B cell antigen receptor and CD40-controlled expression of heparan sulfate proteoglycans. van der Voort, R., Keehnen, R.M., Beuling, E.A., Spaargaren, M., Pals, S.T. J. Exp. Med. (2000) [Pubmed]
  33. Heparin-induced thrombocytopenia and cardiopulmonary bypass. Nash, I. N. Engl. J. Med. (2000) [Pubmed]
  34. Effect of thrombolytic therapy on pulmonary-capillary blood volume in patients with pulmonary embolism. Sharma, G.V., Burleson, V.A., Sasahara, A.A. N. Engl. J. Med. (1980) [Pubmed]
  35. A comparison of low-molecular-weight heparin with unfractionated heparin for acute pulmonary embolism. The THESEE Study Group. Tinzaparine ou Heparine Standard: Evaluations dans l'Embolie Pulmonaire. Simonneau, G., Sors, H., Charbonnier, B., Page, Y., Laaban, J.P., Azarian, R., Laurent, M., Hirsch, J.L., Ferrari, E., Bosson, J.L., Mottier, D., Beau, B. N. Engl. J. Med. (1997) [Pubmed]
  36. Coronary angioplasty with or without stent implantation for acute myocardial infarction. Stent Primary Angioplasty in Myocardial Infarction Study Group. Grines, C.L., Cox, D.A., Stone, G.W., Garcia, E., Mattos, L.A., Giambartolomei, A., Brodie, B.R., Madonna, O., Eijgelshoven, M., Lansky, A.J., O'Neill, W.W., Morice, M.C. N. Engl. J. Med. (1999) [Pubmed]
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