Enoxaparin is a low molecular weight heparin used as anticoagulant medication to treat and prevent deep vein thrombosis (DVT) and pulmonary embolism (PE) including during pregnancy and following certain types of surgery. Enoxaparin is a depolymerized derivative of Unfractionated heparin produced by controlled depolymerization using alkaline hydrolysis of the heparin benzylic ester. Like Unfractionated heparin, its major anticoagulant effect is mediated by interaction with antithrombin III, which in turn inactivates serine proteases like factors IIa (thrombin), IXa and Xa. Therefore, enoxaparin indirectly inhibits the conversion of prothrombin to thrombin and reduces the thrombin-mediated conversion of fibrinogen to fibrin, thus preventing clot formation. Among parenteral anticoagulants, enoxaparin stands out for certain major advantages: rapid onset of action, higher bioavailability, once- or twice-daily dosing that can be administered by patients at home without any need for monitoring, and no reported association with catheter thrombosis. Enoxaparin has been shown to be a safe and effective drug in a wide variety of thromboembolic conditions, and two decades of available data have undoubtedly inspired significant confidence. Although these properties make it a preferred option in a wide range of clinical disorders, lack of reliable antidote and accumulation in renal dysfunction are major concerns associated with its use, which are shared, apart from Unfractionated heparin, by most other available anticoagulants.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28616032
Curator's Comment: When peripherally administered, enoxaparin has the potential to penetrate the blood-brain barrier (BBB)
Approval Year
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Preventing | LOVENOX (PRESERVATIVE FREE) Approved UseLovenox is a low molecular weight heparin (LMWH) indicated for:
• Prophylaxis of deep vein thrombosis (DVT) in abdominal surgery, hip replacement surgery, knee replacement surgery, or medical patients with severely restricted mobility during acute illness (1.1)
• Inpatient treatment of acute DVT with or without pulmonary embolism (1.2)
• Outpatient treatment of acute DVT without pulmonary embolism (1.2)
• Prophylaxis of ischemic complications of unstable angina and non–Q-wave myocardial infarction (MI) (1.3)
• Treatment of acute ST-segment elevation myocardial infarction (STEMI) managed medically or with subsequent percutaneous coronary intervention (PCI) (1.4) Launch Date1993 |
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Primary | LOVENOX (PRESERVATIVE FREE) Approved UseEnoxaparin sodium is a low molecular weight heparin [LMWH Launch Date1993 |
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Preventing | LOVENOX (PRESERVATIVE FREE) Approved UseLovenox is a low molecular weight heparin (LMWH) indicated for:
• Prophylaxis of deep vein thrombosis (DVT) in abdominal surgery, hip replacement surgery, knee replacement surgery, or medical patients with severely restricted mobility during acute illness (1.1)
• Inpatient treatment of acute DVT with or without pulmonary embolism (1.2)
• Outpatient treatment of acute DVT without pulmonary embolism (1.2)
• Prophylaxis of ischemic complications of unstable angina and non–Q-wave myocardial infarction (MI) (1.3)
• Treatment of acute ST-segment elevation myocardial infarction (STEMI) managed medically or with subsequent percutaneous coronary intervention (PCI) (1.4) Launch Date1993 |
PubMed
Title | Date | PubMed |
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[Disseminated intravascular coagulation induced by heparin. Treatment with a combination of low-molecular weight heparin and concentrated antithrombin III]. | 1984 May 26 |
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Heparin-associated thrombocytopenia and thrombosis: a serious clinical problem and potential solution. | 1986 Nov |
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Ancrod anticoagulation for cardiopulmonary bypass in heparin-induced thrombocytopenia and thrombosis. | 1989 Nov |
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Comparison of antithrombotic efficacy and haemorrhagic side-effects of Clivarin versus enoxaparin in patients undergoing total hip replacement surgery. | 1993 Dec |
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Heparin induced thrombosis: an important complication of heparin prophylaxis for thromboembolic disease in surgery. | 1993 Jul 3 |
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Successful administration of low molecular weight heparin in a patient with heparin-induced thrombocytopenia and coumarin-induced skin necrosis. | 1993 Sep-Oct |
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Heparin-associated thrombosis despite normal platelet counts. | 1994 Aug 13 |
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Regression of deep vein thrombosis by i.v.-administration of a low molecular weight heparin--results of a pilot study. | 1994 Mar 1 |
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A comparative study of three low-molecular weight heparins (LMWH) and unfractionated heparin (UH) in healthy volunteers. | 1995 Mar |
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Impairment of renal function after treatment of a burn patient with diclofenac, a non-steroidal antiinflammatory drug. | 1995 Sep |
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Low molecular weight heparin-induced thrombocytopenia and thrombosis. | 1996 May |
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Heparin-induced thrombocytopenia with thrombotic complications during prophylactic treatment with low-molecular-weight heparin. | 1996 Nov |
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[Enoxaparin-induced cutaneous necrosis localized on insulin lipodystrophies]. | 1997 |
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Human urinary soluble thrombomodulin (MR-33) improves disseminated intravascular coagulation without affecting bleeding time in rats: comparison with low molecular weight heparin. | 1997 Apr |
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Enoxaparin-associated dermal necrosis: a consequence of cross-reactivity with heparin-mediated antibodies. | 1997 Mar |
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[Cholesterol crystal embolism during treatment with low-molecular-weight heparin]. | 1997 Sep 13 |
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The incidence of symptomatic venous thromboembolism during and after prophylaxis with enoxaparin: a multi-institutional cohort study of patients who underwent hip or knee arthroplasty. Canadian Collaborative Group. | 1998 Apr 27 |
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Delayed onset of anterior tibial compartment syndrome in a patient receiving low-molecular-weight heparin. A case report. | 1998 Dec |
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Heparin oligosaccharides that pass the blood-brain barrier inhibit beta-amyloid precursor protein secretion and heparin binding to beta-amyloid peptide. | 1998 Feb |
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Administration of dexamethasone induces proteinuria of glomerular origin in mice. | 1998 Mar |
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Enoxaparin increases the incidence of postoperative intracranial hemorrhage when initiated preoperatively for deep venous thrombosis prophylaxis in patients with brain tumors. | 1998 Nov |
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Compartment syndrome in an ELBW infant receiving low-molecular-weight heparins. | 2004 Apr |
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A case of two adverse reactions. | 2004 Aug |
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Hemorrhagic transformation of ischemic stroke associated with enoxaparin and aspirin concomitant therapy. | 2004 Jan |
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Acute myocardial infarction in a young woman with antiphospholipid syndrome and occasional cocaine abuse. | 2005 Nov 2 |
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Low-molecular-weight heparin and postoperative bleeding in rhytidectomy. | 2006 Aug |
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Thrombocytopenia and intra-cerebral complications associated with low-molecular-weight heparin treatment in patients undergoing total hip replacement. A report of two cases. | 2006 Mar |
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[Efficacy and safety of aspirin in prevention of venous thromboembolism after total joint arthroplasty]. | 2007 Dec 18 |
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Enoxaparin-induced skin necrosis: a fatal outcome. | 2007 Jul-Aug |
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Thalidomide and thrombosis. A meta-analysis. | 2007 Jun |
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Oral dabigatran etexilate vs. subcutaneous enoxaparin for the prevention of venous thromboembolism after total knee replacement: the RE-MODEL randomized trial. | 2007 Nov |
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Low-molecular-weight heparin for prevention of thrombosis: inverted role. | 2007 Nov |
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Continuing or discontinuing low-dose aspirin before transrectal prostate biopsy: results of a prospective randomized trial. | 2007 Sep |
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Central venous sinus thrombosis in a young woman taking norethindrone acetate for dysfunctional uterine bleeding: case report and review of literature. | 2008 Aug |
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Major rectus abdominis hematoma complicating low molecular weight heparin therapy. | 2008 Jul |
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Heparin induced thrombocytopenia in a patient with factor V Leiden following cardiac surgery. | 2009 Dec |
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Acute sciatic nerve palsy as a delayed complication of low-molecular-weight heparin prophylaxis after total hip arthroplasty. | 2009 Feb |
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Enoxaparin induced intracerebral haemorrhage after deep brain stimulation surgery. | 2009 Jul |
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Heparin induced thrombocytopenia and thrombosis in a tertiary care hospital. | 2009 Jun |
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Anticoagulation and bleeding: a pooled analysis of lung cancer trials of the NCIC Clinical Trials Group. | 2009 May |
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The Janus face of thromboprophylaxis in patients with high risk for both thrombosis and bleeding during intracranial surgery: report of five exemplary cases. | 2009 Oct |
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Budd-Chiari syndrome and heparin-induced thrombocytopenia in polycythemia vera: successful treatment with repeated TIPS and interferon alpha. | 2009 Oct-Dec |
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Heparin induced thrombocytopenia and re-thrombosis associated with warfarin and fondaparinux in a child. | 2009 Sep |
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[Rectus sheath haematoma--rare complication of anticoagulant therapy]. | 2010 Jul 11 |
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Heparin-induced thrombocytopenia and cerebral venous thrombosis after low-molecular weight heparin. | 2010 Jul-Aug |
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Neuraxial hematoma and paralysis after enoxaparin administration 3 days after attempted spinal anesthesia for total knee arthroplasty. | 2010 Oct |
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Warfarin-induced penile necrosis in a patient with heparin-induced thrombocytopenia. | 2010 Sep |
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One-year outcomes after a strategy using enoxaparin vs. unfractionated heparin in patients undergoing fibrinolysis for ST-segment elevation myocardial infarction: 1-year results of the ExTRACT-TIMI 25 trial. | 2010 Sep |
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Antithrombin III and enoxaparin treatment inhibit contusion-triggered cell death, inflammation, hemorrhage and apoptosis after severe traumatic brain injury in rats. | 2011 |
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Low-molecular-weight heparin added to aspirin in the prevention of recurrent early-onset pre-eclampsia in women with inheritable thrombophilia: the FRUIT-RCT. | 2012 Jan |
Patents
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Polymer
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C2578
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ACTIVE MOIETY |
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Agent Modifications
Modification Process | Modification Role | Modification Type | Amount | Fragment Name | Fragment ID |
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BETA-ELIMINATION | CLEAVAGE | HYDROLYSIS |
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Sodium hydroxide | 55X04QC32I |
PRE-CLEAVAGE | O-ACYLATION |
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BENZOYL CHLORIDE | VTY8706W36 |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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ANTI-FACTOR XA/ANTI-FACTOR II RATIO | ENZYMATIC |
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DEGREE OF SULFATION | PHYSICAL |
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MOL_WEIGHT:NUMBER AVERAGE(HP-SEC) | CHEMICAL |
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MOL_WEIGHT:WEIGHT AVERAGE(HP-SEC) | CHEMICAL |
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