U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
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

Curator's Comment: When peripherally administered, enoxaparin has the potential to penetrate the blood-brain barrier (BBB)

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
LOVENOX (PRESERVATIVE FREE)

Approved Use

Lovenox 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 Date

1993
Primary
LOVENOX (PRESERVATIVE FREE)

Approved Use

Enoxaparin sodium is a low molecular weight heparin [LMWH

Launch Date

1993
Preventing
LOVENOX (PRESERVATIVE FREE)

Approved Use

Lovenox 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 Date

1993
PubMed

PubMed

TitleDatePubMed
Low-molecular-weight heparin added to aspirin in the prevention of recurrent early-onset pre-eclampsia in women with inheritable thrombophilia: the FRUIT-RCT.
2012-01
Antithrombin III and enoxaparin treatment inhibit contusion-triggered cell death, inflammation, hemorrhage and apoptosis after severe traumatic brain injury in rats.
2011
Neuraxial hematoma and paralysis after enoxaparin administration 3 days after attempted spinal anesthesia for total knee arthroplasty.
2010-10
Warfarin-induced penile necrosis in a patient with heparin-induced thrombocytopenia.
2010-09
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.
2010-09
Heparin-induced thrombocytopenia and cerebral venous thrombosis after low-molecular weight heparin.
2010-08-27
[Rectus sheath haematoma--rare complication of anticoagulant therapy].
2010-07-11
Budd-Chiari syndrome and heparin-induced thrombocytopenia in polycythemia vera: successful treatment with repeated TIPS and interferon alpha.
2010-02-18
Heparin induced thrombocytopenia in a patient with factor V Leiden following cardiac surgery.
2009-12
The Janus face of thromboprophylaxis in patients with high risk for both thrombosis and bleeding during intracranial surgery: report of five exemplary cases.
2009-10
Heparin induced thrombocytopenia and re-thrombosis associated with warfarin and fondaparinux in a child.
2009-09
Enoxaparin induced intracerebral haemorrhage after deep brain stimulation surgery.
2009-07
Heparin induced thrombocytopenia and thrombosis in a tertiary care hospital.
2009-06
Anticoagulation and bleeding: a pooled analysis of lung cancer trials of the NCIC Clinical Trials Group.
2009-05
Acute sciatic nerve palsy as a delayed complication of low-molecular-weight heparin prophylaxis after total hip arthroplasty.
2009-02
Central venous sinus thrombosis in a young woman taking norethindrone acetate for dysfunctional uterine bleeding: case report and review of literature.
2008-08
Major rectus abdominis hematoma complicating low molecular weight heparin therapy.
2008-07
[Efficacy and safety of aspirin in prevention of venous thromboembolism after total joint arthroplasty].
2007-12-18
Oral dabigatran etexilate vs. subcutaneous enoxaparin for the prevention of venous thromboembolism after total knee replacement: the RE-MODEL randomized trial.
2007-11
Low-molecular-weight heparin for prevention of thrombosis: inverted role.
2007-11
Continuing or discontinuing low-dose aspirin before transrectal prostate biopsy: results of a prospective randomized trial.
2007-09
Enoxaparin-induced skin necrosis: a fatal outcome.
2007-08-02
Thalidomide and thrombosis. A meta-analysis.
2007-06
Fatal haemorrhage associated with enoxaparin.
2007-03
Massive pontine hemorrhagic transformation associated with an anticoagulant for basilar artery occlusion.
2006-12
How frequently is venous thromboembolism in heparin-treated patients associated with heparin-induced thrombocytopenia?
2006-09
Low-molecular-weight heparin and postoperative bleeding in rhytidectomy.
2006-08
[A case of heparin induced thrombocytopenia treated with lepirudin infusion: case report].
2006
Delayed onset of anterior tibial compartment syndrome in a patient receiving low-molecular-weight heparin. A case report.
1998-12
Enoxaparin increases the incidence of postoperative intracranial hemorrhage when initiated preoperatively for deep venous thrombosis prophylaxis in patients with brain tumors.
1998-11
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.
1998-04-27
Administration of dexamethasone induces proteinuria of glomerular origin in mice.
1998-03
Heparin oligosaccharides that pass the blood-brain barrier inhibit beta-amyloid precursor protein secretion and heparin binding to beta-amyloid peptide.
1998-02
[Cholesterol crystal embolism during treatment with low-molecular-weight heparin].
1997-09-13
Human urinary soluble thrombomodulin (MR-33) improves disseminated intravascular coagulation without affecting bleeding time in rats: comparison with low molecular weight heparin.
1997-04
Enoxaparin-associated dermal necrosis: a consequence of cross-reactivity with heparin-mediated antibodies.
1997-03
[Enoxaparin-induced cutaneous necrosis localized on insulin lipodystrophies].
1997
Heparin-induced thrombocytopenia with thrombotic complications during prophylactic treatment with low-molecular-weight heparin.
1996-11
Low molecular weight heparin-induced thrombocytopenia and thrombosis.
1996-05
Impairment of renal function after treatment of a burn patient with diclofenac, a non-steroidal antiinflammatory drug.
1995-09
A comparative study of three low-molecular weight heparins (LMWH) and unfractionated heparin (UH) in healthy volunteers.
1995-03
Heparin-associated thrombosis despite normal platelet counts.
1994-08-13
Regression of deep vein thrombosis by i.v.-administration of a low molecular weight heparin--results of a pilot study.
1994-03-01
Comparison of antithrombotic efficacy and haemorrhagic side-effects of Clivarin versus enoxaparin in patients undergoing total hip replacement surgery.
1993-12
Successful administration of low molecular weight heparin in a patient with heparin-induced thrombocytopenia and coumarin-induced skin necrosis.
1993-09-01
Heparin induced thrombosis: an important complication of heparin prophylaxis for thromboembolic disease in surgery.
1993-07-03
[Massive pulmonary embolism disclosing thrombocytopenia induced by low molecular weight heparin. Therapeutic success of prostacyclin].
1991-12
Ancrod anticoagulation for cardiopulmonary bypass in heparin-induced thrombocytopenia and thrombosis.
1989-11
Heparin-associated thrombocytopenia and thrombosis: a serious clinical problem and potential solution.
1986-11
[Disseminated intravascular coagulation induced by heparin. Treatment with a combination of low-molecular weight heparin and concentrated antithrombin III].
1984-05-26
Patents

Sample Use Guides

Abdominal Surgery: 40 mg by subcutaneous injection once a day; Hip or Knee Replacement Surgery: 30 mg every 12 hours administered by subcutaneous injection Deep Vein Thrombosis: 1 mg/kg every 12 hours administered subcutaneously
Route of Administration: Other
Substance Class Polymer
Created
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on Tue Apr 01 20:35:37 GMT 2025
Edited
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Record UNII
E47C0NF7LV
Record Status Validated (UNII)
Record Version
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Name Type Language
ENOXAPARIN
VANDF   WHO-DD  
Common Name English
ENOXAPARIN [VANDF]
Preferred Name English
Enoxaparin [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QB01AB05
Created by admin on Tue Apr 01 20:35:37 GMT 2025 , Edited by admin on Tue Apr 01 20:35:37 GMT 2025
NCI_THESAURUS C2578
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NDF-RT N0000007961
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WHO-ATC B01AB05
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LIVERTOX 351
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NDF-RT N0000175586
Created by admin on Tue Apr 01 20:35:37 GMT 2025 , Edited by admin on Tue Apr 01 20:35:37 GMT 2025
Code System Code Type Description
FDA UNII
E47C0NF7LV
Created by admin on Tue Apr 01 20:35:37 GMT 2025 , Edited by admin on Tue Apr 01 20:35:37 GMT 2025
PRIMARY
MESH
D017984
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PRIMARY
DAILYMED
E47C0NF7LV
Created by admin on Tue Apr 01 20:35:37 GMT 2025 , Edited by admin on Tue Apr 01 20:35:37 GMT 2025
PRIMARY
NCI_THESAURUS
C1452
Created by admin on Tue Apr 01 20:35:37 GMT 2025 , Edited by admin on Tue Apr 01 20:35:37 GMT 2025
PRIMARY
RXCUI
67108
Created by admin on Tue Apr 01 20:35:37 GMT 2025 , Edited by admin on Tue Apr 01 20:35:37 GMT 2025
PRIMARY RxNorm
SMS_ID
100000085598
Created by admin on Tue Apr 01 20:35:37 GMT 2025 , Edited by admin on Tue Apr 01 20:35:37 GMT 2025
PRIMARY
DRUG BANK
DB01225
Created by admin on Tue Apr 01 20:35:37 GMT 2025 , Edited by admin on Tue Apr 01 20:35:37 GMT 2025
PRIMARY
LACTMED
Enoxaparin
Created by admin on Tue Apr 01 20:35:37 GMT 2025 , Edited by admin on Tue Apr 01 20:35:37 GMT 2025
PRIMARY
IUPHAR
6811
Created by admin on Tue Apr 01 20:35:37 GMT 2025 , Edited by admin on Tue Apr 01 20:35:37 GMT 2025
PRIMARY
CHEBI
28304
Created by admin on Tue Apr 01 20:35:37 GMT 2025 , Edited by admin on Tue Apr 01 20:35:37 GMT 2025
PRIMARY
CAS
9005-49-6
Created by admin on Tue Apr 01 20:35:37 GMT 2025 , Edited by admin on Tue Apr 01 20:35:37 GMT 2025
GENERIC (FAMILY)
EVMPD
SUB21316
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PRIMARY
Display Structure of ENOXAPARIN
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY

Agent Modifications

Modification Process Modification Role Modification Type Amount Fragment Name Fragment ID
PRE-CLEAVAGE O-ACYLATION BENZOYL CHLORIDE VTY8706W36
BETA-ELIMINATION DEPOLYMERIZATION HYDROLYSIS Sodium Hydroxide 55X04QC32I
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
MOL_WEIGHT:WEIGHT AVERAGE(HP-SEC) CHEMICAL
DEGREE OF SULFATION PHYSICAL
ANTI-FACTOR XA/ANTI-FACTOR II RATIO ENZYMATIC
Biological Half-life PHARMACOKINETIC
MOL_WEIGHT:NUMBER AVERAGE(HP-SEC) CHEMICAL