Identification
- Name
- Enoxaparin
- Accession Number
- DB01225 (APRD00068)
- Type
- Small Molecule
- Groups
- Approved
- Description
Enoxaparin is a low molecular weight heparin. Enoxaparin is used to prevent and treat deep vein thrombosis or pulmonary embolism, and is given as a subcutaneous injection. Enoxaparin binds to and accelerates the activity of antithrombin III. By activating antithrombin III, enoxaparin preferentially potentiates the inhibition of coagulation factors Xa and IIa. Factor Xa catalyzes the conversion of prothrombin to thrombin, so enoxaparin's inhibition of this process results in decreased thrombin and ultimately the prevention of fibrin clot formation. Low molecular weight heparins are less effective at inactivating factor IIa due to their shorter length compared to unfractionated heparin.
- Synonyms
- Not Available
- Product Ingredients
Ingredient UNII CAS InChI Key Enoxaparin sodium 8NZ41MIK1O 679809-58-6 Not applicable - Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Lovenox Injection 300 mg/3mL Intravenous; Subcutaneous sanofi-aventis U.S. LLC 1993-03-29 Not applicable US 
Lovenox Solution 80 mg Subcutaneous Sanofi Aventis 2012-09-11 Not applicable Canada 
Lovenox Injection 80 mg/0.8mL Intravenous; Subcutaneous Physicians Total Care, Inc. 2004-07-28 Not applicable US Lovenox Injection 80 mg/0.8mL Intravenous; Subcutaneous Cardinal Health 1993-03-29 2018-05-09 US Lovenox Injection 100 mg/1mL Intravenous; Subcutaneous Cardinal Health 1993-03-29 2018-03-31 US Lovenox Injection 300 mg/3mL Intravenous; Subcutaneous sanofi-aventis U.S. LLC 1993-03-29 Not applicable US Lovenox Injection 80 mg/0.8mL Subcutaneous sanofi-aventis U.S. LLC 1993-03-29 Not applicable US Lovenox Injection 40 mg/0.4mL Intravenous; Subcutaneous Physicians Total Care, Inc. 2005-10-06 Not applicable US Lovenox Injection 40 mg/0.4mL Intravenous; Subcutaneous Cardinal Health 1993-03-29 2018-05-09 US Lovenox Injection 60 mg/0.6mL Intravenous; Subcutaneous Cardinal Health 1993-03-29 2017-12-31 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Enoxaparin Sodium Injection 100 mg/1mL Subcutaneous Cardinal Health 2010-07-23 2018-06-30 US Enoxaparin Sodium Injection 100 mg/1mL Subcutaneous Amphastar Pharmaceuticals, Inc. 2011-09-19 Not applicable US Enoxaparin Sodium Injection 100 mg/1mL Subcutaneous Sandoz 2010-07-23 2013-07-31 US Enoxaparin Sodium Injection 150 mg/1mL Subcutaneous Amphastar Pharmaceuticals, Inc. 2011-09-19 Not applicable US Enoxaparin Sodium Injection 100 mg/1mL Subcutaneous Sandoz 2010-07-23 Not applicable US Enoxaparin Sodium Injection 150 mg/1mL Subcutaneous Amphastar Pharmaceuticals, Inc. 2011-09-19 Not applicable US Enoxaparin sodium Injection 150 mg/1mL Subcutaneous Fresenius Kabi 2015-02-20 Not applicable US Enoxaparin sodium Injection 100 mg/1mL Subcutaneous Winthrop U.S. 2011-10-03 Not applicable US Enoxaparin Sodium Injection 120 mg/0.8mL Subcutaneous Actavis Pharma Company 2012-02-13 2018-06-30 US Enoxaparin Sodium Injection, solution 60 mg/0.6mL Intravenous; Subcutaneous Teva Parenteral Medicines, Inc. 2014-11-17 Not applicable US - International/Other Brands
- Clexane
- Categories
- UNII
- E47C0NF7LV
- CAS number
- 9005-49-6
- Weight
- Not Available
- Chemical Formula
- Not Available
- InChI Key
- Not Available
- InChI
- Not Available
- IUPAC Name
- Not Available
- SMILES
- Not Available
Pharmacology
- Indication
For the prophylaxis of deep vein thrombosis, which may lead to pulmonary embolism, and also for the prophylaxis of ischemic complications of unstable angina and non-Q-wave myocardial infarction, when concurrently administered with aspirin.
- Associated Conditions
- Pharmacodynamics
Enoxaparin is a highly acidic mucopolysaccharide formed of equal parts of sulfated D-glucosamine and D-glucuronic acid with sulfaminic bridges. The molecular weight ranges from 3800 to 5000 daltons. Enoxaparin occurs in and is obtained from liver, lung, mast cells, etc., of vertebrates. Enoxaparin is a well known and commonly used anticoagulant which has antithrombotic properties. Enoxaparin inhibits reactions that lead to the clotting of blood and the formation of fibrin clots both in vitro and in vivo. Enoxaparin acts at multiple sites in the normal coagulation system. Small amounts of enoxaparin in combination with antithrombin III (enoxaparin cofactor) can inhibit thrombosis by inactivating activated Factor X and inhibiting the conversion of prothrombin to thrombin. Once active thrombosis has developed, larger amounts of enoxaparin can inhibit further coagulation by inactivating thrombin and preventing the conversion of fibrinogen to fibrin. Enoxaparin also prevents the formation of a stable fibrin clot by inhibiting the activation of the fibrin stabilizing factor. Its use should be avoided in patients with a creatinine clearance less than 20mL/min. In these patients, unfractionated heparin should only be used. As for monitoring, active partial thromboplastin time (aPTT) will only increase at high doses of low molecular weight heparins (LMWH). Therefore, monitoring aPTT is not recommended. However, anti-Xa activity can be measured to monitor the efficacy of the LMWH.
- Mechanism of action
The mechanism of action of enoxaparin is antithrombin-dependent. It acts mainly by accelerating the rate of the neutralization of certain activated coagulation factors by antithrombin, but other mechanisms may also be involved. The antithrombotic effect of enoxaparin is well correlated to the inhibition of factor Xa. Enoxaparin interacts with Antithrombin III, Prothrombin and Factor X. Enoxaparin binds to and accelerates the activity of antithrombin III. By activating antithrombin III, enoxaparin preferentially potentiates the inhibition of coagulation factors Xa and IIa.
Target Actions Organism AAntithrombin-III potentiatorHumans ACoagulation factor X inhibitorHumans - Absorption
Mean absolute bioavailability of enoxaparin, after 1.5 mg/kg given subcutaneously, based on anti-Factor Xa activity is approximately 100% in healthy volunteers.
- Volume of distribution
- 4.3 L
- Protein binding
80% bound-albumin
- Metabolism
Undergoes desulfation and polymerization via the liver
- Route of elimination
Enoxaparin sodium is primarily metabolized in the liver by desulfation and/or depolymerization to lower molecular weight species with much reduced biological potency. Renal clearance of active fragments represents about 10% of the administered dose and total renal excretion of active and non-active fragments 40% of the dose.
- Half life
4.5 hours
- Clearance
- Not Available
- Toxicity
Mouse, median lethal dose greater than 5000 mg/kg. Another side effect is heparin induced thrombocytopenia (HIT syndrome). HIT is caused by an immunological reaction that makes platelets form clots within the blood vessels, thereby using up coagulation factors.
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction (1,2,6,7-3H)Testosterone The therapeutic efficacy of Enoxaparin can be increased when used in combination with (1,2,6,7-3H)Testosterone. (R)-warfarin The risk or severity of bleeding can be increased when Enoxaparin is combined with (R)-warfarin. (S)-Warfarin The risk or severity of bleeding can be increased when Enoxaparin is combined with (S)-Warfarin. 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid The risk or severity of hyperkalemia can be increased when 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid is combined with Enoxaparin. 1-Testosterone The therapeutic efficacy of Enoxaparin can be increased when used in combination with 1-Testosterone. 18-methyl-19-nortestosterone The therapeutic efficacy of Enoxaparin can be increased when used in combination with 18-methyl-19-nortestosterone. 4-hydroxycoumarin The risk or severity of bleeding can be increased when Enoxaparin is combined with 4-hydroxycoumarin. 4-Hydroxytestosterone The therapeutic efficacy of Enoxaparin can be increased when used in combination with 4-Hydroxytestosterone. 5beta-dihydrotestosterone The therapeutic efficacy of Enoxaparin can be increased when used in combination with 5beta-dihydrotestosterone. Abciximab The risk or severity of bleeding can be increased when Abciximab is combined with Enoxaparin. - Food Interactions
- Avoid danshen, dong quai, evening primrose oil, gingko, policosanol, willow bark
References
- Synthesis Reference
Jorgen I. Nielsen, "Process of using light absorption to control enzymatic depolymerization of heparin to produce low molecular weight heparin." U.S. Patent US5106734, issued May, 1981.
US5106734- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB14551
- KEGG Drug
- D07510
- PubChem Substance
- 46507450
- ChemSpider
- 751
- ChEMBL
- CHEMBL1201685
- Therapeutic Targets Database
- DAP000616
- PharmGKB
- PA449463
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Enoxaparin_sodium
- ATC Codes
- B01AB05 — Enoxaparin
- AHFS Codes
- 20:12.04.16 — Heparins
- FDA label
- Download (1.44 MB)
Clinical Trials
- Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Cardinal Health
- Lake Erie Medical and Surgical Supply
- Neuman Distributors Inc.
- Physicians Total Care Inc.
- Sanofi-Aventis Inc.
- Dosage forms
Form Route Strength Injection Subcutaneous 100 mg/1mL Injection Subcutaneous 120 mg/0.8mL Injection Subcutaneous 150 mg/1mL Injection Subcutaneous 30 mg/0.3mL Injection Subcutaneous 300 mg/3mL Injection Subcutaneous 40 mg/0.4mL Injection Subcutaneous 60 mg/0.6mL Injection Subcutaneous 80 mg/0.8mL Injection, solution Intravenous; Subcutaneous 100 mg/1mL Injection, solution Intravenous; Subcutaneous 120 mg/0.8mL Injection, solution Intravenous; Subcutaneous 150 mg/1mL Injection, solution Intravenous; Subcutaneous 30 mg/0.3mL Injection, solution Intravenous; Subcutaneous 40 mg/0.4mL Injection, solution Intravenous; Subcutaneous 60 mg/0.6mL Injection, solution Intravenous; Subcutaneous 80 mg/0.8mL Injection Intravenous; Subcutaneous 100 mg/1mL Injection Intravenous; Subcutaneous 120 mg/0.8mL Injection Intravenous; Subcutaneous 30 mg/0.3mL Injection Intravenous; Subcutaneous 300 mg/3mL Injection Intravenous; Subcutaneous 40 mg/0.4mL Injection Intravenous; Subcutaneous 60 mg/0.6mL Injection Intravenous; Subcutaneous 80 mg/0.8mL Solution Subcutaneous 100 mg Solution Subcutaneous 30 mg Solution Subcutaneous 40 mg Solution Subcutaneous 60 mg Solution Subcutaneous 80 mg Solution Subcutaneous 120 mg Solution Subcutaneous 150 mg Solution Subcutaneous 90 mg Solution Intravenous; Subcutaneous 100 mg - Prices
Unit description Cost Unit Lovenox 300 mg/3ml Solution 3ml Vial 281.47USD vial Lovenox 150 mg/ml Solution 1ml Syringe 140.94USD syringe Lovenox 100 mg/ml Solution 1ml Syringe 93.93USD syringe Lovenox 80 mg/0.8ml Solution 0.8ml Syringe 75.14USD syringe Lovenox 60 mg/0.6ml Solution 0.6ml Syringe 56.36USD syringe Lovenox 40 mg/0.4ml Solution 0.4ml Syringe 37.53USD syringe Lovenox Hp (0.8Ml/1Ml Syringe) 150 mg/ml Syringe 34.63USD syringe Lovenox 30 mg/0.3ml Solution 0.3ml Syringe 28.15USD syringe Lovenox (0.4 - 1 Ml Syringe) 100 mg/ml Syringe 23.09USD syringe Lovenox 100 mg/ml 23.09USD syringe Lovenox (0.3 Ml Syringe) 30 mg/syr Syringe 6.97USD syringe DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) US5389618 No 1995-02-14 2012-02-14 US CA2045433 No 2002-07-30 2011-06-25 Canada
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility > 200 mg/mL Not Available logP -13.2 Not Available - Predicted Properties
- Not Available
- Predicted ADMET features
Property Value Probability Human Intestinal Absorption - 0.9215 Blood Brain Barrier - 0.8366 Caco-2 permeable - 0.6496 P-glycoprotein substrate Non-substrate 0.698 P-glycoprotein inhibitor I Non-inhibitor 0.5818 P-glycoprotein inhibitor II Non-inhibitor 0.9771 Renal organic cation transporter Non-inhibitor 0.9454 CYP450 2C9 substrate Non-substrate 0.6694 CYP450 2D6 substrate Non-substrate 0.8196 CYP450 3A4 substrate Non-substrate 0.5842 CYP450 1A2 substrate Non-inhibitor 0.8157 CYP450 2C9 inhibitor Non-inhibitor 0.771 CYP450 2D6 inhibitor Non-inhibitor 0.8869 CYP450 2C19 inhibitor Non-inhibitor 0.7655 CYP450 3A4 inhibitor Non-inhibitor 0.9194 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9232 Ames test Non AMES toxic 0.5957 Carcinogenicity Non-carcinogens 0.694 Biodegradation Not ready biodegradable 0.851 Rat acute toxicity 2.3846 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9589 hERG inhibition (predictor II) Non-inhibitor 0.7157
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
Taxonomy
- Classification
- Not classified
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Serine-type endopeptidase inhibitor activity
- Specific Function
- Most important serine protease inhibitor in plasma that regulates the blood coagulation cascade. AT-III inhibits thrombin, matriptase-3/TMPRSS7, as well as factors IXa, Xa and XIa. Its inhibitory a...
- Gene Name
- SERPINC1
- Uniprot ID
- P01008
- Uniprot Name
- Antithrombin-III
- Molecular Weight
- 52601.935 Da
References
- Peng K, Wang C, Pang BS, Yang YH: [Effects of thrombolysis and anticoagulation on the functions of vascular endothelial cells and coagulation and fibrinolysis in patients with pulmonary thromboembolism]. Zhonghua Jie He He Hu Xi Za Zhi. 2005 Sep;28(9):596-9. [PubMed:16207425]
- Lee S, Gibson CM: Enoxaparin in acute coronary syndromes. Expert Rev Cardiovasc Ther. 2007 May;5(3):387-99. [PubMed:17489664]
- Bisio A, Vecchietti D, Citterio L, Guerrini M, Raman R, Bertini S, Eisele G, Naggi A, Sasisekharan R, Torri G: Structural features of low-molecular-weight heparins affecting their affinity to antithrombin. Thromb Haemost. 2009 Nov;102(5):865-73. doi: 10.1160/TH09-02-0081. [PubMed:19888521]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Serine-type endopeptidase activity
- Specific Function
- Factor Xa is a vitamin K-dependent glycoprotein that converts prothrombin to thrombin in the presence of factor Va, calcium and phospholipid during blood clotting.
- Gene Name
- F10
- Uniprot ID
- P00742
- Uniprot Name
- Coagulation factor X
- Molecular Weight
- 54731.255 Da
References
- Graff J, Picard-Willems B, Harder S: Monitoring effects of direct FXa-inhibitors with a new one-step prothrombinase-induced clotting time (PiCT) assay: comparative in vitro investigation with heparin, enoxaparin, fondaparinux and DX 9065a. Int J Clin Pharmacol Ther. 2007 Apr;45(4):237-43. [PubMed:17474542]
- Berges A, Laporte S, Epinat M, Zufferey P, Alamartine E, Tranchand B, Decousus H, Mismetti P: Anti-factor Xa activity of enoxaparin administered at prophylactic dosage to patients over 75 years old. Br J Clin Pharmacol. 2007 Oct;64(4):428-38. Epub 2007 May 17. [PubMed:17509040]
- Sanchez-Pena P, Hulot JS, Urien S, Ankri A, Collet JP, Choussat R, Lechat P, Montalescot G: Anti-factor Xa kinetics after intravenous enoxaparin in patients undergoing percutaneous coronary intervention: a population model analysis. Br J Clin Pharmacol. 2005 Oct;60(4):364-73. [PubMed:16187968]
- Dalmora SL, Junior LB, Schmidt CA, Vaccari SF, Oliveira PR, Codevilla CF: Validation of the anti-factor Xa assay for the potency assessment of enoxaparin in pharmaceutical formulations. J AOAC Int. 2004 Nov-Dec;87(6):1305-8. [PubMed:15675440]
- Paige JT, Gouda BP, Gaitor-Stampley V, Scalia PG, Klainer TE, Raum WJ, Martin LF: No correlation between anti-factor Xa levels, low-molecular-weight heparin, and bleeding after gastric bypass. Surg Obes Relat Dis. 2007 Jul-Aug;3(4):469-75. Epub 2007 Jun 12. [PubMed:17567541]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Other
- General Function
- Peroxidase activity
- Specific Function
- Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production o...
- Gene Name
- MPO
- Uniprot ID
- P05164
- Uniprot Name
- Myeloperoxidase
- Molecular Weight
- 83867.71 Da
References
- Rudolph TK, Rudolph V, Witte A, Klinke A, Szoecs K, Lau D, Heitzer T, Meinertz T, Baldus S: Liberation of vessel adherent myeloperoxidase by enoxaparin improves endothelial function. Int J Cardiol. 2010 Apr 1;140(1):42-7. doi: 10.1016/j.ijcard.2008.10.035. Epub 2008 Dec 2. [PubMed:19049846]
Drug created on June 13, 2005 07:24 / Updated on January 22, 2019 17:56