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Enoxaparin
Systematic (IUPAC) name
6-[5-acetylamino-4,6-dihydroxy-2- (sulfooxymethyl)tetrahydropyran-3-yl] oxy-3- [5-(6-carboxy-4,5-dihydroxy-3- sulfooxy-tetrahydropyran-2-yl)oxy-6-(hydroxymethyl)- 3-sulfoamino-4-sulfooxy-tetrahydropyran-2-yl] oxy-4-hydroxy-5-sulfooxy-tetrahydropyran-2- carboxylicacid
Identifiers
CAS number	9005-49-6
ATC code	B01AB05
PubChem	772
DrugBank	APRD00068
Chemical data
Formula	(C26H40N2O36S5)n
Mol. mass	4500 daltons (average)
Pharmacokinetic data
Bioavailability	92%
Protein binding	80% bound-albumin
Metabolism	primarily by liver by desulfation and/or depolymerization
Half life	4.5 hours
Excretion	?
Therapeutic considerations
Pregnancy cat.	B
Legal status
Routes	Subcutaneous (SC) Injection and intervenous (IV) per package insert

Enoxaparin is a low molecular weight heparin manufactured by Sanofi-Aventis. It is marketed as Lovenox or Clexane. Enoxaparin injections are derived from the intestinal mucosa of pigs. Enoxaparin is used to prevent and treat deep vein thrombosis or pulmonary embolism, and is given as a subcutaneous injection (by a health care provider or the patient). Its use is evolving in acute coronary syndromes (ACS).

Contents 1 Indications 2 Mechanism of action 3 Monitoring 3.1 Pregnancy 3.2 Side effects 3.3 Reversal Agent 3.4 Availability 3.5 External links

In the UK, enoxaparin is approved for five indications:

• The prophylaxis of thromboembolism disorders of venous origin, in particular those which may be associated with orthopaedic surgery.
• The prophylaxis of venous thromboembolism (VTE) in medical patients bedridden due to acute illness.
• The treatment of venous thromboembolism disease (VTED) presenting with deep vein thrombosis (DVT), pulmonary embolism (PE) or both.
• The treatment of unstable angina (UA) and non-Q-wave myocardial infarction (NQMI), administered concurrently with aspirin.
• The prevention of thrombus formation in the extracorporeal circulation during haemodialysis.

In the United States, enoxaparin is FDA approved for eight indications:

• Prophylaxis of DVT in medically ill patient,
• Total hip & knee replacement,
• Extended hip-replacement,
• Abdominal surgery.
• Treatment of DVT with or with out PE inpatient and
• Treatment of DVT inpatient, with ACS, including STEMI.

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. The anticoagulant effect of enoxaparin can be directly correlated to its ability to inhibit factor Xa. 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.

• Enoxaparin does not affect the INR, PT or aPTT
• Anti-factor Xa levels can be measured, and are often used to monitor enoxaparin activity

• Category B: enoxaprin is safe for use in the second trimester as it does not cross the placenta

• Bleeding
• Thrombocytopenia, i.e. can be associated with heparin-induced thrombocytopenia
• Pain, bruising or irritation; hard, inflamed nodules or an itchy red rash at the injection site
• Symptoms similar to those of hayfever
• Abdominal/chest pain
• Headache

• Protamine, although not as effective at reversal as it is for heparin due to more activity at the Xa clotting factor (enoxaparin); as heparin has both Xa and IIa. Protamine sulfate will reverse enoxaparin by 66% per package insert.

100 mg/mL

• Prefilled Syringes: 30mg/0.3mL, 40mg/0.4mL
• Graduated Prefilled Syringes: 60mg/0.6mL, 80mg/0.8mL, 100mg/1mL
• Multiple Dose Vials: 300mg/3.0mL

150mg/mL

• Graduated Prefilled Syringes: 120mg/0.8mL, 150mg/1mL

• DrugBank Information
• Sanofi-Aventis information
• Lovenox: Prescribing Information

v • d • e Antithrombotics (thrombolytics, anticoagulants and antiplatelet drugs) (B01)
Vitamin K antagonists	Acenocoumarol • Clorindione • Coumatetralyl • Dicumarol (Dicoumarol) • Diphenadione • Ethyl biscoumacetate • Phenprocoumon • Phenindione • Tioclomarol • Warfarin
Heparin group	Antithrombin III • Danaparoid • Heparin • Sulodexide • low molecular weight heparin (Bemiparin, Dalteparin, Enoxaparin, Nadroparin, Parnaparin, Reviparin, Tinzaparin)
Glycoprotein IIb/IIIa inhibitors	Abciximab • Eptifibatide • Tirofiban
Other platelet aggregation inhibitors	Acetylsalicylic acid/Aspirin • Aloxiprin • Ditazole • Carbasalate calcium • Cloricromen • Dipyridamole • Indobufen • Picotamide • Triflusal • ADP receptor inhibitors (Clopidogrel, Ticlopidine, Prasugrel) • prostaglandin analogue (Beraprost, Prostacyclin, Iloprost, Treprostinil)
Enzymes	plasminogen activators (Alteplase/Reteplase/Tenecteplase, Streptokinase, Urokinase/Saruplase, Anistreplase) • other serine endopeptidases (Ancrod, Drotrecogin alfa/Protein C, Fibrinolysin) • Brinase
Direct thrombin inhibitors	Argatroban • Bivalirudin • Dabigatran • Desirudin • Hirudin • Lepirudin • Melagatran • Ximelagatran
Other antithrombotics	Defibrotide • Dermatan sulfate • Fondaparinux • Rivaroxaban
Non-medicinal	Citrate • EDTA • Oxalate