Enoxaparin

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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	?
Half life	4.5 hours
Excretion	?
Therapeutic considerations
Pregnancy cat.	B
Legal status
Routes	Subcutaneous (SC) Injection

Enoxaparin is a low molecular weight heparin manufactured by Sanofi-Aventis. It is marketed as Lovenox or Clexane.

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.

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 extracorpreal circulation during haemodialysis.

[edit] Mechanism of Action

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.

[edit] Side effects

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

[edit] External links

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