Drug/Small Molecule:

enoxaparin

Overview

Generic Names:	LMWH; Low Molecular Weight Heparin; enoxaparin
IUPAC Name:	6-[5-acetamido-4,6-dihydroxy-2-(sulfooxymethyl)oxan-3-yl]oxy-3-[5-(6-carboxy-4,5-dihydroxy-3-sulfooxyoxan-2-yl)oxy-6-(hydroxymethyl)-3-(sulfoamino)-4-sulfooxyoxan-2-yl]oxy-4-hydroxy-5-sulfooxyoxane-2-carboxylic acid
Trade Names:	Clexane; Lovenox; Lovenox HP
PharmGKB Accession Id:	PA449463

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.

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.

ATC Therapeutic Category

• B01AB:Heparin group

Pharmacology and Interactions

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.

Pharmacology

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 six to twenty thousand. 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.

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Hepatic.

Protein Binding

80% bound-albumin

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.

Half Life

4.5 hours

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.

Chemical Properties

Chemical Formula:

C₂₆H₄₂N₂O₃₇S₅

SMILES Code:

CC(=O)N[C@@H]1[C@H]([C@@H]([C@@H](O[C@H]1O)COS(=O)(=O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C(=O)O)O
[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O[C@@H]4[C@H]([C@@H]([C@H]([C@@H](O4)C(=O)O)O)O)OS(=O)(=O)O)OS
(=O)(=O)O)NS(=O)(=O)O)O)OS(=O)(=O)O)O

(Format: OpenEye Isomeric)

Molecular Weight ( average / monoisotopic )

1134.928 / 1134.007

Non-Curated Information

A list of non-curated publications that mention this drug along with other genes is available.

Drug Targets

• F2
• F10
• SERPINC1

Non-Curated Information

A list of non-curated publications that mention this drug along with other drugs is available.

Curated Information

The following diseases are in curated knowledge about this drug.

	Disease	Relationship	Evidence
	Hemorrhage	CO	Publications
	Pulmonary Embolism	CO	Publications
	venous thromboembolism	CO	Publications
	Venous Thrombosis	CO	Publications

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Non-Curated Publications

A list of non-curated publications that mention this drug is available.