Enoxaparin is a low molecular weight heparin manufactured by Sanofi-Aventis. It is marketed as Lovenox or Clexane. Lovenox enoxaparin sodium injections are derived 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.

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.

In France enoxaparin is often used for the prophylaxis of thromboembolism disorders of venous origin when casts are used to immobilize bone fractures.

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.

Monitoring

Enoxaparin sodium
	File:Lovenox2.gif
Clinical data
Pregnancy; category	B;
Routes of; administration	Subcutaneous (SC) Injection
ATC code	B01AB05 (WHO) ;
Legal status
Legal status	US: WARNING;
Pharmacokinetic data
Bioavailability	92%
Protein binding	80% bound-albumin
Metabolism	primarily by liver by desulfation and/or depolymerization
Elimination half-life	4.5 hours
Identifiers
	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;
CAS Number	9005-49-6;
PubChem CID	772;
DrugBank	APRD00068;
CompTox Dashboard (EPA)	DTXSID0045969 ;
ECHA InfoCard	100.029.698
Chemical and physical data
Formula	(C26H40N2O36S5)n
Molar mass	4500 daltons (average)

INR, PT, CBC with platelets, aPTT (not as useful as in Heparin)

Pregnancy

Category B

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

Reversal Agent

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.

Availability

100mg/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

External links

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^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.

[FDA-AllBoxedWarnings-1] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.

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