Enoxaparin sodium

Enoxaparin sodium

Clinical data
Trade names	Lovenox, Clexane
AHFS/Drugs.com	monograph
MedlinePlus	a696006
Licence data	US FDA:link
Pregnancy category	B
Legal status	UK: Prescription-only (POM) US: ℞-only
Routes of administration	Subcutaneous (SC) Injection and intravenous (IV) per package insert
Pharmacokinetic data
Bioavailability	92%
Protein binding	80% bound-albumin
Metabolism	primarily by kidneys
Half-life	4.5 hours
Identifiers
CAS Registry Number	9005-49-6 Y
ATC code	B01AB05
PubChem	CID 772
DrugBank	DB01225 N
UNII	8NZ41MIK1O N
KEGG	D07510 Y
ChEMBL	CHEMBL1201685 N
Chemical data
Formula	(C26H40N2O36S5)n
Molecular mass	4500 daltons (average)
N (what is this?)  (verify)

Enoxaparin is a low molecular weight heparin marketed under the trade names Lovenox, Xaparin and Clexane, among others. It is an anticoagulant 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).

Enoxaparin is manufactured by Sanofi and is derived from the intestinal mucosa of pigs. Generic versions are available from Amphastar Pharmaceuticals and Sandoz.

Indications

• treatment of unstable angina (UA) and non-Q-wave myocardial infarction (NQMI), administered concurrently with aspirin
• prophylaxis of DVT
• total hip and knee replacement
• abdominal surgery
• treatment of DVT with or without PE
• treatment of DVT inpatient, with ACS, including STEMI
• antiphospholipid syndrome

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.

Alternatively: Enoxaparin binds to Factor Xa. It does not bind ATIII as the signal peptide is not long enough to bind to ATIII or thrombin.

Monitoring

• Anti-factor Xa levels can be measured, and are generally used to monitor enoxaparin activity in certain subgroups of patients. Anti-factor Xa levels may be recommended in underweight, obese, pregnant, or renally impaired patients. Anti-Xa levels should be checked at their peak at 4 hours after dosing (both q12 and q24 variations). Since the action on F10a/F2a generation is much more important than just anti-F10a concentration LMWH should be monitored by an ultra-specific and ultra-sensitive thrombin generation assay (INCA or EXCA). Because enoxaparin is dosed by weight, weight should also be monitored.^[1]

Pregnancy

Enoxaparin is a FDA pregnancy category B drug, and is not expected to harm an unborn baby. Enoxaparin does not cross the placenta. In animal models, there was no evidence of teratogenic effects or fetotoxicity due to enoxaparin. Pregnancy alone can raise a woman's risk of life-threatening thromboembolic event. Enoxaparin can be used during all stages of pregnancy; however, it should be closely monitored by a physician.

Side effects

• Bleeding^[2] Note that great care must be taken in use of low molecular weight heparin after major surgery, particularly neurosurgical procedures involving the brain and spine. The risk of inducing or potentiating post-operative bleeding must be balanced against the additional benefit of chemical thromboprophylaxis, over and above the benefits of mechanical means (stockings, boots) of preventing thromboembolism.
• Thrombocytopenia, i.e. can be associated with heparin-induced thrombocytopenia (0.5-5.0% of patients treated for at least five days^[3]
• Pain, bruising or irritation; hard, inflamed nodules or an itchy red rash at the injection site
• Symptoms similar to those of hay fever
• Abdominal/chest pain
• Headache
• Hyperkalemia^[4]
• Transaminitis

Reversal agent

Protamine is less effective at reversing enoxaparin compared to heparin, with a maximum neutralisation of approximately 60% of the anti-factor Xa effect.^[5]

Availability

100 mg/mL concentration

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

150 mg/mL concentration

• Graduated Prefilled Syringes: 120 mg/0.8mL, 150 mg/1mL
• There are many other L.M.W.H agonists, like Fragmin (dalteparin sodium).

Cost and market

Annual sales approximately $4.06 billion.

Enoxaparin is not protected by US patent due to inequitable conduct on the filing of Patent No. 5,389,618.^[6]

Trademark

Clexane®, Klexane®, Lovenox®, Xaparin, ENOXAPARIN u.a.

References

External links

• Official website
• DrugBank Information
• Lovenox: Prescribing Information
• "Enoxaparin Sodium". Daily Med.