Enoxaparin sodium

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Enoxaparin sodium
EnoxaparinSodium.png
Enoxaparin sodium ball-and-stick.png
Clinical data
Trade namesLovenox, Clexane
AHFS/Drugs.commonograph
MedlinePlusa696006
Licence dataUS FDA:link
Pregnancy cat.B
Legal statusPOM (UK) -only (US)
RoutesSubcutaneous (SC) Injection and intravenous (IV) per package insert
Pharmacokinetic data
Bioavailability92%
Protein binding80% bound-albumin
Metabolismprimarily by kidneys
Half-life4.5 hours
Identifiers
CAS number9005-49-6 YesY
ATC codeB01AB05
PubChemCID 772
DrugBankDB01225
UNII8NZ41MIK1O N
KEGGD07510 YesY
ChEMBLCHEMBL1201685 N
Chemical data
Formula(C26H40N2O36S5)n
Mol. mass4500 daltons (average)
 N (what is this?)  (verify)
 
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Enoxaparin sodium
EnoxaparinSodium.png
Enoxaparin sodium ball-and-stick.png
Clinical data
Trade namesLovenox, Clexane
AHFS/Drugs.commonograph
MedlinePlusa696006
Licence dataUS FDA:link
Pregnancy cat.B
Legal statusPOM (UK) -only (US)
RoutesSubcutaneous (SC) Injection and intravenous (IV) per package insert
Pharmacokinetic data
Bioavailability92%
Protein binding80% bound-albumin
Metabolismprimarily by kidneys
Half-life4.5 hours
Identifiers
CAS number9005-49-6 YesY
ATC codeB01AB05
PubChemCID 772
DrugBankDB01225
UNII8NZ41MIK1O N
KEGGD07510 YesY
ChEMBLCHEMBL1201685 N
Chemical data
Formula(C26H40N2O36S5)n
Mol. mass4500 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[edit]

Mechanism of action[edit]

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[edit]

[citation needed]

Pregnancy[edit]

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[edit]

Reversal agent[edit]

Protamine is less effective at reversing enoxaparin compared to heparin, with a maximum neutralisation of approximately 60% of the anti-factor Xa effect.[4]

Availability[edit]

100 mg/mL concentration

150 mg/mL concentration

Cost and Market[edit]

Annual sales approx $3.17 billion.[citation needed]

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

Trademark[edit]

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

References[edit]

External links[edit]