Enoxaparin

drugbox
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

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width = 300px
CAS_number = 9005-49-6
ChemSpiderID = 751
ATC_prefix = B01
ATC_suffix = AB05
ATC_supplemental =
PubChem = 772
DrugBank = APRD00068
chemical_formula = (C₂₆H₄₀N₂O₃₆S₅)n
molecular_weight = 4500 daltons (average)
bioavailability = 92%
protein_bound = 80% bound-albumin
metabolism = primarily by liver by desulfation and/or depolymerization
elimination_half-life = 4.5 hours
pregnancy_category = B
legal_UK = POM
legal_US = Rx-only
legal_status =
routes_of_administration = Subcutaneous (SC) Injection and intervenous (IV) per package insert

Enoxaparin is a low molecular weight heparin manufactured by Sanofi-Aventis. It is marketed as Lovenox or Clexane. Enoxaparin injections are derived from 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 (ACS).

Indications

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. There is limited evidence supporting the use of enoxaparin in orthoapedic patients [Warwick D, Williams MH, Bannister GC. Death and thromboembolic disease after total hip replacement. A series of 1162 cases with no routine chemical prophylaxis. J Bone Joint Surg Br. 1995 Jan;77(1):6-10. PMID 7822397] , although evidence is reasonable for colorectal patients [Bergqvist D. Venous thromboembolism: a review of risk and prevention in colorectal surgery patients. Dis Colon Rectum. 2006 Oct;49(10):1620-8. PMID 17019655]
* 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 extracorporeal circulation during haemodialysis. In the United States, enoxaparin is FDA approved for eight indications:
* Prophylaxis of DVT in medically ill patient,
* Total hip & knee replacement,
* Extended hip-replacement,
* Abdominal surgery.
* Treatment of DVT with or without PE inpatient and
* Treatment of DVT inpatient, with ACS, including STEMI.

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 does not affect the INR, PT or aPTT
* Anti-factor Xa levels can be measured, and are often used to monitor enoxaparin activity

Pregnancy

* Category B: enoxaprin is safe for use in the second trimester as it does not cross the placenta and safe while breast feeding

ide effects

* Bleeding [Warwick D, Bannister GC, Glew D, Mitchelmore A, Thornton M, Peters TJ, Brookes S. Perioperative low-molecular-weight heparin. Is it effective and safe. J Bone Joint Surg Br. 1995 Sep;77(5):715-9. PMID 7559695]
* Thrombocytopenia, i.e. can be associated with heparin-induced thrombocytopenia (0.5-5.0% of patients treated for at least five days [Levy JH, Tanaka KA, Hursting MJ. Reducing thrombotic complications in the perioperative setting: an update on heparin-induced thrombocytopenia. Anesth Analg. 2007 Sep;105(3):570-82. PMID 17717208]
* 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. Protamine sulfate will reverse enoxaparin by 66% per package insert.

Availability

100 mg/mL
* Prefilled Syringes: 30mg/0.3mL, 40mg/0.4mL
* Graduated Prefilled Syringes: 60mg/0.6mL, 80mg/0.8mL, 100mg/1mL, 120mg/0.8mL, 150mg/1mL

* Multiple Dose Vials: 300mg/3.0mL150mg/mL

References

External links

* [http://redpoll.pharmacy.ualberta.ca/drugbank/cgi-bin/getCard.cgi?CARD=APRD00068 DrugBank Information]
* [http://en.sanofi-aventis.com/group/products/p_group_products_cardio_lovenox.asp Sanofi-Aventis information]
* [http://products.sanofi-aventis.us/lovenox/lovenox.html Lovenox: Prescribing Information]