Enoxaparin sodium

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Enoxaparin sodium
Clinical data
Trade names Lovenox, Clexane
AHFS/Drugs.com monograph
MedlinePlus a696006
Licence data US FDA:link
Pregnancy cat. B
Legal status POM (UK) ℞-only (US)
Routes 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 number 9005-49-6 YesY
ATC code B01AB05
PubChem CID 772
DrugBank DB01225
UNII 8NZ41MIK1O N
KEGG D07510 YesY
ChEMBL CHEMBL1201685 N
Chemical data
Formula (C26H40N2O36S5)n
Mol. 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

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

[citation needed]

  • 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).

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

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.[3]

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 L.M.W.H agonists, like Fragmin (dalteparin sodium).

Cost and Market

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.[4]

Trademark

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

References

  1. ↑ Warwick, D; Bannister, GC; Glew, D; Mitchelmore, A; Thornton, M; Peters, TJ; Brookes, S (1995). "Perioperative low-molecular-weight heparin. Is it effective and safe". The Journal of bone and joint surgery. British volume 77 (5): 715–9. PMID 7559695. 
  2. ↑ Levy, JH; Tanaka, KA; Hursting, MJ (2007). "Reducing thrombotic complications in the perioperative setting: an update on heparin-induced thrombocytopenia". Anesthesia and Analgesia 105 (3): 570–82. doi:10.1213/01.ane.0000277497.70701.47. PMID 17717208. 
  3. ↑ http://products.sanofi.ca/en/lovenox.pdf
  4. ↑ Fed. Cir. 2008 No. 2007-1280 Aventis Pharma v. Amphastar and Teva

External links

Antiplatelet drugs
Thromboxane inhibitors
Other
Anticoagulants
Factor Xa inhibitors
(with some II inhibition)
Other
Thrombolytic drugs/
fibrinolytics
Non-medicinal

M: MYL

cell/phys (coag, heme, immu, gran), csfs

rbmg/mogr/tumr/hist, sysi/epon, btst

drug (B1/2/3+5+6), btst, trns

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