Enoxaparin sodium

Enoxaparin sodium
Clinical data
Trade names Lovenox, Clexane, Oksapar, other
AHFS/Drugs.com Monograph
MedlinePlus a696006
License data
Pregnancy
category
  • B
Routes of
administration		 Subcutaneous (SC) Injection and intravenous (IV) per package insert
ATC code B01AB05 (WHO)
Legal status
Legal status
Pharmacokinetic data
Biological half-life 4.5 hours
Identifiers
CAS Number 9005-49-6 YesY
PubChem (CID) 772
IUPHAR/BPS 6811
DrugBank DB01225 N
ChemSpider none
UNII 8NZ41MIK1O N
KEGG D07510 YesY
ChEMBL CHEMBL1201685 N
ECHA InfoCard 100.029.698
Chemical and physical data
Formula (C26H40N2O36S5)n
Molar mass 4500 g/mol (average)
 NYesY (what is this?)  (verify)

Enoxaparin sodium is a low molecular weight heparin marketed under the trade names Lovenox, Xaparin and Clexane, among others.[1] It is an anticoagulant used to prevent deep vein thrombosis (DVT) or to treat acute deep vein thrombosis with or without pulmonary embolism (PE).[2] It is given as an injection just under the skin or intravenously.[2] Its use is evolving in acute coronary syndromes (ACS).[3]

Enoxaparin is available from its originator as well as generic companies.[4]

It is on the WHO Model List of Essential Medicines, the most important medications needed in a basic health system.[5]

Medical uses

Monitoring

Enoxaparin has predictable absorption, bioavailability, and distribution therefore monitoring is not typically done. However, there are instances where monitoring may be beneficial for special populations, for example individuals with kidney insufficiency or those that are obese. In this case, anti-Xa units can be measured and dosing adjusted accordingly.[2]

Reversal agent

Protamine sulfate is less effective at reversing enoxaparin compared to heparin, with a maximum neutralization of approximately 60% of the anti-factor Xa effect.[2]

Pregnancy

Side effects

Uncommon (<1%)

Common (>1%)

Frequency under investigation

Boxed warning

The FDA issued a revision to the boxed warning for enoxaparin in October 2013.[8] The revision recommends exercising caution regarding when spinal catheters are placed and removed in persons taking enoxaparin for spinal puncture or neuroaxial anesthesia.[9] It may be necessary to delay anticoagulant dosing in these persons in order to decrease the risk for spinal or epidural hematomas, which can manifest as permanent or long-term paralysis.[9] Persons at risk for hematomas may present with indwelling epidural catheters, concurrent use of medications that worsen bleeding states such as non-steroidal anti-inflammatory drugs (NSAIDs), or a past medical history of epidural or spinal punctures, spinal injury, or spinal deformations.[8] The FDA recommends that at-risk persons be monitored for bleeding and neurological changes.[8][10]

Pharmacology

Mechanism of action

Enoxaparin binds to antithrombin (a circulating anticoagulant) to form a complex that irreversibly inactivates clotting factor Xa.[11] It has less activity against factor IIa (thrombin) compared to unfractionated heparin (UFH) due to its low molecular weight.[12]

Pharmacokinetics

Absorption: Bioavailability (subcutaneous injection) ~ 100%[8]

Distribution: Volume of distribution (anti-Factor Xa activity) = 4.3 liters[8]

Metabolism: Enoxaparin is metabolized in the liver into low molecular weight species by either or both desulfation and depolymerization.[8]

Elimination: A single dose of a subcutaneous injection of enoxaparin has an elimination half-life of 4.5 hours.[8] Approximately 10%-40% of the active and inactive fragments from a single dose are excreted by the kidneys.[8] Dose adjustments based on kidney function are necessary in persons with reduced kidney function.[8]

Drug class

Enoxaparin belongs to the class of drugs known as low molecular weight heparins. Other drugs in this class include dalteparin, fondaparinux and tinzaparin.[13]

References

  1. ↑ Issa, Abdelfatah Abou; Simman, Richard (2015-03-18). "Lovenox Induced Tissue Necrosis, a Case Report and Literature Review". The Journal of the American College of Clinical Wound Specialists. 5 (3): 66–68. doi:10.1016/j.jccw.2015.03.001. ISSN 2213-5103. PMC 4495755Freely accessible. PMID 26199895.
  2. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 "Lovenox® (enoxaparin sodium injection) for subcutaneous and intravenous use Prescribing Information". products.sanofi.us. Retrieved 2015-11-03.
  3. ↑ Lee, Sinjin; Gibson, C. Michael (2007-05-01). "Enoxaparin in acute coronary syndromes". Expert Review of Cardiovascular Therapy. 5 (3): 387–399. doi:10.1586/14779072.5.3.387. ISSN 1744-8344. PMID 17489664.
  4. ↑ Mourier, Pierre A. J.; Agut, Christophe; Souaifi-Amara, Hajer; Herman, Fréderic; Viskov, Christian (2015-11-10). "Analytical and statistical comparability of generic enoxaparins from the US market with the originator product". Journal of Pharmaceutical and Biomedical Analysis. 115: 431–442. doi:10.1016/j.jpba.2015.07.038. ISSN 1873-264X. PMID 26280926.
  5. ↑ "19th WHO Model List of Essential Medicines (April 2015)" (PDF). WHO. April 2015. Retrieved May 10, 2015.
  6. ↑ Gershanik, Juan; Boecler, Betty; Ensley, Harry; McCloskey, Sharon; George, William (1982-11-25). "The Gasping Syndrome and Benzyl Alcohol Poisoning". New England Journal of Medicine. 307 (22): 1384–1388. doi:10.1056/NEJM198211253072206. ISSN 0028-4793. PMID 7133084.
  7. ↑ "Reducing Thrombotic Complications in the Perioperative Setti... : Anesthesia & Analgesia" (PDF). LWW. Retrieved 2015-11-05.
  8. 1 2 3 4 5 6 7 8 9 10 "DailyMed - ENOXAPARIN SODIUM- enoxaparin sodium injection". dailymed.nlm.nih.gov. Retrieved 2015-11-05.
  9. 1 2 Research, Center for Drug Evaluation and. "Drug Safety and Availability - FDA Drug Safety Communication: Updated recommendations to decrease risk of spinal column bleeding and paralysis in patients on low molecular weight heparins". www.fda.gov. Retrieved 2015-11-05.
  10. ↑ Commissioner, Office of the. "Safety Information - Lovenox (enoxaparin sodium) injection". www.fda.gov. Retrieved 2015-11-05.
  11. ↑ Alldredge, Brian; Corelli, Robin; Ernst, Michael; Guglielmo, B. Joseph; Jacobson, Pamela; Kradjan, Wayne; Williams, Bradley. Koda-Kimble and Young's Applied Therapeutics: The Clinical Use of Drugs (Tenth ed.). pp. 347–348. ISBN 1-60913-713-2.
  12. ↑ Trevor, Anthony J., Bertram G. Katzung, and Susan B. Masters. Basic & clinical pharmacology. McGraw-Hill Medical, 2012.
  13. ↑ "LowMolecularWeightHeparins". livertox.nih.gov. Retrieved 2015-11-05.
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