Enoxaparin sodium explained

Verifiedfields:changed
Watchedfields:changed
Verifiedrevid:407062079
Width:300
Tradename:Lovenox, Clexane, Xaparin, others
Dailymedid:Enoxaparin
Pregnancy Au:C
Pregnancy Au Comment:[1]
Routes Of Administration:Subcutaneous, intravenous
Atc Prefix:B01
Atc Suffix:AB05
Biosimilars:Arovi, Axberi,[2] Axberi HP, Exarane, Exarane Forte, Enoxapo, Inclunox, Inclunox HP, Inhixa, Noromby, Noromby HP, Redesca, Redesca HP, Thorinane
Legal Au:S4
Legal Au Comment:[3] [4] [5]
Legal Ca:Rx-only
Legal Ca Comment:/Schedule D[6]
Legal Uk:POM
Legal Us:Rx-only
Legal Us Comment:[7]
Legal Eu:Rx-only
Elimination Half-Life:4.5 hours
Cas Number:679809-58-6
Pubchem:772
Iuphar Ligand:6811
Drugbank:DB01225
Chemspiderid:none
Unii:8NZ41MIK1O
Kegg:D07510
Chembl:1201685
Chemical Formula:(C26H40N2O36S5)n
Molecular Weight:4500
Molecular Weight Comment:g/mol (average)

Enoxaparin sodium, sold under the brand name Lovenox among others, is an anticoagulant medication (blood thinner). It is used to treat and prevent deep vein thrombosis (DVT) and pulmonary embolism (PE) including during pregnancy and following certain types of surgery. It is also used in those with acute coronary syndrome (ACS) and heart attacks. It is given by injection just under the skin or into a vein. It is also used during hemodialysis.[8]

Common side effects include bleeding, fever, and swelling of the legs. Bleeding may be serious especially in those who are undergoing a spinal tap. Use during pregnancy appears to be safe for the baby. Enoxaparin is in the low molecular weight heparin family of medications.

Enoxaparin was first made in 1981 and approved for medical use in 1993.[9] It is on the World Health Organization's List of Essential Medicines.[10] Enoxaparin is sold under several brand names and is available as a generic medication.[9] Enoxaparin is made from heparin.[11] In 2020, it was the 350th most commonly prescribed medication in the United States, with more than 500thousand prescriptions.[12]

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.

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.

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.[15] The revision recommends exercising caution regarding when spinal catheters are placed and removed in persons taking enoxaparin for spinal puncture or neuroaxial anesthesia.[16] 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. 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. The FDA recommends that at-risk persons be monitored for bleeding and neurological changes.[17]

Pharmacology

Mechanism of action

Enoxaparin binds to and potentiates antithrombin (a circulating anticoagulant) to form a complex that irreversibly inactivates clotting factor Xa.[18] It has less activity against factor IIa (thrombin) compared to unfractionated heparin (UFH) due to its low molecular weight.[19]

Pharmacokinetics

Absorption: Bioavailability (subcutaneous injection) ~ 100%

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

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

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

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.[20]

Biosimilars

See also: Biosimilars.

In September 2016, Inhixa and Thorinane were approved for use in the European Union.[21] [22] Thorinane was withdrawn from the market in October 2019.[23]

In March 2017, Enoxaparin BECAT, Laboratorios ROVI (Spain) obtained marketing authorization in twenty six countries in Europe. The product is now available in Europe.[24]

In October 2020, Noromby and Noromby HP, were approved for medical use in Canada.[25]

In November 2020, Inclunox and Inclunox HP were approved for medical use in Canada.[26]

In December 2020, Redesca and Redesca HP were approved for medical use in Canada.[27]

Notes and References

  1. Web site: Enoxaparin Use During Pregnancy . Drugs.com . 15 July 2019 . 16 August 2020 . 27 October 2020 . https://web.archive.org/web/20201027035539/https://www.drugs.com/pregnancy/enoxaparin.html . live .
  2. Web site: Summary Basis of Decision (SBD) for Axberi/Axberi HP . . 26 January 2024 . 24 February 2024 . 24 February 2024 . https://web.archive.org/web/20240224070452/https://dhpp.hpfb-dgpsa.ca/review-documents/resource/SBD1706623043472 . live .
  3. Web site: Enoxapo Australian prescription medicine decision summary . Therapeutic Goods Administration (TGA) . 28 February 2020 . 17 August 2020 . 26 February 2020 . https://web.archive.org/web/20200226120650/https://www.tga.gov.au/apm-summary/enoxapo . live .
  4. Web site: Exarane/Exarane Forte . Therapeutic Goods Administration (TGA) . 2023-08-07 . 2024-07-04 . 2 January 2024 . https://web.archive.org/web/20240102022215/https://www.tga.gov.au/resources/auspmd/exaraneexarane-forte . dead .
  5. Web site: AusPAR: Exarane/Exarane Forte . Therapeutic Goods Administration (TGA) . 4 March 2024 . 31 March 2024 . 31 March 2024 . https://web.archive.org/web/20240331035015/https://www.tga.gov.au/resources/auspar/auspar-exaraneexarane-forte . live .
  6. Web site: Summary Basis of Decision - Elonox/Elonox HP . . 28 March 2023 . 24 April 2023 . 25 April 2023 . https://web.archive.org/web/20230425001504/https://hpr-rps.hres.ca/reg-content/summary-basis-decision-detailTwo.php?linkID=SBD00632&lang=en . live .
  7. Web site: Lovenox- enoxaparin sodium injection . DailyMed . U.S. National Library of Medicine . 28 April 2020 . 16 August 2020 . 4 August 2020 . https://web.archive.org/web/20200804165635/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=5017a927-2a24-4f27-89f9-27c805bf7d59 . live .
  8. Web site: Clexane Forte Syringes - Summary of Product Characteristics (SmPC) . emc . 12 October 2020 . 26 September 2018 . https://web.archive.org/web/20180926014357/https://www.medicines.org.uk/emc/product/1695/smpc . live .
  9. Web site: Enoxaparin Sodium. The American Society of Health-System Pharmacists. 8 December 2016. live. https://web.archive.org/web/20161221011322/https://www.drugs.com/monograph/enoxaparin-sodium.html. 21 December 2016.
  10. Book: ((World Health Organization)) . World Health Organization model list of essential medicines: 21st list 2019 . 2019 . 10665/325771 . World Health Organization . World Health Organization . Geneva . WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO . free .
  11. Book: Northern Neonatal Network . Enoxaparin . Neonatal Formulary: Drug Use in Pregnancy and the First Year of Life. 2008. John Wiley & Sons. 9780470750353. 96. https://books.google.com/books?id=aumIBqHmChwC&pg=PA96. en. live. https://web.archive.org/web/20161220133303/https://books.google.ca/books?id=aumIBqHmChwC&pg=PA96. 2016-12-20.
  12. Web site: Enoxaparin - Drug Usage Statistics . ClinCalc . 7 October 2022 . 7 November 2022 . https://web.archive.org/web/20221107021541/https://clincalc.com/DrugStats/Drugs/Enoxaparin . live .
  13. Gershanik J, Boecler B, Ensley H, McCloskey S, George W . The gasping syndrome and benzyl alcohol poisoning . The New England Journal of Medicine . 307 . 22 . 1384–1388 . November 1982 . 7133084 . 10.1056/NEJM198211253072206 .
  14. Levy JH, Tanaka KA, Hursting MJ . Reducing thrombotic complications in the perioperative setting: an update on heparin-induced thrombocytopenia . Anesthesia and Analgesia . 105 . 3 . 570–582 . September 2007 . 17717208 . 10.1213/01.ane.0000277497.70701.47 . 25103749 . free .
  15. Web site: ENOXAPARIN SODIUM- enoxaparin sodium injection. DailyMed . U.S. National Library of Medicine . 2015-11-05. live. https://web.archive.org/web/20151019091929/http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3e6bf2b3-9339-4104-bda3-ad86a1949703#S2. 2015-10-19.
  16. Web site: 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. 2015-11-05. Center for Drug Evaluation and Research . U.S. Food and Drug Administration . live . https://web.archive.org/web/20151030045440/https://www.fda.gov/Drugs/DrugSafety/ucm373595.htm . 2015-10-30 .
  17. Web site: Safety Information - Lovenox (enoxaparin sodium) injection. U.S. Food and Drug Administration . 2015-11-05. Office of the Commissioner. live. https://web.archive.org/web/20160304180930/https://www.fda.gov/Safety/MedWatch/SafetyInformation/ucm180210.htm. 2016-03-04.
  18. Book: Koda-Kimble and Young's Applied Therapeutics: The Clinical Use of Drugs. Alldredge BK, Corelli RL, Ernst ME, Guglielmo BJ, Jacobson PA, Kradjan WA, Williams BR . 978-1-60913-713-7. 347–348. Tenth . February 2012. Lippincott Williams & Wilkins .
  19. Book: Trevor AJ, Katzung BG, Masters SB . Basic & Clinical Pharmacology . McGraw-Hill Medical . 2012 . 978-0-07-176401-8 .
  20. LowMolecularWeightHeparins . 2012 . 31643176 . livertox.nih.gov . 2015-11-05 . live . https://web.archive.org/web/20150828060257/http://livertox.nih.gov/LowMolecularWeightHeparins.htm . 2015-08-28 .
  21. Web site: Inhixa EPAR . European Medicines Agency (EMA) . 17 September 2018 . 2 April 2020 . 29 October 2020 . https://web.archive.org/web/20201029200312/https://www.ema.europa.eu/en/medicines/human/EPAR/inhixa . live .
  22. Web site: Thorinane EPAR . European Medicines Agency (EMA) . 17 September 2018 . 2 April 2020 . 30 December 2019 . https://web.archive.org/web/20191230161610/https://www.ema.europa.eu/en/medicines/human/EPAR/thorinane . live .
  23. Web site: Public statement on Thorinane: Cessation of validity of the marketing authorisation in the European Union . 2 April 2020 . 28 August 2021 . https://web.archive.org/web/20210828073816/https://www.ema.europa.eu/en/documents/public-statement/public-statement-thorinane-cessation-validity-marketing-authorisation-european-union_en.pdf . live .
  24. Web site: To The National Stock Market Commission . 29 May 2020 . 28 August 2021 . https://web.archive.org/web/20210828073818/https://www.rovi.es/sites/default/files/196i.pdf . live .
  25. Web site: Summary Basis of Decision (SBD) for Noromby/Noromby HP . Health Canada . 23 October 2014 . 29 May 2022 . 30 May 2022 . https://web.archive.org/web/20220530051353/https://hpr-rps.hres.ca/reg-content/summary-basis-decision-detailTwo.php?linkID=SBD00513&lang=en . live .
  26. Web site: Summary Basis of Decision (SBD) for Inclunox/Inclunox HP . Health Canada . 23 October 2014 . 29 May 2022 . 30 May 2022 . https://web.archive.org/web/20220530050038/https://hpr-rps.hres.ca/reg-content/summary-basis-decision-detailTwo.php?linkID=SBD00517&lang=en . live .
  27. Web site: Summary Basis of Decision (SBD) for Redesca/Redesca HP . Health Canada . 23 October 2014 . 29 May 2022 . 30 May 2022 . https://web.archive.org/web/20220530040901/https://hpr-rps.hres.ca/reg-content/summary-basis-decision-detailTwo.php?linkID=SBD00540&lang=en . live .

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