Revision as of 12:53, 10 January 2011 editAnypodetos (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers39,350 editsm Copyedit← Previous edit |
Latest revision as of 23:58, 12 January 2025 edit undoArthurfragoso (talk | contribs)Extended confirmed users, Template editors4,591 edits dark mode fix |
(331 intermediate revisions by more than 100 users not shown) |
Line 1: |
Line 1: |
|
|
{{Short description|Anticoagulant medication (blood thinner)}} |
|
{{drugbox |
|
|
|
{{Use dmy dates|date=April 2020}} |
|
| IUPAC_name = |
|
|
|
{{Infobox drug |
|
|
| Verifiedfields = changed |
|
|
| Watchedfields = changed |
|
|
| verifiedrevid = 407062079 |
|
| image = EnoxaparinSodium.png |
|
| image = EnoxaparinSodium.png |
|
|
| image_class = skin-invert-image |
|
| width = 300px |
|
|
| CAS_number = 9005-49-6 |
|
| width = 300 |
|
|
| alt = |
|
| ChemSpiderID = |
|
|
|
| image2 = Enoxaparin sodium ball-and-stick.png |
|
|
| image_class2 = bg-transparent |
|
|
| width2 = |
|
|
| alt2 = |
|
|
| caption = |
|
|
|
|
|
<!-- Clinical data --> |
|
|
| pronounce = |
|
|
| tradename = Lovenox, Clexane, Xaparin, others |
|
|
| Drugs.com = {{drugs.com|monograph|enoxaparin_sodium}} |
|
|
| MedlinePlus = a696006 |
|
|
| DailyMedID = Enoxaparin |
|
|
| pregnancy_AU = C |
|
|
| pregnancy_AU_comment = <ref name="Drugs.com pregnancy">{{cite web | title=Enoxaparin Use During Pregnancy | website=Drugs.com | date=15 July 2019 | url=https://www.drugs.com/pregnancy/enoxaparin.html | access-date=16 August 2020 | archive-date=27 October 2020 | archive-url=https://web.archive.org/web/20201027035539/https://www.drugs.com/pregnancy/enoxaparin.html | url-status=live }}</ref><ref name="Enoxapo APMDS" /><ref name="Exarane APMDS" /> |
|
|
| pregnancy_category = |
|
|
| routes_of_administration = ], ] |
|
|
| class = |
|
| ATC_prefix = B01 |
|
| ATC_prefix = B01 |
|
| ATC_suffix = AB05 |
|
| ATC_suffix = AB05 |
|
| ATC_supplemental = |
|
| ATC_supplemental = |
|
|
| biosimilars = Arovi, Axberi,<ref name="Axberi SBD">{{cite web | title=Summary Basis of Decision (SBD) for Axberi/Axberi HP | website=] | date=26 January 2024 | url=https://dhpp.hpfb-dgpsa.ca/review-documents/resource/SBD1706623043472 | access-date=24 February 2024 | archive-date=24 February 2024 | archive-url=https://web.archive.org/web/20240224070452/https://dhpp.hpfb-dgpsa.ca/review-documents/resource/SBD1706623043472 | url-status=live }}</ref> Axberi HP,<ref name="Axberi SBD" /> Exarane,<ref name="Exarane APMDS" /> Exarane Forte,<ref name="Exarane APMDS" /> Enoxapo,<ref name="Enoxapo APMDS" /> Inclunox, Inclunox HP, Inhixa, Noromby, Noromby HP, Redesca, Redesca HP, Thorinane |
|
|
|
|
|
<!-- Legal status --> |
|
|
| legal_AU = S4 |
|
|
| legal_AU_comment = <ref name="Enoxapo APMDS">{{cite web | title=Enoxapo Australian prescription medicine decision summary | website=Therapeutic Goods Administration (TGA) | date=28 February 2020 | url=https://www.tga.gov.au/apm-summary/enoxapo | access-date=17 August 2020 | archive-date=26 February 2020 | archive-url=https://web.archive.org/web/20200226120650/https://www.tga.gov.au/apm-summary/enoxapo | url-status=live }}</ref><ref name="Exarane APMDS">{{cite web | title=Exarane/Exarane Forte | website=Therapeutic Goods Administration (TGA) | date=2023-08-07 | url=https://www.tga.gov.au/resources/auspmd/exaraneexarane-forte | access-date=2024-07-04 | archive-date=2 January 2024 | archive-url=https://web.archive.org/web/20240102022215/https://www.tga.gov.au/resources/auspmd/exaraneexarane-forte | url-status=dead }}</ref><ref>{{cite web | title=AusPAR: Exarane/Exarane Forte | website=Therapeutic Goods Administration (TGA) | date=4 March 2024 | url=https://www.tga.gov.au/resources/auspar/auspar-exaraneexarane-forte | access-date=31 March 2024 | archive-date=31 March 2024 | archive-url=https://web.archive.org/web/20240331035015/https://www.tga.gov.au/resources/auspar/auspar-exaraneexarane-forte | url-status=live }}</ref> |
|
|
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F --> |
|
|
| legal_BR_comment = |
|
|
| legal_CA = Rx-only |
|
|
| legal_CA_comment = /{{nbsp}}Schedule D<ref>{{cite web | title=Summary Basis of Decision - Elonox/Elonox HP | website=] | date=28 March 2023 | url=https://hpr-rps.hres.ca/reg-content/summary-basis-decision-detailTwo.php?linkID=SBD00632&lang=en | access-date=24 April 2023 | archive-date=25 April 2023 | archive-url=https://web.archive.org/web/20230425001504/https://hpr-rps.hres.ca/reg-content/summary-basis-decision-detailTwo.php?linkID=SBD00632&lang=en | url-status=live }}</ref> |
|
|
| legal_DE = <!-- Anlage I, II, III or Unscheduled --> |
|
|
| legal_DE_comment = |
|
|
| legal_NZ = <!-- Class A, B, C --> |
|
|
| legal_NZ_comment = |
|
|
| legal_UK = POM |
|
|
| legal_UK_comment = <ref name="Clexane Forte SmPC" /> |
|
|
| legal_US = Rx-only |
|
|
| legal_US_comment = <ref name="FDA Lovenox label">{{cite web | title=Lovenox- enoxaparin sodium injection | work = DailyMed | publisher = U.S. National Library of Medicine | date=28 April 2020 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=5017a927-2a24-4f27-89f9-27c805bf7d59 | access-date=16 August 2020 | archive-date=4 August 2020 | archive-url=https://web.archive.org/web/20200804165635/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=5017a927-2a24-4f27-89f9-27c805bf7d59 | url-status=live }}</ref> |
|
|
| legal_EU = Rx-only |
|
|
| legal_EU_comment = <ref name="Inhixa EPAR" /> |
|
|
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV --> |
|
|
| legal_UN_comment = |
|
|
| legal_status = <!-- For countries not listed above --> |
|
|
|
|
|
<!-- Pharmacokinetic data --> |
|
|
| bioavailability = |
|
|
| protein_bound = |
|
|
| metabolism = |
|
|
| metabolites = |
|
|
| onset = |
|
|
| elimination_half-life = 4.5 hours |
|
|
| duration_of_action = |
|
|
| excretion = |
|
|
|
|
|
<!-- Identifiers --> |
|
|
| CAS_number_Ref = {{cascite|correct|??}} |
|
|
| CAS_number = 679809-58-6 |
|
|
| CAS_supplemental = |
|
| PubChem = 772 |
|
| PubChem = 772 |
|
|
| IUPHAR_ligand = 6811 |
|
| DrugBank = APRD00068 |
|
|
|
| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
|
|
| DrugBank = DB01225 |
|
|
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
|
|
| ChemSpiderID = none |
|
|
| UNII_Ref = {{fdacite|changed|FDA}} |
|
|
| UNII = 8NZ41MIK1O |
|
|
| KEGG_Ref = {{keggcite|correct|kegg}} |
|
| KEGG = D07510 |
|
| KEGG = D07510 |
|
|
| ChEBI_Ref = |
|
|
| ChEBI = |
|
|
| ChEMBL_Ref = {{ebicite|changed|EBI}} |
|
|
| ChEMBL = 1201685 |
|
|
| NIAID_ChemDB = |
|
|
| PDB_ligand = |
|
|
| synonyms = |
|
|
|
|
|
<!-- Chemical and physical data --> |
|
|
| IUPAC_name = |
|
| chemical_formula = (C<sub>26</sub>H<sub>40</sub>N<sub>2</sub>O<sub>36</sub>S<sub>5</sub>)n |
|
| chemical_formula = (C<sub>26</sub>H<sub>40</sub>N<sub>2</sub>O<sub>36</sub>S<sub>5</sub>)n |
|
|
| C= | H= | Ag= | Al= | As= | Au= | B= | Bi= | Br= | Ca= | Cl= | Co= | F= | Fe= | Gd= | I= |
|
| molecular_weight = 4500 ] (average) |
|
|
|
| K= | Li= | Mg= | Mn= | N= | Na= | O= | P= | Pt= | S= | Sb= | Se= | Sr= | Tc= | Zn= | charge= |
|
| bioavailability = 92% |
|
|
|
| molecular_weight = 4500 |
|
| protein_bound = 80% bound-albumin |
|
|
|
| molecular_weight_comment = g/mol (average) |
|
| metabolism = primarily by kidneys |
|
|
|
| SMILES = |
|
| elimination_half-life = 4.5 hours |
|
|
|
| StdInChI = |
|
| pregnancy_category = B |
|
|
|
| StdInChI_comment = |
|
| legal_UK = POM |
|
|
|
| StdInChIKey = |
|
| legal_US = Rx-only |
|
|
| legal_status = |
|
| density = |
|
|
| density_notes = |
|
| routes_of_administration = Subcutaneous (SC) Injection and intervenous (IV) per package insert |
|
|
|
| melting_point = |
|
|
| melting_high = |
|
|
| melting_notes = |
|
|
| boiling_point = |
|
|
| boiling_notes = |
|
|
| solubility = |
|
|
| sol_units = |
|
|
| specific_rotation = |
|
}} |
|
}} |
|
'''Enoxaparin''' is a ] marketed as '''Lovenox''' or '''Clexane''', as '''Indenox''' (India, ]) and '''Xaparin''' (India, New Medicon Pharma). |
|
|
It is used to prevent and treat ] or ], and is given as a ] injection (by a health care provider or the patient). Its use is evolving in ]s (ACS). |
|
|
|
|
|
|
|
<!-- Definition and medical uses --> |
|
Enoxaparin is manufactured by ] and is derived from the ] ] of pigs. |
|
|
|
'''Enoxaparin sodium''', sold under the brand name '''Lovenox''' among others, is an ] medication (blood thinner).<ref name=AHFS2016/> It is used to treat and prevent ] (DVT) and ] (PE) including during ] and following certain types of surgery.<ref name=AHFS2016/> It is also used in those with ] (ACS) and ]s.<ref name=AHFS2016/> It is given by ] or ].<ref name=AHFS2016/> It is also used during ].<ref name="Clexane Forte SmPC">{{cite web | title=Clexane Forte Syringes - Summary of Product Characteristics (SmPC) | website=emc | url=https://www.medicines.org.uk/emc/product/1695/smpc | access-date=12 October 2020 | archive-date=26 September 2018 | archive-url=https://web.archive.org/web/20180926014357/https://www.medicines.org.uk/emc/product/1695/smpc | url-status=live }}</ref><ref name="Inhixa EPAR" /> |
|
|
|
|
|
|
<!-- Side effects and mechanism --> |
|
==Indications== |
|
|
|
Common side effects include bleeding, fever, and ].<ref name=AHFS2016/> Bleeding may be serious especially in those who are undergoing a ].<ref name=AHFS2016/> Use during ] appears to be safe for the baby.<ref name=AHFS2016/> Enoxaparin is in the ] family of medications.<ref name=AHFS2016/> |
|
In the ] and ], enoxaparin is approved for six indications: |
|
|
* The prophylaxis of ] disorders of venous origin, in particular those which may be associated with ]. There is limited evidence supporting the use of enoxaparin in orthopaedic patients<ref>{{cite journal | last1 = Warwick | first1 = D | last2 = Williams | first2 = MH | last3 = Bannister | first3 = GC | title = Death and thromboembolic disease after total hip replacement. A series of 1162 cases with no routine chemical prophylaxis | journal = The Journal of bone and joint surgery. British volume | volume = 77 | issue = 1 | pages = 6–10 | year = 1995 | pmid = 7822397 }}</ref>, although evidence is reasonable for colorectal patients<ref>{{cite journal | last1 = Bergqvist | first1 = D | title = Venous thromboembolism: a review of risk and prevention in colorectal surgery patients | journal = Diseases of the colon and rectum | volume = 49 | issue = 10 | pages = 1620–8 | year = 2006 | pmid = 17019655 | doi = 10.1007/s10350-006-0693-0 }}</ref> |
|
|
* The prophylaxis of ] (VTE) in medical patients bedridden due to acute ]. |
|
|
* The treatment of venous thromboembolism disease (VTED) presenting with ] (DVT), ] (PE) or both. |
|
|
* The treatment of unstable ] (UA) and non-Q-wave ] (NQMI), administered concurrently with ]. |
|
|
* The prevention of thrombus formation in the extracorporeal circulation during ]. |
|
|
* The prevention of thrombus formation during episodes of lone ], administered concurrently with ] (in the absence of long term blood thinning treatment with ]). |
|
|
In the ], enoxaparin is ] approved for seven indications: |
|
|
* The treatment of unstable ] (UA) and non-Q-wave ] (NQMI), administered concurrently with ]. |
|
|
* Prophylaxis of DVT in medically ill patient, |
|
|
* Total hip & knee replacement, |
|
|
* Extended hip-replacement, |
|
|
* Abdominal surgery. |
|
|
* Treatment of DVT with or without PE. |
|
|
* Treatment of DVT inpatient, with ACS, including STEMI. |
|
|
|
|
|
|
|
<!-- History, society and culture --> |
|
==Mechanism of action== |
|
|
|
Enoxaparin was first made in 1981 and approved for medical use in 1993.<ref name=Net2008/><ref name=AHFS2016>{{cite web|title=Enoxaparin Sodium|url=https://www.drugs.com/monograph/enoxaparin-sodium.html|publisher=The American Society of Health-System Pharmacists|access-date=8 December 2016|url-status=live|archive-url=https://web.archive.org/web/20161221011322/https://www.drugs.com/monograph/enoxaparin-sodium.html|archive-date=21 December 2016}}</ref> It is on the ].<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref> Enoxaparin is sold under several brand names and is available as a ].<ref name=AHFS2016/> Enoxaparin is made from ].<ref name=Net2008>{{cite book | author = Northern Neonatal Network | chapter = Enoxaparin |title=Neonatal Formulary: Drug Use in Pregnancy and the First Year of Life|date=2008|publisher=John Wiley & Sons|isbn=9780470750353|page=96| chapter-url = https://books.google.com/books?id=aumIBqHmChwC&pg=PA96|language=en|url-status=live|archive-url=https://web.archive.org/web/20161220133303/https://books.google.ca/books?id=aumIBqHmChwC&pg=PA96|archive-date=2016-12-20}}</ref> In 2020, it was the 350th most commonly prescribed medication in the United States, with more than 500{{nbsp}}thousand prescriptions.<ref>{{cite web | title = Enoxaparin - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Enoxaparin | access-date = 7 October 2022 | archive-date = 7 November 2022 | archive-url = https://web.archive.org/web/20221107021541/https://clincalc.com/DrugStats/Drugs/Enoxaparin | url-status = live }}</ref> |
|
Enoxaparin binds to and accelerates the activity of ]. By activating antithrombin III, enoxaparin preferentially potentiates the inhibition of ] Xa and IIa. The anticoagulant effect of enoxaparin can be directly correlated to its ability to inhibit ]. Factor Xa catalyzes the conversion of prothrombin to ], so enoxaparin’s inhibition of this process results in decreased thrombin and ultimately the prevention of ] clot formation. |
|
|
|
|
|
|
==Monitoring== |
|
==Medical uses== |
|
|
* Treatment of unstable ] (UA) and non-ST elevated ] (NSTEMI), administered concurrently with ] |
|
* Enoxaparin does NOT affect the international normalized ratio (INR), ] or ] {{Citation needed|reason=Anecdotally, I've often seen LMWHs raise APTT to a lesser extent than unfractionated heparin. They also have less or no effect on thrombin time, depending on which LMWH. However, I don't know at which dosage.|date=October 2010}} |
|
|
|
* DVT and pulmonary embolism prophylaxis in bed-ridden patients |
|
* Anti-] levels can be measured, and are often used to monitor enoxaparin activity |
|
|
|
* DVT prophylaxis in knee replacement surgery |
|
|
* DVT prophylaxis in hip replacement surgery |
|
|
* DVT prophylaxis in abdominal surgery |
|
|
* Treatment of DVT with or without pulmonary embolism |
|
|
* Treatment of DVT inpatient, with ] (STEMI)<ref name="FDA Lovenox label" /> |
|
|
* Bridging treatment for those with INR below therapeutic range |
|
|
|
|
|
==Pregnancy== |
|
===Monitoring=== |
|
|
Enoxaparin has predictable absorption, ], and distribution therefore monitoring is not typically done. However, there are instances where monitoring may be beneficial for special populations, for example individuals with ] or those that are obese. In this case, ] can be measured and dosing adjusted accordingly.<ref name="FDA Lovenox label" /> |
|
* Category B: enoxaprin is safe for use in the ] as it does not cross the ] and safe while breast feeding |
|
|
|
|
|
|
|
===Reversal agent=== |
|
==Dosing in patients with renal failure== |
|
|
|
] is less effective at reversing enoxaparin compared to ], with a maximum neutralization of approximately 60% of the anti-factor Xa effect.<ref name="FDA Lovenox label" /> |
|
Decreased dose is recommended in renal failure or ESRD patients. For DVT prophylaxis in a patient with GFR < 30, a dose of 30 mg daily is recommended. For DVT prophylaxis in a patient with GFR > 30, full dose (40 mg daily) can be given. For treatment of DVT/PE, the standard recommended dose is 1.5 mg/kg once daily. If the GFR < 30, the dose should be changed to 1 mg/kg daily. |
|
|
|
|
|
|
===Pregnancy=== |
|
|
* Enoxaparin is a FDA ] B drug which means enoxaparin is not expected to cause harm to an unborn baby when used during pregnancy.<ref name="FDA Lovenox label" /> |
|
|
* Enoxaparin does not cross the placenta therefore it is unlikely an unborn baby would be exposed to it.<ref name="FDA Lovenox label" /> |
|
|
* Some fetal deaths have been reported by women who used enoxaparin during pregnancy, but it is unclear if enoxaparin caused these deaths.<ref name="FDA Lovenox label" /> |
|
|
* The multiple-dose vials of the brand name enoxaparin (Lovenox) contain 15 mg ] per 1 mL as a preservative. Premature infants who have been given large amounts of benzyl alcohol (99–405 mg/kg/day) have experienced "gasping syndrome".<ref name="FDA Lovenox label" /><ref>{{cite journal | vauthors = Gershanik J, Boecler B, Ensley H, McCloskey S, George W | title = The gasping syndrome and benzyl alcohol poisoning | journal = The New England Journal of Medicine | volume = 307 | issue = 22 | pages = 1384–1388 | date = November 1982 | pmid = 7133084 | doi = 10.1056/NEJM198211253072206 }}</ref> |
|
|
* Although enoxaparin is used to prevent blood clots, pregnancy alone can raise a woman's risk of clotting.<ref name="FDA Lovenox label" /> |
|
|
|
|
|
==Side effects== |
|
==Side effects== |
|
|
'''Uncommon (<1%)''' |
|
* ]<ref>{{cite journal | last1 = Warwick | first1 = D | last2 = Bannister | first2 = GC | last3 = Glew | first3 = D | last4 = Mitchelmore | first4 = A | last5 = Thornton | first5 = M | last6 = Peters | first6 = TJ | last7 = Brookes | first7 = S | title = Perioperative low-molecular-weight heparin. Is it effective and safe | journal = The Journal of bone and joint surgery. British volume | volume = 77 | issue = 5 | pages = 715–9 | year = 1995 | pmid = 7559695 }}</ref> |
|
|
|
* In people with unstable angina or non-Q-wave myocardial infarction: |
|
* ], i.e. can be associated with ] (0.5-5.0% of patients treated for at least five days<ref>{{cite journal | last1 = Levy | first1 = JH | last2 = Tanaka | first2 = KA | last3 = Hursting | first3 = MJ | title = Reducing thrombotic complications in the perioperative setting: an update on heparin-induced thrombocytopenia | journal = Anesthesia and analgesia | volume = 105 | issue = 3 | pages = 570–82 | year = 2007 | pmid = 17717208 | doi = 10.1213/01.ane.0000277497.70701.47 }}</ref> |
|
|
|
** ], ], lung edema, ]: ≥ 0.5%v |
|
* ], ] or ]; hard, inflamed ]s or an itchy red ] at the ] site |
|
|
|
'''Common (>1%)''' |
|
* Symptoms similar to those of ] |
|
|
|
* ], i.e. can be associated with ] (0.5-5.0% of persons treated for at least five days)<ref>{{cite journal | vauthors = Levy JH, Tanaka KA, Hursting MJ | title = Reducing thrombotic complications in the perioperative setting: an update on heparin-induced thrombocytopenia | journal = Anesthesia and Analgesia | volume = 105 | issue = 3 | pages = 570–582 | date = September 2007 | pmid = 17717208 | doi = 10.1213/01.ane.0000277497.70701.47 | s2cid = 25103749 | doi-access = free }}</ref> |
|
* ]/] pain |
|
|
|
* Elevations in serum ]: 5.9%-6.1%<ref name="FDA Lovenox label" /> |
|
* ] |
|
|
|
* In people undergoing abdominal or colorectal surgery: |
|
* ] |
|
|
|
** Bleeding, anemia, ]: ≥ 2%<ref name="FDA Lovenox label" /> |
|
* ] |
|
|
|
* In persons undergoing hip or knee replacement: |
|
|
** Fever, nausea, ], edema, peripheral edema: ≥ 2%<ref name="FDA Lovenox label" /> |
|
|
* In persons with severely restricted mobility during acute illness: |
|
|
** ], thrombocytopenia, confusion, diarrhea, nausea: ≥ 2%<ref name="FDA Lovenox label" /> |
|
|
* In people being treated for deep vein thrombosis: |
|
|
** Injection site hemorrhage, injection site pain, ]: ≥ 2%<ref name="FDA Lovenox label" /> |
|
|
'''Frequency under investigation''' |
|
|
* Local reactions: local irritation, pain, ], ecchymosis, erythema<ref name="FDA Lovenox label" /> |
|
|
* ]<ref name="FDA Lovenox label" /> |
|
|
* ]<ref name="FDA Lovenox label" /> |
|
|
* ]<ref name="FDA Lovenox label" /> |
|
|
* ]<ref name="FDA Lovenox label" /> |
|
|
|
|
|
|
=== Boxed warning === |
|
==Reversal agent== |
|
|
|
The FDA issued a revision to the ] for enoxaparin in October 2013.<ref name="DailyMed">{{Cite web|title = ENOXAPARIN SODIUM- enoxaparin sodium injection|url = http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3e6bf2b3-9339-4104-bda3-ad86a1949703#S2 | work = DailyMed | publisher = U.S. National Library of Medicine |access-date = 2015-11-05|url-status = live|archive-url = https://web.archive.org/web/20151019091929/http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3e6bf2b3-9339-4104-bda3-ad86a1949703#S2|archive-date = 2015-10-19}}</ref> The revision recommends exercising caution regarding when spinal ]s are placed and removed in persons taking enoxaparin for spinal puncture or neuroaxial ].<ref name="Center for Drug Evaluation and Research">{{Cite web|title = 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|url = https://www.fda.gov/Drugs/DrugSafety/ucm373595.htm |access-date = 2015-11-05| work = Center for Drug Evaluation and Research | publisher = U.S. Food and Drug Administration |url-status = live |archive-url = https://web.archive.org/web/20151030045440/https://www.fda.gov/Drugs/DrugSafety/ucm373595.htm |archive-date = 2015-10-30 }}</ref> 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 ].<ref name="Center for Drug Evaluation and Research" /> Persons at risk for hematomas may present with indwelling epidural catheters, concurrent use of medications that worsen bleeding states such as ], or a past medical history of epidural or spinal punctures, spinal injury, or spinal deformations.<ref name="DailyMed" /> The FDA recommends that at-risk persons be monitored for bleeding and neurological changes.<ref name="DailyMed" /><ref>{{Cite web|title = Safety Information - Lovenox (enoxaparin sodium) injection|url = https://www.fda.gov/safety/medwatch/safetyinformation/ucm180210.htm| publisher = U.S. Food and Drug Administration |access-date = 2015-11-05| author = Office of the Commissioner|url-status = live|archive-url = https://web.archive.org/web/20160304180930/https://www.fda.gov/Safety/MedWatch/SafetyInformation/ucm180210.htm|archive-date = 2016-03-04}}</ref> |
|
* ], 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== |
|
== Pharmacology == |
|
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 |
|
|
|
|
|
|
|
=== Mechanism of action === |
|
==Market== |
|
|
|
Enoxaparin binds to and activates ] (a circulating anticoagulant) to form a complex that irreversibly inactivates ] ].<ref>{{Cite book|title = Koda-Kimble and Young's Applied Therapeutics: The Clinical Use of Drugs| vauthors = Alldredge BK, Corelli RL, Ernst ME, Guglielmo BJ, Jacobson PA, Kradjan WA, Williams BR |isbn = 978-1-60913-713-7|pages = 347–348|edition = Tenth |date = February 2012| publisher = Lippincott Williams & Wilkins }}</ref> It has less activity against ] (thrombin) compared to unfractionated heparin (UFH) due to its low molecular weight.<ref>{{cite book | vauthors = Trevor AJ, Katzung BG, Masters SB | title = Basic & Clinical Pharmacology | publisher = McGraw-Hill Medical | date = 2012 | isbn = 978-0-07-176401-8 }}</ref> |
|
Annual sales approx $3.1bn. Enoxaparin is no longer protected by US patent due to inequitable conduct on the filing of Patent No. 5,389,618 () |
|
|
|
|
|
|
|
=== Pharmacokinetics === |
|
==References== |
|
|
|
Absorption: Bioavailability (subcutaneous injection) ~ 100%<ref name="DailyMed" /> |
|
{{reflist|2}} |
|
|
|
|
|
|
|
Distribution: Volume of distribution (anti-Factor Xa activity) = 4.3 liters<ref name="DailyMed" /> |
|
==External links== |
|
|
|
|
|
* |
|
|
|
Metabolism: Enoxaparin is metabolized in the liver into low molecular weight species by either or both desulfation and depolymerization.<ref name="DailyMed" /> |
|
* |
|
|
|
|
|
* |
|
|
|
Elimination: A single dose of a subcutaneous injection of enoxaparin has an elimination half-life of 4.5 hours.<ref name="DailyMed" /> Approximately 10–40% of the active and inactive fragments from a single dose are excreted by the kidneys.<ref name="DailyMed" /> Dose adjustments based on kidney function are necessary in persons with reduced kidney function.<ref name="DailyMed" /> |
|
|
|
|
|
===Drug class=== |
|
|
Enoxaparin belongs to the class of drugs known as low molecular weight heparins. Other drugs in this class include ], ] and ].<ref>{{cite journal | vauthors = | title = LowMolecularWeightHeparins | year = 2012 | pmid = 31643176 | url = http://livertox.nih.gov/LowMolecularWeightHeparins.htm | website = livertox.nih.gov | access-date = 2015-11-05 | url-status = live | archive-url = https://web.archive.org/web/20150828060257/http://livertox.nih.gov/LowMolecularWeightHeparins.htm | archive-date = 2015-08-28 }}</ref> |
|
|
|
|
|
==Biosimilars== |
|
|
{{see also|Biosimilars}} |
|
|
|
|
|
In September 2016, Inhixa and Thorinane were approved for use in the European Union.<ref name="Inhixa EPAR">{{cite web | title=Inhixa EPAR | website=] (EMA) | date=17 September 2018 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/inhixa | access-date=2 April 2020 | archive-date=29 October 2020 | archive-url=https://web.archive.org/web/20201029200312/https://www.ema.europa.eu/en/medicines/human/EPAR/inhixa | url-status=live }}</ref><ref name="Thorinane EPAR">{{cite web | title=Thorinane EPAR | website=] (EMA) | date=17 September 2018 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/thorinane | access-date=2 April 2020 | archive-date=30 December 2019 | archive-url=https://web.archive.org/web/20191230161610/https://www.ema.europa.eu/en/medicines/human/EPAR/thorinane | url-status=live }}</ref> Thorinane was withdrawn from the market in October 2019.<ref>{{cite web | url=https://www.ema.europa.eu/documents/public-statement/public-statement-thorinane-cessation-validity-marketing-authorisation-european-union_en.pdf | title=Public statement on Thorinane: Cessation of validity of the marketing authorisation in the European Union | access-date=2 April 2020 | archive-date=28 August 2021 | archive-url=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 | url-status=live }}</ref> |
|
|
|
|
|
In March 2017, Enoxaparin BECAT, Laboratorios ROVI (Spain) obtained marketing authorization in twenty six countries in Europe. The product is now available in Europe.<ref>{{cite web |title=To The National Stock Market Commission |url=https://www.rovi.es/sites/default/files/196i.pdf |access-date=29 May 2020 |archive-date=28 August 2021 |archive-url=https://web.archive.org/web/20210828073818/https://www.rovi.es/sites/default/files/196i.pdf |url-status=live }}</ref> |
|
|
|
|
|
In October 2020, Noromby and Noromby HP, were approved for medical use in Canada.<ref>{{cite web | title=Summary Basis of Decision (SBD) for Noromby/Noromby HP | website=Health Canada | date=23 October 2014 | url=https://hpr-rps.hres.ca/reg-content/summary-basis-decision-detailTwo.php?linkID=SBD00513&lang=en | access-date=29 May 2022 | archive-date=30 May 2022 | archive-url=https://web.archive.org/web/20220530051353/https://hpr-rps.hres.ca/reg-content/summary-basis-decision-detailTwo.php?linkID=SBD00513&lang=en | url-status=live }}</ref> |
|
|
|
|
|
In November 2020, Inclunox and Inclunox HP were approved for medical use in Canada.<ref>{{cite web | title=Summary Basis of Decision (SBD) for Inclunox/Inclunox HP | website=Health Canada | date=23 October 2014 | url=https://hpr-rps.hres.ca/reg-content/summary-basis-decision-detailTwo.php?linkID=SBD00517&lang=en | access-date=29 May 2022 | archive-date=30 May 2022 | archive-url=https://web.archive.org/web/20220530050038/https://hpr-rps.hres.ca/reg-content/summary-basis-decision-detailTwo.php?linkID=SBD00517&lang=en | url-status=live }}</ref> |
|
|
|
|
|
In December 2020, Redesca and Redesca HP were approved for medical use in Canada.<ref>{{cite web | title=Summary Basis of Decision (SBD) for Redesca/Redesca HP | website=Health Canada | date=23 October 2014 | url=https://hpr-rps.hres.ca/reg-content/summary-basis-decision-detailTwo.php?linkID=SBD00540&lang=en | access-date=29 May 2022 | archive-date=30 May 2022 | archive-url=https://web.archive.org/web/20220530040901/https://hpr-rps.hres.ca/reg-content/summary-basis-decision-detailTwo.php?linkID=SBD00540&lang=en | url-status=live }}</ref> |
|
|
|
|
|
== References == |
|
|
{{Reflist}} |
|
|
|
|
|
{{Antithrombotics}} |
|
{{Antithrombotics}} |
|
|
{{Portal bar | Medicine}} |
|
|
|
|
|
{{DEFAULTSORT:Enoxaparin Sodium}} |
|
{{DEFAULTSORT:Enoxaparin Sodium}} |
|
] |
|
|
] |
|
] |
|
|
] |
|
|
|
|
|
] |
|
] |
|
|
|
] |
|
] |
|
|
] |
|
|
] |
|