Enoxaparin sodium

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Enoxaparin sodium
EnoxaparinSodium.png
Enoxaparin sodium ball-and-stick.png
Clinical data
Trade names Lovenox, Clexane, Xaparin, others
Biosimilars Arovi, Axberi, [1] Axberi HP, [1] Exarane, [2] Exarane Forte, [2] Enoxapo, [3] Inclunox, Inclunox HP, Inhixa, Noromby, Noromby HP, Redesca, Redesca HP, Thorinane
AHFS/Drugs.com Monograph
MedlinePlus a696006
License data
Pregnancy
category
Routes of
administration
Subcutaneous, intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
Elimination half-life 4.5 hours
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
  • none
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.029.698 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula (C26H40N2O36S5)n
Molar mass 4500g/mol (average)
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Enoxaparin sodium, sold under the brand name Lovenox among others, is an anticoagulant medication (blood thinner). [11] It is used to treat and prevent deep vein thrombosis (DVT) and pulmonary embolism (PE) including during pregnancy and following certain types of surgery. [11] It is also used in those with acute coronary syndrome (ACS) and heart attacks. [11] It is given by injection just under the skin or into a vein. [11] It is also used during hemodialysis. [7] [10]

Contents

Common side effects include bleeding, fever, and swelling of the legs. [11] Bleeding may be serious especially in those who are undergoing a spinal tap. [11] Use during pregnancy appears to be safe for the baby. [11] Enoxaparin is in the low molecular weight heparin family of medications. [11]

Enoxaparin was first made in 1981 and approved for medical use in 1993. [12] [11] It is on the World Health Organization's List of Essential Medicines. [13] Enoxaparin is sold under several brand names and is available as a generic medication. [11] Enoxaparin is made from heparin. [12] In 2020, it was the 350th most commonly prescribed medication in the United States, with more than 500 thousand prescriptions. [14]

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. [9]

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. [9]

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. [17] The revision recommends exercising caution regarding when spinal catheters are placed and removed in persons taking enoxaparin for spinal puncture or neuroaxial anesthesia. [18] 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. [18] 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. [17] The FDA recommends that at-risk persons be monitored for bleeding and neurological changes. [17] [19]

Pharmacology

Mechanism of action

Enoxaparin binds to and activates antithrombin (a circulating anticoagulant) to form a complex that irreversibly inactivates clotting factor Xa. [20] It has less activity against factor IIa (thrombin) compared to unfractionated heparin (UFH) due to its low molecular weight. [21]

Pharmacokinetics

Absorption: Bioavailability (subcutaneous injection) ~ 100% [17]

Distribution: Volume of distribution (anti-Factor Xa activity) = 4.3 liters [17]

Metabolism: Enoxaparin is metabolized in the liver into low molecular weight species by either or both desulfation and depolymerization. [17]

Elimination: A single dose of a subcutaneous injection of enoxaparin has an elimination half-life of 4.5 hours. [17] Approximately 10–40% of the active and inactive fragments from a single dose are excreted by the kidneys. [17] Dose adjustments based on kidney function are necessary in persons with reduced kidney function. [17]

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. [22]

Biosimilars

In September 2016, Inhixa and Thorinane were approved for use in the European Union. [10] [23] Thorinane was withdrawn from the market in October 2019. [24]

In March 2017, Enoxaparin BECAT, Laboratorios ROVI (Spain) obtained marketing authorization in twenty six countries in Europe. The product is now available in Europe. [25]

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

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

In December 2020, Redesca and Redesca HP were approved for medical use in Canada. [28]

Related Research Articles

<span class="mw-page-title-main">Anticoagulant</span> Class of drugs

An anticoagulant, commonly known as a blood thinner, is a chemical substance that prevents or reduces the coagulation of blood, prolonging the clotting time. Some occur naturally in blood-eating animals, such as leeches and mosquitoes, which help keep the bite area unclotted long enough for the animal to obtain blood.

<span class="mw-page-title-main">Venous thrombosis</span> Blood clot (thrombus) that forms within a vein

Venous thrombosis is the blockage of a vein caused by a thrombus. A common form of venous thrombosis is deep vein thrombosis (DVT), when a blood clot forms in the deep veins. If a thrombus breaks off (embolizes) and flows to the lungs to lodge there, it becomes a pulmonary embolism (PE), a blood clot in the lungs. The conditions of DVT only, DVT with PE, and PE only, are all captured by the term venous thromboembolism (VTE).

<span class="mw-page-title-main">Warfarin</span> Anticoagulant medication

Warfarin is an anticoagulant used as a medication under several brand names including Coumadin. While the drug is described as a "blood thinner", it does not reduce viscosity but rather inhibits coagulation. Accordingly, it is commonly used to prevent blood clots in the circulatory system such as deep vein thrombosis and pulmonary embolism, and to protect against stroke in people who have atrial fibrillation, valvular heart disease, or artificial heart valves. Less commonly, it is used following ST-segment elevation myocardial infarction (STEMI) and orthopedic surgery. It is usually taken by mouth, but may also be administered intravenously.

<span class="mw-page-title-main">Heparin</span> Anticoagulant

Heparin, also known as unfractionated heparin (UFH), is a medication and naturally occurring glycosaminoglycan. Heparin is a blood anticoagulant that increases the activity of antithrombin. It is used in the treatment of heart attacks and unstable angina. It can be given intravenously or by injection under the skin. Its anticoagulant properties make it useful to prevent blood clotting in blood specimen test tubes and kidney dialysis machines.

<span class="mw-page-title-main">Naproxen</span> Nonsteroidal anti-inflammatory drug (NSAID) used to treat pain

Naproxen, sold under the brand name Aleve among others, is a nonsteroidal anti-inflammatory drug (NSAID) used to treat pain, menstrual cramps, and inflammatory diseases such as rheumatoid arthritis, gout and fever. It is taken orally. It is available in immediate and delayed release formulations. Onset of effects is within an hour and lasts for up to twelve hours.

<span class="mw-page-title-main">Filgrastim</span> Medication

Filgrastim, sold under the brand name Neupogen among others, is a medication used to treat low neutrophil count. Low neutrophil counts may occur with HIV/AIDS, following chemotherapy or radiation poisoning, or be of an unknown cause. It may also be used to increase white blood cells for gathering during leukapheresis. It is given either by injection into a vein or under the skin. Filgrastim is a leukocyte growth factor.

Low-molecular-weight heparin (LMWH) is a class of anticoagulant medications. They are used in the prevention of blood clots and, in the treatment of venous thromboembolism, and the treatment of myocardial infarction.

<span class="mw-page-title-main">Argatroban</span> Pharmaceutical drug

Argatroban is an anticoagulant that is a small molecule direct thrombin inhibitor. In 2000, argatroban was licensed by the US Food and Drug Administration (FDA) for prophylaxis or treatment of thrombosis in people with heparin-induced thrombocytopenia (HIT). In 2002, it was approved for use during percutaneous coronary interventions in people who have HIT or are at risk for developing it. In 2012, it was approved by the UK Medicines and Healthcare products Regulatory Agency for anticoagulation in people with heparin-induced thrombocytopenia Type II (HIT) who require parenteral antithrombotic therapy.

<span class="mw-page-title-main">Fondaparinux</span> Chemical compound

Fondaparinux is an anticoagulant medication chemically related to low molecular weight heparins. It is marketed by Viatris. A generic version developed by Alchemia is marketed within the US by Dr. Reddy's Laboratories.

<span class="mw-page-title-main">Rivaroxaban</span> Anticoagulant drug

Rivaroxaban, sold under the brand name Xarelto among others, is an anticoagulant medication used to treat and prevent blood clots. Specifically it is used to treat deep vein thrombosis and pulmonary emboli and prevent blood clots in atrial fibrillation and following hip or knee surgery. It is taken by mouth.

<span class="mw-page-title-main">Dalteparin sodium</span> Pharmaceutical drug

Dalteparin is a low molecular weight heparin. It is marketed as Fragmin. Like other low molecular weight heparins, dalteparin is used for prophylaxis or treatment of deep vein thrombosis and pulmonary embolism to reduce the risk of a stroke or heart attack. Dalteparin acts by potentiating the activity of antithrombin III, inhibiting formation of both Factor Xa and thrombin. It is normally administered by self-injection.

<span class="mw-page-title-main">Tirofiban</span> Antiplatelet drug

Tirofiban, sold under the brand name Aggrastat, is an antiplatelet medication. It belongs to a class of antiplatelets named glycoprotein IIb/IIIa inhibitors. Tirofiban is a small molecule inhibitor of the protein-protein interaction between fibrinogen and the platelet integrin receptor GP IIb/IIIa and is the first drug candidate whose origins can be traced to a pharmacophore-based virtual screening lead.

Prothrombin complex concentrate (PCC), also known as factor IX complex, sold under the brand name Kcentra among others, is a combination medication made up of blood clotting factors II, IX, and X(3-factor PCC) or, when also containing factor VII as does Kcentra, 4-factor PCC. It is used to treat and prevent bleeding in hemophilia B if pure factor IX is not available. It may also be used for reversal of warfarin therapy. It is given by slow injection into a vein. Another product, activated prothrombin complex concentrate or FEIBA, may be used for acquired hemophilia.

<span class="mw-page-title-main">Bemiparin sodium</span> Chemical compound

Bemiparin is an antithrombotic and belongs to the group of low molecular weight heparins (LMWH).

<span class="mw-page-title-main">Tinzaparin sodium</span> Pharmaceutical drug

Tinzaparin is an antithrombotic drug in the heparin group. It is a low molecular weight heparin (LMWH) marketed as Innohep worldwide. It has been approved by the U.S. Food and Drug Administration (FDA) for once daily treatment and prophylaxis of deep vein thrombosis (DVT) and pulmonary embolism (PE).

<span class="mw-page-title-main">Edoxaban</span> Anticoagulant medication

Edoxaban, sold under the brand name Lixiana among others, is an anticoagulant medication and a direct factor Xa inhibitor. It is taken by mouth.

<span class="mw-page-title-main">Apixaban</span> Anticoagulant medication

Apixaban, sold under the brand name Eliquis, is an anticoagulant medication used to treat and prevent blood clots and to prevent stroke in people with nonvalvular atrial fibrillation through directly inhibiting factor Xa. It is used an alternative to warfarin to prevent blood clots following hip or knee replacement and in those with a history of prior clots. and does not require monitoring by blood tests or dietary restrictions. It is taken by mouth.

Direct thrombin inhibitors (DTIs) are a class of anticoagulant drugs that can be used to prevent and treat embolisms and blood clots caused by various diseases. They inhibit thrombin, a serine protease which affects the coagulation cascade in many ways. DTIs have undergone rapid development since the 90's. With technological advances in genetic engineering the production of recombinant hirudin was made possible which opened the door to this new group of drugs. Before the use of DTIs the therapy and prophylaxis for anticoagulation had stayed the same for over 50 years with the use of heparin derivatives and warfarin which have some well known disadvantages. DTIs are still under development, but the research focus has shifted towards factor Xa inhibitors, or even dual thrombin and fXa inhibitors that have a broader mechanism of action by both inhibiting factor IIa (thrombin) and Xa. A recent review of patents and literature on thrombin inhibitors has demonstrated that the development of allosteric and multi-mechanism inhibitors might lead the way to a safer anticoagulant.

Fremanezumab, sold under the brand name Ajovy, is a medication used to prevent migraines in adults. It is given by injection under the skin.

<span class="mw-page-title-main">Relugolix/estradiol/norethisterone acetate</span> Combination medication

Relugolix/estradiol/norethisterone acetate, sold under the brand names Myfembree and Ryeqo, is a fixed-dose combination hormonal medication which is used for the treatment of heavy menstrual bleeding associated with uterine leiomyomas (fibroids) and for moderate to severe pain associated with endometriosis. It contains relugolix, an orally active gonadotropin-releasing hormone antagonist, estradiol, an estrogen, and norethisterone acetate, a progestin. The medication is taken by mouth.

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