Enoxaparin sodium

Structural formula
${\displaystyle {\mathsf {(4n+3)\ Na^{+}}}}$
Possible structural section of enoxaparin sodium
General
Surname	Enoxaparin sodium
CAS number	679809-58-6
Monomers / partial structures	glycosidically linked glucosamine and uronic acid building blocks
PubChem	772
ATC code	B01 AB05
DrugBank	DB01225
Brief description	crystalline solid
Drug information
Drug class	anticoagulant
properties
Melting point	140 ° C
safety instructions
Please note the restricted labeling requirements for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Enoxaparin sodium is a drug used to prevent blood clotting .

Chemical structure

Enoxaparin sodium is one of the low-molecular-weight heparins , i.e. it has the same structural elements as standard unfractionated heparin, but has a smaller average molecular size than this. Enoxaparin is a complex mixture of oligosaccharides , the chains of which are made up of glucosamine and uronic acid building blocks , which are glycosidically linked. The molecular chains consist of four to 24 monomers . Most chains have a 4-enopyranoseuronate structure at the non-reducing end. 15 to 25 percent of the components have a 1,6-anhydro structure at the reducing chain end.

The specification of the European Pharmacopoeia defines a degree of sulfation of around 2 per disaccharide unit and an average relative molecular weight in the range from 3800 to 5000, the characteristic value being around 4500. The sodium content is 11.3 to 13.5 percent, based on the dried substance.

Clinical information

application areas

Enoxaparin sodium inhibits the coagulation-promoting factor Xa . It is used for the treatment and prophylaxis of thrombosis (blood clots). It is suitable for the primary prophylaxis of deep vein thromboses in surgical and non-surgical patients at risk of thromboembolic events, for thrombosis prophylaxis and anticoagulation in extracorporeal circulation during hemodialysis , for the treatment of deep vein thromboses with and without pulmonary embolism . Furthermore, low molecular weight heparins (LMWH) represent an alternative to unfractionated heparin (UFH) in the treatment of unstable angina pectoris and non-Q-wave myocardial infarction (UA / NQMI). In patients with unstable angina pectoris or a myocardial infarction without ST- Elevation , enoxaparin reduces the frequency of clinical events in the acute phase of treatment by 20%.

Enoxaparin is approved for the following areas of application:

• all strengths: thrombosis prophylaxis and anticoagulation in extracorporeal circulation during hemodialysis.
• 20 mg / day: Primary prophylaxis of deep vein thrombosis: peri and postoperatively in patients with a low or medium thromboembolic risk (e.g. general surgery ).
• 40 mg / day: primary prophylaxis of deep vein thrombosis: peri- and postoperatively in patients with a high thromboembolic risk (e.g. in orthopedic surgery), primary prophylaxis of deep vein thrombosis in non-surgical patients with a medium or high thromboembolic risk in acute severe internal diseases ( Heart failure NYHA III or IV, infections , respiratory diseases) with extensive immobilization .
• 60 - 100 mg / day: Therapy of deep vein thrombosis with and without pulmonary embolism, therapy of unstable angina pectoris and non-ST segmentation myocardial infarction, therapy of acute ST segmentation myocardial infarction (STEMI), conservative or with subsequent PCI (Percutaneous coronary intervention).

type of application

Enoxaparin is injected under the skin , most commonly under the skin of the abdomen. It is intended for subcutaneous injection and must not be administered intramuscularly . Patients with renal insufficiency can be bridged by anticoagulation with enoxaparin with a corresponding dose reduction.

Contraindications

Enoxaparin sodium must not be used in case of hypersensitivity to enoxaparin or other low molecular weight heparins, nor in case of recent bleeding (e.g. from injury or surgery, clinically relevant gastrointestinal or urogenital bleeding, haemorrhagic stroke or other intracranial bleeding). It is also not allowed to be used in the case of clinically relevant coagulation disorders, gastric or intestinal ulcers, imminent abortion, severe liver or pancreatic diseases, uncontrollable severe hypertension or endocarditis.

Extraction and properties

As a low molecular weight heparin, enoxaparin is produced by the chemical depolymerization of porcine intestinal heparin. The processing ( extraction , fractionation ) of this raw material of biological origin determines the properties of the active ingredient.

Enoxaparin sodium, which is the reference for new agents in this area, has a characteristic and reproducible oligosaccharide profile , which is responsible for the specific pharmacological properties: Enoxaparin sodium has a higher and more uniform bioavailability after subcutaneous administration than unfractionated heparin has a longer plasma half-life and is less bound to plasma proteins.

Biosimilars for enoxaparin sodium have been on the market since 2017.

Trade names

Trade names: Clexane , Lovenox (manufacturer: Sanofi ) u. a.

Biosimilars : Hepaxane (manufacturer: ITF Pharma), Enoxaparin BECAT (manufacturer: Rovi ), Inhixa (manufacturer: Techdow), Thorinane (manufacturer: Pharmathen)

See also

• Anticoagulation
• Hemostasis
• Heparin-induced thrombocytopenia

Web links

• Enoxaparin Injection MedlinePlus

Individual evidence

1. ↑ ^{a b c d} data sheet Enoxaparin Sodium CRS (PDF) at EDQM , accessed on November 4, 2018.
2. ↑ Entry on enoxaparin. In: Römpp Online . Georg Thieme Verlag, accessed on December 28, 2014.
3. ↑ European Pharmacopoeia 8th Edition, 1st Supplement (2014), page 5427.
4. ^ Meyer Michel Samama et al .: A Comparison of Enoxaparin with Placebo for the Prevention of Venous Thromboembolism in Acutely Ill Medical Patients . In: The New England Journal of Medicine , 341, 1999, pp. 793-800. doi: 10.1056 / NEJM199909093411103
5. ↑ Clexane 20 mg / 40 mg ( Memento from February 17, 2015 in the Internet Archive ) (PDF; 77 kB) and Clexane Multidose 20/40/60/80/100/500/1000 mg (PDF; 109 kB) Specialist information: Summary the characteristics of the drug. Retrieved December 20, 2017.
6. ↑ Afshin Assadian : Enoxaparin in vascular surgery . ( Memento from February 21, 2014 in the Internet Archive ) Springer Verlag, 2009.
7. ↑ Antman EM, Cohen M, McCabe C, Goodman SG, Murphy SA, Braunwald E: Enoxaparin is superior to unfractionated heparin for preventing clinical events at 1-year follow-up of TIMI 11B and ESSENCE . In: European Heart Journal . 23, No. 4, February 2002, pp. 308-314. doi : 10.1053 / euhj.2001.2779 . PMID 11812067 .
8. ↑ Approval for Clexane ^® (enoxaparin sodium) extended to include ST elevation myocardial infarction (PDF) sanofi-aventis.de. September 24, 2007. Archived from the original on November 17, 2008. Retrieved on July 19, 2012.
9. ↑ H. Darius, K. Hester, G.-J. Sanderink, WD Paar, Antithrombotic therapy with low molecular weight heparins in renal insufficiency , Austrian Journal of Cardiology, 2004.
10. ↑ ^{a b} Brief description of Clexane ( Memento from November 5, 2013 in the Internet Archive ).
11. ^ Heyder Omran et al .: Perioperative bridging anticoagulation with enoxaparin . In: Medical Clinic , Volume 102, Number 10, 2007, pp. 809-815, doi: 10.1007 / s00063-007-1098-0 .
12. ↑ EMA (Ed.): Guideline on Non-Clinical and Clinical Development of Similar Biological Medicinal Products Containing Low-Molecular-Weight-Heparins . November 10, 2016 ( europa.eu [PDF; 64 kB ; accessed on November 4, 2018]).
13. ↑ C. Houiste et al .: Quantitative PCR and Disaccharide Profiling to Characterize the Animal Origin of Low-Molecular-Weight Heparins . In: Clinical and applied thrombosis / hemostasis. Volume 15, Number 1, February 2009, pp. 50-58, doi: 10.1177 / 1076029608320831 , PMID 18805847 .
14. ↑ J. Fareed, D. Hoppensteadt, J. Walenga, O. Iqbal, Q. Ma, W. Jeske, T. Sheikh: Pharmacodynamic and pharmacokinetic properties of enoxaparin: implications for clinical practice. In: Clinical Pharmacokinetics . Volume 42, number 12, 2003, pp. 1043-1057, doi: 10.2165 / 00003088-200342120-00003 , PMID 12959635 (review).
15. ↑ aerztezeitung.de: Enoxaparin biosimilar expands therapy options , October 20, 2017, accessed on November 4, 2018.
16. ↑ Enoxaparin Biosimilar made in Europe , PM on journalonko, accessed on November 14, 2018
17. ↑ Enoxaparinbecat.de , website of the manufacturer, accessed on November 14, 2018

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