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Wikipedia - Fondaparinux

Fondaparinux
Systematic (IUPAC) name
2-deoxy-6-O-sulfo-2-(sulfoamino)-a-D-glucopyranosyl-(1?

4)-O-ß-D-glucopyranuronosyl-(1?4)-O-2-deoxy-3,6-di-O-sulfo-2- (sulfoamino)-a-D-glucopyranosyl-(1?4)-O-2-O-sulfo-a-L-idopyranouronosyl-(1? 4)-O-methyl-2-deoxy-6-O-sulfo-2-(sulfoamino)-a-D-glucopyranoside, decasodium salt.
Identifiers
CAS number 114870-03-0
ATC code B01AX05
PubChem CID 636380
DrugBank APRD00500
Chemical data
Formula C31H43N3Na10O49S8 
Mol. mass 1726.77 g/mol
Pharmacokinetic data
Bioavailability N/A
Protein binding 94%
Metabolism renally excreted unchanged
Half-life 17-21 hours
Therapeutic considerations
Licence data

EU EMA:link, US FDA:link
Pregnancy cat.  ?
Legal status POM (UK) ?-only (US)
Routes subcutaneous

Fondaparinux (Arixtra) is an anticoagulant medication.

It is marketed by GlaxoSmithKline.

Contents

[edit] Structure and mechanism

See also: Heparin#Mechanism of action

Fondaparinux is a synthetic pentasaccharide as evident by its chemical structure on the right. Apart from the O-methyl group at the reducing end of the molecule, the identity and sequence of the five monomeric sugar units contained in fondaparinux is identical to a sequence of five monomeric sugar units that can be isolated after either chemical or enzymatic cleavage of the polymeric glycosaminoglycans heparin and heparan sulfate (HS). Within heparin and heparan sulfate this monomeric sequence is thought to form the high affinity binding site for the anti-coagulant factor antithrombin III (ATIII). Binding of heparin/HS to ATIII has been shown to increase the anti-coagulant activity of antithrombin III 1000 fold.

[edit] Administration

Fondaparinux is given subcutaneously daily. Clinically, it is used for the prevention of deep vein thrombosis in patients who have had orthopedic surgery as well as for the treatment of deep vein thrombosis and pulmonary embolism.

[edit] Comparison to other agents

One potential advantage of fondaparinux over LMWH or unfractionated heparin is that the risk for heparin-induced thrombocytopenia is substantially lower. Furthermore, there have been case reports of fondaparinux being used to anticoagulate patients with established HIT as it has no affinity to PF-4. However, its renal excretion precludes its use in patients with renal dysfunction.

Unlike direct factor Xa inhibitors, it mediates its effects indirectly through antithrombin III, but unlike heparin, it is selective for factor Xa.[1]

[edit] Uses

Fondaparinux is similar to enoxaparin in reducing the risk of ischemic events at nine days, but it substantially reduces major bleeding and improves long term mortality and morbidity.[2]

It has been investigated for use in conjunction with streptokinase.[3]

[edit] Chemical structure

[edit] Abbreviations

  • GlcNS(6S) = 2-deoxy-6-O-sulfo-2-(sulfoamino)-a-D-glucopyranoside
  • GlcA = ß-D-glucopyranuronosyl
  • GlcNS(3S,6S) = 2-deoxy-3,6-di-O-sulfo-2-(sulfoamino)-a-D-glucopyranosyl
  • IdoA(2S) = 2-O-sulfo-a-L-idopyranuronosyl
  • GlcNS(6S)OMe = methyl-O-2-deoxy-6-O-sulfo-2-(sulfoamino)-a-D-glucopyranoside
Fondaparinux

[edit] References

  1. ^ "Medscape.com". http://www.medscape.com/viewarticle/456874_5. Retrieved 2009-01-23. 
  2. ^ "NEJM -- Comparison of Fondaparinux and Enoxaparin in Acute Coronary Syndromes". http://content.nejm.org/cgi/content/abstract/354/14/1464. Retrieved 2009-01-23. 
  3. ^ Peters RJ, Joyner C, Bassand JP, et al. (February 2008). "The role of fondaparinux as an adjunct to thrombolytic therapy in acute myocardial infarction: a subgroup analysis of the OASIS-6 trial". Eur. Heart J. 29 (3): 324–31. doi:10.1093/eurheartj/ehm616. PMID 18245119. http://eurheartj.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=18245119. 

[edit] External links

v • d • e
Antithrombotics (thrombolytics, anticoagulants and antiplatelet drugs) (B01)
Antiplatelet drugs
Thromboxane inhibitors
Other
Anticoagulants
Factor Xa inhibitors
(with some II inhibition)
Other
Thrombolytic drugs/
fibrinolytics
Non-medicinal
Citrate • EDTA • Oxalate
Retrieved from "http://en.wikipedia.org/wiki/Fondaparinux"

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Fondaparinux".

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