Fondaparinux

drugbox


width = 500
IUPAC_name =2-deoxy-6-O-sulfo-2-(sulfoamino)-α-D-glucopyranosyl-(1→4)-O-β-D-glucopyranuronosyl-(1→4)-O-2-deoxy-3,6-di-O-sulfo-2-(sulfoamino)-α-D-glucopyranosyl-(1→4)-O-2-O-sulfo-α-L-idopyranouronosyl-(1→4)-O-methyl-2-deoxy-6-O-sulfo-2-(sulfoamino)-α-D-glucopyranoside, decasodium salt.
CAS_number = 114870-03-0
ATC_prefix = B01
ATC_suffix = AX05
ATC_supplemental =
PubChem = 636380
DrugBank = APRD00500
C=31 | H=43 | N=3 | Na=10 | O=49 | S=8
molecular_weight = 1726.77 g/mol
bioavailability = N/A
protein_bound = 94%
metabolism = renally excreted unchanged
elimination_half-life = 17-21 hours
pregnancy_category =
legal_UK = POM
legal_US = Rx-only
legal_status =
routes_of_administration = subcutaneous
licence_EU =Arixtra
licence_US =Fondaparinux

Fondaparinux (Arixtra) is an anticoagulant medication.

As shown in the box to the right, fondaparinux is a synthetic pentasaccharide. 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. See the heparin article for a detailed rationale behind the development of fondaparinux as an anticoagulant.

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.

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.

Randomized Controlled Trials

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. [http://content.nejm.org/cgi/content/abstract/354/14/1464]

Chemical structure

Abbreviations

*GlcNS(6S) = 2-deoxy-6-O-sulfo-2-(sulfoamino)-α-D-glucopyranoside
*GlcA = β-D-glucopyranuronosyl
*GlcNS(3S,6S) = 2-deoxy-3,6-di-O-sulfo-2-(sulfoamino)-α-D-glucopyranosyl
*IdoA(2S) = 2-O-sulfo-α-L-idopyranuronosyl
*GlcNS(6S)OMe = methyl-O-2-deoxy-6-O-sulfo-2-(sulfoamino)-α-D-glucopyranoside

External links

* [http://www.arixtra.com/ Arixtra home page]