| Catalog Number | I000553 |
| CAS Number | 114870-03-0 |
| Synonyms | Fondaparinux sodium
|
| Molecular Formula | C31H44N3Na10O49S8 |
| Purity | ≥95% |
| Target | Factor Xa |
| Solubility | H2O: ≥ 30 mg/mL |
| Storage | Store at -20°C |
| IUPAC Name | decasodium;(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5R,6R)-6-[(2R,3S,4S,5R,6R)-2-carboxylato-4-hydroxy-6-[(2R,3S,4R,5R,6S)-4-hydroxy-6-methoxy-5-(sulfonatoamino)-2-(sulfonatooxymethyl)oxan-3-yl]oxy-5-sulfonatooxyoxan-3-yl]oxy-5-(sulfonatoamino)-4-sulfonatooxy-2-(sulfonatooxymethyl)oxan-3-yl]oxy-3-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-(sulfonatoamino)-6-(sulfonatooxymethyl)oxan-2-yl]oxy-4,5-dihydroxyoxane-2-carboxylate |
| InChI | InChI=1S/C31H53N3O49S8.10Na/c1-69-27-9(33-85(48,49)50)13(37)17(6(74-27)3-71-88(57,58)59)76-31-22(83-91(66,67)68)16(40)21(24(81-31)26(43)44)79-29-10(34-86(51,52)53)19(82-90(63,64)65)18(7(75-29)4-72-89(60,61)62)77-30-15(39)14(38)20(23(80-30)25(41)42)78-28-8(32-84(45,46)47)12(36)11(35)5(73-28)2-70-87(54,55)56;;;;;;;;;;/h5-24,27-40H,2-4H2,1H3,(H,41,42)(H,43,44)(H,45,46,47)(H,48,49,50)(H,51,52,53)(H,54,55,56)(H,57,58,59)(H,60,61,62)(H,63,64,65)(H,66,67,68);;;;;;;;;;/q;10*+1/p-10/t5-,6-,7-,8-,9-,10-,11-,12-,13-,14-,15-,16+,17-,18-,19-,20+,21+,22-,23+,24-,27+,28-,29-,30-,31-;;;;;;;;;;/m1........../s1 |
| InChIKey | XEKSTYNIJLDDAZ-JASSWCPGSA-D |
| SMILES | CO[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)COS(=O)(=O)[O-])O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](O2)C(=O)[O-])O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)COS(=O)(=O)[O-])O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C(=O)[O-])O[C@@H]5[C@@H]([C@H]([C@@H]([C@H](O5)COS(=O)(=O)[O-])O)O)NS(=O)(=O)[O-])O)O)OS(=O)(=O)[O-])NS(=O)(=O)[O-])O)OS(=O)(=O)[O-])O)NS(=O)(=O)[O-].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+] |
| Reference | 1. Drugs. 2004;64(14):1575-96. <br />
Fondaparinux sodium: a review of its use in the prevention of venous
thromboembolism following major orthopaedic surgery. <br />
Reynolds NA(1), Perry CM, Scott LJ. <br />
Author information: <br />
(1)Adis International Limited, 41 Centorian Drive, PB 65901, Mairangi Bay,
Auckland 1311, New Zealand. [email protected] <br />
Fondaparinux sodium (Arixtra; fondaparinux) is the first of a new class of
synthetic pentasaccharide anticoagulants that bind to antithrombin and inhibit
the action of factor Xa. In three large, well designed trials, subcutaneous
fondaparinux 2.5mg once daily was more effective than subcutaneous enoxaparin
sodium (enoxaparin) 30 mg twice daily or 40 mg once daily at preventing venous
thromboembolism (VTE) at day 11 in patients undergoing hip replacement, elective
major knee or hip fracture surgery; a fourth trial demonstrated similar efficacy
to enoxaparin 30 mg twice daily in hip replacement. Fondaparinux recipients had a
lower incidence of proximal deep vein thrombosis (DVT) in two studies. In a
meta-analysis of the four trials, patients receiving fondaparinux had a >50%
reduction in the relative risk of VTE at day 11. Fondaparinux compared favourably
with enoxaparin in several pharmacoeconomic analyses. In a large, controlled
trial in hip fracture patients, extended prophylaxis with fondaparinux (duration
25-31 days) substantially reduced the incidence of VTE at day 25-32 compared with
prophylaxis for 6-8 days, and was a cost-effective treatment strategy. Moreover,
extended prophylaxis significantly decreased the rate of proximal, total and
distal DVT and symptomatic VTE. Fondaparinux was generally well tolerated in
clinical trials in patients undergoing major orthopaedic surgery. However,
following major knee surgery and in a meta-analysis of pooled data from four
trials, fondaparinux recipients had a significantly higher incidence of overt
bleeding with a bleeding index > or =2, but no increase in fatal bleeding,
bleeding into a critical organ or bleeding leading to reoperation. The bleeding
risk is related to the timing of the first dose and when fondaparinux was
initiated between 6 and 8 hours after surgery, the bleeding risk was similar to
enoxaparin. Extended prophylaxis with fondaparinux was not associated with a
significantly increased risk of bleeding events. In conclusion, fondaparinux is
more effective than enoxaparin at preventing postoperative VTE in patients
undergoing elective hip replacement, major knee or hip fracture surgery. Extended
therapy with fondaparinux considerably increases its efficacy without a
significant increase in the incidence of bleeding episodes. Fondaparinux was
generally well tolerated in clinical trials. Fondaparinux is an effective and
useful alternative to low molecular weight heparins for the prevention of VTE
following major orthopaedic surgery. <br />
2. Am J Health Syst Pharm. 2001 Nov 1;58 Suppl 2:S14-7. <br />
Fondaparinux sodium: a selective inhibitor of factor Xa. <br />
Bauer KA(1). <br />
Author information: <br />
(1)Hematology Section, VA Boston Healthcare System, Beth Israel Deaconess Medical
Center, MA, USA. [email protected] <br />
The pharmacology and mechanism of action of fondaparinux sodium are described.
Fondaparinux sodium is the first agent of a new class of anticoagulants that
selectively target factor Xa. It has a linear, dose-dependent pharmacokinetic
profile, which provides a highly predictable response. It is 100% bioavailable,
has a rapid onset of action, and has a half-life of 14 to 16 hours, allowing for
sustained antithrombotic activity over a 24-hour period. The drug does not affect
prothrombin time or activated partial thromboplastin time, nor does it affect
platelet function or aggregation. Studies in patients with confirmed
heparin-induced thrombocytopenia demonstrate that the drug is not associated with
in vitro cross-reactivity to heparin antibodies. Fondaparinux sodium appears to
meet the criteria for an ideal antithrombotic agent: equal or better
effectiveness than currently available agents, a low bleeding risk, no need for
laboratory monitoring, and once-daily administration. <br />
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