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'''Idraparinux sodium''' is an [[anticoagulant]] medication in development by [[Sanofi-Aventis]].<ref name="pmid18294998">{{cite journal |author=Bousser MG, Bouthier J, Büller HR, ''et al.'' |title=Comparison of idraparinux with vitamin K antagonists for prevention of thromboembolism in patients with atrial fibrillation: a randomised, open-label, non-inferiority trial |journal=Lancet |volume=371 |issue=9609 |pages=315–21 |year=2008 |month=January |pmid=18294998 |doi=10.1016/S0140-6736(08)60168-3 |url=http://linkinghub.elsevier.com/retrieve/pii/S0140-6736(08)60168-3}}</ref>
'''Idraparinux sodium''' is an [[anticoagulant]] medication in development by [[Sanofi-Aventis]].<ref name="pmid18294998">{{cite journal |author=Bousser MG, Bouthier J, Büller HR, ''et al.'' |title=Comparison of idraparinux with vitamin K antagonists for prevention of thromboembolism in patients with atrial fibrillation: a randomised, open-label, non-inferiority trial |journal=Lancet |volume=371 |issue=9609 |pages=315–21 |date=January 2008 |pmid=18294998 |doi=10.1016/S0140-6736(08)60168-3 |url=http://linkinghub.elsevier.com/retrieve/pii/S0140-6736(08)60168-3}}</ref>


It has a similar chemical structure and the same method of action as [[fondaparinux]], but with an elimination half-life about five to six times longer (an increase from fondaparinux's 17 hours to approximately 80 hours), which means that the drug should only need to be injected once a week.
It has a similar chemical structure and the same method of action as [[fondaparinux]], but with an elimination half-life about five to six times longer (an increase from fondaparinux's 17 hours to approximately 80 hours), which means that the drug should only need to be injected once a week.
Line 57: Line 57:


==Method of action==
==Method of action==
Idraparinux selectively blocks [[coagulation factor Xa]].<ref name="pmid17855670">{{cite journal |author=Buller HR, Cohen AT, Davidson B, ''et al.'' |title=Idraparinux versus standard therapy for venous thromboembolic disease |journal=N. Engl. J. Med. |volume=357 |issue=11 |pages=1094–104 |year=2007 |month=September |pmid=17855670 |doi=10.1056/NEJMoa064247 |url=http://content.nejm.org/cgi/pmidlookup?view=short&pmid=17855670&promo=ONFLNS19}}</ref>
Idraparinux selectively blocks [[coagulation factor Xa]].<ref name="pmid17855670">{{cite journal |author=Buller HR, Cohen AT, Davidson B, ''et al.'' |title=Idraparinux versus standard therapy for venous thromboembolic disease |journal=N. Engl. J. Med. |volume=357 |issue=11 |pages=1094–104 |date=September 2007 |pmid=17855670 |doi=10.1056/NEJMoa064247 |url=http://content.nejm.org/cgi/pmidlookup?view=short&pmid=17855670&promo=ONFLNS19}}</ref>


See [[Heparin#Mechanism of anticoagulant action|Heparin: Mechanism of anticoagulant action]] for a comparison of the mechanism of heparin, low-molecular-weight heparins, fondaparinux and idraparinux.
See [[Heparin#Mechanism of anticoagulant action|Heparin: Mechanism of anticoagulant action]] for a comparison of the mechanism of heparin, low-molecular-weight heparins, fondaparinux and idraparinux.

Revision as of 20:35, 21 January 2014

Idraparinux
Clinical data
Routes of
administration		Subcutaneous
ATC code
  • none
Legal status
Legal status
  • Investigational
Pharmacokinetic data
Elimination half-life80-130 hours
Identifiers
  • Nonasodium (2S,3S,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-6-
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC38H55Na9O49S7
Molar mass1727.17683 g/mol g·mol−1
3D model (JSmol)
  • CO[C@@H]1[C@H](O[C@@H]([C@@H]([C@H]1OC)OC)O[C@H]2[C@@H]([C@H]([C@@H](O[C@@H]2C(=O)[O-])O[C@@H]3[C@H](O[C@@H]([C@@H]([C@H]3OS(=O)(=O)[O-])OS(=O)(=O)[O-])O[C@H]4[C@@H]([C@H]([C@@H](O[C@H]4C(=O)[O-])O[C@@H]5[C@H](O[C@@H]([C@@H]([C@H]5OS(=O)(=O)[O-])OS(=O)(=O)[O-])OC)COS(=O)(=O)[O-])OC)OC)COS(=O)(=O)[O-])OC)OC)COS(=O)(=O)[O-].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+]
  • InChI=1S/C38H64O49S7.9Na/c1-64-15-12(9-72-88(43,44)45)76-35(27(68-5)18(15)65-2)80-21-19(66-3)28(69-6)37(82-25(21)32(39)40)79-17-14(11-74-90(49,50)51)77-38(31(87-94(61,62)63)24(17)85-92(55,56)57)81-22-20(67-4)29(70-7)36(83-26(22)33(41)42)78-16-13(10-73-89(46,47)48)75-34(71-8)30(86-93(58,59)60)23(16)84-91(52,53)54;;;;;;;;;/h12-31,34-38H,9-11H2,1-8H3,(H,39,40)(H,41,42)(H,43,44,45)(H,46,47,48)(H,49,50,51)(H,52,53,54)(H,55,56,57)(H,58,59,60)(H,61,62,63);;;;;;;;;/q;9*+1/p-9/t12-,13-,14-,15-,16-,17-,18+,19+,20+,21+,22+,23+,24+,25+,26-,27-,28-,29-,30-,31-,34+,35-,36-,37-,38-;;;;;;;;;/m1........./s1 checkY
  • Key:MVPQUSQUURLQKF-MCPDASDXSA-E checkY
  (verify)

Idraparinux sodium is an anticoagulant medication in development by Sanofi-Aventis.[1]

It has a similar chemical structure and the same method of action as fondaparinux, but with an elimination half-life about five to six times longer (an increase from fondaparinux's 17 hours to approximately 80 hours), which means that the drug should only need to be injected once a week.

As of July 2007, it has completed the Phase III clinical trial AMADEUS.

Method of action

Idraparinux selectively blocks coagulation factor Xa.[2]

See Heparin: Mechanism of anticoagulant action for a comparison of the mechanism of heparin, low-molecular-weight heparins, fondaparinux and idraparinux.

References

  1. ^ Bousser MG, Bouthier J, Büller HR; et al. (January 2008). "Comparison of idraparinux with vitamin K antagonists for prevention of thromboembolism in patients with atrial fibrillation: a randomised, open-label, non-inferiority trial". Lancet. 371 (9609): 315–21. doi:10.1016/S0140-6736(08)60168-3. PMID 18294998. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)
  2. ^ Buller HR, Cohen AT, Davidson B; et al. (September 2007). "Idraparinux versus standard therapy for venous thromboembolic disease". N. Engl. J. Med. 357 (11): 1094–104. doi:10.1056/NEJMoa064247. PMID 17855670. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)
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