Idraparinux

Idraparinux
Clinical data
Routes of; administration	Subcutaneous
ATC code	none;
Legal status
Legal status	Investigational;
Pharmacokinetic data
Elimination half-life	80-130 hours
Identifiers
	IUPAC name Nonasodium (2S,3S,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-6-;
CAS Number	149920-56-9 ;
PubChem CID	3083444;
ChemSpider	2340656 ;
Chemical and physical data
Formula	C38H55Na9O49S7
Molar mass	1727.17683 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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 ; Key:MVPQUSQUURLQKF-MCPDASDXSA-E ;
	(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.

Sanofi discontinued the development of idraparinux sodium.

Negative clinical trial

A phase III trial of idraparinux sodium for stroke prevention in patients with AF (AMADEUS) was halted prematurely due to excessive clinically relevant and intracranial bleeding. Sanofi discontinued the development of idraparinux sodium in favour of a biotinylated formulation of the drug called idrabiotaparinux sodium.^[2]^[3]

Method of action

Idraparinux selectively blocks coagulation factor Xa.^[4]

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

Spin off: idrabiotaparinux sodium

Sanofi conducted three phase III trials of idrabiotaparinux sodium between 2006 and 2008 in approximately 13,550 patients. In one phase III trial, idrabiotaparinux sodium was non-inferior to warfarin in preventing the recurrent VTE at three months in patients with pulmonary embolism and the incidence of clinically relevant bleeding was lower in the idrabiotaparinux sodium arm. The drug was expected to be filed for stroke prevention in patients with AF in 2011. However, Sanofi has since discontinued its development. The company announced in May 2011 that the drug is available for licensing. ^[5]

References

^ 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)
^ Modern anticoagulants threaten status quo http://www.pmlive.com/pharma_intelligence/modern_anticoagulants_threaten_status_quo_411610
^ The Amadeus investigators. Comparison of idraparinux with vitamin K antagonists for prevention of thromboembolism in patients with atrial fibrillation: a randomised, open-label, non-inferiority trial. Lancet 2008; 371:315-321.
^ 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)
^ Modern anticoagulants threaten status quo http://www.pmlive.com/pharma_intelligence/modern_anticoagulants_threaten_status_quo_411610

[pmid18294998-1] 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] Modern anticoagulants threaten status quo http://www.pmlive.com/pharma_intelligence/modern_anticoagulants_threaten_status_quo_411610

[3] The Amadeus investigators. Comparison of idraparinux with vitamin K antagonists for prevention of thromboembolism in patients with atrial fibrillation: a randomised, open-label, non-inferiority trial. Lancet 2008; 371:315-321.

[pmid17855670-4] 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)

[5] Modern anticoagulants threaten status quo http://www.pmlive.com/pharma_intelligence/modern_anticoagulants_threaten_status_quo_411610

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