Idraparinux: Difference between revisions

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-; [(2R,3S,4S,5R,6R)-2-carboxylato-; 4,5-dimethoxy-6-[(2R,3R,4S,5R,6S)-6-methoxy-4,5-; disulfonatooxy-2-(sulfonatooxymethyl)oxan-3-yl]; oxyoxan-3-yl]oxy-4,5-disulfonatooxy-; 2-(sulfonatooxymethyl)oxan-3-yl]oxy-4,5-dimethoxy-; 3-[(2R,3R,4S,5R,6R)-3,4,5-trimethoxy-; 6-(sulfonatooxymethyl)oxan-2-yl]oxyoxane-; 2-carboxylate;
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+];

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Revision as of 12:36, 1 November 2010

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^[update], 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

^ Bousser MG, Bouthier J, Büller HR; et al. (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); Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
^ Buller HR, Cohen AT, Davidson B; et al. (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); Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

[pmid18294998-1] Bousser MG, Bouthier J, Büller HR; et al. (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); Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

[pmid17855670-2] Buller HR, Cohen AT, Davidson B; et al. (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); Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)

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@@ Line 9: / Line 9: @@
 -(sulfonatooxymethyl)oxan-2-yl]oxyoxane-<br>2-carboxylate
 | image             = Idraparinux.png
+| ChemSpiderID = 2340656
+| InChI1 = 1/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
+| InChIKey1 = MVPQUSQUURLQKF-KRAUNZEEBS
 | CAS_number        = 149920-56-9
 | CAS_supplemental  =