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Updating {{drugbox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref') per Chem/Drugbox validation (report [[Wikipedia talk:Wi
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{{Drugbox
{{Drugbox
| verifiedrevid = 400114453
| verifiedrevid = 400114453
| IUPAC_name = Nonasodium (2''S'',3''S'',4''S'',5''R'',6''R'')-6-[(2''R'',3''R'',4''S'',5''R'',6''R'')-6-<br>
| IUPAC_name = Nonasodium (2''S'',3''S'',4''S'',5''R'',6''R'')-6-[(2''R'',3''R'',4''S'',5''R'',6''R'')-6-<br>
⚫
| image = Idraparinux.png
[(2''R'',3''S'',4''S'',5''R'',6''R'')-2-carboxylato-<br>

4,5-dimethoxy-6-[(2''R'',3''R'',4''S'',5''R'',6''S'')-6-methoxy-4,5-<br>
<!--Clinical data-->
disulfonatooxy-2-(sulfonatooxymethyl)oxan-3-yl]<br>
| tradename =
oxyoxan-3-yl]oxy-4,5-disulfonatooxy-<br>
⚫
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
2-(sulfonatooxymethyl)oxan-3-yl]oxy-4,5-dimethoxy-<br>
⚫
| pregnancy_US = <!-- A / B / C / D / X -->
3-[(2''R'',3''R'',4''S'',5''R'',6''R'')-3,4,5-trimethoxy-<br>
⚫
| pregnancy_category =
6-(sulfonatooxymethyl)oxan-2-yl]oxyoxane-<br>2-carboxylate
⚫
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
⚫
| image = Idraparinux.png
⚫
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
⚫
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
⚫
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
⚫
| legal_status = Investigational
⚫
| routes_of_administration = Subcutaneous

<!--Pharmacokinetic data-->
⚫
| bioavailability =
⚫
| protein_bound =
⚫
| metabolism =
⚫
| elimination_half-life = 80-130 hours
⚫
| excretion =

<!--Identifiers-->
⚫
| CAS_number = 149920-56-9
⚫
| ATC_prefix = none
⚫
| ATC_suffix =
⚫
| ATC_supplemental =
⚫
| PubChem = 3083444
⚫
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2340656
| ChemSpiderID = 2340656

<!--Chemical data-->
⚫
| chemical_formula =
⚫
| C=38 | H=55 | Na=9 | O=49 | S=7
⚫
| molecular_weight = 1727.17683 g/mol
⚫
| 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 = 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
| InChI = 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
| InChIKey = MVPQUSQUURLQKF-KRAUNZEEBS
| InChIKey = MVPQUSQUURLQKF-KRAUNZEEBS
Line 18: Line 44:
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MVPQUSQUURLQKF-MCPDASDXSA-E
| StdInChIKey = MVPQUSQUURLQKF-MCPDASDXSA-E
⚫
| CAS_number = 149920-56-9
| CAS_supplemental =
⚫
| ATC_prefix = none
⚫
| ATC_suffix =
⚫
| ATC_supplemental =
⚫
| PubChem = 3083444
⚫
| DrugBank =
⚫
| chemical_formula =
⚫
| C=38 | H=55 | Na=9 | O=49 | S=7
⚫
| molecular_weight = 1727.17683 g/mol
⚫
| 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+]
⚫
| bioavailability =
⚫
| protein_bound =
⚫
| metabolism =
⚫
| elimination_half-life = 80-130 hours
⚫
| excretion =
⚫
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫
| pregnancy_US = <!-- A / B / C / D / X -->
⚫
| pregnancy_category=
⚫
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
⚫
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
⚫
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
⚫
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
⚫
| legal_status = Investigational
⚫
| routes_of_administration = Subcutaneous
}}
}}
<!-- MeSHName=SANORG+34006 -->
<!-- MeSHName=SANORG+34006 -->

Revision as of 07:18, 3 September 2011

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. (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)
  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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