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Revision as of 12:52, 2 December 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: InChI1->InChI StdInChI StdInChIKey.← Previous edit Revision as of 13:03, 2 December 2010 edit undoCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref') per Chem/Drugbox validation (report [[Misplaced Pages talk:WiNext edit →
Line 1: Line 1:
{{Drugbox {{Drugbox
| 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>
[(2''R'',3''S'',4''S'',5''R'',6''R'')-2-carboxylato-<br> [(2''R'',3''S'',4''S'',5''R'',6''R'')-2-carboxylato-<br>
Line 9: Line 10:
6-(sulfonatooxymethyl)oxan-2-yl]oxyoxane-<br>2-carboxylate 6-(sulfonatooxymethyl)oxan-2-yl]oxyoxane-<br>2-carboxylate
| image = Idraparinux.png | image = Idraparinux.png
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2340656 | ChemSpiderID = 2340656
| 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
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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 | StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MVPQUSQUURLQKF-MCPDASDXSA-E | StdInChIKey = MVPQUSQUURLQKF-MCPDASDXSA-E
| CAS_number = 149920-56-9 | CAS_number = 149920-56-9

Revision as of 13:03, 2 December 2010

Pharmaceutical compound
Idraparinux
Clinical data
Routes of
administration		Subcutaneous
ATC code
  • none
Legal status
Legal status
  • Investigational
Pharmacokinetic data
Elimination half-life80-130 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
PubChem CID
ChemSpider
Chemical and physical data
FormulaC38H55Na9O49S7
Molar mass1727.17683 g/mol g·mol
3D model (JSmol)
SMILES
  • CO1(O((1OC)OC)O2(((O2C(=O))O3(O((3OS(=O)(=O))OS(=O)(=O))O4(((O4C(=O))O5(O((5OS(=O)(=O))OS(=O)(=O))OC)COS(=O)(=O))OC)OC)COS(=O)(=O))OC)OC)COS(=O)(=O).........
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.

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.

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)
Antithrombotics (thrombolytics, anticoagulants and antiplatelet drugs) (B01)
Antiplatelet drugs
Glycoprotein IIb/IIIa inhibitors
ADP receptor/P2Y12 inhibitors
Prostaglandin analogue (PGI2)
COX inhibitors
Thromboxane inhibitors
Phosphodiesterase inhibitors
Other
Anticoagulants
Vitamin K antagonists
(inhibit II, VII, IX, X)
Factor Xa inhibitors
(with some II inhibition)
Heparin group/
glycosaminoglycans/
(bind antithrombin)
Direct Xa inhibitors ("xabans")
Direct thrombin (IIa) inhibitors
Other
Thrombolytic drugs/
fibrinolytics
Non-medicinal
Categories: