MedKoo Cat#: 585216 | Name: Idraparinux

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Idraparinux is a synthetic pentasaccharide that binds to antithrombin with high affinity.

Chemical Structure

Idraparinux
Idraparinux
CAS#162610-17-5 (free base)

Theoretical Analysis

MedKoo Cat#: 585216

Name: Idraparinux

CAS#: 162610-17-5 (free base)

Chemical Formula: C38H64O49S7

Exact Mass: 1528.0561

Molecular Weight: 1529.30

Elemental Analysis: C, 29.84; H, 4.22; O, 51.26; S, 14.67

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
149920-56-9 (Na); 162610-17-5 (free base)
Synonym
Idraparinux; SR 34006; SR-34006; SR34006
IUPAC/Chemical Name
(2S,3S,4S,5R,6R)-6-[(2R,3R,4S,5R,6R)-6-[(2R,3S,4S,5R,6R)-2-carboxy-4,5-dimethoxy-6-[(2R,3R,4S,5R,6S)-6-methoxy-4,5-disulfooxy-2-(sulfooxymethyl)oxan-3-yl]oxyoxan-3-yl]oxy-4,5-disulfooxy-2-(sulfooxymethyl)oxan-3-yl]oxy-4,5-dimethoxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trimethoxy-6-(sulfooxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
InChi Key
AJBMORBNKXNZSF-COSHMZDQSA-N
InChi Code
InChI=1S/C38H64O49S7/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)/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
SMILES Code
O=C([C@H]1O[C@@H](O[C@@H]2[C@@H](COS(=O)(O)=O)O[C@H](O[C@@H]3[C@H](C(O)=O)O[C@@H](O[C@@H]4[C@@H](COS(=O)(O)=O)O[C@H](OC)[C@H](OS(=O)(O)=O)[C@H]4OS(=O)(O)=O)[C@H](OC)[C@H]3OC)[C@H](OS(=O)(O)=O)[C@H]2OS(=O)(O)=O)[C@H](OC)[C@@H](OC)[C@@H]1O[C@H]5O[C@H](COS(=O)(O)=O)[C@@H](OC)[C@H](OC)[C@H]5OC)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 1,529.30 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
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PubMed PMID: 29920657; PubMed Central PMCID: PMC6389342. 3: Farge D, Debourdeau P, Beckers M, Baglin C, Bauersachs RM, Brenner B, Brilhante D, Falanga A, Gerotzafias GT, Haim N, Kakkar AK, Khorana AA, Lecumberri R, Mandala M, Marty M, Monreal M, Mousa SA, Noble S, Pabinger I, Prandoni P, Prins MH, Qari MH, Streiff MB, Syrigos K, Bounameaux H, Büller HR. International clinical practice guidelines for the treatment and prophylaxis of venous thromboembolism in patients with cancer. J Thromb Haemost. 2013 Jan;11(1):56-70. doi: 10.1111/jth.12070. Review. PubMed PMID: 23217107. 4: Herbert JM, Hérault JP, Bernat A, van Amsterdam RG, Lormeau JC, Petitou M, van Boeckel C, Hoffmann P, Meuleman DG. Biochemical and pharmacological properties of SANORG 34006, a potent and long-acting synthetic pentasaccharide. Blood. 1998 Jun 1;91(11):4197-205. PubMed PMID: 9596667. 5: Łopatkiewicz G, Buda S, Mlynarski J. Application of the EF and GH Fragments to the Synthesis of Idraparinux. J Org Chem. 2017 Dec 1;82(23):12701-12714. doi: 10.1021/acs.joc.7b02497. Epub 2017 Nov 7. PubMed PMID: 29087187. 6: Idraparinux sodium: SANORG 34006, SR 34006. Drugs R D. 2004;5(3):164-5. Review. PubMed PMID: 15139779. 7: Harenberg J. Idraparinux and idrabiotaparinux. Expert Rev Clin Pharmacol. 2010 Jan;3(1):9-16. doi: 10.1586/ecp.09.55. PubMed PMID: 22111528. 8: Brandao GM, Junqueira DR, Rollo HA, Sobreira ML. Pentasaccharides for the treatment of deep vein thrombosis. Cochrane Database Syst Rev. 2017 Dec 2;12:CD011782. doi: 10.1002/14651858.CD011782.pub2. Review. PubMed PMID: 29199766; PubMed Central PMCID: PMC6486040. 9: Trellu M, Fau JB, Cortez P, Cheng S, Paty I, Boëlle E, Donat F, Sanderink GJ. Bioequipotency of idraparinux and idrabiotaparinux after once weekly dosing in healthy volunteers and patients treated for acute deep vein thrombosis. Br J Clin Pharmacol. 2013 May;75(5):1255-64. doi: 10.1111/bcp.12009. PubMed PMID: 23078631; PubMed Central PMCID: PMC3635596. 10: Prandoni P, Tormene D, Perlati M, Brandolin B, Spiezia L. Idraparinux: review of its clinical efficacy and safety for prevention and treatment of thromboembolic disorders. Expert Opin Investig Drugs. 2008 May;17(5):773-7. doi: 10.1517/13543784.17.5.773 . Review. PubMed PMID: 18447601. 11: van Gogh Investigators, Buller HR, Cohen AT, Davidson B, Decousus H, Gallus AS, Gent M, Pillion G, Piovella F, Prins MH, Raskob GE. Idraparinux versus standard therapy for venous thromboembolic disease. N Engl J Med. 2007 Sep 13;357(11):1094-104. PubMed PMID: 17855670. 12: Bijsterveld NR, Vink R, van Aken BE, Fennema H, Peters RJ, Meijers JC, Büller HR, Levi M. Recombinant factor VIIa reverses the anticoagulant effect of the long-acting pentasaccharide idraparinux in healthy volunteers. Br J Haematol. 2004 Mar;124(5):653-8. PubMed PMID: 14871253. 13: Bruins Slot KM, Berge E. Factor Xa inhibitors versus vitamin K antagonists for preventing cerebral or systemic embolism in patients with atrial fibrillation. Cochrane Database Syst Rev. 2018 Mar 6;3:CD008980. doi: 10.1002/14651858.CD008980.pub3. Review. PubMed PMID: 29509959; PubMed Central PMCID: PMC6494202. 14: van Gogh Investigators, Buller HR, Cohen AT, Davidson B, Decousus H, Gallus AS, Gent M, Pillion G, Piovella F, Prins MH, Raskob GE. Extended prophylaxis of venous thromboembolism with idraparinux. N Engl J Med. 2007 Sep 13;357(11):1105-12. PubMed PMID: 17855671. 15: Harenberg J. Development of idraparinux and idrabiotaparinux for anticoagulant therapy. Thromb Haemost. 2009 Nov;102(5):811-5. doi: 10.1160/TH09-08-0555. Review. PubMed PMID: 19888513. 16: Veyrat-Follet C, Vivier N, Trellu M, Dubruc C, Sanderink GJ. The pharmacokinetics of idraparinux, a long-acting indirect factor Xa inhibitor: population pharmacokinetic analysis from Phase III clinical trials. J Thromb Haemost. 2009 Apr;7(4):559-65. doi: 10.1111/j.1538-7836.2009.03298.x. Epub 2009 Jan 24. PubMed PMID: 19187079. 17: van Doormaal FF, Cohen AT, Davidson BL, Decousus H, Gallus AS, Gent M, Piovella F, Prins MH, Raskob GE, Büller HR. Idraparinux versus standard therapy in the treatment of deep venous thrombosis in cancer patients: a subgroup analysis of the Van Gogh DVT trial. Thromb Haemost. 2010 Jul;104(1):86-91. doi: 10.1160/TH09-12-0870. Epub 2010 May 27. PubMed PMID: 20508907. 18: Mező E, Eszenyi D, Varga E, Herczeg M, Borbás A. A Modular Synthetic Approach to Isosteric Sulfonic Acid Analogues of the Anticoagulant Pentasaccharide Idraparinux. Molecules. 2016 Nov 11;21(11). pii: E1497. PubMed PMID: 27845725; PubMed Central PMCID: PMC6274384. 19: Amadeus Investigators, Bousser MG, Bouthier J, Büller HR, Cohen AT, Crijns H, Davidson BL, Halperin J, Hankey G, Levy S, Pengo V, Prandoni P, Prins MH, Tomkowski W, Torp-Pedersen C, Wyse DG. 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 Jan 26;371(9609):315-21. doi: 10.1016/S0140-6736(08)60168-3. Erratum in: Lancet. 2008 Dec 13;372(9655):2022.. Thorp-Pedersen, C [corrected to Torp-Pedersen, C]. PubMed PMID: 18294998. 20: Dong K, Song Y, Li X, Ding J, Gao Z, Lu D, Zhu Y. Pentasaccharides for the prevention of venous thromboembolism. Cochrane Database Syst Rev. 2016 Oct 31;10:CD005134. Review. PubMed PMID: 27797404; PubMed Central PMCID: PMC6463830.