Idraparinux

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

MedKoo CAT#: 585216

CAS#: 162610-17-5

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


Chemical Structure

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Idraparinux
CAS# 162610-17-5

Theoretical Analysis

MedKoo Cat#: 585216
Name: Idraparinux
CAS#: 162610-17-5
Chemical Formula: C38H64O49S7
Exact Mass: 1528.0561
Molecular Weight: 1529.301
Elemental Analysis: C, 29.84; H, 4.22; O, 51.26; S, 14.67

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

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

Preparing Stock Solutions

The following data is based on the product molecular weight 1529.301 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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1: Song Y, Li X, Pavithra S, Li D. Idraparinux or idrabiotaparinux for long-term venous thromboembolism treatment: a systematic review and meta-analysis of randomized controlled trials. PLoS One. 2013 Nov 20;8(11):e78972. doi: 10.1371/journal.pone.0078972. eCollection 2013. Review. PubMed PMID: 24278113; PubMed Central PMCID: PMC3835858.

2: Kahale LA, Hakoum MB, Tsolakian IG, Matar CF, Terrenato I, Sperati F, Barba M, Yosuico VE, Schünemann H, Akl EA. Anticoagulation for the long-term treatment of venous thromboembolism in people with cancer. Cochrane Database Syst Rev. 2018 Jun 19;6:CD006650. doi: 10.1002/14651858.CD006650.pub5. Review. 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.