Otamixaban
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MedKoo CAT#: 326792

CAS#: 193153-04-7 (free base)

Description: Otamixaban, also known as XRP0673, is an experimental injectable anticoagulant direct factor Xa inhibitor, that was investigated for the treatment for acute coronary syndrome. In 2013, Sanofi announced that it had ended development of the drug candidate after poor performance in a Phase III clinical trial.


Chemical Structure

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Otamixaban
CAS# 193153-04-7 (free base)

Theoretical Analysis

MedKoo Cat#: 326792
Name: Otamixaban
CAS#: 193153-04-7 (free base)
Chemical Formula: C25H26N4O4
Exact Mass: 446.1954
Molecular Weight: 446.507
Elemental Analysis: C, 67.25; H, 5.87; N, 12.55; O, 14.33

Price and Availability

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10.0mg USD 695.0 2 Weeks
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Related CAS #: 409081-12-5 (HCl); 193153-04-7 (free base)  

Synonym: XRP0673; XRP-0673; XRP 0673; Otamixaban

IUPAC/Chemical Name: Methyl (2R,3R)-2-(3-carbamimidoylbenzyl)-3-((4-(1-oxidopyridin-4-yl)benzoyl)amino)butanoate

InChi Key: PFGVNLZDWRZPJW-OPAMFIHVSA-N

InChi Code: InChI=1S/C25H26N4O4/c1-16(22(25(31)33-2)15-17-4-3-5-21(14-17)23(26)27)28-24(30)20-8-6-18(7-9-20)19-10-12-29(32)13-11-19/h3-14,16,22H,15H2,1-2H3,(H3,26,27)(H,28,30)/t16-,22-/m1/s1

SMILES Code: C[C@@H](NC(C1=CC=C(C2=CC=[N+]([O-])C=C2)C=C1)=O)[C@@H](CC3=CC=CC(C(N)=N)=C3)C(OC)=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: >2 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 446.507 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: Roberts A. Anticoagulation therapy: Otamixaban fails in NSTE-ACS. Nat Rev Cardiol. 2013 Nov;10(11):615. doi: 10.1038/nrcardio.2013.134. Epub 2013 Sep 17. PubMed PMID: 24042230.

2: Steg PG, Mehta SR, Pollack CV Jr, Bode C, Cohen M, French WJ, Hoekstra J, Rao SV, Ruzyllo W, Ruiz-Nodar JM, Sabaté M, Widimsky P, Kiss RG, Navarro Estrada JL, Hod H, Kerkar P, Guneri S, Sezer M, Ruda M, Nicolau JC, Cavallini C, Ebrahim I, Petrov I, Kim JH, Jeong MH, Ramos Lopez GA, Laanmets P, Kovar F, Gaudin C, Fanouillere KC, Minini P, Hoffman EB, Moryusef A, Wiviott SD, Sabatine MS; TAO Investigators. Anticoagulation with otamixaban and ischemic events in non-ST-segment elevation acute coronary syndromes: the TAO randomized clinical trial. JAMA. 2013 Sep 18;310(11):1145-55. doi: 10.1001/jama.2013.277165. PubMed PMID: 23995608.

3: Steg PG, Mehta SR, Pollack CV Jr, Bode C, Gaudin C, Fanouillere K, Moryusef A, Wiviott SD, Sabatine MS. Design and rationale of the treatment of acute coronary syndromes with otamixaban trial: a double-blind triple-dummy 2-stage randomized trial comparing otamixaban to unfractionated heparin and eptifibatide in non-ST-segment elevation acute coronary syndromes with a planned early invasive strategy. Am Heart J. 2012 Dec;164(6):817-24.e13. doi: 10.1016/j.ahj.2012.10.001. Epub 2012 Nov 7. PubMed PMID: 23194481.

4: Doggrell SA. New drugs for the treatment of coronary artery syndromes: otamixaban and ticagrelor. Expert Opin Pharmacother. 2010 Feb;11(2):325-9. doi: 10.1517/14656560903473173. PubMed PMID: 20088750.

5: Eikelboom JW, Weitz JI. Otamixaban in acute coronary syndromes. Lancet. 2009 Sep 5;374(9692):762-4. doi: 10.1016/S0140-6736(09)61529-4. Epub 2009 Aug 28. PubMed PMID: 19717186.

6: Sabatine MS, Antman EM, Widimsky P, Ebrahim IO, Kiss RG, Saaiman A, Polasek R, Contant CF, McCabe CH, Braunwald E. Otamixaban for the treatment of patients with non-ST-elevation acute coronary syndromes (SEPIA-ACS1 TIMI 42): a randomised, double-blind, active-controlled, phase 2 trial. Lancet. 2009 Sep 5;374(9692):787-95. doi: 10.1016/S0140-6736(09)61454-9. Epub 2009 Aug 28. Erratum in: Lancet. 2009 Oct 31;374(9700):1502. PubMed PMID: 19717184.

7: Guertin KR, Choi YM. The discovery of the Factor Xa inhibitor otamixaban: from lead identification to clinical development. Curr Med Chem. 2007;14(23):2471-81. Review. PubMed PMID: 17979700.

8: Cohen M, Bhatt DL, Alexander JH, Montalescot G, Bode C, Henry T, Tamby JF, Saaiman J, Simek S, De Swart J; SEPIA-PCI Trial Investigators. Randomized, double-blind, dose-ranging study of otamixaban, a novel, parenteral, short-acting direct factor Xa inhibitor, in percutaneous coronary intervention: the SEPIA-PCI trial. Circulation. 2007 May 22;115(20):2642-51. Epub 2007 May 14. PubMed PMID: 17502577.

9: Hinder M, Frick A, Jordaan P, Hesse G, Gebauer A, Maas J, Paccaly A. Direct and rapid inhibition of factor Xa by otamixaban: a pharmacokinetic and pharmacodynamic investigation in patients with coronary artery disease. Clin Pharmacol Ther. 2006 Dec;80(6):691-702. PubMed PMID: 17178269.

10: Nutescu EA, Pater K. Drug evaluation: the directly activated Factor Xa inhibitor otamixaban. IDrugs. 2006 Dec;9(12):854-65. Review. PubMed PMID: 17139573.

11: Sakai T, Kawamoto Y, Tomioka K. Asymmetric synthesis of intermediates for otamixaban and premafloxacin by the chiral ligand-controlled asymmetric conjugate addition of a lithium amide. J Org Chem. 2006 Jun 9;71(12):4706-9. PubMed PMID: 16749814.

12: Hinder M, Frick A, Rosenburg R, Hesse G, Ozoux ML, Laux V, Scholtz H, Gebauer A, Paccaly A. Anticoagulant and anti-platelet effects are maintained following coadministration of otamixaban, a direct factor Xa inhibitor, and acetylsalicylic acid. Thromb Haemost. 2006 Feb;95(2):224-8. PubMed PMID: 16493482.

13: Paccaly A, Ozoux ML, Chu V, Simcox K, Marks V, Freyburger G, Sibille M, Shukla U. Pharmacodynamic markers in the early clinical assessment of otamixaban, a direct factor Xa inhibitor. Thromb Haemost. 2005 Dec;94(6):1156-63. PubMed PMID: 16411387.

14: Paccaly A, Frick A, Ozoux ML, Chu V, Rosenburg R, Hinder M, Shukla U, Jensen BK. Pharmacokinetic/pharmacodynamic relationships for otamixaban, a direct factor Xa inhibitor, in healthy subjects. J Clin Pharmacol. 2006 Jan;46(1):45-51. PubMed PMID: 16397283.

15: Paccaly A, Frick A, Rohatagi S, Liu J, Shukla U, Rosenburg R, Hinder M, Jensen BK. Pharmacokinetics of otamixaban, a direct factor Xa inhibitor, in healthy male subjects: pharmacokinetic model development for phase 2/3 simulation of exposure. J Clin Pharmacol. 2006 Jan;46(1):37-44. PubMed PMID: 16397282.

16: Hinder M, Paccaly A, Frick A, Shukla U, Simcox K, Miller B, Gebauer A. Anticoagulant and anti-platelet effects are maintained following coadministration of otamixaban, a direct factor Xa inhibitor, with tirofiban in healthy volunteers. Thromb Haemost. 2005 Apr;93(4):794-5. PubMed PMID: 15841331.