Otamixaban | CAS# 193153-04-7 (free base) | Xa inhibitor

Otamixaban
featured

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

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

Otamixaban

CAS# 193153-04-7 (free base)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 326792
Name: Otamixaban
CAS#: 193153-04-7 (free base)
Chemical Formula: C25H26N4O4
Exact Mass: 446.20
Molecular Weight: 446.507
Elemental Analysis: C, 67.25; H, 5.87; N, 12.55; O, 14.33

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 695	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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

More Info:

Product Data:

Product Data

Instruction:

View handling instruction

Biological target:	Otamixaban (FXV673) is a potent (Ki = 0.5 nM), selective, rapid acting, competitive and reversible fXa inhibitor.
In vitro activity:	This study reports that a late-stage drug candidate, otamixaban, inhibits SARS-CoV-2 cell entry. This study shows that otamixaban suppresses TMPRSS2 activity and SARS-CoV-2 infection of a human lung cell line, although with lower potency than camostat or nafamostat. In contrast, otamixaban inhibits SARS-CoV-2 infection of precision cut lung slices with the same potency as camostat. Furthermore, this study reports that otamixaban's potency can be significantly enhanced by (sub-) nanomolar nafamostat or camostat supplementation. Reference: Chem Sci. 2021 Aug 26;12(38):12600-12609. https://pubmed.ncbi.nlm.nih.gov/34703545/
In vivo activity:	TBD

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	50.0	119.98

Preparing Stock Solutions

The following data is based on the product molecular weight 446.51 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.

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

Formulation protocol:	Hempel T, Elez K, Krüger N, Raich L, Shrimp JH, Danov O, Jonigk D, Braun A, Shen M, Hall MD, Pöhlmann S, Hoffmann M, Noé F. Synergistic inhibition of SARS-CoV-2 cell entry by otamixaban and covalent protease inhibitors: pre-clinical assessment of pharmacological and molecular properties. Chem Sci. 2021 Aug 26;12(38):12600-12609. doi: 10.1039/d1sc01494c. PMID: 34703545; PMCID: PMC8494051.
In vitro protocol:	Hempel T, Elez K, Krüger N, Raich L, Shrimp JH, Danov O, Jonigk D, Braun A, Shen M, Hall MD, Pöhlmann S, Hoffmann M, Noé F. Synergistic inhibition of SARS-CoV-2 cell entry by otamixaban and covalent protease inhibitors: pre-clinical assessment of pharmacological and molecular properties. Chem Sci. 2021 Aug 26;12(38):12600-12609. doi: 10.1039/d1sc01494c. PMID: 34703545; PMCID: PMC8494051.
In vivo protocol:	TBD

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.

Mass

Concentration

Volume

M. Wt* g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

Volume (to add to vial)

Mass (in vial)

Desired Reconstitution Concentration

Dilution Calculator

Calculate the dilution required to prepare a stock solution.

Concentration 1

Volume 1

Concentration 2

Volume 2

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.

Your view history

Otamixaban featured