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Otamixaban (formerly FXV-673; XRP0673 and XRP-0673) is an intravenous, rapid acting, competitive and reversible direct factor Xa inhibitor used as an injectable anticoagulant. It was investigated for the treatment for acute coronary syndrome.
Physicochemical Properties
| Molecular Formula | C25H26N4O4 |
| Molecular Weight | C25H26N4O4 |
| Exact Mass | 446.195 |
| CAS # | 193153-04-7 |
| Related CAS # | 409081-12-5 (HCl); 193153-04-7; |
| PubChem CID | 5496659 |
| Appearance | Light yellow to yellow solid powder |
| Density | 1.3±0.1 g/cm3 |
| Index of Refraction | 1.619 |
| LogP | 0.58 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 9 |
| Heavy Atom Count | 33 |
| Complexity | 671 |
| Defined Atom Stereocenter Count | 2 |
| SMILES | C[C@H]([C@@H](CC1=CC(=CC=C1)C(=N)N)C(=O)OC)NC(=O)C2=CC=C(C=C2)C3=CC=[N+](C=C3)[O-] |
| 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 |
| Chemical Name | Methyl (2R,3R)-2-(3-carbamimidoylbenzyl)-3-((4-(1-oxidopyridin-4-yl)benzoyl)amino)butanoate |
| Synonyms | XRP673 XRP0673XRP-673 XRP-0673XRP 673 XRP 0673 |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| References | Anticoagulation therapy: Otamixaban fails in NSTE-ACS. Nat Rev Cardiol. 2013 Nov;10(11):615. |
| Additional Infomation |
Otamixaban is a novel direct Factor Xa (FXa) inhibitor. It is currently being developed by the French pharmaceutical company Sanofi-Aventis as a treatment for acute coronary syndrome. Otamixaban is an inhibitor of coagulation factor Xa (activated factor X) with anticoagulant activity. Otamixaban has a short half-life of 1.5 to 3 hours. Drug Indication Investigated for use/treatment in thrombosis. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~50 mg/mL (~111.98 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.75 mg/mL (6.16 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.75 mg/mL (6.16 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.75 mg/mL (6.16 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |