Otamixaban

Base Information

• Chemical Name: Otamixaban
• CAS No.: 193153-04-7
• Molecular Formula: C25H26N4O4
• Molecular Weight: 446.50
• UNII: S173RED00L
• DSSTox Substance ID: DTXSID40172917
• Nikkaji Number: J1.584.766B
• Wikipedia: Otamixaban
• Wikidata: Q7108427
• NCI Thesaurus Code: C90704
• Pharos Ligand ID: GBFPV22VMKVW
• Metabolomics Workbench ID: 149873
• ChEMBL ID: CHEMBL46618
• Mol file: 193153-04-7.mol

Synonyms:2-(3-carbamimidoylbenzyl)-3-(4-(1-oxypyridin-4-yl)benzoylamino)butyric acid methyl ester;2-(R)-(3-carbamimidoylbenzyl)-3-(R)-(4-(1-oxypyridin-4-yl)benzoylamino)butyric acid methyl ester;benzenepropanoic acid, 3-((Z)-aminoiminomethyl)-alpha-((1R)-1-((4-(1-oxido-4-pyridinyl)benzoyl)amino)ethyl)-, methyl ester, (alphaR)-;FXV 673;FXV-673;FXV673;otamixaban;RPR-130673;RPR130673

Chemical Property of Otamixaban

Chemical Property:

• PKA: 13.38±0.46(Predicted)
• PSA: 130.73000
• Density: 1.25
• LogP: 4.40730
• Solubility.: ≥22.35 mg/mL in DMSO; insoluble in H2O; ≥55 mg/mL in EtOH with gentle warming
• XLogP3: 2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 446.19540532
• Heavy Atom Count: 33
• Complexity: 671

Purity/Quality:

97% ^*data from raw suppliers

Otamixaban ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(CC1=CC(=CC=C1)C(=N)N)C(=O)OC)NC(=O)C2=CC=C(C=C2)C3=CC=[N+](C=C3)[O-]
• Isomeric 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-]
• Recent ClinicalTrials: Effect of Otamixaban Versus Unfractionated Heparin + Eptifibatide in Patients With Unstable Angina/Non ST Elevation Myocardial Infarction Undergoing Early Invasive Strategy
• Recent EU Clinical Trials: Randomized, double-blind, triple-dummy trial to compare the efficacy of otamixaban with Unfractionated Heparin + eptifibatide, in patients with Unstable angina/Non ST segment Elevation Myocardial infarction scheduled to undergo an early invasive strategy
• Uses: A potent (Ki = 0.5 nM), selective, rapid acting, competitive and reversible fXa inhibitor that effectively inhibits both free and prothrombinase-bound fXa. Clinical studies show that it is efficacious , safe and well tolerated in humans and therefore has considerable potential for the treatment of acute coronary syndrome. A potent (Ki = 0.5 nM), selective, rapid acting, competitive and reversible fXa inhibitor that effectively inhibits both free and prothrombinase-bound fXa. Clinical studies show that it is efficacious, safe and well tolerated in humans and therefore has considerable potential for the treatment of acute coronary syndrome.

Technology Process of Otamixaban

There total 3 articles about Otamixaban which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

4-(4-pyridinyl)benzoic acid (4385-76-6) → methyl (2R,3R)-2-{3-[amino(imino)methyl]benzyl}-3-{[4-(1-oxido-4-pyridinyl)benzoyl]amino}butanoate hydrochloride (193153-04-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 1.5 h / 20 °C

2: magnesium bis(monoperoxyphthalate)hexahydrate / water; dichloromethane / 5 h

3: hydrogenchloride / methanol / 16 h / -5 - 0 °C / 100 Torr / Sealed tube

With 4-methyl-morpholine; hydrogenchloride; magnesium bis(monoperoxyphthalate)hexahydrate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

(2R,3R)-2-(3-Cyano-benzyl)-3-[4-(1-oxy-pyridin-4-yl)-benzoylamino]-butyric acid methyl ester (193153-02-5) → methyl (2R,3R)-2-{3-[amino(imino)methyl]benzyl}-3-{[4-(1-oxido-4-pyridinyl)benzoyl]amino}butanoate hydrochloride (193153-04-7)

Guidance literature:

(2R,3R)-2-(3-Cyano-benzyl)-3-[4-(1-oxy-pyridin-4-yl)-benzoylamino]-butyric acid methyl ester; With hydrogenchloride; In methanol; at -5 - 0 ℃; for 16h;

With ammonia; In methanol; at 0 - 20 ℃;

Reference yield:

(2R,3R)-3-Amino-2-(3-cyano-benzyl)-butyric acid methyl ester (193152-96-4) → methyl (2R,3R)-2-{3-[amino(imino)methyl]benzyl}-3-{[4-(1-oxido-4-pyridinyl)benzoyl]amino}butanoate hydrochloride (193153-04-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 1.5 h / 20 °C

2: magnesium bis(monoperoxyphthalate)hexahydrate / water; dichloromethane / 5 h

3: hydrogenchloride / methanol / 16 h / -5 - 0 °C / 100 Torr / Sealed tube

With 4-methyl-morpholine; hydrogenchloride; magnesium bis(monoperoxyphthalate)hexahydrate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

(2R,3R)-2-(3-Cyano-benzyl)-3-[4-(1-oxy-pyridin-4-yl)-benzoylamino]-butyric acid methyl ester

(2R,3R)-3-Amino-2-(3-cyano-benzyl)-butyric acid methyl ester

4-(4-pyridinyl)benzoic acid

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