otamixaban   Click here for help

GtoPdb Ligand ID: 10732

Synonyms: compound 9c [PMID: 12039587] | FXV-673 | FXV673 | XRP-0673 | XRP0673
PDB Ligand
Compound class: Synthetic organic
Comment: Otamixaban (FXV673) is an anticoagulant that was originally reported by Aventis Pharmaceuticals (Sanofi) [1]. It is a potent and selective direct inhibitor of coagulation factor Xa that is delivered intravenously. The INN record stipulates the (2R,3R) configuration. Virtual docking studies suggest that otamixaban may bind to the serine protease TMPRSS2 [2-3], which is linked to host cell entry by a number of viruses, in particular influenza viruses and respiratory viruses such as SARS-CoV-2. Inhibition of TMPRSS2 is being examined for antiviral activity. The TMPRSS2 inhibitory activity of otamixaban is reported in [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 10
Topological polar surface area 132.21
Molecular weight 446.2
XLogP 4.35
No. Lipinski's rules broken 0
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Canonical SMILES COC(=O)[C@@H]([C@H](NC(=O)c1ccc(cc1)c1cc[n+](cc1)[O-])C)Cc1cccc(c1)C(=N)N
Isomeric SMILES COC(=O)[C@@H]([C@H](NC(=O)c1ccc(cc1)c1cc[n+](cc1)[O-])C)Cc1cccc(c1)C(=N)N
InChI 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
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
methyl (2R,3R)-2-[(3-carbamimidoylphenyl)methyl]-3-[[4-(1-oxidopyridin-1-ium-4-yl)benzoyl]amino]butanoate
International Nonproprietary Names Click here for help
INN number INN
8096 otamixaban
Synonyms Click here for help
compound 9c [PMID: 12039587] | FXV-673 | FXV673 | XRP-0673 | XRP0673
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9682033
Reactome Reaction Reactome logo R-HSA-9681514
Other databases
BindingDB Ligand 50114539
CAS Registry No. 193153-04-7 (source: WHO INN record)
ChEMBL Ligand CHEMBL46618
GtoPdb PubChem SID 405067325
PubChem CID 5496659
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UniChem Compound Search for chemical match using the InChIKey PFGVNLZDWRZPJW-OPAMFIHVSA-N
UniChem Connectivity Search for chemical match using the InChIKey PFGVNLZDWRZPJW-OPAMFIHVSA-N