otamixaban   

GtoPdb Ligand ID: 10732

Synonyms: compound 9c [PMID: 12039587] | FXV-673 | FXV673 | XRP-0673 | XRP0673
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], 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 potential and/or antiviral activity of otamixaban have not yet been determined.
2D Structure
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Physico-chemical Properties
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
SMILES / InChI / InChIKey
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
InChI Key PFGVNLZDWRZPJW-OPAMFIHVSA-N
Classification
Compound class Synthetic organic
IUPAC Name
methyl (2R,3R)-2-[(3-carbamimidoylphenyl)methyl]-3-[[4-(1-oxidopyridin-1-ium-4-yl)benzoyl]amino]butanoate
International Nonproprietary Names
INN number INN
8096 otamixaban
Synonyms
compound 9c [PMID: 12039587] | FXV-673 | FXV673 | XRP-0673 | XRP0673
Comments
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], 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 potential and/or antiviral activity of otamixaban have not yet been determined.
Database Links
BindingDB Ligand 50114539
CAS Registry No. 193153-04-7 (source: WHO INN record)
ChEMBL Ligand CHEMBL46618
GtoPdb PubChem SID 405067325
PubChem CID 5496659
RCSB PDB Ligand FXV
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