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
1. Guertin KR, Gardner CJ, Klein SI, Zulli AL, Czekaj M, Gong Y, Spada AP, Cheney DL, Maignan S, Guilloteau JP et al.. (2002)
Optimization of the beta-aminoester class of factor Xa inhibitors. Part 2: Identification of FXV673 as a potent and selective inhibitor with excellent In vivo anticoagulant activity.
Bioorg Med Chem Lett, 12 (12): 1671-4. [PMID:12039587]
2. Hu X, Shrimp JH, Guo H, Xu M, Chen CZ, Zhu W, Zakharov AV, Jain S, Shinn P, Simeonov A et al.. (2021)
Discovery of TMPRSS2 Inhibitors from Virtual Screening as a Potential Treatment of COVID-19.
ACS Pharmacol Transl Sci, 4 (3): 1124-1135. [PMID:34136758]
3. Rensi S, Altman RB, Liu T, Lo YC, McInnes G, Derry A, Keys A. (2020)
Homology Modeling of TMPRSS2 Yields Candidate Drugs That May Inhibit Entry of SARS-CoV-2 into Human Cells.
ChemRxiv, [Preprint]. DOI: 10.26434/chemrxiv.12009582 [PMID:32511288]
4. Steg PG, Mehta SR, Pollack Jr CV, Bode C, Cohen M, French WJ, Hoekstra J, Rao SV, Ruzyllo W, Ruiz-Nodar JM et al.. (2013)
Anticoagulation with otamixaban and ischemic events in non-ST-segment elevation acute coronary syndromes: the TAO randomized clinical trial.
JAMA, 310 (11): 1145-55. [PMID:23995608]