upamostat   Click here for help

GtoPdb Ligand ID: 6497

Synonyms: WX-671
Compound class: Synthetic organic
Comment: Upamostat (WX-671) is an oral serine protease inhibitor prodrug. Its principal molecular target is plasminogen activator, urokinase (uPA; PLAU) [2]. The uPA system plays an important role in tumour invasion and metastasis. The active substance is WX-UK1.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 3
Rotatable bonds 15
Topological polar surface area 149.02
Molecular weight 629.32
XLogP 6.24
No. Lipinski's rules broken 2
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Canonical SMILES CCOC(=O)N1CCN(CC1)C(=O)C(NS(=O)(=O)c1c(cc(cc1C(C)C)C(C)C)C(C)C)Cc1cccc(c1)C=NNO
Isomeric SMILES CCOC(=O)N1CCN(CC1)C(=O)[C@@H](NS(=O)(=O)c1c(cc(cc1C(C)C)C(C)C)C(C)C)Cc1cccc(c1)/C=N/NO
InChI InChI=1S/C32H47N5O6S/c1-8-43-32(39)37-14-12-36(13-15-37)31(38)29(17-24-10-9-11-25(16-24)20-33-35-40)34-44(41,42)30-27(22(4)5)18-26(21(2)3)19-28(30)23(6)7/h9-11,16,18-23,29,34-35,40H,8,12-15,17H2,1-7H3/b33-20+/t29-/m0/s1
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Summary of Clinical Use Click here for help
Upamostat was originally developed for anti-tumour potential [3-4]. It has been realigned and is being evaluated for clinical efficacy in non-hospitalised COVID-19 patients.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT04723537 Upamostat, a Serine Protease Inhibitor, or Placebo for Treatment of COVID-19 Disease Phase 2/Phase 3 Interventional RedHill Biopharma Limited
NCT00615940 Combination of Oral WX-671 Plus Capecitabine vs. Capecitabine Monotherapy in First-line Her2-negative Metastatic Breast Cancer Phase 2 Interventional Heidelberg Pharma AG
NCT00499265 Gemcitabine With or Without WX-671 in Treating Patients With Locally Advanced Pancreatic Cancer That Cannot Be Removed By Surgery Phase 2 Interventional Heidelberg Pharma AG 3