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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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
InChI Key CYCFEEXTLQGJEL-XEOXDSMQSA-N
No information available.
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