nafamostat   Click here for help

GtoPdb Ligand ID: 4262

Synonyms: CKD-314 | CKD314 | FUT-175 | Nafabelltan®
Approved drug PDB Ligand
nafamostat is an approved drug (Japan only)
Compound class: Synthetic organic
Comment: Nafamostat is a guanidinobenzoate-containing inhibitor, with activity against a range of serine proteases. Some data is attached to nafamostat mesylate (PubChem CID 5311180).
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
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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Click here for structure editor
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 6
Hydrogen bond donors 4
Rotatable bonds 5
Topological polar surface area 140.57
Molecular weight 347.14
XLogP 2.98
No. Lipinski's rules broken 0
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 NC(=Nc1ccc(cc1)C(=O)Oc1ccc2c(c1)ccc(c2)C(=N)N)N
Isomeric SMILES NC(=Nc1ccc(cc1)C(=O)Oc1ccc2c(c1)ccc(c2)C(=N)N)N
InChI InChI=1S/C19H17N5O2/c20-17(21)14-2-1-13-10-16(8-5-12(13)9-14)26-18(25)11-3-6-15(7-4-11)24-19(22)23/h1-10H,(H3,20,21)(H4,22,23,24)
InChI Key MQQNFDZXWVTQEH-UHFFFAOYSA-N
References
1. Chen X, Numata T, Li M, Mori Y, Orser BA, Jackson MF, Xiong ZG, MacDonald JF. (2010)
The modulation of TRPM7 currents by nafamostat mesilate depends directly upon extracellular concentrations of divalent cations.
Mol Brain, 3: 38. [PMID:21122141]
2. Hays SJ, Caprathe BW, Gilmore JL, Amin N, Emmerling MR, Michael W, Nadimpalli R, Nath R, Raser KJ, Stafford D et al.. (1998)
2-amino-4H-3,1-benzoxazin-4-ones as inhibitors of C1r serine protease.
J Med Chem, 41 (7): 1060-7. [PMID:9544206]
3. Hoffmann M, Schroeder S, Kleine-Weber H, Müller MA, Drosten C, Pöhlmann S. (2020)
Nafamostat Mesylate Blocks Activation of SARS-CoV-2: New Treatment Option for COVID-19.
Antimicrob Agents Chemother, 64 (6). DOI: 10.1128/AAC.00754-20 [PMID:32312781]
4. Mori S, Itoh Y, Shinohata R, Sendo T, Oishi R, Nishibori M. (2003)
Nafamostat mesilate is an extremely potent inhibitor of human tryptase.
J Pharmacol Sci, 92 (4): 420-3. [PMID:12939527]
5. The University of Tokyo Hospital. 
Therapy with Favipiravir and Nafamostat in Patients with COVID-19.
Accessed on 18/05/2020. Modified on 18/05/2020. The University of Tokyo Hospital/articles, https://www.u-tokyo.ac.jp/focus/en/articles/z0103_00019.html
6. Ugawa S, Ishida Y, Ueda T, Inoue K, Nagao M, Shimada S. (2007)
Nafamostat mesilate reversibly blocks acid-sensing ion channel currents.
Biochem Biophys Res Commun, 363 (1): 203-8. [PMID:17826743]
7. Yamamoto M, Matsuyama S, Li X, Takeda M, Kawaguchi Y, Inoue JI, Matsuda Z. (2016)
Identification of Nafamostat as a Potent Inhibitor of Middle East Respiratory Syndrome Coronavirus S Protein-Mediated Membrane Fusion Using the Split-Protein-Based Cell-Cell Fusion Assay.
Antimicrob Agents Chemother, 60 (11): 6532-6539. [PMID:27550352]