nafamostat   Click here for help

GtoPdb Ligand ID: 4262

Synonyms: CKD-314 | CKD314 | FUT-175 | Nafabelltan®
Approved drug
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).
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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)
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,
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]