Compound: Nafamostat
SMILES: O=C(Oc1cc2c(cc(C(=N)N)cc2)cc1)c3ccc(N=C(N)N)cc3
InChIKey: MQQNFDZXWVTQEH-UHFFFAOYSA-N
Synonyms: Nafamostat, 81525-10-2, Nafamostatum, 6-Amidino2-naphthyl 4-guanidinobenzoate, Y25LQ0H97D, p-Guanidinobenzoic acid ester with 6-hydroxy-2-naphthamidine, CKD314, 6-(Aminoiminomethyl)-2-naphthalenyl 4-((aminoiminomethyl)amino)benzoate, Benzoic acid, 4-((aminoiminomethyl)amino)-, 6-(aminoiminomethyl)-2-naphthalenyl ester, 6-carbamimidoylnaphthalen-2-yl 4-((diaminomethylidene)amino)benzoate, 6-carbamimidoylnaphthalen-2-yl 4-[(diaminomethylidene)amino]benzoate, 6'-amidino-2-naphthyl 4-guanidinobenzoate, RefChem:831686, 6-carbamimidoylnaphthalen-2-yl 4-carbamimidamidobenzoate, Benzoic acid, 4-((aminoiminomethyl)amino)-, 6-(aminoiminomethyl)-2-naphthalenyl ester, dihydrochloride, Nafamostat [INN], Nafamstat, (6-carbamimidoylnaphthalen-2-yl) 4-(diaminomethylideneamino)benzoate, 6-carbamimidoylnaphthalen-2-yl 4-guanidinobenzoate, CHEMBL273264, Nafamostat (INN), Benzoic acid, 4-[(aminoiminomethyl)amino]-,6-(aminoiminomethyl)-2-naphthalenyl ester, Nafamostatum [Latin], (6-carbamimidoylnaphthalen-2-yl) 4-carbamimidamidobenzoate, NCGC00160398-01, UNII-Y25LQ0H97D, Nafabelltan, NAFAMOSTAT [MI], NAFAMOSTAT [WHO-DD], BSPBio_001194, SCHEMBL135503, SCHEMBL135504, GTPL4262, orb1704313, DTXSID0048420, SCHEMBL29358879, SCHEMBL29360143, SCHEMBL29429443, SCHEMBL29429445, CHEBI:135466, HMS3742K19, ALBB-027243, GDA52510, HY-B0190, BDBM50063698, AKOS017259237, DB12598, 6-amidino-2-naphthyl p-guanidinobenzoate, NCGC00160398-02, NCGC00160398-03, NCGC00160398-04, NCGC00160398-13, BS-17665, NS00069533, D08240, G78310, MLS-0435512.0001, AB01566816_01, (6-carbamimidoyl-2-naphthyl) 4-guanidinobenzoate, BRD-K06674495-334-03-2, BRD-K06674495-334-04-0, Q15409374, 4-Guanidino-benzoic acid 6-carbamimidoyl-naphthalen-2-yl ester, 6-Carbamimidoylnaphthalen-2-yl 4-(carbamimidoylamino)benzoate, 4-Guanidino-benzoic acid 6-carbamimidoyl-naphthalen-2-yl ester(FUT-175), 7RF
Theoretical properties:
molecular_formula: C19H17N5O2
molecular_weight: 347.4 g/mol
exact_mass: 347.13822480 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 4
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 5
heavy_atom_count: 26
topological_polar_surface_area: 141 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Nafamostat is a member of benzoic acids and a member of guanidines.
chembl: NAFAMOSTAT is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: Nafamostat mesylate (INN), a synthetic serine protease inhibitor, is a short-acting anticoagulant, and it is also used for the treatment of pancreatitis. It also has some potential antiviral and anti-cancer properties. Nafamostat is a fast-acting proteolytic inhibitor and used during hemodialysis to prevent the proteolysis of fibrinogen into fibrin.  The mechanism of action of nafamostat is as a slow tight-binding substrate, trapping the target protein in the acyl-enzyme intermediate form, resulting in apparent observed inhibition.
It inhibits a large number of Lys/Arg specific serine proteinases, and is also a tryptase inhibitor, which is implicated in leaking blood vessels which is symptomatic of dengue hemorrhagic fever and of end-stage dengue shock syndrome.  It is available in a generic form already used for the treatment of certain bleeding complications in some countries, there are risks of severe complications such as: agranulocytosis,  hyperkalemia, and anaphylaxis which must be weighed in non-emergency care. In some countries, it used as a treatment for pancreatitis and pancreatic cancer.
This drug has been identified as a potential therapy for COVID-19, with clinical trials in Japan possibly set to begin in March 2020. With evidence that nafamostat is a potent anti-viral inhibitor in lung cells, a second round of clinical trials in Korea has begun with 10 hospitals participating. Multiple Phase 2/3 and Phase 3 clinical trials for COVID-19 in different countries are ongoing.
It has also been reported to target tubulin, favorizing its polymerization.