Basic information
- CAS
81525-10-2- Standard SMILES
N=C(N)c1ccc2cc(OC(=O)c3ccc(N=C(N)N)cc3)ccc2c1- InChIKey
MQQNFDZXWVTQEH-UHFFFAOYSA-N- Molecular formula
- C19H17N5O2
- Average molar mass
- 347.4 g/mol
- Monoisotopic mass
- 347.1382248
Overview
Nafamostat is a member of benzoic acids and a member of guanidines.
Names & identifiers
- Preferred name
- Nafamostat
- IUPAC
- (6-carbamimidoylnaphthalen-2-yl) 4-(diaminomethylideneamino)benzoate
- English name
- Nafamostat
- Molecular formula
- C19H17N5O2
- Molecular weight
- 347.37
Names & synonyms
Nafamostat81525-10-2Nafamostatum6-Amidino2-naphthyl 4-guanidinobenzoateY25LQ0H97Dp-Guanidinobenzoic acid ester with 6-hydroxy-2-naphthamidineCKD3146-(Aminoiminomethyl)-2-naphthalenyl 4-((aminoiminomethyl)amino)benzoateBenzoic acid, 4-((aminoiminomethyl)amino)-, 6-(aminoiminomethyl)-2-naphthalenyl ester6-carbamimidoylnaphthalen-2-yl 4-((diaminomethylidene)amino)benzoate6-carbamimidoylnaphthalen-2-yl 4-[(diaminomethylidene)amino]benzoate6'-amidino-2-naphthyl 4-guanidinobenzoate
Show more names
NAFAMOSTAT MESILATEFUT-175FUTHANNafamstatNaphthalmostatMesylate nafaMostatNafamostat (FUT-175)NafamostatMesilateBase
RefChem:8316866-carbamimidoylnaphthalen-2-yl 4-carbamimidamidobenzoateBenzoic acid, 4-((aminoiminomethyl)amino)-, 6-(aminoiminomethyl)-2-naphthalenyl ester, dihydrochlorideNafamostat [INN](6-carbamimidoylnaphthalen-2-yl) 4-(diaminomethylideneamino)benzoate6-carbamimidoylnaphthalen-2-yl 4-guanidinobenzoateCHEMBL273264Nafamostat (INN)
Properties
Computed structural properties
- XLogP
- 2
- Topological polar surface area
- 141 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 5
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 552
Experimental & physicochemical properties
Drugs
Pharmaceutical
Pharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Boiling point
- 586 · 586.0±60.0 °C(Predicted)
- Density
- 1.39 · 1.39±0.1 g/cm3(Predicted)
- storage temp.
- 2 · under inert gas (nitrogen or Argon) at 2–8 °C
- solubility
- Soluble in DMSO
- form
- Powder
- pka
- 11.3 · 11.30±0.30(Predicted)
- FDA UNII
- 25 LQ0H97D · Y25LQ0H97D
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Nafamostat
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Chemistry & industry
Pharmacology
Pharmacodynamics
Nafamostat is a fast-acting proteolytic inhibitor used during hemodialysis to prevent the proteolysis of fibrinogen into fibrin by competitively inhibiting several serine proteases including thrombin. It improves acute pancreatitis and prevents blood clot formation during extracorporeal circulation and has an anti-inflammatory effect in vitro. A study suggets that nafamostat has a neuroprotective role during ischemia-induced brain injury from antithrombin activity.
Mechanism of Action
Nafamostat mesilate inhibits various enzyme systems, such as coagulation and fibrinolytic systems (thrombin, Xa, and XIIa), the kallikrein–kinin system, the complement system, pancreatic proteases and activation of protease-activated receptors (PARs). Nafamostat inhibits lipopolysaccharide-induced nitric oxide production, apoptosis, and interleukin (IL)-6 and IL-8 levels in cultured human trophoblasts. It is shown to act as an antioxidant in TNF-α-induced ROS production.
Biological Half-LifeApproximately 8 minutes
Metabolism/MetabolitesNafamostat is mainly hydrolyzed by hepatic carboxyesterase and long-chain acyl-CoA hydrolase in human liver cytosol. Main metabolites are p-guanidinobenzoic acid (PGBA) and 6-amidino-2-naphthol (AN) as inactive protease inhibitors.
MeSH Pharmacological Classification
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.
Agents that prevent BLOOD CLOTTING.
Compounds which inhibit or antagonize biosynthesis or actions of proteases (ENDOPEPTIDASES).
Serine proteinase inhibitors which inhibit trypsin. They may be endogenous or exogenous compounds.
Exogenous or endogenous compounds which inhibit SERINE ENDOPEPTIDASES.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…