HuagongsheHuagongshe Chemistry Print Report · For research reference only
Nafamostat
NAFAMOSTAT MESILATE · FUT-175 · 6-Carbamimidoylnaphthalen-2-yl 4-guanidinobenzoate · FUTHAN · Nafamstat · NAFAMOSTAT · Naphthalmostat · Mesylate nafaMostat
Identifiers & Physical Properties
| CAS No. | 81525-10-2 |
|---|---|
| Molecular formula | C19H17N5O2 |
| Average molar mass | 347.4 g/mol |
| Monoisotopic mass | 347.1382248 g/mol |
| SMILES | N=C(N)c1ccc2cc(OC(=O)c3ccc(N=C(N)N)cc3)ccc2c1 |
| InChIKey | MQQNFDZXWVTQEH-UHFFFAOYSA-N |
| PubChem CID | 4413 |
| ChEMBL | CHEMBL273264 |
| ChEBI | CHEBI:135466 |
| DTXSID | DTXSID0048420 |
Chemical & Physical Properties
| XLogP | 2 |
|---|---|
| Topological polar surface area | 141 |
| Hydrogen bond donors | 4 |
| Hydrogen bond acceptors | 4 |
| Rotatable bonds | 5 |
| Heavy atoms | 26 |
| Formal charge | 0 |
| Complexity | 552 |
| Drugs | PharmaceuticalPharmaceuticals -> Listed in ZINC15 |
| Boiling point | 586.0±60.0 °C(Predicted) |
| Density | 1.39±0.1 g/cm3(Predicted) |
| Storage conditions | under inert gas (nitrogen or Argon) at 2–8 °C |
| Solubility | Soluble in DMSO |
| Physical state | Powder |
| pKa (acidity coefficient) | 11.30±0.30(Predicted) |
| FDA UNII | Y25LQ0H97D |
Safety & Regulations
| Drug Induced Liver Injury | Drug-Induced Liver Injury Severity and Toxicity (DILIst)NafamostatDILI PositiveDOI:10.1016/j.drudis.2019.09.022 |
|---|
Applications & Uses
Uses
Nafamostat is a non-peptide synthetic protease inhibitor with broad-spectrum and potent enzyme inhibition. For the treatment of acute pancreatitis. It can improve acute symptoms of acute pancreatitis, acute exacerbation of chronic pancreatitis, and post-traumatic pancreatitis.
Preparation & Synthesis
Preparation
6-Bromo-2-naphthol reacts with copper cyanide in dimethylformamide to generate 6-cyano-2-naphthol, which is methanolylated and then aminolyzed to generate 6-amidino-2-naphthol , and finally esterification with p-guanidinobenzoic acid to generate nafamostat.