82956-11-4

Basic information

• Product Name: Nafamostat mesylate
• Synonyms: 4-((aminoiminomethyl)amino)-benzoicaci6-(aminoiminomethyl)-2-naphthalenyl;6-carbaMiMidoylnaphthalen-2-yl 4-guanidinobenzoate diMethanesulfonate;[amino-[6-[[4-(diaminomethyleneazaniumyl)phenyl]-oxomethoxy]-2-naphthyl]methylene]ammonium;[amino-[6-[4-(diaminomethyleneazaniumyl)benzoyl]oxy-2-naphthyl]methylene]ammonium;[amino-[6-[4-(diaminomethylideneazaniumyl)benzoyl]oxynaphthalen-2-yl]methylidene]azanium;[amino-[6-[4-(diaminomethylideneazaniumyl)phenyl]carbonyloxynaphthalen-2-yl]methylidene]azanium;6-[amino(imino)methyl]-2-naphthyl 4-{[amino(imino)methyl]amino}benzoate dimethanesulfonate;Nafamostat mesylate, >=98%
• CAS NO: 82956-11-4
• Molecular Formula: 2CH₄O₃S*C₁₉H₁₇N₅O₂
• Molecular Weight: 539.58
• EINECS: 1806241-263-5
• Product Categories: Inhibitor;API;Futhan, FUT-175;Inhibitors;APIs;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;ProteaseInhibitors
• Mol File: 82956-11-4.mol

Chemical Properties

• Melting Point: 259-261°C
• Boiling Point: 637.2 °C at 760 mmHg
• Flash Point: 339.1 °C
• Appearance: Tan to pale orange solid
• Vapor Pressure: 3.9E-16mmHg at 25°C
• Storage Temp.: Room temp
• Solubility: Soluble in Water (up to 25 mg/ml).
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in distilled water may be stored at 4°C for up to 1 month, or at -80°C for up to 6 months.
• Merck: 14,6350
• CAS DataBase Reference: Nafamostat mesylate(CAS DataBase Reference)
• NIST Chemistry Reference: Nafamostat mesylate(82956-11-4)
• EPA Substance Registry System: Nafamostat mesylate(82956-11-4)

Safety Data

• RIDADR: 3077
• WGK Germany: nwg
• RTECS: DG2736000
• Hazardous Substances Data: 82956-11-4(Hazardous Substances Data)

Usage

Uses

Used in Acute Pancreatitis Treatment:
Nafamostat mesylate is used as a protease inhibitor for the treatment of acute pancreatitis, helping to manage the condition and alleviate symptoms.
Used in Autoimmune Disease Treatment:
Nafamostat mesylate is used as a potential treatment for autoimmune diseases due to its anticomplement, anticoagulant, and other activities, which may help in managing the symptoms and progression of these conditions.
Used in Disseminated Intravascular Coagulation Treatment:
Nafamostat mesylate is used as a treatment for disseminated intravascular coagulation, a serious medical condition characterized by abnormal blood clotting, due to its anticoagulant properties.
Used in Asthma Management:
Nafamostat mesylate is used as an anticoagulant and broad-spectrum serine protease inhibitor for reducing eosinophil infiltration, mast cell activation, and airway responsiveness in a murine model of asthma, potentially offering a novel therapeutic approach for managing this respiratory condition.

Originator

Torii (Japan)

Biological Activity

Broad spectrum serine protease inhibitor. Displays selectivity for human tryptase when used at relatively low concentrations. Reduces eosinophil infiltration, mast cell activation and airway responsiveness in a murine model of asthma.

Biochem/physiol Actions

Nafamostat mesylate is a broad spectrum serine protease inhibitor, kallikrein inhibitor, and inhibits blood coagulation. It is also a possible complement inhibitor.

References

1) Han et al. (2019) Identification of nafamostat mesilate as an inhibitor of the fat mass and obesity-associated protein (FTO) demethylase; Chem. Biol. Interact., 297 80

InChI:InChI=1/C19H17N5O2.CH4O3S/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;1-5(2,3)4/h1-10H,(H3,20,21)(H4,22,23,24);1H3,(H,2,3,4)

Upstream product

• 2386-57-4 methanesulfonic acid sodium salt 
• 80251-32-7 Nafamostat hydrochloride 
• 75-75-2 methanesulfonic acid 
• 52927-22-7 6-cyano-2-naphthol 
• 82957-06-0 6-amidino-2-naphthol methanesulfonate 
• 78119-82-1 6-hydroxynaphthalene-2-carbaldehyde 

Relevant articles and documents

Process for Preparing Nafamostat Mesilate and Intermediate Thereof

The present invention provides a method for efficiently producing astaxmostat mesylate through a simple process and a method for producing 6 - amidino -2 - naphthol mesylate in high yield under mild conditions.

Production of [...] acid salt

The purpose of the present invention is to provide a process for producing nafamostat mesylate without via nafamostat bicarbonate and while avoiding inclusion of sodium mesylate. The process for producing nafamostat mesylate comprises (1) a step in which an anion-exchange resin in which the anion is a mesylic acid ion is prepared, (2) a step in which the anion-exchange resin obtained in the step (1) is brought into contact with a nafamostat salt which is neither nafamostat bicarbonate nor nafamostat mesylate, in the presence of a solvent to thereby convert the nafamostat salt into nafamostat mesylate by salt exchange, and (3) a step in which the nafamostat mesylate obtained in the step (2) is crystallized.

Method for preparing of nafamostat mesilate

The present invention discloses a manufacturing method for nafamostat mesylate used as blood coagulation inhibitor where crystalline II type nafamostat mesylate is obtained with high purity and quality as well as regularity. According to the present invention, the manufacturing method for nafamostat mesylate comprises the following steps of: (a) initiating a chemical reaction between 4-guanidino benzoic acidic hydrochloride and 6-amidino-2-naphthol methanesulfonate with the existence of N,N′-Diisopropylcarbodiimide to manufacture the compound shown in Formula 1; (b) adding the manufactured compound in Formula 1 to solvent mixed with water H_2O and saturated sodium hydrogen carbonate NaHCO_3 to manufacture the compound shown in Formula 2; and (c) adding the compound in Formula 2 to solvent, and then adding methanesulfonate to manufacture the nafamostat mesylate compound shown in Formula 3.

AMIDINE COMPOUND

Amidino compounds represented by the formula STR1 and pharmaceutically acceptable acid addition salts thereof are novel compounds and are useful as powerful antitrypsine, antiplasmin, antikallikrein and antithrombin agents. Having strong anti-C1 (C1r, C1s) activities and an anticomplement activity, they are also useful as anticomplement agents. These amidino compounds are prepared by usual esterification of carboxylic acid compounds represented by the formula STR2 with 6-amidino-2-naphthol and, if necessary, can be transformed into pharmaceuticlly acceptable acid addition salts thereof.