Camostat mesylate

Base Information

• Chemical Name: Camostat mesylate
• CAS No.: 59721-29-8
• Molecular Formula: C20H22N4O5^.CH4O3S
• Molecular Weight: 494.525
• Hs Code.: 2934999090
• European Community (EC) Number: 694-565-6
• UNII: 451M50A1EQ
• DSSTox Substance ID: DTXSID0020238
• Wikidata: Q23731028
• NCI Thesaurus Code: C96364
• Pharos Ligand ID: P67GSQDASQ14
• ChEMBL ID: CHEMBL85164
• Mol file: 59721-29-8.mol

Synonyms:camostat;camostat mesilate;camostat mesylate;camostate;camostate-mesilate;Foipan;FOY 305;FOY S 980;Foy-305;foypan;N,N-dimethylcarbamoylmethyl-4-(4-guanidinobenzoyloxy)phenylacetate methanesulfonate;p-guanidinobenzoic acid, ester with (p-hydroxyphenyl)acetic acid, ester with N,N-dimethylglycolamide

Chemical Property of Camostat mesylate

Chemical Property:

• Appearance/Colour: crystalline solid
• Vapor Pressure: 5.22E-16mmHg at 25°C
• Melting Point: 150-155 °C
• Boiling Point: 634.6 °C at 760 mmHg
• Flash Point: 337.6 °C
• PSA: 197.56000
• LogP: 2.84290
• Storage Temp.: Desiccate at RT
• Solubility.: H2O: ≥24mg/mL
• Water Solubility.: Soluble in water (100 mM), DMSO (100 mM), and ethanol (<1 mg/ml).
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 494.14713497
• Heavy Atom Count: 34
• Complexity: 695

Purity/Quality:

99%min, ^*data from raw suppliers

Camostat Mesylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N
• Hazard Codes: Xi,N
• Statements: 36/37/38-50
• Safety Statements: 26-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C(=O)COC(=O)CC1=CC=C(C=C1)OC(=O)C2=CC=C(C=C2)N=C(N)N.CS(=O)(=O)O
• Recent ClinicalTrials: Camostat Mesylate for Protein-losing Enteropathy After Fontan Operation
• Recent EU Clinical Trials: The DAWN camostat trial: the efficacy of camostat for COVID-19 infections presenting to ambulatory care: a randomized controlled trial.
• Recent NIPH Clinical Trials: Safety and efficacy of favipiravir and camostat mesilate in patients with COVID-19.
• Description: Camostat mesylate is a broad spectrum protease inhibitor useful in the treatment of chronic pancreatitis.
• Uses: It is used as a protease and Trypsin inhibitor. Furthermore it was found that this water induction and bicarbonate secretion increase was achieved via direct regulation of ductular cells of the dog pancreas. Other studies have shown Camostat mesylate to suppress spinal Fos expression in the rat, which is a marker for neuronal activation. In addition it was shown that this compound may prevent or depress pancreatitis-induced referred allodynia/hyperalgesia in rat models. Camostat mesylate has also demonstrated the ability to prevent Trypsin attack of microspheres, which causes the degradation product N-benzoyl-dl-arginine. Camostat mesylate is an inhibitor of KLK, plasminogen, Prothrombin and Trypsin. Orally active, non-peptide proteolitic enzyme inhibitor with anti-trypsin and anti-plasmin activities, related structurally to gabexate. Protease inhibitor

Technology Process of Camostat mesylate

There total 2 articles about Camostat mesylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

p-hydroxyphenylacetic acid-N, N-dimethylcarbamoylmethyl ester (59721-16-3) → camostat mesylate (59721-29-8)

Guidance literature:

With sodium hydrogencarbonate; In pyridine; methanol; diethyl ether;

Reference yield:

methanesulfonic acid (75-75-2,98527-29-8) + camostat (59721-28-7) → camostat mesylate (59721-29-8)

Guidance literature:

In acetone; at 15 - 25 ℃; for 1h;

Reference yield:

camostat mesylate (59721-29-8) → 2-hydroxy-N,N-dimethylacetamide (14658-93-6) + 4-hydroxyphenylacetate (156-38-7) + 4-guanidinobenzoic acid (16060-65-4)

Guidance literature:

With Tris-HCl buffer; human liver carboxylesterase pI 4.5; at 37 ℃; pH=7.4; Enzyme kinetics;

DOI:10.1248/bpb.20.869

upstream raw materials:

p-hydroxyphenylacetic acid-N, N-dimethylcarbamoylmethyl ester

methanesulfonic acid

camostat

Downstream raw materials:

4-guanidinobenzoic acid

4-(4-guanidinobenzoyloxy)phenylacetic acid

2-hydroxy-N,N-dimethylacetamide

4-hydroxyphenylacetate

Refernces

• 1、 -. "Guanidinobenzoic acid derivatives". . . Retrieved 2008/06/13.