Sivelestat

Base Information

• Chemical Name: Sivelestat
• CAS No.: 127373-66-4
• Molecular Formula: C20H22N2O7S
• Molecular Weight: 434.47
• Hs Code.: 2935009090
• European Community (EC) Number: 695-701-7
• UNII: DWI62G0P59
• DSSTox Substance ID: DTXSID9048304
• Nikkaji Number: J464.383F
• Wikipedia: Sivelestat
• Wikidata: Q5646925
• NCI Thesaurus Code: C66539
• Pharos Ligand ID: TLSLCZ1VM11W
• Metabolomics Workbench ID: 153764
• ChEMBL ID: CHEMBL76688
• Mol file: 127373-66-4.mol

Synonyms:N-(2-(4-(2,2-dimethylpropionyloxy)phenylsulfonylamino)benzoyl)aminoacetic acid;ONO 5046;ONO-5046;Ono-EI-600;sivelestat

Chemical Property of Sivelestat

Chemical Property:

• Melting Point: 218-220°
• Refractive Index: 1.598
• PKA: 3.67±0.10(Predicted)
• PSA: 147.25000
• Density: 1.369 g/cm³
• LogP: 3.79800
• Storage Temp.: room temp
• Solubility.: DMSO: soluble10mg/mL, clear
• XLogP3: 3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 434.11477222
• Heavy Atom Count: 30
• Complexity: 731

Purity/Quality:

99%min, ^*data from raw suppliers

Sivelestat sodium salt hydrate ≥98% (HPLC), solid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C(=O)OC1=CC=C(C=C1)S(=O)(=O)NC2=CC=CC=C2C(=O)NCC(=O)O
• Recent ClinicalTrials: Protective Effect of Sivelestat Sodium on ARDS in Patients With Sepsis
• Recent EU Clinical Trials: Exercise-induced cardiac adaptions in rheumatoid arthritis patients during interleukin-6 vs. tumor necrosis factor antibody therapy: a randomised controlled study (RABEX).
• Recent NIPH Clinical Trials: Effect of sivelestat, a neutrophil elastase inhibitor on cardiac surgical patients after cardiopulmonary bypass
• Uses: Treatment of acute lung injury; acute respiratory distress syndrome (elastase inhibitor). Sivelestat is an inhibitor of neutrophil elastase that prevents neutrophil extracellular trap formation and rescues mice from endotoxic shock. The inhibition of neutropil elastase by Sivelestat is a promising therapeutic strategy to inhibit glial scar and promote functional recovery by upregulating angiopoietin-1 after spinal cord injury.

Technology Process of Sivelestat

There total 12 articles about Sivelestat 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: 94.5%

4-(N-(2-(2-(benzyloxy)-2-oxoethylcarbamoyl)phenyl)sulfamoyl)phenylpivalic acid (150374-98-4) → N-[o-(p-pivaloyloxybenzenesulfonylamino)benzoyl]glycine (127373-66-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 - 25 ℃; for 2h; under 2280.15 Torr; Pressure; Autoclave;

Reference yield: 73.6%

pivaloyl chloride (3282-30-2) + sodium p-hydroxybenzenesulfonate (825-90-1) + benzyl 2-(2-aminobenzamido)acetate → N-[o-(p-pivaloyloxybenzenesulfonylamino)benzoyl]glycine (127373-66-4)

Guidance literature:

pivaloyl chloride; sodium p-hydroxybenzenesulfonate; With triethylamine; In dichloromethane; at 20 - 25 ℃; for 2.08333h;

With thionyl chloride; In N,N-dimethyl-formamide; at 20 - 25 ℃; for 2.25h;

benzyl 2-(2-aminobenzamido)acetate; Further stages;

Reference yield: 70.0%

N-(2-aminobenzoyl)-glycine (526-21-6) + p-pivaloyloxybenzenesulfonyl chloride (150374-99-5) → N-[o-(p-pivaloyloxybenzenesulfonylamino)benzoyl]glycine (127373-66-4)

Guidance literature:

N-(2-aminobenzoyl)-glycine; With pyridine; chloro-trimethyl-silane; In dichloromethane; at 25 - 30 ℃; for 0.25h;

p-pivaloyloxybenzenesulfonyl chloride; In dichloromethane; at 25 - 30 ℃; Further stages.;

DOI:10.1080/00397910801982373

upstream raw materials:

4-(N-(2-(2-(benzyloxy)-2-oxoethylcarbamoyl)phenyl)sulfamoyl)phenylpivalic acid

pivaloyl chloride

sodium p-hydroxybenzenesulfonate

p-pivaloyloxybenzenesulfonyl chloride