Lodoxamide

Base Information

• Chemical Name: Lodoxamide
• CAS No.: 53882-12-5
• Molecular Formula: C11H6ClN3O6
• Molecular Weight: 311.638
• Hs Code.: 2926909090
• UNII: SPU695OD73
• DSSTox Substance ID: DTXSID9057767
• Nikkaji Number: J10.842A
• Wikipedia: Lodoxamide
• Wikidata: Q6666510
• NCI Thesaurus Code: C61813
• RXCUI: 52151
• Pharos Ligand ID: LW979CKK6W71
• Metabolomics Workbench ID: 149990
• ChEMBL ID: CHEMBL1201266
• Mol file: 53882-12-5.mol

Synonyms:diethyl N,N'-(2-chloro-5-cyano-m-phenylene)dioxamate;lodoxamide;lodoxamide ethyl;U-42,718

Chemical Property of Lodoxamide

Chemical Property:

• Melting Point: 212° (dec)
• Boiling Point: °Cat760mmHg
• PKA: 2.07±0.50(Predicted)
• Flash Point: °C
• PSA: 156.59000
• Density: 1.78g/cm³
• LogP: 0.40388
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 310.9945126
• Heavy Atom Count: 21
• Complexity: 489

Purity/Quality:

99% ^*data from raw suppliers

Lodoxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=C(C(=C1NC(=O)C(=O)O)Cl)NC(=O)C(=O)O)C#N
• Uses: Harmful Lodoxamide is an antiallergic drug that acts as a mast cell stabilizer. It is effective in the treatment of allergic conjunctivitis and in decreasing vascular permeability.

Technology Process of Lodoxamide

There total 5 articles about Lodoxamide 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: 93.8%

oxalyl dichloride (79-37-8) + 2-chloro-5-cyano-1,3-phenylenediamine (34207-46-0) → N,N'-(2-chloro-5-cyano-m-phenylene)dioxamic acid (53882-12-5)

Guidance literature:

In dichloromethane; at -10 - 0 ℃; for 0.5h; Solvent;

Reference yield:

diethyl N,N'-(2-chloro-5-cyano-m-phenylene)dioxamate (53882-13-6) → N,N'-(2-chloro-5-cyano-m-phenylene)dioxamic acid (53882-12-5)

Guidance literature:

With sodium hydroxide; In dichloromethane;

DOI:10.1021/jm00207a016

Reference yield:

4-chloro-3,5-dinitrobenzonitrile (1930-72-9) → N,N'-(2-chloro-5-cyano-m-phenylene)dioxamic acid (53882-12-5)

Guidance literature:

Multi-step reaction with 3 steps

1: SnCl₂, aq. HCl

2: Et₃N / dimethylformamide

3: aq. NaOH / CH₂Cl₂

With hydrogenchloride; sodium hydroxide; triethylamine; tin(ll) chloride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00207a016

upstream raw materials:

diethyl N,N'-(2-chloro-5-cyano-m-phenylene)dioxamate

4-chloro-3,5-dinitrobenzonitrile

2-chloro-5-cyano-1,3-phenylenediamine

oxalyl dichloride

Downstream raw materials:

lodoxamide tromethamine

Refernces

• 1、 -. "Cytoprotective use of oxamate derivatives". . . Retrieved 2008/06/13.