Lodoxamide Chemical Properties

Melting point:

212° (dec)

Density 

1.78±0.1 g/cm3(Predicted)

storage temp. 

Store at -20°C

solubility 

DMF: 3 mg/ml; DMSO: 5 mg/ml; PBS (pH 7.2): 2 mg/mL

form 

A solid

pka

2.07±0.50(Predicted)

color 

Off-white to pink

Stability:

Hygroscopic

Lodoxamide Usage And Synthesis

Description

Trometamol (2-amino-2-(hydroxymethyl)-1,3- propanediol) salt . Lodoxamide is an antiallergic drug acting as a mast-cell stabilizer, which is effective in the treatment of allergic conjunctivitis .

Originator

Lodoxamide,Alcon,USA

Uses

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.

Uses

Harmful

Definition

ChEBI: Lodoxamide is an organooxygen compound and an organonitrogen compound. It is functionally related to an alpha-amino acid.

Manufacturing Process

To a solution of 1.56 mole of stannous chloride dihydrate in 860 ml of concentrated hydrochloric acid is added 0.2195 mole of 4-chloro-3,5- dinitrobenzonitrile. The mixture is stirred at room temperature for 2 hours and cooled to 0°C in an ice-salt bath. A cold solution of 50% sodium hydroxide is added to the mixture until strongly basic. During the addition the temperature is kept below 30°C.The precipitate is removed by filtration and extracted three times with 400 ml of ethyl acetate. The extracts are combined and added to the aqueous filtrate. The phases are shaken well for ten minutes and separated. The organic phase is evaporated to dryness in vacuo. The solid residue is recrystallized from ethanol-water. There is obtained 25.0 g (68%) of 4-chloro-3,5-diaminobenzonitrile, melting point 169-170°C.
To a solution of 0.34 mole of 4-chloro-3,5-diaminobenzonitrile in 160 ml of dry DMF is added 0.82 mole of triethylamine. The solution is cooled to 5°C andthere is added 0.82 mole of ethyloxalyl chloride dropwise, keeping the temperature less than 15°C. The mixture is stirred for 1 hour and warmed to room temperature. The mixture is stirred at room temperature for 24 hours. The precipitate is removed by filtration and washed two times with ethyl acetate. The filtrate and washes are combined and the ethyl acetate distilled off in vacuo. The DMF solution is poured into 3 L of water. The semi-solid residue is removed by filtration. The residue is recrystallized from ethanol. There is obtained 72.4 g (58%) of diethyl N,N'-(2-chloro-5-cyano-mphenylene)dioxamate, melting point 177-179°C.
A solution of 0.197 mole of diethyl (N,N'-(2-chloro-5-cyano-m-phenylene) dioxamate in 750 ml of methylene chloride is extracted with 465 ml of 1 N sodium hydroxide. The aqueous phase is separated and stirred for 20 min at room temperature. The solution is acidified with dilute hydrochloric acid. The precipitate is removed by filtration and washed with water. There is obtained 59.1 g (96%) of N,N'-(2-chloro-5-cyano-m-phenylene)dioxamic acid, melting point 212°C (dec.).

brand name

Alomide (Alcon).

Therapeutic Function

Anti-asthmatic, Antiallergic

Biochem/physiol Actions

Lodoxamide Tromethamine is a potent agonist of GPR35 in both human and rat, and an antiallergic mast cell stabilizer used clinically in the UK for treatment of allergic conjunctivitis.

Lodoxamide(53882-12-5)Related Product Information

• 3,5-DIAMINOBENZONITRILE
• Lodoxamidetromethamine
• Lodoxamide
• lodoxamide ethyl
• 3-AMINO-4-CHLOROBENZONITRILE
• 4-Chlorobenzonitrile