5555. Lodoxamide

Nomenclature

CAS number: 53882-12-5
2,2′-[(2-Chloro-5-cyano-1,3-phenylene)diimino]bis(2-oxoacetic acid); N,N′-(2-chloro-5-cyano-m-phenylene)dioxamic acid.
C11H6ClN3O6; mol wt 311.63.
C 42.40%, H 1.94%, Cl 11.38%, N 13.48%, O 30.80%.

Description and references

Mast cell stabilizer. Prepn: C. M. Hall, J. B. Wright, DE 2362409; eidem, US 3993679 (1974, 1976 both to Upjohn); J. B. Wright et al., J. Med. Chem. 21, 930 (1978). HPLC determn in human plasma: I. L. Honigberg et al., J. Chromatogr. 276, 213 (1983). Mechanism of action study: M. K. Church, J. Hiroi, Br. J. Pharmacol. 90, 421 (1987). Clinical evaluation in asthma: R. L. Case et al., J. Am. Med. Assoc. 247, 661 (1982); in allergic eye disease: G. T. Fahy et al., Eur. J. Ophthalmol. 2, 144 (1992).

Chemical structure

Properties

mp 212° (dec). uv max (0.1N NaOH) 239.5 (ε 23800).

Derivative

Diethyl ester.

Nomenclature

CAS number: 53882-13-6
Diethyl N,N′-(2-chloro-5-cyano-m-phenylene)dioxamate; lodoxamide ethyl; U-42718.
C15H14ClN3O6; mol wt 367.74.
C 48.99%, H 3.84%, Cl 9.64%, N 11.43%, O 26.10%.

Properties

Crystals from ethanol, mp 177-179°.

Derivative

Tromethamine salt.

Nomenclature

CAS number: 63610-09-3
Lodoxamide tromethamine; lodoxamide trometamol; U-42585E; Alomide (Alcon).
C11H6ClN3O6.2C4H11NO3; mol wt 553.90.
C 41.20%, H 5.10%, Cl 6.40%, N 12.64%, O 34.66%.

Therapeutic Category

Antiallergic; topically in allergic conjunctivitis.

Keywords

Antiallergic