Lodoxamide

Names

[ Name ]:
Lodoxamide

[Synonym ]:
UNII-SPU695OD73
Acetic acid,2,2'-((2-chloro-5-cyano-1,3-phenylene)diimino)bis(2-oxo
Lodoxamidum [INN-Latin]
N,N'-(2-Chlor-5-cyan-m-phenylen)-dioxamsaeure
Alomide (TN)
Lodoxamidum
Lodoxamida [INN-Spanish]
N,N'-(2-Chlor-5-cyan-3-phenylen)dioxamsaeure
N-N'-(2-chloro-5-cyano-m-phenylene)dioxamic acid
Lodoxamida
diesters of N,N'-(2-chloro-5-cyano-m-phenylene)dioxamic acid
Lodoxamide

Biological Activity

[Description]:

Lodoxamide is an antiallergic compound acting as a mast-cell stabilizer for the treatment of asthma and allergic conjunctivitis.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Histamine Receptor

Signaling Pathways >> Immunology/Inflammation >> Histamine Receptor

Research Areas >> Inflammation/Immunology

[In Vitro]

Lodoxamide inhibits compound 48/80-induced histamine release and ionophore-induced 45Ca influx with associated histamine release in purified rat peritoneal mast cells[1]. The chemotactic response of eosinophils to fMLP as well as to IL-5 is significant and dose-dependent inhibited by Lodoxamide. Lodoxamide is also able to strongly inhibit the release of eosinophil peroxidase after IgA-dependent activation and, to a lesser extent, the release of eosinophil cationic protein and eosinophil-derived neurotoxin[2].

[In Vivo]

Lodoxamide has been demonstrated to have cromolyn-like activity when studied in the rat peritoneal mast cell assay (PCA) model3 and in Ascaris antigen-sensitized rhesus monkeys. When given intravenously, orally, or intrabronchially by aerosol, lodoxamide significantly inhibits the increased respiratory frequency and decreased tidal volume induced by antigen challenge in Ascaris-sensitized. anesthetized rhesus monkeys[1]. Addition of lodoxamide tromethamine to Euro-Collins or University of Wisconsin solution results in a marked decrease in lung reperfusion injury as demonstrated by increased oxygenation, decreased microvascular permeability, and increased compliance[3]. Patients treated with lodoxamide tromethamine demonstrate an improvement in daytime breathing difficulty, cough, sputum production, and sleep[4].

[References]

[1]. Watt GD, et al. Protective effect opf lodoxamide tromethamine on allergen inhalation challenge. J Allergy Clin Immunol. 1980 Oct;66(4):286-94.

[2]. Capron M,et al. Inhibitory effects of lodoxamide on eosinophil activation. Int Arch Allergy Immunol. 1998 Jun;116(2):140-6.

[3]. Barr ML, et al. Addition of a mast cell stabilizing compound to organ preservation solutions decreases lung reperfusion injury. J Thorac Cardiovasc Surg. 1998 Mar;115(3):631-6; discussion 636-7.

[4]. Mann JS, et al. Inhaled lodoxamide tromethamine in the treatment of perennial asthma: a double-blind placebo-controlled study. J Allergy Clin Immunol. 1985 Jul;76(1):83-90.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.78g/cm3

[ Molecular Formula ]:
C₁₁H₆ClN₃O₆

[ Molecular Weight ]:
311.63500

[ Exact Mass ]:
310.99500

[ PSA ]:
156.59000

[ LogP ]:
0.40388

[ Index of Refraction ]:
1.673

[ Storage condition ]:
2-8℃

Safety Information

[ HS Code ]:
2926909090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2926909090

[ Summary ]:
HS:2926909090 other nitrile-function compounds VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%