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Lodoxamide

Lodoxamide structure

CAS No:
53882-12-5
Formula:
C11H6ClN3O6
Chemical Name:
Lodoxamide
Synonyms:
Acetic acid,2,2′-[(2-chloro-5-cyano-1,3-phenylene)diimino]bis[2-oxo-;2,2′-[(2-Chloro-5-cyano-1,3-phenylene)diimino]bis[2-oxoacetic acid];Lodoxamide;Thilomide;2,2′-((2-chloro-5-cyano-1,3-phenylene)bis(azanediyl))bis(2-oxoacetic acid);2-[2-Chloro-5-cyano-3-(oxaloamino)anilino]-2-oxoacetic acid
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

Lodoxamide is an organooxygen compound and an organonitrogen compound. It derives from an alpha-amino acid.|Lodoxamide is a mast-cell stabilizer for topical administration into the eye. Mast-cell stabilizers, first one approved being cromolyn sodium, are used in treatment of ocular hypersensitivity reactions such as vernal conjunctivitis. These conditions often require treatment with anti-inflammatory medications such as ophthalmic NSAIDs or topical steroids which may cause systemic or toxic effects long-term. Although less effective than topical steroids at decreasing inflammation, mast-cell stabilizers offer another treatment option and exhibit minimal adverse effects. Lodoxamide is marketed under the brand name Alomide by Alcon.|Lodoxamide is a Mast Cell Stabilizer. The physiologic effect of lodoxamide is by means of Decreased Histamine Release.|Lodoxamide is a synthetic mast cell stabilizing compound with anti-inflammatory activity. Lodoxamide appears to inhibit the antigen-stimulated calcium transport across the mast cell membrane, thereby inhibiting mast cell degranulation and the release of histamine, leukotrienes, and other substances that cause hypersensitivity reactions. Lodoxamide also inhibits eosinophil chemotaxis. When applied topically to the eye, this drug prevents the symptoms associated with keratitis or conjunctivitis.

Lodoxamide Basic Attributes

Molecular Weight：

311.63500

Exact Mass：

311.63

UNII：

SPU695OD73

DSSTox ID：

DTXSID9057767

NCI Thesaurus Code：

C61813

ATC Code：

S01GX05|S - Sensory organs

HScode：

2926909090

Characteristics

PSA：

156.59000

XLogP3：

0.40388

Density：

1.78g/cm3

Melting Point：

212 °C (decomp)

Refractive Index：

1.673

Drug Information

Drug Indication：

Indicated in the treatment of the ocular disorders referred to by the terms vernal keratoconjunctivitis, vernal conjunctivitis, and vernal keratitis.|FDA Label

Pharmacology：

Lodoxamide is a mast cell stabilizer that inhibits the in vivo Type 1 immediate hypersensitivity reaction. Lodoxamide therapy inhibits the increases in cutaneous vascular permeability that are associated with reagin or IgE and antigen-mediated reactions.

MeSH：

Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475) (See all compounds classified as Anti-Allergic Agents.)

Absorption：

In a study of twelve healthy adult volunteers, topical administration of lodoxamide tromethamine ophthalmic solution 0.1%, one drop in each eye four times per day for ten days, did not result in any measurable lodoxamide plasma levels at a detection limit of 2.5 ng/mL.|Urinary excretion is the major route of elimination.

Biological Half-Life：

Elimination half-life was 8.5 hours in urine.

Mechanism of Action：

Although lodoxamide's precise mechanism of action is unknown, it is postulated that it prevents calcium influx into mast cells upon antigen stimulation and therefore stabilizes the membrane. By stabilizing the mast cell membrane from degranulation, lodoxamide consequently inhibits the release of intracellular histamine and other chemoattractant factors that primarily cause ocular symptoms. Lodoxamide's mechanism of action may be similar to cromolyn sodium, as both exhibit cross-tachyphylaxis.

MeSH Entry Terms：

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

Lodoxamide Use and Manufacturing

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:311.63
XLogP3:0.5
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:4
Exact Mass:310.9945126
Monoisotopic Mass:310.9945126
Topological Polar Surface Area:157
Heavy Atom Count:21
Complexity:489
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Loxamic acid is a mast cell stabilizer that can inhibit type I immediate allergic reactions in animals and humans, prevent the release of histamine caused by specific antigens, prevent the release of mast cells and other inflammatory mediators, and prevent the transfer of calcium ions into mast cells after stimulation. It is used to treat allergic eye diseases.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Lodoxamide eye drops
Ingredients	Lemimin Eye Drops is a sterilized, isotonic and buffered ophthalmic preparation that can be used multiple times. Each milliliter contains 1.78 mg of the active ingredient tromethamine and loxamic acid (equivalent to 1 mg of loxamic acid) and appropriate amounts of benzyl chloride, mannitol, hydroxypropyl methylcellulose and other auxiliary agents.
Specifications	5 ml: 5 mg (0.1%)