Basic information
- CAS
53882-12-5- Standard SMILES
N#Cc1cc(NC(=O)C(=O)O)c(Cl)c(NC(=O)C(=O)O)c1- InChIKey
RVGLGHVJXCETIO-UHFFFAOYSA-N- Molecular formula
- C11H6ClN3O6
- Average molar mass
- 311.63 g/mol
- Monoisotopic mass
- 310.9945126
Overview
Lodoxamide is an organonitrogen compound and an organooxygen compound. It is functionally related to an alpha-amino acid.
Names & identifiers
- Preferred name
- Lodoxamide
- IUPAC
- 2-[2-chloro-5-cyano-3-(oxaloamino)anilino]-2-oxoacetic acid
- English name
- Lodoxamide
- Molecular formula
- C11H6ClN3O6
- Molecular weight
- 311.63
Names & synonyms
Lodoxamide53882-12-5LodoxamidaLodoxamidumDTXSID9057767SPU695OD73DTXCID0031556N,N'-(2-chloro-5-cyano-m-phenylene)dioxamateAcetic acid, 2,2'-((2-chloro-5-cyano-1,3-phenylene)diimino)bis(2-oxo-{[3-(carboxyformamido)-2-chloro-5-cyanophenyl]carbamoyl}formic acidAcetic acid, 2,2'-[(2-chloro-5-cyano-1,3-phenylene)diimino]bis[2-oxo-((3-(carboxyformamido)-2-chloro-5-cyanophenyl)carbamoyl)formic acid
Show more names
Unii-spu695od73LODOXAMIDE USP/EP/BPLodoxamide (U42585E)Lodoxamide lmpurity 16Lodoxamide lmpurity 01Lodoxamidum [inn-latin]Lodoxamida [inn-spanish]Lodoxamide, 10 mM in DMSO
2-((2-chloro-5-cyano-3-(oxaloamino)phenyl)amino)-2-oxoacetic acid2-[[2-chloro-5-cyano-3-(oxaloamino)phenyl]amino]-2-oxoacetic acidRefChem:58567S01GX052-[2-chloro-5-cyano-3-(oxaloamino)anilino]-2-oxoacetic acid2,2'-((2-Chloro-5-cyano-1,3-phenylene)bis(azanediyl))bis(2-oxoacetic acid)U-42585E (free acid)Lodoxamide (INN)
Properties
Computed structural properties
- XLogP
- 0.5
- Topological polar surface area
- 157 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 4
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 489
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Human DrugsBreast Feeding; Lactation; Milk, Human; Anti-Allergic Agents; Histamine Antagonists
Physicochemical properties
- Melting point
- 212 ° · 212° (dec)
- Density
- 1.78 · 1.78±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 3 mg/ml; · DMF: 3 mg/ml; DMSO: 5 mg/ml; PBS (pH 7.2): 2 mg/mL
- form
- A solid
- pka
- 2.07 · 2.07±0.50(Predicted)
- color
- Off-white to pink
- Stability
- Hygroscopic
- InChI
- 1S/C11H6ClN3O6/c12-7-5(14-8(16)10(18)19)1-4(3-13)2-6(7)15-9(17)11(20)21/h1-2H,(H,14,16)(H,15,17)(H,18,19)(H,20,21)
- InChIKey
- RVGLGHVJXCETIO-UHFFFAOYSA-N
- SMILES
- Clc1c(cc(cc1NC(=O)C(=O)O)C#N)NC(=O)C(=O)O
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- wgk
- WGK 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
ATC Code
S01GX05
S - Sensory organs
QS - Sensory organs
Pharmacodynamics
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.
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.
Biological Half-LifeElimination half-life was 8.5 hours in urine.
FDA Pharmacological Classification
SPU695OD73
LODOXAMIDE
Physiologic Effects [PE] - Decreased Histamine Release
Established Pharmacologic Class [EPC] - Mast Cell Stabilizer
Lodoxamide is a Mast Cell Stabilizer. The physiologic effect of lodoxamide is by means of Decreased Histamine Release.
MeSH Pharmacological Classification
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)
Absorption, Distribution and Excretion
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.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…