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Nedocromil

Nedocromil structure

CAS No:
69049-73-6
Formula:
C19H17NO7
Chemical Name:
Nedocromil
Synonyms:
4H-Pyrano[3,2-g]quinoline-2,8-dicarboxylic acid,9-ethyl-6,9-dihydro-4,6-dioxo-10-propyl-;9-Ethyl-6,9-dihydro-4,6-dioxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid;Nedocromil;FPL 59002
Categories:
Active Pharmaceutical Ingredients > Respiratory Drugs

Description

Nedocromil suppresses the action or formation of multiple mediators, including histamine, leukotriene C4 (LTC4), and prostaglandin D2 (PGD2).

Solid

Nedocromil is a dicarboxylic acid and an organic heterotricyclic compound. It has a role as a non-steroidal anti-inflammatory drug, an anti-asthmatic drug and an anti-allergic agent. It is a conjugate acid of a nedocromil(2-).|A pyranoquinolone derivative that inhibits activation of inflammatory cells which are associated with asthma, including eosinophils, neutrophils, macrophages, mast cells, monocytes, and platelets.|Nedocromil is a Mast Cell Stabilizer. The physiologic effect of nedocromil is by means of Decreased Histamine Release.|A pyranoquinolone derivative that inhibits activation of inflammatory cells which are associated with ASTHMA, including EOSINOPHILS; NEUTROPHILS; MACROPHAGES; MAST CELLS; MONOCYTES; AND PLATELETS.

Nedocromil Basic Attributes

Molecular Weight：

371.34

Exact Mass：

371.34

UNII：

0B535E0BN0

DSSTox ID：

DTXSID7023356

ATC Code：

R - Respiratory system|S - Sensory organs

Characteristics

PSA：

121

XLogP3：

2.6

Appearance：

white to beige

Density：

1.5±0.1 g/cm3

Melting Point：

299 °C (decomp)

Boiling Point：

645.5±55.0 °C at 760 mmHg

Flash Point：

344.2±31.5 °C

Refractive Index：

1.641

Water Solubility：

DMSO: soluble 2mg/mL, clear (warmed)

Storage Conditions：

2-8°C

Safety Information

Transport codes：

NONH for all modes of transport

hazard class code：

safety instructions：

Marks：

Precautionary statement(s)：

P305 + P351 + P338

Hazard Statements：

H319

Toxicity

Toxicity Summary：

Side effects include headache, nasal congestion, ocular burning, irritation and stinging, unpleasant taste, cough, difficulty breathing, noisy breathing, shortness of breath, tightness in chest, wheezing, conjunctivitis, blurred vision, change in color vision, difficulty seeing at night, increased sensitivity of eyes to sunlight.

Protein Binding：

approximately 89% protein bound in human plasma over a concentration range of 0.5 to 50 µg/mL

Drug Information

Drug Indication：

For the treatment of mild to moderate asthma|FDA Label

Pharmacology：

Nedocromil is a anti-inflammatory agent and can be administered directly to the bronchial mucosa. It has significant inhibitory effect on allergen-induced early and late asthmatic reactions and on bronchial hyperresponsiveness.

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.)|Drugs that are used to treat asthma. (See all compounds classified as Anti-Asthmatic Agents.)|Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)|Compounds that prevent the release of inflammatory mediators from MAST CELLS. (See all compounds classified as Mast Cell Stabilizers.)

Absorption：

Low|It is not metabolized and is eliminated primarily unchanged in urine (70%) and feces (30%).

Metabolism/Metabolites：

Nedocromil is not metabolized after IV administration and is excreted unchanged.

Biological Half-Life：

~3.3 hours

Mechanism of Action：

Nedocromil has been shown to inhibit the in vitro activation of, and mediator release from, a variety of inflammatory cell types associated with asthma, including eosinophils, neutrophils, macrophages, mast cells, monocytes, and platelets. Nedocromil inhibits activation and release of inflammatory mediators such as histamine, prostaglandin D2 and leukotrienes c4 from different types of cells in the lumen and mucosa of the bronchial tree. These mediators are derived from arachidonic acid metabolism through the lipoxygenase and cyclo-oxygenase pathways. The mechanism of action of nedocromil may be due partly to inhibition of axon reflexes and release of sensory neuropeptides, such as substance P, neurokinin A, and calcitonin-geneñrelated peptides. The result is inhibition of bradykinin-induced bronchoconstriction. Nedocromil does not posess any bronchodilator, antihistamine, or corticosteroid activity.

MeSH Entry Terms：

9-Ethyl-6,9-dihydro-4,6-dioxo-10-propyl-4H-pyrano(3,2-g)quinoline-2,8-dicarboxylic acid

Nedocromil Use and Manufacturing

Uses

Asthma prevention drugs must be administered by inhalation. This product is excreted in its original form and is not metabolized, so long-term use will not produce accumulation. Reversible airway obstructive diseases, including bronchial asthma, asthmatic bronchitis, new-onset asthma, and labor-induced asthma, can be used for frequent preventive treatment.

Use Classification：

Pharmaceuticals

Computed Properties

Molecular Weight:371.3
XLogP3:2.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:5
Exact Mass:371.10050188
Monoisotopic Mass:371.10050188
Topological Polar Surface Area:121
Heavy Atom Count:27
Complexity:753
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Sodium bicarbonate

Polyphosphoric acids

Diethyl oxalate