nedocromil   

GtoPdb Ligand ID: 7607

Synonyms: FPL-59002 | nedocromil sodium | Rapitil® | Tilade®
nedocromil is an approved drug (FDA (1992))
Compound class: Synthetic organic
Comment: Nedocromil is considered to be a mast cell stabilising drug. Chemically it belongs to the benzopyrone family of compounds. In the US, production of inhaled nedocromil was terminated in 2008.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 126.81
Molecular weight 371.1
XLogP 5.15
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CCCc1c2oc(cc(=O)c2cc2c1n(CC)c(cc2=O)C(=O)O)C(=O)O
Isomeric SMILES CCCc1c2oc(cc(=O)c2cc2c1n(CC)c(cc2=O)C(=O)O)C(=O)O
InChI InChI=1S/C19H17NO7/c1-3-5-9-16-10(13(21)7-12(18(23)24)20(16)4-2)6-11-14(22)8-15(19(25)26)27-17(9)11/h6-8H,3-5H2,1-2H3,(H,23,24)(H,25,26)
InChI Key RQTOOFIXOKYGAN-UHFFFAOYSA-N
No information available.
Summary of Clinical Use
Used as an inhlation drug to alleviate bronchconstriction in asthma [1], and may be used in eye-drops to treat allergic eye reactions. The use of some formulations of this drug has been discontinued in the US.
Mechanism Of Action and Pharmacodynamic Effects
Nedocromil predominantly stabilises mast cells and inhibits their degranulation. This action supresses the release of histamine and tryptase, thus reducing the synthesis of pro-inflammatory prostaglandins and leukotrienes. The drug also inhibits the activity of other types of inflammatory cells (eg eosinophils, neutrophils, macrophages, monocytes, and platelets) which are associated with asthma. However, as mast cell stabilisation is not sufficient on its own to explain the anti-asthmatic activity of this chromone type drug, other as yet incompletely resolved mechanisms must be involved.
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