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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2017-10-23 19:06:24 UTC
HMDB IDHMDB0014854
Secondary Accession Numbers
  • HMDB14854
Metabolite Identification
Common NameNedocromil
DescriptionNedocromil is only found in individuals that have used or taken this drug. It is a pyranoquinolone derivative that inhibits activation of inflammatory cells which are associated with asthma, including eosinophils, neutrophils, macrophages, mast cells, monocytes, and platelets. [PubChem]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.
Structure
Thumb
Synonyms
ValueSource
9-Ethyl-6,9-dihydro-4,6-dioxo-10-propyl-4H-pyrano(3,2-g)chinolin-2,8-dicarbonsaeureChEBI
9-Ethyl-6,9-dihydro-4,6-dioxo-10-propyl-4H-pyrano(3,2-g)quinoline-2,8-dicarboxylic acidChEBI
NedocromiloChEBI
NedocromilumChEBI
9-Ethyl-6,9-dihydro-4,6-dioxo-10-propyl-4H-pyrano(3,2-g)quinoline-2,8-dicarboxylateGenerator
Aventis brand OF nedocromil sodiumMeSH
Fisons brand OF nedocromil sodiumMeSH
IrtanMeSH
Nedocromil, disodium salt, hydrateMeSH
Rhône-poulenc rorer brand OF nedocromil sodiumMeSH
Vita brand OF nedocromil sodiumMeSH
Calcium, nedocromilMeSH
Nedocromil calciumMeSH
RapitilMeSH
TiladeMeSH
Allergan brand OF nedocromil sodiumMeSH
AlocrilMeSH
CetimilMeSH
Nedocromil sodiumMeSH
Pantheon brand OF nedocromil sodiumMeSH
TilaireMeSH
ASTA medica brand OF nedocromil sodiumMeSH
Aventis behring brand OF nedocromil sodiumMeSH
BrionilMeSH
HalamidMeSH
Lesvi brand OF nedocromil sodiumMeSH
Nedocromil, calcium salt (1:1)MeSH
Nedocromil, disodium saltMeSH
Sodium, nedocromilMeSH
TiladMeSH
TilavistMeSH
Chemical FormulaC19H17NO7
Average Molecular Weight371.3408
Monoisotopic Molecular Weight371.100501903
IUPAC Name9-ethyl-4,6-dioxo-10-propyl-4H,6H,9H-chromeno[7,6-b]pyridine-2,8-dicarboxylic acid
Traditional Namenedocromil
CAS Registry Number69049-73-6
SMILES
CCCC1=C2N(CC)C(=CC(=O)C2=CC2=C1OC(=CC2=O)C(O)=O)C(O)=O
InChI Identifier
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 KeyRQTOOFIXOKYGAN-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as chromenopyridines. These are aromatic heterocyclic compounds structurally characterized by a pyridine ring fused to a chromene moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct ParentChromenopyridines
Alternative Parents
Substituents
  • Chromenopyridine
  • Quinoline-2-carboxylic acid
  • Chromone
  • Dihydroquinolone
  • Dihydroquinoline
  • Quinoline
  • Pyridine carboxylic acid
  • Pyridine carboxylic acid or derivatives
  • Pyranone
  • Benzenoid
  • Pyridine
  • Pyran
  • Dicarboxylic acid or derivatives
  • Vinylogous amide
  • Heteroaromatic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Azacycle
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point299 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.046 g/LNot Available
LogP2.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.046 g/LALOGPS
logP2.18ALOGPS
logP2.5ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)2.28ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area121.21 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity98.09 m³·mol⁻¹ChemAxon
Polarizability36.95 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fi3-1079000000-d564312728bd150fe31cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0ufr-5005970000-97881ce64a88f76b15bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0009000000-57e9552f630a97a5246dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kdi-0019000000-6cb1f3659f43e7f5db29View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001l-2090000000-e8513d13fffe0f308201View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-0009000000-3558ecfc138178587c69View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00c0-0049000000-2dd8dd6be40621ec07acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05gj-1091000000-9a4f3989d5b3fd23a494View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00716 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00716 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00716
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID45608
KEGG Compound IDC07255
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNedocromil
METLIN IDNot Available
PubChem Compound50294
PDB IDNot Available
ChEBI ID7492
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
High affinity receptor for N-formyl-methionyl peptides, which are powerful neutrophils chemotactic factors. Binding of FMLP to the receptor causes activation of neutrophils. This response is mediated via a G-protein that activates a phosphatidylinositol-calcium second messenger system
Gene Name:
FPR1
Uniprot ID:
P21462
Molecular weight:
38445.1
References
  1. Peroni DG, Melotti P, Piacentini GL, Bonizzato C, Boner AL: Effects of nedocromil sodium on the binding of N-formyl-methionyl-leucyl-phenylalanine in human neutrophils. Agents Actions. 1992 Jul;36(3-4):212-4. [PubMed:1326878 ]
  2. Carolan EJ, Casale TB: Effects of nedocromil sodium and WEB 2086 on chemoattractant-stimulated neutrophil migration through cellular and noncellular barriers. Ann Allergy. 1992 Oct;69(4):323-8. [PubMed:1329582 ]
  3. Warringa RA, Mengelers HJ, Maikoe T, Bruijnzeel PL, Koenderman L: Inhibition of cytokine-primed eosinophil chemotaxis by nedocromil sodium. J Allergy Clin Immunol. 1993 Mar;91(3):802-9. [PubMed:8384226 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for cysteinyl leukotrienes mediating bronchoconstriction of individuals with and without asthma. Stimulation by LTD4 results in the contraction and proliferation of smooth muscle, edema, eosinophil migration and damage to the mucus layer in the lung. This response is mediated via a G-protein that activates a phosphatidylinositol-calcium second messenger system. The rank order of affinities for the leukotrienes is LTD4 >> LTE4 = LTC4 >> LTB4
Gene Name:
CYSLTR1
Uniprot ID:
Q9Y271
Molecular weight:
38540.5
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Monteseirin J, Chacon P, Vega A, Sanchez-Monteseirin H, Asturias JA, Martinez A, Guardia P, Perez-Cano R, Conde J: L-selectin expression on neutrophils from allergic patients. Clin Exp Allergy. 2005 Sep;35(9):1204-13. [PubMed:16164449 ]
  4. Yazid S, Leoni G, Getting SJ, Cooper D, Solito E, Perretti M, Flower RJ: Antiallergic cromones inhibit neutrophil recruitment onto vascular endothelium via annexin-A1 mobilization. Arterioscler Thromb Vasc Biol. 2010 Sep;30(9):1718-24. doi: 10.1161/ATVBAHA.110.209536. Epub 2010 Jun 17. [PubMed:20558817 ]
  5. Radeau T, Godard P, Chavis C, Michel FB, Descomps B, Damon M: Effect of nedocromil sodium on sulfidopeptide leukotrienes-stimulated human alveolar macrophages in asthma. Pulm Pharmacol. 1993 Mar;6(1):27-31. [PubMed:8386571 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for cysteinyl leukotrienes. The response is mediated via a G-protein that activates a phosphatidylinositol- calcium second messenger system. Stimulation by BAY u9773, a partial agonist, induces specific contractions of pulmonary veins and might also have an indirect role in the relaxation of the pulmonary vascular endothelium. The rank order of affinities for the leukotrienes is LTC4 = LTD4 >> LTE4
Gene Name:
CYSLTR2
Uniprot ID:
Q9NS75
Molecular weight:
39634.8
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Monteseirin J, Chacon P, Vega A, Sanchez-Monteseirin H, Asturias JA, Martinez A, Guardia P, Perez-Cano R, Conde J: L-selectin expression on neutrophils from allergic patients. Clin Exp Allergy. 2005 Sep;35(9):1204-13. [PubMed:16164449 ]
  4. Yazid S, Leoni G, Getting SJ, Cooper D, Solito E, Perretti M, Flower RJ: Antiallergic cromones inhibit neutrophil recruitment onto vascular endothelium via annexin-A1 mobilization. Arterioscler Thromb Vasc Biol. 2010 Sep;30(9):1718-24. doi: 10.1161/ATVBAHA.110.209536. Epub 2010 Jun 17. [PubMed:20558817 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for prostaglandin D2 (PGD2). The activity of this receptor is mainly mediated by G(s) proteins that stimulate adenylate cyclase, resulting in an elevation of intracellular cAMP. A mobilization of calcium is also observed, but without formation of inositol 1,4,5-trisphosphate
Gene Name:
PTGDR
Uniprot ID:
Q13258
Molecular weight:
40270.1
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Lane SJ, Lee TH: Mast cell effector mechanisms. J Allergy Clin Immunol. 1996 Nov;98(5 Pt 2):S67-71; discussion S71-2. [PubMed:8939179 ]
  4. Ahluwalia P, Anderson DF, Wilson SJ, McGill JI, Church MK: Nedocromil sodium and levocabastine reduce the symptoms of conjunctival allergen challenge by different mechanisms. J Allergy Clin Immunol. 2001 Sep;108(3):449-54. [PubMed:11544467 ]
General function:
Involved in ATP binding
Specific function:
Molecular chaperone. Has ATPase activity
Gene Name:
HSP90AA1
Uniprot ID:
P07900
Molecular weight:
84659.0
References
  1. Okada M, Itoh H, Hatakeyama T, Tokumitsu H, Kobayashi R: Hsp90 is a direct target of the anti-allergic drugs disodium cromoglycate and amlexanox. Biochem J. 2003 Sep 1;374(Pt 2):433-41. [PubMed:12803546 ]
  2. Nishikawa M, Takemoto S, Takakura Y: Heat shock protein derivatives for delivery of antigens to antigen presenting cells. Int J Pharm. 2008 Apr 16;354(1-2):23-7. Epub 2007 Sep 29. [PubMed:17980980 ]