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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:46 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
Data?1582753228
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 sodiumHMDB
Fisons brand OF nedocromil sodiumHMDB
IrtanHMDB
Nedocromil, disodium salt, hydrateHMDB
Rhône-poulenc rorer brand OF nedocromil sodiumHMDB
Vita brand OF nedocromil sodiumHMDB
Calcium, nedocromilHMDB
Nedocromil calciumHMDB
RapitilHMDB
TiladeHMDB
Allergan brand OF nedocromil sodiumHMDB
AlocrilHMDB
CetimilHMDB
Nedocromil sodiumHMDB
Pantheon brand OF nedocromil sodiumHMDB
TilaireHMDB
ASTA medica brand OF nedocromil sodiumHMDB
Aventis behring brand OF nedocromil sodiumHMDB
BrionilHMDB
HalamidHMDB
Lesvi brand OF nedocromil sodiumHMDB
Nedocromil, calcium salt (1:1)HMDB
Nedocromil, disodium saltHMDB
Sodium, nedocromilHMDB
TiladHMDB
TilavistHMDB
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
Description 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point299 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.046 g/LNot Available
LogP2.6Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+185.9131661259
DarkChem[M-H]-183.87731661259
DeepCCS[M+H]+183.68130932474
DeepCCS[M-H]-181.32330932474
DeepCCS[M-2H]-215.21730932474
DeepCCS[M+Na]+191.38330932474
AllCCS[M+H]+184.332859911
AllCCS[M+H-H2O]+181.332859911
AllCCS[M+NH4]+187.132859911
AllCCS[M+Na]+187.932859911
AllCCS[M-H]-188.732859911
AllCCS[M+Na-2H]-188.632859911
AllCCS[M+HCOO]-188.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NedocromilCCCC1=C2N(CC)C(=CC(=O)C2=CC2=C1OC(=CC2=O)C(O)=O)C(O)=O3772.1Standard polar33892256
NedocromilCCCC1=C2N(CC)C(=CC(=O)C2=CC2=C1OC(=CC2=O)C(O)=O)C(O)=O2370.8Standard non polar33892256
NedocromilCCCC1=C2N(CC)C(=CC(=O)C2=CC2=C1OC(=CC2=O)C(O)=O)C(O)=O3583.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Nedocromil,1TMS,isomer #1CCCC1=C2OC(C(=O)O[Si](C)(C)C)=CC(=O)C2=CC2=C1N(CC)C(C(=O)O)=CC2=O3248.7Semi standard non polar33892256
Nedocromil,1TMS,isomer #2CCCC1=C2OC(C(=O)O)=CC(=O)C2=CC2=C1N(CC)C(C(=O)O[Si](C)(C)C)=CC2=O3269.2Semi standard non polar33892256
Nedocromil,2TMS,isomer #1CCCC1=C2OC(C(=O)O[Si](C)(C)C)=CC(=O)C2=CC2=C1N(CC)C(C(=O)O[Si](C)(C)C)=CC2=O3188.6Semi standard non polar33892256
Nedocromil,1TBDMS,isomer #1CCCC1=C2OC(C(=O)O[Si](C)(C)C(C)(C)C)=CC(=O)C2=CC2=C1N(CC)C(C(=O)O)=CC2=O3476.3Semi standard non polar33892256
Nedocromil,1TBDMS,isomer #2CCCC1=C2OC(C(=O)O)=CC(=O)C2=CC2=C1N(CC)C(C(=O)O[Si](C)(C)C(C)(C)C)=CC2=O3475.7Semi standard non polar33892256
Nedocromil,2TBDMS,isomer #1CCCC1=C2OC(C(=O)O[Si](C)(C)C(C)(C)C)=CC(=O)C2=CC2=C1N(CC)C(C(=O)O[Si](C)(C)C(C)(C)C)=CC2=O3578.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Nedocromil GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fi3-1079000000-d564312728bd150fe31c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nedocromil GC-MS (2 TMS) - 70eV, Positivesplash10-0ufr-5005970000-97881ce64a88f76b15bd2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nedocromil GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nedocromil GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nedocromil 10V, Negative-QTOFsplash10-00fr-0009000000-3558ecfc138178587c692016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nedocromil 20V, Negative-QTOFsplash10-00c0-0049000000-2dd8dd6be40621ec07ac2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nedocromil 40V, Negative-QTOFsplash10-05gj-1091000000-9a4f3989d5b3fd23a4942016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nedocromil 10V, Negative-QTOFsplash10-001i-0097000000-0ffc03875f16aae689cc2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nedocromil 20V, Negative-QTOFsplash10-0002-0093000000-47cd9e316569c13d535d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nedocromil 40V, Negative-QTOFsplash10-0002-0092000000-2cbe85dde82b160a062c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nedocromil 10V, Positive-QTOFsplash10-0uk9-0009000000-57e9552f630a97a5246d2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nedocromil 20V, Positive-QTOFsplash10-0kdi-0019000000-6cb1f3659f43e7f5db292016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nedocromil 40V, Positive-QTOFsplash10-001l-2090000000-e8513d13fffe0f3082012016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nedocromil 10V, Positive-QTOFsplash10-00di-0009000000-62e4880ac1e3f7a379c22021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nedocromil 20V, Positive-QTOFsplash10-00b9-0029000000-828027fa080faa0ba1002021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nedocromil 40V, Positive-QTOFsplash10-053s-0091000000-e7da9ff3f608a7d6d7b42021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00716 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00716 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00716
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]