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Record Information
Version3.6
Creation Date2012-09-06 15:16:50 UTC
Update Date2017-03-02 21:33:25 UTC
HMDB IDHMDB14725
Secondary Accession NumbersNone
Metabolite Identification
Common NameCinalukast
DescriptionUsed in the treatment of asthma, cinalukast selectively antagonizes leukotriene D4 (LTD4) at the cysteinyl leukotriene receptor, CysLT1, in the human airway. Cinalukast inhibits the actions of LTD4 at the CysLT1 receptor, preventing airway edema, smooth muscle contraction, and enhanced secretion of thick, viscous mucus.
Structure
Thumb
Synonyms
ValueSource
3'-((e)-2-(4-Cyclobutyl-2-thiazolyl)vinyl)-2,2-diethylsuccinanilic acidChEBI
3'-((e)-2-(4-Cyclobutyl-2-thiazolyl)vinyl)-2,2-diethylsuccinanilateGenerator
4-(3-(2-(4-Cyclobutyl-2-thiazolyl)ethenyl)phenylamino)-2,2-diethyl-4-oxobutanoic acidMeSH
Chemical FormulaC23H28N2O3S
Average Molecular Weight412.545
Monoisotopic Molecular Weight412.182063462
IUPAC Name3-({3-[(E)-2-(4-cyclobutyl-1,3-thiazol-2-yl)ethenyl]phenyl}carbamoyl)-2,2-diethylpropanoic acid
Traditional Namecinalukast
CAS Registry Number128312-51-6
SMILES
CCC(CC)(CC(=O)NC1=CC=CC(\C=C\C2=NC(=CS2)C2CCC2)=C1)C(O)=O
InChI Identifier
InChI=1S/C23H28N2O3S/c1-3-23(4-2,22(27)28)14-20(26)24-18-10-5-7-16(13-18)11-12-21-25-19(15-29-21)17-8-6-9-17/h5,7,10-13,15,17H,3-4,6,8-9,14H2,1-2H3,(H,24,26)(H,27,28)/b12-11+
InChI KeyBZMKNPGKXJAIDV-VAWYXSNFSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAnilides
Direct ParentAnilides
Alternative Parents
Substituents
  • Anilide
  • Styrene
  • N-arylamide
  • 2,4-disubstituted 1,3-thiazole
  • Fatty amide
  • Fatty acyl
  • Azole
  • Heteroaromatic compound
  • Thiazole
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Antiarrhythmic Agents
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility8.72e-04 g/LNot Available
LogP4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000872 mg/mLALOGPS
logP4.98ALOGPS
logP5.48ChemAxon
logS-5.7ALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)2.44ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area79.29 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity116.75 m3·mol-1ChemAxon
Polarizability45.8 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00587 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00587 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00587
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4940804
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB14725
Metagene LinkHMDB14725
METLIN IDNot Available
PubChem Compound6436135
PDB IDNot Available
ChEBI ID126598
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:
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. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Adelroth E, Inman MD, Summers E, Pace D, Modi M, O'Byrne PM: Prolonged protection against exercise-induced bronchoconstriction by the leukotriene D4-receptor antagonist cinalukast. J Allergy Clin Immunol. 1997 Feb;99(2):210-5. [PubMed:9042047 ]
  3. Foller M, Mahmud H, Gu S, Wang K, Floride E, Kucherenko Y, Luik S, Laufer S, Lang F: Participation of leukotriene C(4) in the regulation of suicidal erythrocyte death. J Physiol Pharmacol. 2009 Sep;60(3):135-43. [PubMed:19826192 ]