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Identification
NameCinalukast
Accession NumberDB00587  (APRD00637)
TypeSmall Molecule
GroupsApproved
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
3'-((e)-2-(4-Cyclobutyl-2-thiazolyl)vinyl)-2,2-diethylsuccinanilic acid
Cinalukast
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII5E1O433QAI
CAS number128312-51-6
WeightAverage: 412.545
Monoisotopic: 412.182063462
Chemical FormulaC23H28N2O3S
InChI KeyBZMKNPGKXJAIDV-VAWYXSNFSA-N
InChI
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+
IUPAC Name
3-({3-[(E)-2-(4-cyclobutyl-1,3-thiazol-2-yl)ethenyl]phenyl}carbamoyl)-2,2-diethylpropanoic acid
SMILES
CCC(CC)(CC(=O)NC1=CC=CC(\C=C\C2=NC(=CS2)C2CCC2)=C1)C(O)=O
Pharmacology
IndicationFor Protection against second- phase inflamation in exercise-induced bronchoconstriction and Asthma.
Structured Indications Not Available
PharmacodynamicsUsed 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.
Mechanism of actionBinds to the cysteinyl leukotriene receptor. The cysteinyl leukotrienes (LTC4, LTD4, LTE4) are products of arachidonic acid metabolism and are released from various cells, including mast cells and eosinophils. These eicosanoids bind to cysteinyl leukotriene receptors (CysLT) found in the human airway. Cysteinyl leukotrienes and leukotriene receptor occupation have been correlated with the pathophysiology of asthma, including airway edema, smooth muscle contraction, and altered cellular activity associated with the inflammatory process, which contribute to the signs and symptoms of asthma.
TargetKindPharmacological actionActionsOrganismUniProt ID
Cysteinyl leukotriene receptor 1Proteinyes
antagonist
HumanQ9Y271 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9315
Blood Brain Barrier+0.8337
Caco-2 permeable-0.6145
P-glycoprotein substrateSubstrate0.5433
P-glycoprotein inhibitor INon-inhibitor0.939
P-glycoprotein inhibitor IINon-inhibitor0.9373
Renal organic cation transporterNon-inhibitor0.9402
CYP450 2C9 substrateNon-substrate0.7695
CYP450 2D6 substrateNon-substrate0.8402
CYP450 3A4 substrateNon-substrate0.5901
CYP450 1A2 substrateNon-inhibitor0.7134
CYP450 2C9 inhibitorNon-inhibitor0.6524
CYP450 2D6 inhibitorNon-inhibitor0.9247
CYP450 2C19 inhibitorNon-inhibitor0.6193
CYP450 3A4 inhibitorInhibitor0.7242
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5806
Ames testNon AMES toxic0.7982
CarcinogenicityNon-carcinogens0.857
BiodegradationNot ready biodegradable0.9763
Rat acute toxicity2.5159 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9993
hERG inhibition (predictor II)Non-inhibitor0.9064
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
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
Mass Spec (NIST)Not Available
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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-arylamides. These are organic compounds that contain a carboxamide group that is N-linked to a aryl group. They have the generic structure RC(=O)N(R')H, R = organyl group and R'= aryl group.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassN-arylamides
Sub ClassNot Available
Direct ParentN-arylamides
Alternative Parents
Substituents
  • N-arylamide
  • Styrene
  • 2,4-disubstituted 1,3-thiazole
  • Fatty acyl
  • Benzenoid
  • Fatty amide
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Thiazole
  • Cyclic alcohol
  • Azole
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Leukotriene receptor activity
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 affini...
Gene Name:
CYSLTR1
Uniprot ID:
Q9Y271
Molecular Weight:
38540.55 Da
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23