Record Information
Version1.0
Creation Date2016-05-25 18:20:37 UTC
Update Date2026-08-22 11:43:15 UTC
Accession NumberCHEM022113
Identification
Common NameMontelukast
ClassSmall Molecule
Description
Montelukast was first approved for clinical use by the US FDA in 1998 as Merck's brand name Singulair. The medication is a member of the leukotriene receptor antagonist (LTRA) category of drugs. Although capable of demonstrating effectiveness, the use of such LTRAs like montelukast is typically in addition to or complementary with the use of inhaled corticosteroids or other agents in asthma step therapy. Regardless, in 2008-2009, there were FDA-led investigations into the possibility of montelukast to elicit neuropsychiatric effects like agitation, hallucinations, suicidal behaviour, and others in individuals who used the medication. And although these kinds of effects are currently included in the official prescribing information for montelukast, the drug still sees extensive use worldwide via millions of prescriptions annually and has since become available as a generic and as a brand name product.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
(R-(e))-1-(((1-(3-(2-(7-Chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropaneacetic acidChEBI
1-[[[(1 R)-1-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl] phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]sulfanyl]methyl]cyclopropaneacetic acidChEBI
BrondilatKegg
(R-(e))-1-(((1-(3-(2-(7-Chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropaneacetateGenerator
1-[[[(1 R)-1-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl] phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]sulfanyl]methyl]cyclopropaneacetateGenerator
1-[[[(1 R)-1-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl] phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]sulphanyl]methyl]cyclopropaneacetateGenerator
1-[[[(1 R)-1-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl] phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]sulphanyl]methyl]cyclopropaneacetic acidGenerator
Merck brand OF montelukast sodiumHMDB
SingulairHMDB
Montelukast sodiumHMDB
Sodium 1-(((1-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methyl)cyclopropylacetateHMDB
Cahill may roberts brand OF montelukast sodiumHMDB
Merck frosst brand OF montelukast sodiumHMDB
Merck sharp and dohme brand OF montelukast sodiumHMDB
Chemical FormulaC35H36ClNO3S
Average Molecular Mass586.183 g/mol
Monoisotopic Mass585.210 g/mol
CAS Registry Number158966-92-8
IUPAC Name2-[1-({[(1R)-1-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-[2-(2-hydroxypropan-2-yl)phenyl]propyl]sulfanyl}methyl)cyclopropyl]acetic acid
Traditional Namemontelukast
SMILESOC(=O)CC1(CC1)CS[C@H](CCC1=CC=CC=C1C(O)(C)C)C1=CC=CC(\C=C\C2=NC3=C(C=CC(Cl)=C3)C=C2)=C1
InChI IdentifierInChI=1S/C35H36ClNO3S/c1-34(2,40)30-9-4-3-7-25(30)13-17-32(41-23-35(18-19-35)22-33(38)39)27-8-5-6-24(20-27)10-15-29-16-12-26-11-14-28(36)21-31(26)37-29/h3-12,14-16,20-21,32,40H,13,17-19,22-23H2,1-2H3,(H,38,39)/b15-10+/t32-/m1/s1
InChI KeyUCHDWCPVSPXUMX-TZIWLTJVSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as linear 1,3-diarylpropanoids. These are organic compounds with a structure based on a C6-C3-C6 skeleton, where the two benzene rings are not linked together.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassLinear 1,3-diarylpropanoids
Sub ClassNot Available
Direct ParentLinear 1,3-diarylpropanoids
Alternative Parents
Substituents
  • Linear 1,3-diarylpropanoid
  • Haloquinoline
  • Chloroquinoline
  • Quinoline
  • Phenylpropane
  • Styrene
  • Hydroxy fatty acid
  • Thia fatty acid
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Pyridine
  • Fatty acyl
  • Benzenoid
  • Heteroaromatic compound
  • Tertiary alcohol
  • Thioether
  • Dialkylthioether
  • Sulfenyl compound
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organosulfur compound
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.2e-06 g/LALOGPS
logP7.25ALOGPS
logP8.49ChemAxon
logS-7.8ALOGPS
pKa (Strongest Acidic)4.4ChemAxon
pKa (Strongest Basic)3.12ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70.42 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity169.5 m³·mol⁻¹ChemAxon
Polarizability66.36 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB00471
HMDB IDHMDB0014614
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDMTK
Wikipedia LinkMontelukast
Chemspider ID4444507
ChEBI ID50730
PubChem Compound ID5281040
Kegg Compound IDC07482
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References