Zafirlukast (CHEM016937)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:48:09 UTC
Update Date2016-11-09 01:15:30 UTC
Accession NumberCHEM016937
Identification
Common NameZafirlukast
ClassSmall Molecule
DescriptionZafirlukast is an oral leukotriene receptor antagonist (LTRA) for the maintenance treatment of asthma, often used in conjunction with an inhaled steroid and/or long-acting bronchodilator. It is available as a tablet and is usually dosed twice daily. Another leukotriene receptor antagonist is montelukast (Singulair), which is usually taken just once daily. Zafirlukast blocks the action of the cysteinyl leukotrienes on the CysLT1 receptors, thus reducing constriction of the airways, build-up of mucus in the lungs and inflammation of the breathing passages.
Contaminant Sources
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
4-(5-Cyclopentyloxycarbonylamino-1-methyl-1H-indol-3-ylmethyl)-3-methoxy-N-O-tolylsulfonylbenzamideChEBI
AccolateChEBI
Cyclopentyl 3-(2-methoxy-4-((O-tolylsulfonyl)carbamoyl)benzyl)-1-methylindole-5-carbamateChEBI
4-(5-Cyclopentyloxycarbonylamino-1-methyl-1H-indol-3-ylmethyl)-3-methoxy-N-O-tolylsulphonylbenzamideGenerator
Accolic acidGenerator
Cyclopentyl 3-(2-methoxy-4-((O-tolylsulfonyl)carbamoyl)benzyl)-1-methylindole-5-carbamic acidGenerator
Cyclopentyl 3-(2-methoxy-4-((O-tolylsulphonyl)carbamoyl)benzyl)-1-methylindole-5-carbamateGenerator
Cyclopentyl 3-(2-methoxy-4-((O-tolylsulphonyl)carbamoyl)benzyl)-1-methylindole-5-carbamic acidGenerator
AeronixHMDB
4-(5-Cyclopentyloxycarbonylamino-2-methylindol-3-yl-methyl)-3-methoxy-N-O-tolylsulfonylbenzamideHMDB
OlmoranHMDB
Chemical FormulaC31H33N3O6S
Average Molecular Mass575.675 g/mol
Monoisotopic Mass575.209 g/mol
CAS Registry Number107753-78-6
IUPAC Namecyclopentyl N-[3-({2-methoxy-4-[(2-methylbenzenesulfonyl)carbamoyl]phenyl}methyl)-1-methyl-1H-indol-5-yl]carbamate
Traditional Namezafirlukast
SMILESCOC1=C(CC2=CN(C)C3=C2C=C(NC(=O)OC2CCCC2)C=C3)C=CC(=C1)C(=O)NS(=O)(=O)C1=CC=CC=C1C
InChI IdentifierInChI=1S/C31H33N3O6S/c1-20-8-4-7-11-29(20)41(37,38)33-30(35)22-13-12-21(28(17-22)39-3)16-23-19-34(2)27-15-14-24(18-26(23)27)32-31(36)40-25-9-5-6-10-25/h4,7-8,11-15,17-19,25H,5-6,9-10,16H2,1-3H3,(H,32,36)(H,33,35)
InChI KeyYEEZWCHGZNKEEK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentBenzenesulfonamides
Alternative Parents
Substituents
  • Benzenesulfonamide
  • N-alkylindole
  • 3-alkylindole
  • Benzoic acid or derivatives
  • Benzenesulfonyl group
  • Indole
  • Indole or derivatives
  • Phenoxy compound
  • Anisole
  • Benzoyl
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • Toluene
  • N-methylpyrrole
  • Substituted pyrrole
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Pyrrole
  • Carbamic acid ester
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Carbonic acid derivative
  • Organoheterocyclic compound
  • Azacycle
  • Ether
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organosulfur compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • 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 Solubility0.00096 g/LALOGPS
logP4.84ALOGPS
logP6.4ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)4.29ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area115.73 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity158.58 m³·mol⁻¹ChemAxon
Polarizability62.06 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9330620000-fc40738dd1a7e2c81dc5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00di-0001190000-27c5d161a5754e1434f4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00di-0001190000-27c5d161a5754e1434f4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0292-0940000000-f369442eba5344b3ecb4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0292-0940000000-f369442eba5344b3ecb4Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-0003191000-ba3996913abfda3b22c4Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4r-0259300000-1440474b4cb47824c9f2Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-0001191000-58bcdb71b459847fc794Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0ap0-0149300000-896e679131032968db95Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000i-0029300000-c82ecc534ef9c1eb1c1fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00di-0000090000-e0b91fc76d38f979eccaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002r-9110380000-9e5c8dd5fdec56391e67Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9012110000-e33cb25b1e67d0d2bf04Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9021000000-1a28cc2a5255b3c26347Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-3000940000-d189a5e1b668abe5609eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-7511930000-ba1443db38e17f7c56c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000m-9601600000-7d2519b7cb04660b56f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0008290000-74ba6045634101ef1590Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052o-9217440000-736a786992f3e2189ffdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ou-9051430000-b689491e7cebb735e1b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000090000-08c3cf635346a0e9b809Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-7300490000-1baf05db9dff2aaf16eaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-4201390000-a227805ba727dea02ed8Spectrum
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
DrugBank IDDB00549
HMDB IDHMDB0014689
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkZafirlukast
Chemspider ID5515
ChEBI ID10100
PubChem Compound ID5717
Kegg Compound IDC07206
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11888331
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19331987
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22159431
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22614107
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24258705
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=25798389
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=25834030