Israpafant (CHEM016265)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:25:11 UTC
Update Date2016-11-09 01:15:22 UTC
Accession NumberCHEM016265
Identification
Common NameIsrapafant
ClassSmall Molecule
DescriptionIsrapafant (Y-24180) is a drug which acts as a selective antagonist for the platelet-activating factor receptor, and was originally developed for the treatment of asthma. Its chemical structure is a thienotriazolodiazepine, closely related to the sedative benzodiazepine derivative etizolam. However israpafant binds far more tightly to the platelet-activating factor receptor, with an IC50 of 0.84nM for inhibiting PAF-induced human platelet aggregation (compared to etizolam's IC50 of 998nM at this target), while it binds only weakly to benzodiazepine receptors, with a Ki of 3680nM. Israpafant has been found to inhibit the activation of eosinophil cells, and consequently delays the development of immune responses. It has also been shown to have anti-nephrotoxic properties, and to mobilize calcium transport.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
4-(2-Chlorophenyl)-2-(2-(4-isobutylphenyl)ethyl)-6,9-dimethyl-6H-thieno(3,2-F)(1,2,4)triazolo(4,3-a)(1,4)diazepineMeSH
Chemical FormulaC28H29ClN4S
Average Molecular Mass489.080 g/mol
Monoisotopic Mass488.180 g/mol
CAS Registry Number117279-73-9
IUPAC Name7-(2-chlorophenyl)-9,13-dimethyl-4-{2-[4-(2-methylpropyl)phenyl]ethyl}-3-thia-1,8,11,12-tetraazatricyclo[8.3.0.0²,⁶]trideca-2(6),4,7,10,12-pentaene
Traditional Name7-(2-chlorophenyl)-9,13-dimethyl-4-{2-[4-(2-methylpropyl)phenyl]ethyl}-3-thia-1,8,11,12-tetraazatricyclo[8.3.0.0²,⁶]trideca-2(6),4,7,10,12-pentaene
SMILESCC(C)CC1=CC=C(CCC2=CC3=C(S2)N2C(C)=NN=C2C(C)N=C3C2=CC=CC=C2Cl)C=C1
InChI IdentifierInChI=1S/C28H29ClN4S/c1-17(2)15-21-11-9-20(10-12-21)13-14-22-16-24-26(23-7-5-6-8-25(23)29)30-18(3)27-32-31-19(4)33(27)28(24)34-22/h5-12,16-18H,13-15H2,1-4H3
InChI KeyRMSWMRJVUJSDGN-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as thienodiazepines. These are heteropolycyclic containing a thiophene ring fused to a diazepine ring. Thiophene is 5-membered ring consisting of four carbon and one sulfur atoms. Diazepine is a 7-membered ring consisting of five carbon and two nitrogen atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassThienodiazepines
Sub ClassNot Available
Direct ParentThienodiazepines
Alternative Parents
Substituents
  • Thieno-para-diazepine
  • Phenylpropane
  • 2,3,5-trisubstituted thiophene
  • Para-diazepine
  • Chlorobenzene
  • Halobenzene
  • Aryl halide
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl chloride
  • Heteroaromatic compound
  • Azole
  • 1,2,4-triazole
  • Thiophene
  • Ketimine
  • Organic 1,3-dipolar compound
  • Azacycle
  • Propargyl-type 1,3-dipolar organic compound
  • Organochloride
  • Organohalogen compound
  • Imine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.0029 g/LALOGPS
logP5.76ALOGPS
logP7.9ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)16.71ChemAxon
pKa (Strongest Basic)4.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.07 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity152.71 m³·mol⁻¹ChemAxon
Polarizability55.26 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
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, Positivesplash10-0007-9602600000-a7dfba49ef684a7ca7a5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0022900000-f0578f72f5711a3c31f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dr-1901200000-c6f68be13a58f04ba613Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08g0-2921100000-a38b43bbcdd0d7fa9d8bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-94af3b4780f01e5dbd07Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0191100000-4540859c608407687a5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00e9-6369400000-be8d6ca54ba6c0fe10fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-d33c50a12c619036870cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0019-4000900000-c8269e00ee52b7c30a50Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-7119400000-2edc6347b719dd28fe75Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000900000-faffabfc4c4b683e536fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1000900000-a2c2309953ac93c223a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-8402900000-6391d61a3ab878cd4365Spectrum
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 IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkIsrapafant
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID119175
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available