azilsartan (CHEM045660)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 13:33:49 UTC
Update Date2016-11-09 01:23:23 UTC
Accession NumberCHEM045660
Identification
Common Nameazilsartan
ClassSmall Molecule
DescriptionA benzimidazolecarboxylic acid that is benzimidazole-7-carboxylic acid substituted at position 2 by a methoxy group and at position 1 by a 2'-[(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl group. Used (as the prodrug, azilsartan medoxomil) for treatment of hypertension.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
TAK 536ChEBI
TAK-536ChEBI
AzilvaKegg
2-Ethoxy-1-((2'-(5-oxo-2,5-dihydro-1,2,4-oxadiazol-3-yl)-biphenyl-4-yl)methyl)-1H-benzimidazole-7-carboxylic acidMeSH
2-Ethoxy-1-{[2'-(5-oxo-2,5-dihydro-1,2,4-oxadiazol-3-yl)-[1,1'-biphenyl]-4-yl]methyl}-1H-1,3-benzodiazole-7-carboxylateGenerator
Chemical FormulaC25H20N4O5
Average Molecular Mass456.458 g/mol
Monoisotopic Mass456.143 g/mol
CAS Registry Number147403-03-0
IUPAC Name2-ethoxy-1-{[2'-(5-oxo-2,5-dihydro-1,2,4-oxadiazol-3-yl)-[1,1'-biphenyl]-4-yl]methyl}-1H-1,3-benzodiazole-7-carboxylic acid
Traditional Name2-ethoxy-3-{[2'-(5-oxo-2H-1,2,4-oxadiazol-3-yl)-[1,1'-biphenyl]-4-yl]methyl}-1,3-benzodiazole-4-carboxylic acid
SMILESCCOC1=NC2=CC=CC(C(O)=O)=C2N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NC(=O)ON1
InChI IdentifierInChI=1S/C25H20N4O5/c1-2-33-24-26-20-9-5-8-19(23(30)31)21(20)29(24)14-15-10-12-16(13-11-15)17-6-3-4-7-18(17)22-27-25(32)34-28-22/h3-13H,2,14H2,1H3,(H,30,31)(H,27,28,32)
InChI KeyKGSXMPPBFPAXLY-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBiphenyls and derivatives
Direct ParentBiphenyls and derivatives
Alternative Parents
Substituents
  • Biphenyl
  • Phenyl-1,2,4-oxadiazole
  • Benzimidazole
  • Alkyl aryl ether
  • N-substituted imidazole
  • 1,2,4-oxadiazole
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Oxadiazole
  • Vinylogous amide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen 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 Solubility0.012 g/LALOGPS
logP4.54ALOGPS
logP4.61ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)3.52ChemAxon
pKa (Strongest Basic)1.76ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area115.04 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity133.8 m³·mol⁻¹ChemAxon
Polarizability46.36 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0194500000-df27d34aa2f83656a214Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0010900000-32267dd1d4b63950bee2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dr-0028900000-1765c453df741674e701Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0096100000-9bf752eea1a45025244fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-08fr-0001900000-15e4bb7ab4f590efe40bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0102900000-c0617e7b705c6071beb2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxr-1139000000-d3fcd3cc57c3eff9efa3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0000900000-93b0af2cfa3cb6391352Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0013900000-1158bad8ebb3216b1001Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-0597100000-b41a92820f638c2c1d34Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0006900000-f08e2fd0336f593224ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02t9-0009400000-3df799b934a96ee951d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gbc-2229200000-a30a382d4b50df751547Spectrum
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 LinkAzilsartan
Chemspider ID8001032
ChEBI ID68850
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21749604
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21983318
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21986624
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22278628
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22365278
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22399858
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22661897
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22728984
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22745562
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22975662
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=23012812
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=23034464
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23051655