2-ethoxy-1-({4-[2-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)phenyl]phenyl}methyl)-1H-1,3-benzodiazole-7-carboxylic acid

• ChemBase ID: 161080
• Molecular Formular: C25H20N4O5
• Molecular Mass: 456.4501
• Monoisotopic Mass: 456.14336976
• SMILES: c1cc(c2c(c1)nc(n2Cc1ccc(cc1)c1ccccc1c1[nH]c(=O)on1)OCC)C(=O)O
• Canonical SMILES: CCOc1nc2c(n1Cc1ccc(cc1)c1ccccc1c1noc(=O)[nH]1)c(ccc2)C(=O)O
• InChI: InChI=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)
• InChIKey: KGSXMPPBFPAXLY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-ethoxy-1-({4-[2-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)phenyl]phenyl}methyl)-1H-1,3-benzodiazole-7-carboxylic acid
• IUPAC Traditional name: azilsartan
• Synonyms: 2-Ethoxy-1-[[2'-(4,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylic Acid; TAK 536; Azilsartan; 1-[[2'-(2,5-Dihydro-5-oxo-1,2,4-oxadiazol-3-yl)[1,1'-biphenyl]-4-yl]methyl]-2-ethoxy-1H-benzimidazole-7-carboxylic Acid

Database IDs

• CAS Number: 147403-03-0
• PubChem SID: 162255215
• PubChem CID: 9825285

CALCULATED PROPERTIES

• Acid pKa: 2.9726665
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 2.5378458
• LogD (pH = 7.4): 1.5937049
• Log P: 4.820512
• Molar Refractivity: 123.3836 cm^3
• Polarizability: 49.204304 Å^3
• Polar Surface Area: 115.04 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: >171°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - A926900

Azilsartan is an analgesic and antiinflammatory drugs containing angiotensin II antagonists.

REFERENCES

• Kohara, Y., et al.: J. Med. Chem., 39, 5228 (1996)
• Plomgaard, P., et al.: Diabetes, 54, 2939 (1996)
• Fenton, C., et al.: Drugs, 2005, 65, 537,