2-{[(cyclohexyloxy)carbonyl]oxy}ethyl 2-ethoxy-1-({4-[2-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-1,3-benzodiazole-7-carboxylate

• ChemBase ID: 124975
• Molecular Formular: C33H34N6O6
• Molecular Mass: 610.65966
• Monoisotopic Mass: 610.25398284
• SMILES: n1(c(nc2c1c(C(=O)OCCOC(=O)OC1CCCCC1)ccc2)OCC)Cc1ccc(c2c(c3nnn[nH]3)cccc2)cc1
• Canonical SMILES: CCOc1nc2c(n1Cc1ccc(cc1)c1ccccc1c1nnn[nH]1)c(ccc2)C(=O)OCCOC(=O)OC1CCCCC1
• InChI: InChI=1S/C33H34N6O6/c1-2-42-32-34-28-14-8-13-27(31(40)43-19-20-44-33(41)45-24-9-4-3-5-10-24)29(28)39(32)21-22-15-17-23(18-16-22)25-11-6-7-12-26(25)30-35-37-38-36-30/h6-8,11-18,24H,2-5,9-10,19-21H2,1H3,(H,35,36,37,38)
• InChIKey: NQZDOSXQAGAIAB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[(cyclohexyloxy)carbonyl]oxy}ethyl 2-ethoxy-1-({4-[2-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-1,3-benzodiazole-7-carboxylate
• IUPAC Traditional name: 2-{[(cyclohexyloxy)carbonyl]oxy}ethyl 2-ethoxy-3-({4-[2-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1,3-benzodiazole-4-carboxylate; 2-{[(cyclohexyloxy)carbonyl]oxy}ethyl 2-ethoxy-1-({4-[2-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-1,3-benzodiazole-7-carboxylate
• Synonyms: 2-(((cyclohexyloxy)carbonyl)oxy)ethyl 1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate; Candesartan Cilexetil

Database IDs

• CAS Number: 145040-37-5
• PubChem SID: 162219328
• PubChem CID: 15225138

CALCULATED PROPERTIES

• Acid pKa: 4.2330327
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 6.063863
• LogD (pH = 7.4): 5.5917697
• Log P: 7.1918874
• Molar Refractivity: 177.7682 cm^3
• Polarizability: 66.53383 Å^3
• Polar Surface Area: 143.34 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Angiotensin II receptor antagonist

Product Information

• Application(s): Antihypertensive agent; Renoprotective effects

REFERENCES

• Eur. Pat., 1991, Takeda, 459 136; CA, 116, 128924, (synth, pharmacol)
• Mizuno, K. et al., Life Sci., 1992, 51, PL183, (Candesartan cilexitil)
• Kubo, K. et al., J. Med. Chem., 1993, 36, 2182; 2343, (synth, pmr, ir, pharmacol)
• Shibouta, Y. et al., J. Pharmacol. Exp. Ther., 1993, 266, 114, (pharmacol)
• Morimoto, S. et al., Cardiovasc. Drug Rev., 1994, 12, 153, (rev)
• Arakawa, K. et al., J. Hypertens., Suppl. 9, 1994, 12, (pharmacol, rev)
• Flesch, M. et al., Eur. J. Pharmacol., 1995, 289, 399, (pharmacol)
• Delacrtaz, E. et al., Hypertension (Dallas), 1995, 25, 14, (pharmacol, man)
• Lee, J.W. et al., J. Chromatogr., B: Biomed. Appl., 1995, 670, 287, (hplc)
• McClellan, K.J. et al., Drugs, 1998, 56, 847-869, (rev)
• Matsunaga, H. et al., Chem. Pharm. Bull., 1999, 47, 182-186, (Candesartan ciloxetil, cmr, cryst struct)
• Drugs of Today (Barcelona), 1999, 35, 11-16; 105-115; 117-126