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

• ChemBase ID: 70763
• Molecular Formular: C33H34N6O6
• Molecular Mass: 610.65966
• Monoisotopic Mass: 610.25398284
• SMILES: c1(n(c2c(n1)cccc2C(=O)OC(C)OC(=O)OC1CCCCC1)Cc1ccc(cc1)c1c(cccc1)c1n[nH]nn1)OCC
• Canonical SMILES: CCOc1nc2c(n1Cc1ccc(cc1)c1ccccc1c1n[nH]nn1)c(ccc2)C(=O)OC(OC(=O)OC1CCCCC1)C
• InChI: InChI=1S/C33H34N6O6/c1-3-42-32-34-28-15-9-14-27(31(40)43-21(2)44-33(41)45-24-10-5-4-6-11-24)29(28)39(32)20-22-16-18-23(19-17-22)25-12-7-8-13-26(25)30-35-37-38-36-30/h7-9,12-19,21,24H,3-6,10-11,20H2,1-2H3,(H,35,36,37,38)
• InChIKey: GHOSNRCGJFBJIB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{[(cyclohexyloxy)carbonyl]oxy}ethyl 2-ethoxy-1-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-1,3-benzodiazole-7-carboxylate; 1-{[(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: 1-{[(cyclohexyloxy)carbonyl]oxy}ethyl 2-ethoxy-3-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1,3-benzodiazole-4-carboxylate; 1-{[(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
• Synonyms: 1-(((Cyclohexyloxy)carbonyl)oxy)ethyl 1-((2'-(2H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate; 2-Ethoxy-1-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1H-benzimidazole-7-carboxylic Acid 1-[[(Cyclohexyloxy)carbonyl]oxy]ethyl Ester; TCV 116; Atacand; Amias; Blopress; Candesartan cilexetil

Database IDs

• CAS Number: 145040-37-5
• MDL Number: MFCD00871371
• PubChem SID: 162036474
• PubChem CID: 2540

CALCULATED PROPERTIES

• Acid pKa: 7.399701
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 8.160056
• LogD (pH = 7.4): 7.8762803
• Log P: 8.165408
• Molar Refractivity: 177.42 cm^3
• Polarizability: 66.530426 Å^3
• Polar Surface Area: 143.34 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 168-170°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• Storage Warning: IRRITANT
• TSCA Listed: false

Product Information

• Purity: 95+%

DETAILS

Selleck Chemicals - S2037

Research Area: Cardiovascular Disease
Biological Activity:
Candesartan cilexetil (Atacand) is a specific nonpeptide Ang II receptor (ATR) antagonist and the prodrug of candesartan which is an ATR antagonist with an IC50 of 15 µg/kg. Candesartan cilexetil (Atacand) efficacy is entirely due to its active metabolite candesartan (CV-11794) and is dose-dependent over the range of 1–8 mg and its clinical antihypertensive dose is stated to be around 4 mg/day.Candesartan cilexetil (Atacand) is administered as a pro-drug that undergoes activation during gastrointestinal absorption. In clinical trials, candesartan cilexetil (Atacand) has produced a dose-dependent effect when given in dosages of 2-32 mg/day. Observed trough-to-peak blood pressure ratios support a once-daily dosage regimen. The antihypertensive effect of candesartan cilexetil (Atacand) 4-16 mg/day was as great as that of enalapril 10-20 mg/day and amlodipine 5 mg/day and larger than that of losartan potassium 50 mg/day. Adding candesartan cilexetil (Atacand)  to hydrochlorothiazide 12.5-25 mg/day and amlodipine 5 mg/day led to enhanced blood-pressure reductions and was well tolerated. [1][2]

Toronto Research Chemicals - C175580

Ester prodrug; hydrolized in vivo to the active carboxylic acid. Used in treatment of congestive heart failure. Antihypertensive.

REFERENCES

• http://en.wikipedia.org/wiki/Candesartan
• Shibouta, Y., et al.: J. Pharmacol. Exp. Ther., 266, 114 (1993)
• Ogihara, T., et al.: Clin. Ther., 16, 74 (1994)