N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-[2-(1H-1,2,3,4-tetrazol-5-yl)pyridin-4-yl]pyrimidin-4-yl]-5-(propan-2-yl)pyridine-2-sulfonamide

• ChemBase ID: 178317
• Molecular Formular: C27H27N9O6S
• Molecular Mass: 605.62498
• Monoisotopic Mass: 605.18050063
• SMILES: O(c1nc(nc(c1Oc1ccccc1OC)NS(=O)(=O)c1ccc(cn1)C(C)C)c1cc(ncc1)c1nnn[nH]1)CCO
• Canonical SMILES: OCCOc1nc(nc(c1Oc1ccccc1OC)NS(=O)(=O)c1ccc(cn1)C(C)C)c1ccnc(c1)c1[nH]nnn1
• InChI: InChI=1S/C27H27N9O6S/c1-16(2)18-8-9-22(29-15-18)43(38,39)34-26-23(42-21-7-5-4-6-20(21)40-3)27(41-13-12-37)31-24(30-26)17-10-11-28-19(14-17)25-32-35-36-33-25/h4-11,14-16,37H,12-13H2,1-3H3,(H,30,31,34)(H,32,33,35,36)
• InChIKey: TUYWTLTWNJOZNY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-[2-(1H-1,2,3,4-tetrazol-5-yl)pyridin-4-yl]pyrimidin-4-yl]-5-(propan-2-yl)pyridine-2-sulfonamide
• IUPAC Traditional name: N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-[2-(1H-1,2,3,4-tetrazol-5-yl)pyridin-4-yl]pyrimidin-4-yl]-5-isopropylpyridine-2-sulfonamide
• Synonyms: N-[6-(2-Hydroxyethoxy)-5-(2-methoxyphenoxy)-2-[2-(2H-tetrazol-5-yl)-4-pyridinyl]-4-pyrimidinyl]-5-(1-methylethyl)-2-pyridinesulfonamide; Tezosentan

Database IDs

• CAS Number: 180384-57-0
• PubChem SID: 164234227
• PubChem CID: 151174

CALCULATED PROPERTIES

• Acid pKa: 3.5314944
• H Acceptors: 12
• H Donor: 3
• LogD (pH = 5.5): 1.8932104
• LogD (pH = 7.4): 1.1273187
• Log P: 3.55952
• Molar Refractivity: 178.2328 cm^3
• Polarizability: 60.60846 Å^3
• Polar Surface Area: 200.11 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T321500

A potent dual endothelian (ETA/ETB) receptor antagonist optimized from Bosentan (B675900). It is used in the treatment of congestive heart failure.

REFERENCES

• Clozel, M., et al.: J. Pharmacol. Exp. Ther., 290, 840 (1999)
• Dingemanse, J., et al.: Br. J. Clin. Pharmacol., 53, 355 (1999)
• Schalcher, C., et al.: Am. Heart J., 142, 340 (1999)