sodium 1-[3-({[4-chloro-3-(13C)methyl(3,4,5-13C3)-1,2-oxazol-5-yl]azanidyl}sulfonyl)thiophen-2-yl]-2-(6-methyl-2H-1,3-benzodioxol-5-yl)ethan-1-one

• ChemBase ID: 177790
• Molecular Formular: C18H14ClN2NaO6S2
• Molecular Mass: 480.85694935
• Monoisotopic Mass: 480.00136949
• SMILES: c1c(c(sc1)C(=O)Cc1cc2c(cc1C)OCO2)S(=O)(=O)[N-][13c]1[13c]([13c](no1)[13CH3])Cl.[Na+]
• Canonical SMILES: O=C(c1sccc1S(=O)(=O)[N-][13c]1on[13c]([13c]1Cl)[13CH3])Cc1cc2OCOc2cc1C.[Na+]
• InChI: InChI=1S/C18H14ClN2O6S2.Na/c1-9-5-13-14(26-8-25-13)7-11(9)6-12(22)17-15(3-4-28-17)29(23,24)21-18-16(19)10(2)20-27-18;/h3-5,7H,6,8H2,1-2H3;/q-1;+1/i2+1,10+1,16+1,18+1
• InChIKey: MDTNUYUCUYPIHE-BRXLKHJYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 1-[3-({[4-chloro-3-(^1^3C)methyl(3,4,5-^1^3C₃)-1,2-oxazol-5-yl]azanidyl}sulfonyl)thiophen-2-yl]-2-(6-methyl-2H-1,3-benzodioxol-5-yl)ethan-1-one
• IUPAC Traditional name: sodium 1-(3-{[4-chloro-3-(^1^3C)methyl(3,4,5-^1^3C₃)-1,2-oxazol-5-yl]azanidylsulfonyl}thiophen-2-yl)-2-(6-methyl-2H-1,3-benzodioxol-5-yl)ethanone
• Synonyms: N-(4-Chloro-3-methyl-5-isoxazolyl-13C4)-2-[2-(6-methyl-1,3-benzodioxol-5-yl)acetyl]-3-thiophenesulfonamide Sodium; IPI 1040-13C4; Sitax-13C4; Sitaxentan-13C4 Sodium; TBC 11251-13C4; Thelin-13C4; Sitaxsentan-13C4 Sodium

Database IDs

• PubChem SID: 164233700
• PubChem CID: 46782926

CALCULATED PROPERTIES

• Acid pKa: 6.8883305
• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 3.0762916
• LogD (pH = 7.4): 2.6002722
• Log P: 3.091686
• Molar Refractivity: 105.0045 cm^3
• Polarizability: 41.088886 Å^3
• Polar Surface Area: 104.93 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S493502

Labelled Sitaxsentan. Selective endothelin A (ETA) receptor antagonist. Antihypertensive. Used in treatment of chronic heart failure.

REFERENCES

• Wu, C., et al.: J. Med. Chem., 40, 1690 (1997)
• Tilton, R.G., et al.: Pulm. Pharmacol. Ther., 13, 87 (1997)
• Horn, E.M., et al.: Expert. Opin. Invest. Drugs, 13, 1483 (1997)
• Langleben, D., et al.: Chest, 126, 1377 (1997)