2-[(1Z)-5-fluoro-1-[(4-methanesulfinylphenyl)methylidene]-2-methyl-1H-inden-3-yl]acetic acid

• ChemBase ID: 178011
• Molecular Formular: C20H17FO3S
• Molecular Mass: 356.4105832
• Monoisotopic Mass: 356.08824362
• SMILES: c1(ccc2c(c1)C(=C(/C/2=C/c1ccc(cc1)[S@@](=O)C)C)CC(=O)O)F
• Canonical SMILES: OC(=O)CC1=C(C)/C(=C/c2ccc(cc2)[S@@](=O)C)/c2c1cc(F)cc2
• InChI: InChI=1S/C20H17FO3S/c1-12-17(9-13-3-6-15(7-4-13)25(2)24)16-8-5-14(21)10-19(16)18(12)11-20(22)23/h3-10H,11H2,1-2H3,(H,22,23)/b17-9-/t25-/m0/s1
• InChIKey: MLKXDPUZXIRXEP-WXKFDZDZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1Z)-5-fluoro-1-[(4-methanesulfinylphenyl)methylidene]-2-methyl-1H-inden-3-yl]acetic acid
• IUPAC Traditional name: [(3Z)-6-fluoro-3-({4-[(S)-methanesulfinyl]phenyl}methylidene)-2-methylinden-1-yl]acetic acid
• Synonyms: (1Z)-5-Fluoro-2-methyl-1-[[4-[(S)-methylsulfinyl]phenyl]methylene]-1H-indene-3-acetic Acid; S-Sulindac Sulfoxide; (S)-Sulindac

Database IDs

• CAS Number: 149116-77-8
• PubChem SID: 164233921
• PubChem CID: 11245227

CALCULATED PROPERTIES

• Acid pKa: 4.090206
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.5030619
• LogD (pH = 7.4): -0.17891507
• Log P: 2.9261546
• Molar Refractivity: 99.5588 cm^3
• Polarizability: 37.41637 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S699210

(S)-Sulindac is the S-epimer metabolite of Sulinac (S699215). (S)-Sulindac increases the activity of the P 450 system better than (R)-Sulindac, but both epimers increase primarily the enzymes that oxidize (R)-Sulindac.

REFERENCES

• Duggan, D., et al.: J. Pharmacol. Exp. Ther., 1977, 201, 8 (1977)
• Hamman, M., et al.: Biochem. Pharmacol., 60, 7 (1977)
• Grimaud, R., et al.: J. Biol. Chem., 276, 48915 (1977)