(3S)-3-benzyl-1,1-dioxo-6-(trifluoromethyl)-3,4-dihydro-2H-1λ6,2,4-benzothiadiazine-7-sulfonamide

• ChemBase ID: 161189
• Molecular Formular: C15H14F3N3O4S2
• Molecular Mass: 421.4145696
• Monoisotopic Mass: 421.0377826
• SMILES: c1(c(cc2c(c1)N[C@@H](NS2(=O)=O)Cc1ccccc1)S(=O)(=O)N)C(F)(F)F
• Canonical SMILES: O=S1(=O)N[C@@H](Cc2ccccc2)Nc2c1cc(c(c2)C(F)(F)F)S(=O)(=O)N
• InChI: InChI=1S/C15H14F3N3O4S2/c16-15(17,18)10-7-11-13(8-12(10)26(19,22)23)27(24,25)21-14(20-11)6-9-4-2-1-3-5-9/h1-5,7-8,14,20-21H,6H2,(H2,19,22,23)/t14-/m0/s1
• InChIKey: HDWIHXWEUNVBIY-AWEZNQCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-benzyl-1,1-dioxo-6-(trifluoromethyl)-3,4-dihydro-2H-1λ^6,2,4-benzothiadiazine-7-sulfonamide
• IUPAC Traditional name: bendroflumethazide
• Synonyms: (3S)-3,4-Dihydro-3-(phenylmethyl)-6-(trifluoromethyl)-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-Dioxide; (S)-Bendroflumethiazide

Database IDs

• CAS Number: 1245935-40-3
• PubChem SID: 162255324
• PubChem CID: 6604206

CALCULATED PROPERTIES

• Acid pKa: 9.043274
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.6982855
• LogD (pH = 7.4): 1.6896976
• Log P: 1.698396
• Molar Refractivity: 93.6846 cm^3
• Polarizability: 35.91275 Å^3
• Polar Surface Area: 118.36 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B133510

The S-enatiomer of the diuretic Bendroflumethiazide (B133500).

REFERENCES

• Mone, M.K. et al.: Chromatographia, 73, 985 (2011)
• Atkinson, A., et al.: Drug Metab. Dispos., 33, 1637 (2011)
• Ayrton, A., et al.: Xenobiotica, 38, 676 (2011)
• Diao, L., et al.: Pharm. Res., 26, 1890 (2011)