2-{4-[(2-benzenesulfonamidoethyl)sulfanyl]-2,6-difluorophenoxy}acetamide

• ChemBase ID: 153787
• Molecular Formular: C16H16F2N2O4S2
• Molecular Mass: 402.4360464
• Monoisotopic Mass: 402.05195544
• SMILES: c1ccc(cc1)S(=O)(=O)NCCSc1cc(c(c(c1)F)OCC(=O)N)F
• Canonical SMILES: NC(=O)COc1c(F)cc(cc1F)SCCNS(=O)(=O)c1ccccc1
• InChI: InChI=1S/C16H16F2N2O4S2/c17-13-8-11(9-14(18)16(13)24-10-15(19)21)25-7-6-20-26(22,23)12-4-2-1-3-5-12/h1-5,8-9,20H,6-7,10H2,(H2,19,21)
• InChIKey: GTACSIONMHMRPD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{4-[(2-benzenesulfonamidoethyl)sulfanyl]-2,6-difluorophenoxy}acetamide
• IUPAC Traditional name: pepa (drug)
• Synonyms: PEPA; 2,6-Difluoro-4-[2-(phenylsul-fonyl-amino)-ethyl-thio]-phenoxy-acet-amide

Database IDs

• CAS Number: 141286-78-4
• MDL Number: MFCD04974493
• PubChem SID: 162247926; 24278571
• PubChem CID: 6603828

CALCULATED PROPERTIES

• Acid pKa: 10.182477
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.7719705
• LogD (pH = 7.4): 1.7713448
• Log P: 1.7719785
• Molar Refractivity: 94.9665 cm^3
• Polarizability: 37.009434 Å^3
• Polar Surface Area: 98.49 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: white solid

Safety Information

• Storage Condition: protect from light
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... GRIA1(2890), GRIA2(2891), GRIA3(2892), GRIA4(2893)

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C16H16N2O4S2F2

DETAILS

Sigma Aldrich - D8941

Biochem/physiol Actions
2,6-Difluoro-4-[2-(phenylsul-fonyl-amino)-ethyl-thio]-phenoxy-acet-amide is a structurally novel, selective, high affinity AMPA ionotropic glutamate receptor agonist that reduces ischemia-induced performance deficits in rats.