(2S)-2-[4-(4-bromophenyl)benzenesulfonamido]-3-methylbutanoic acid hydrate

• ChemBase ID: 154459
• Molecular Formular: C17H20BrNO5S
• Molecular Mass: 430.3134
• Monoisotopic Mass: 429.02455575
• SMILES: CC(C)[C@@H](C(=O)O)NS(=O)(=O)c1ccc(cc1)c1ccc(cc1)Br.O
• Canonical SMILES: Brc1ccc(cc1)c1ccc(cc1)S(=O)(=O)N[C@H](C(=O)O)C(C)C.O
• InChI: InChI=1S/C17H18BrNO4S.H2O/c1-11(2)16(17(20)21)19-24(22,23)15-9-5-13(6-10-15)12-3-7-14(18)8-4-12;/h3-11,16,19H,1-2H3,(H,20,21);1H2/t16-;/m0./s1
• InChIKey: LUKRECOTGXWIDO-NTISSMGPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[4-(4-bromophenyl)benzenesulfonamido]-3-methylbutanoic acid hydrate
• IUPAC Traditional name: (2S)-2-[4-(4-bromophenyl)benzenesulfonamido]-3-methylbutanoic acid hydrate
• Synonyms: (S)-2-(4′-Bromo-biphenyl-4-sulfonylamino)-3-methyl-butyric acid hydrate; PD166793 hydrate

Database IDs

• MDL Number: MFCD12912437
• PubChem SID: 162248598
• PubChem CID: 71311869

CALCULATED PROPERTIES

• Acid pKa: 3.3274448
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.9963862
• LogD (pH = 7.4): 0.7323953
• Log P: 4.1531734
• Molar Refractivity: 95.4457 cm^3
• Polarizability: 39.020336 Å^3
• Polar Surface Area: 83.47 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: solid

Safety Information

• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C17H18BrNO4S · xH2O

DETAILS

Sigma Aldrich - P0047

Biochem/physiol Actions
PD166793 is a broad spectrum, but class-selective, MMP inhibitor (low nM at MMP-2 & 3 and low μM at MMP-1, 7 & 9). Adding PD166793 to the high-fat diet substantially reduced the rise in blood glucose. The improvement of glucose homeostasis in PD166793-treated ZDF rats was a result of the enhancement of β-cell function. It prevents β-cell dysfunction and diabetes in female ZDF rats on a high-fat diet. It has been shown to block left ventricular remodeling and dysfunction in a rat model of heart failure. Preservation of normoglycemia and normal glucose tolerance in compound PD166793-treated animals is accompanied by preservation of the high serum insulin levels that are a consequence of the insulin resistance present in these animals. It is not reversing insulin resistance these animals. The most striking effect of the compound is on pancreatic insulin content and β-cell volume.