phenylethynesulfonamide

• ChemBase ID: 58730
• Molecular Formular: C8H7NO2S
• Molecular Mass: 181.21168
• Monoisotopic Mass: 181.01974947
• SMILES: c1cccc(c1)C#CS(=O)(=O)N
• Canonical SMILES: NS(=O)(=O)C#Cc1ccccc1
• InChI: InChI=1S/C8H7NO2S/c9-12(10,11)7-6-8-4-2-1-3-5-8/h1-5H,(H2,9,10,11)
• InChIKey: ZZUZYEMRHCMVTB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: phenylethynesulfonamide
• IUPAC Traditional name: phenylethynesulfonamide
• Synonyms: 2-Phenylacetylenesulfonamide; 2-Phenyl-ethynesulfoanide; PFT-μ; 2-Phenylethynesulfonamide; PFTμ; Pifithrin-μ; Phenyl-ethynesulfonic Acid Amide; Pifithrin-υ; PFTυ; Phenylethynsulfonic Acid Amide; NSC 303580; Pifithrin-μ

Database IDs

• CAS Number: 64984-31-2
• MDL Number: MFCD00181531
• PubChem SID: 24724568; 162063493
• PubChem CID: 327653

CALCULATED PROPERTIES

• Acid pKa: 9.702303
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.0943747
• LogD (pH = 7.4): 1.0923963
• Log P: 1.0944
• Molar Refractivity: 42.1889 cm^3
• Polarizability: 18.226824 Å^3
• Polar Surface Area: 60.16 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL; H2O: <2 mg/mL
• Apperance: solid
• Melting Point: 136 - 138°C
• Hydrophobicity(logP): 0.335

Safety Information

• Storage Condition: desiccated
• Storage Warning: IRRITANT
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: p53

Product Information

• Purity: ≥97% (HPLC); 95%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C8H7NO2S

DETAILS

Sigma Aldrich - P0122

Biochem/physiol Actions
Pifithrin-μ is an inhibitor of p53 binding and anti-apoptotic, which directly inhibits p53 binding to mitochondria as well as to Bcl-xL and Bcl-2 proteins. PFTμ rescues cells from lethal γ-irradiation-induced cell death. Because pifithrin-μ shuts down only the p53-mitochondrial pathway without affecting the transcriptional functions of p53, it is superior to pifithrin-α.

Toronto Research Chemicals - P321575

A small molecule inhibitor of p53 binding to mitochondria protects mice from gamma radiation.

REFERENCES

• Strom, E., et al.: Nature Chemical Biology, 2, 474 (2006)