N-{4-[(4-nitrophenyl)sulfamoyl]phenyl}acetamide

• ChemBase ID: 104658
• Molecular Formular: C14H13N3O5S
• Molecular Mass: 335.33512
• Monoisotopic Mass: 335.05759153
• SMILES: CC(=O)Nc1ccc(cc1)S(=O)(=O)Nc1ccc(cc1)[N+](=O)[O-]
• Canonical SMILES: CC(=O)Nc1ccc(cc1)S(=O)(=O)Nc1ccc(cc1)[N+](=O)[O-]
• InChI: InChI=1S/C14H13N3O5S/c1-10(18)15-11-4-8-14(9-5-11)23(21,22)16-12-2-6-13(7-3-12)17(19)20/h2-9,16H,1H3,(H,15,18)
• InChIKey: GWBPFRGXNGPPMF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{4-[(4-nitrophenyl)sulfamoyl]phenyl}acetamide
• IUPAC Traditional name: sulfanitran
• Synonyms: Sulfanitran; Acetyl(p-nitrophenyl)sulfanilamide; SULFANITRAN; N4-Acetyl-N1-(4-nitrophenyl)sulfanilamide; 4'-[(p-Nitrophenyl)sulfamoyl]acetanilide; N4-Acetyl-4'-nitrosulfanilanilide; N4-Acetyl-N1-(p-nitrophenyl)sulfanilamide; NSC 217299; NSC 77120; N4-乙酰基-N1-(4-硝基苯)磺胺; 磺胺硝苯

Database IDs

• CAS Number: 122-16-7
• MDL Number: MFCD00024598
• Beilstein Number: 2952955
• PubChem SID: 24899645; 24870538; 162092187
• PubChem CID: 5334

CALCULATED PROPERTIES

• Acid pKa: 7.6228285
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.635718
• LogD (pH = 7.4): 1.4635335
• Log P: 1.6386057
• Molar Refractivity: 85.0779 cm^3
• Polarizability: 32.031273 Å^3
• Polar Surface Area: 121.09 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥85%; ~85%
• Grade: VETRANAL™, analytical standard
• Empirical Formula (Hill Notation): C14H13N3O5S

DETAILS

MP Biomedicals - 02156717

Purity: >85%

Sigma Aldrich - S5272

Application
Sulfanitran is used to stimulate MRP2. It is used to stimulate the MRP2-mediated transport of lipophilic amphipathic drugs1. It is used to study the efflux of chemotherapeutics in tumor cell lines1.
Biochem/physiol Actions
Sulfanitran stimulates the ATP binding cassette family transporter multidrug resistance protein 2 (MRP2). Sulfanitran increases the affinity of MRP2 for estradiol-17-β-D-glucuronide2. It stimulates the vectorial transport of saquinavir, a MRP2 substrate, across polarized MDCKII monolayers2.

Sigma Aldrich - 46882

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - S689040

Sulfanitran is a sulfanomide derivative used as an anticoccidial drug. Sulfanitran is added to the drinking water of chickens as an aid in the treatment of coccidiosis caused by E. tenella, E. necatrix, and E. acervulina.

REFERENCES

• Morehouse, N.F. et al.: Exp. Parasitol., 28, 25 (1970)
• Reid, W.M. et al.: Acta Vet. Brno, 38, 137 (1970)
• McLoughlin, D.K. et al.: Avian Dis., 10, 410 (1970)