4-(hydroxyamino)-N-(5-methyl-1,2-oxazol-3-yl)benzene-1-sulfonamide

• ChemBase ID: 171322
• Molecular Formular: C10H11N3O4S
• Molecular Mass: 269.27704
• Monoisotopic Mass: 269.04702685
• SMILES: c1(ccc(cc1)NO)S(=O)(=O)Nc1noc(c1)C
• Canonical SMILES: ONc1ccc(cc1)S(=O)(=O)Nc1noc(c1)C
• InChI: InChI=1S/C10H11N3O4S/c1-7-6-10(12-17-7)13-18(15,16)9-4-2-8(11-14)3-5-9/h2-6,11,14H,1H3,(H,12,13)
• InChIKey: MJAMPGKHIZXVFJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(hydroxyamino)-N-(5-methyl-1,2-oxazol-3-yl)benzene-1-sulfonamide
• IUPAC Traditional name: sulfamethoxazole hydroxylamine
• Synonyms: 4-(Hydroxyamino)-N-(5-methyl-3-isoxazolyl)-benzenesulfonamide; Sulfamethoxazole N4-Hydroxylamine; Sulfamethoxazole Hydroxylamine; NSC 665547; N-Hydroxy Sulfamethoxazole

Database IDs

• CAS Number: 114438-33-4
• PubChem SID: 164227232
• PubChem CID: 114821

CALCULATED PROPERTIES

• Acid pKa: 6.065392
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.0302716
• LogD (pH = 7.4): 0.31231305
• Log P: 1.1277453
• Molar Refractivity: 66.7826 cm^3
• Polarizability: 24.833904 Å^3
• Polar Surface Area: 104.46 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: >130°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - H953800

A Sulfamethoxazole metabolite.

REFERENCES

• Gill, H., et al.: Br. J. Clin. Pharmacol., 42, 347 (1996)
• Winter, H., et al.: Clin. Pharmacol. Ther., 76, 579 (1996)
• Vyas, P., et al.: Biochem. Pharmacol., 70, 275 (1996)
• Vyas, P., et al.: Drug Metab. Dispos., 34, 16 (1996)