4-amino-N-(5-methyl-1,2-oxazol-3-yl)(2H4)benzene-1-sulfonamide

• ChemBase ID: 177987
• Molecular Formular: C10H11N3O3S
• Molecular Mass: 253.27764
• Monoisotopic Mass: 253.05211223
• SMILES: c1(ccc(cc1)N)S(=O)(=O)Nc1noc(c1)C
• Canonical SMILES: Nc1ccc(cc1)S(=O)(=O)Nc1noc(c1)C
• InChI: InChI=1S/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13)
• InChIKey: JLKIGFTWXXRPMT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-N-(5-methyl-1,2-oxazol-3-yl)(^2H₄)benzene-1-sulfonamide
• IUPAC Traditional name: 4-amino-N-(5-methyl-1,2-oxazol-3-yl)(^2H₄)benzenesulfonamide
• Synonyms: 4-Amino-N-(5-methyl-3-isoxazolyl)(benzene-d4)sulfonamide; 3-(p-Amino(benzene-d4)sulfonamido)-5-methylisoxazole; Sulfamethoxazole-d4; 3-Sulfanilamido-5-methylisoxazole-d4; 5-Methyl-3-sulfanilamidoisoxazole-d4; Gantanol-d4; MS 53-d4; Radonil-d4; Ro 4-2130-d4; STX 608-d4; Sinomin-d4; Sulfamethoxazole-d4

Database IDs

• PubChem SID: 164233897
• PubChem CID: 45040440

CALCULATED PROPERTIES

• Acid pKa: 6.1607323
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.71531665
• LogD (pH = 7.4): 9.2554867E-4
• Log P: 0.7905494
• Molar Refractivity: 64.4958 cm^3
• Polarizability: 24.185614 Å^3
• Polar Surface Area: 98.22 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Light Yellow Solid
• Melting Point: 162-165°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - S699087

The isotopically labelled antibacterial drug Sulfamethoxazole. Sulfonamide antibiotic that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase.

REFERENCES

• Rudy, B.C., et al.: Anal. Profiles Drug Subs., 2, 467 (1973)
• Wormser, G.P., et al.: Drugs, 24, 459 (1973)
• Wharton, M., et al.: Ann. Intern. Med., 105, 37 (1973)