4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzene-1-sulfonamide sodium

• ChemBase ID: 132304
• Molecular Formular: C12H14N4NaO2S
• Molecular Mass: 301.31993
• Monoisotopic Mass: 301.07351599
• SMILES: Cc1cc(nc(n1)NS(=O)(=O)c1ccc(cc1)N)C.[Na]
• Canonical SMILES: Nc1ccc(cc1)S(=O)(=O)Nc1nc(C)cc(n1)C.[Na]
• InChI: InChI=1S/C12H14N4O2S.Na/c1-8-7-9(2)15-12(14-8)16-19(17,18)11-5-3-10(13)4-6-11;/h3-7H,13H2,1-2H3,(H,14,15,16)
• InChIKey: MNWVJNSMYXMEIX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzene-1-sulfonamide sodium
• IUPAC Traditional name: sulfamethazine sodium
• Synonyms: 4-Amino-N-(4,6-dimethyl-2-pyrimidinyl)benzenesulfonamide; Sulfamethazine sodium salt; 磺胺二甲基嘧啶 钠盐

Database IDs

• CAS Number: 1981-58-4
• EC Number: 217-840-0
• MDL Number: MFCD00068333
• PubChem SID: 162226581; 24899666
• PubChem CID: 16219973

CALCULATED PROPERTIES

• Acid pKa: 6.99357
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.63772017
• LogD (pH = 7.4): 0.21068367
• Log P: 0.65000117
• Molar Refractivity: 73.3839 cm^3
• Polarizability: 28.103605 Å^3
• Polar Surface Area: 97.97 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98%

DETAILS

Sigma Aldrich - S5637

Application
Sulfamethazine is an antibiotic used to clinically treat bronchitis, prostatitis and urinary tract infections1. It is used in disposition and depletion kinetic studies2,3. It is used to develop detection techniques for quantification in fluids such as cows’ milk, honey and swine urine4.
Biochem/physiol Actions
Sulfamethazine is an antimicrobial sulfur drug that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase. Sulfamethazine is a competitive inhibitor of bacterial para-aminobenzoic acid (PABA), which is required for bacterial synthesis of folic acid1. It induces CYP3A4 expression and is acetylated by N-acetyltransferase. It exhibits sex dependent pharmacokinetics, metabolized by the male specific isoform CYP2C11. Sulfamethazine is bacteriostatic.