4-amino-N-(1-ethyl-2-oxo-1,2-dihydropyrimidin-4-yl)benzene-1-sulfonamide

• ChemBase编号: 1150
• 分子式: C12H14N4O3S
• 平均质量: 294.32956
• 单一同位素质量: 294.07866133
• SMILES: S(=O)(=O)(Nc1nc(=O)n(CC)cc1)c1ccc(N)cc1
• Canonical SMILES: CCn1ccc(nc1=O)NS(=O)(=O)c1ccc(cc1)N
• InChI: InChI=1S/C12H14N4O3S/c1-2-16-8-7-11(14-12(16)17)15-20(18,19)10-5-3-9(13)4-6-10/h3-8H,2,13H2,1H3,(H,14,15,17)
• InChIKey: SIBQAECNSSQUOD-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 4-amino-N-(1-ethyl-2-oxo-1,2-dihydropyrimidin-4-yl)benzene-1-sulfonamide
• IUPAC传统名: sulfacytine
• 商标名: Renoquid
• 别名: 1-ethyl N4-sulfanilylcytosin; 1-ethyl-N-sulfanilylcytosine; N-sulfanilyl-l-ethylcytosine; Sulfacitina [inn-spanish]; Sulfacitinum [inn-latin]; Sulfacytine

登记号

• CAS号: 17784-12-2
• PubChem SID: 160964613; 46505483
• PubChem CID: 5322

理论计算性质

JChem

• Acid pKa: 10.5525875
• 质子受体: 5
• 质子供体: 2
• LogD (pH = 5.5): 0.054794375
• LogD (pH = 7.4): 0.05472528
• Log P: 0.054998476
• 摩尔折射率: 75.488 cm^3
• 极化性: 28.825743 Å^3
• 极化表面积: 104.86 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.51
• LOG S: -2.8
• 溶解度: 4.68e-01 g/l

分子性质

理化性质

• 溶解度: 1.75 mg/mL at 37 oC [MERCK INDEX (1996); pH 5]

详细说明

DrugBank - DB01298

• Drug Groups: approved
• Description: Sulfacytine is a short-acting sulfonamide. The sulfonamides are synthetic bacteriostatic antibiotics with a wide spectrum against most gram-positive and many gram-negative organisms. However, many strains of an individual species may be resistant. Sulfonamides inhibit multiplication of bacteria by acting as competitive inhibitors of p-aminobenzoic acid in the folic acid metabolism cycle. Bacterial sensitivity is the same for the various sulfonamides, and resistance to one sulfonamide indicates resistance to all. Most sulfonamides are readily absorbed orally. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. The sulfonamides are widely distributed throughout all tissues. High levels are achieved in pleural, peritoneal, synovial, and ocular fluids. Although these drugs are no longer used to treat meningitis, CSF levels are high in meningeal infections.; ; Sulfacytine is a competitive inhibitor of the enzyme dihydropteroate synthetase. It inhibits bacterial synthesis of of dihydrofolic acid by preventing the condensation of the pteridine with para-aminobenzoic acid (PABA), a substrate of the enzyme dihydropteroate synthetase. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.
• Indication: Used orally in the treatment of acute urinary tract infections.
• Pharmacology: Sulfacytine is a short-acting sulfonamide. The sulfonamides are synthetic bacteriostatic antibiotics with a wide spectrum against most gram-positive and many gram-negative organisms. However, many strains of an individual species may be resistant. Sulfonamides inhibit multiplication of bacteria by acting as competitive inhibitors of p-aminobenzoic acid in the folic acid metabolism cycle. Bacterial sensitivity is the same for the various sulfonamides, and resistance to one sulfonamide indicates resistance to all. Most sulfonamides are readily absorbed orally. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. The sulfonamides are widely distributed throughout all tissues. High levels are achieved in pleural, peritoneal, synovial, and ocular fluids. Although these drugs are no longer used to treat meningitis, CSF levels are high in meningeal infections. Their antibacterial action is inhibited by pus.
• Affected Organisms: Bacteria
• Absorption: Well absorbed following oral administration.