4-amino-N-(3-methoxypyrazin-2-yl)benzene-1-sulfonamide

• ChemBase编号: 546
• 分子式: C11H12N4O3S
• 平均质量: 280.30298
• 单一同位素质量: 280.06301126
• SMILES: S(=O)(=O)(Nc1nccnc1OC)c1ccc(N)cc1
• Canonical SMILES: COc1nccnc1NS(=O)(=O)c1ccc(cc1)N
• InChI: InChI=1S/C11H12N4O3S/c1-18-11-10(13-6-7-14-11)15-19(16,17)9-4-2-8(12)3-5-9/h2-7H,12H2,1H3,(H,13,15)
• InChIKey: KXRZBTAEDBELFD-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 4-amino-N-(3-methoxypyrazin-2-yl)benzene-1-sulfonamide
• IUPAC传统名: sulfametopyrazine; longum; 4-amino-N-(3-methoxypyrazin-2-yl)benzene-1-sulfonamide
• 商标名: Dalysep; Farmitalia 204/122; Kelfizin; Kelfizina; Kelfizine; Kelfizine W; Longum; Polycidal; SMP; SMP2; Solfametopirazina [Dcit]; Sulfalen; Sulfalene; Sulfalene [Usan:Inn]; Sulfaleno [INN-Spanish]; Sulfalenum [INN-Latin]; Sulfamethopyrazine; Sulfamethoxypyrazine; Sulfamethoxysuccinate; Sulfametoxypyridazin; Sulfapyrazinemethoxine; Sulfapyrazinemethoxyine; Sulfapyrazinemethoxyne
• 别名: Sulfametopyrazine; 4-Amino-N-(3-methoxy-2-pyrazinyl)-benzenesulfonamide; 4-amino-N-(3-methoxypyrazin-2-yl)benzene-1-sulfonamide; F.I. 5978; Farmitalia 204/122; Kelfizin; Kelfizina; Kelfizine W; Longum; N1-(3-Methoxy-2-pyrazinyl)sulfanilamide; NSC 110433; Policydal; Polycidal; SMP2; Sulfalene; Sulfamethopyrazine; Sulfamethoxypyrazine; Sulfametopyrazine; Sulfapyrazinemethoxine; Sulfapyrazinemethoxyine; Sulfapyrazinemethoxyne; Vetkelfizina; Sulfamethoxypyrazine; 4-Amino-N-(3-methoxypyrazinyl)-benzenesulfonamide; N1-(3-Methoxypyrazinyl)-sulfanilamide; 2-Methoxy-3-sulfanilamidopyrazine; 2-Sulfanilamido-3-methoxypyrazine; 3-Methoxy-2-sulfanilamidopyrazine; 3-Methoxy-2-sulfapyrazine; 3-Methoxypyrazine Sulfanilamide; AS 18908; Dalysep; Kelfizine; Sulfalene

登记号

• CAS号: 152-47-6
• MDL号: MFCD00437754
• PubChem SID: 160964009; 46505111
• PubChem CID: 9047

理论计算性质

JChem

• Acid pKa: 5.91424
• 质子受体: 6
• 质子供体: 2
• LogD (pH = 5.5): 0.104915224
• LogD (pH = 7.4): -0.61960566
• Log P: 0.22788408
• 摩尔折射率: 70.367 cm^3
• 极化性: 27.139517 Å^3
• 极化表面积: 107.2 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: 0.41
• LOG S: -2.84
• 溶解度: 4.06e-01 g/l

分子性质

理化性质

• 溶解度: 4030 mg/L; Dichloromethane; Methanol
• 外观: Yellow Solid
• 熔点: 168 - 170°C
• 疏水性(logP): 0.7; 1.048

安全信息

• 保存条件: -20°C Freezer
• 保存注意事项: IRRITANT
• TSCA收录: false

药理学性质

• 生物活性机理: Competitive inhibitor of bacterial 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

产品相关信息

• 纯度: 95%
• 应用领域: Antiseptic; Long-acting sulfonamide used in treatment of respiratory and urinary-tract infections

详细说明

DrugBank - DB00664

• Drug Groups: approved; withdrawn
• Description: Long-acting plasma-bound sulfonamide used for respiratory and urinary tract infections and also for malaria. [PubChem]
• Indication: For the treatment of urinary tract infection and chronic bronchitis.
• Pharmacology: Sulfametopyrazine is a sulfonamide antibiotic. 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: Gram negative, positive bacteria and plasmodium

Toronto Research Chemicals - S699230

A possible antimalarial drug.

参考文献

• Davidson D.E.Jr. et al; Am. J. Trop. Med. Hyg. 25, 26 (1976)
• Launchbury, A.P., Pharm. J., 1975, 214, 14, (pharmacol)
• Kracmar, J. et al., Pharmazie, 1975, 30, 447, (uv)
• Padeiskaya, E.N. et al., Khim.-Farm. Zh., 1977, 11, 141, (rev, pharmacol)
• Botta, M. et al., J. Het. Chem., 1979, 16, 193, (synth)
• Anisimova, O.S. et al., Khim.-Farm. Zh., 1980, 14, 92, (ms)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 205
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, MFN500