4-amino-N-(dimethyl-1,3-oxazol-2-yl)benzene-1-sulfonamide

• ChemBase编号: 6399
• 分子式: C11H13N3O3S
• 平均质量: 267.30422
• 单一同位素质量: 267.06776229
• SMILES: S(=O)(=O)(Nc1oc(c(n1)C)C)c1ccc(N)cc1
• Canonical SMILES: Nc1ccc(cc1)S(=O)(=O)Nc1oc(c(n1)C)C
• InChI: InChI=1S/C11H13N3O3S/c1-7-8(2)17-11(13-7)14-18(15,16)10-5-3-9(12)4-6-10/h3-6H,12H2,1-2H3,(H,13,14)
• InChIKey: CYFLXLSBHQBMFT-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 4-amino-N-(dimethyl-1,3-oxazol-2-yl)benzene-1-sulfonamide
• IUPAC传统名: sulfamoxole
• 商标名: Sulfavigor; Justamil; Sulfmidil; Tardamid; Vetranal; Nuprin
• 别名: 4-氨基-N-(4,5-二甲基-2-恶唑)苯磺酰胺; N1-(4,5-二甲基噁唑-2-基)磺胺; 磺胺噁唑; Sulphamoxole; Sulfamoxol; Sulfamoxolum; Sulfono; Sulfamoxole; N1-(4,5-dimethyl-2-oxazolyl)sulfanilamide; 2-(p-Aminobenzolsulfonamido)-4,5-dimethyloxazole; 2-Sulfanilamido-4,5-dimethyloxazole; Justamil; NSC 683535; N'-(4,5-Dimethyl-2-oxazolyl)sulfanilamide; Oxasulfa; Sulfabutin; Sulfadimethyloxazole; Sulfano; Sulfavigor; Sulfmidil; Sulfune; Sulfuno; Tardamid; Tardamide; 4-Amino-N-(4,5-dimethyl-2-oxazolyl)benzenesulfonamide; N1-(4,5-Dimethyloxazol-2-yl)sulfanilamide; Sulfamoxole

登记号

• CAS号: 729-99-7
• EC号: 211-982-7
• MDL号: MFCD00005303
• Beilstein号: 248434
• PubChem SID: 160969706; 24870529
• PubChem CID: 12894
• CHEBI ID: 55548
• ATC码: J01EC03
• Chemspider ID: 12361
• DrugBank ID: DB08798
• KEGG ID: D02516
• 美国药典/FDA物质标识码: HGG82XE020
• 维基百科标题: Sulfamoxole

理论计算性质

JChem

• Acid pKa: 6.8086896
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 0.57054317
• LogD (pH = 7.4): 0.058534656
• Log P: 0.58905804
• 摩尔折射率: 67.5145 cm^3
• 极化性: 25.918407 Å^3
• 极化表面积: 98.22 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.04
• LOG S: -3.0
• 溶解度: 2.67e-01 g/l

分子性质

理化性质

• 溶解度: DMSO; Methanol
• 外观: Pale Yellow Solid
• 熔点: 176-178°C

安全信息

• 保存条件: Refrigerator, Under Inert Atmosphere
• RTECS编号: WO9150000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 2
• 危险公开号: 43
• 安全公开号: 36/37
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H317
• GHS警示性声明: P280
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

产品相关信息

• 纯度: ≥80%
• 级别: VETRANAL™, analytical standard
• Empirical Formula (Hill Notation): C11H13N3O3S

详细说明

DrugBank - DB08798

• Drug Groups: approved
• Description: Sulfamoxole is a sulfonamide antibacterial.
• Indication: For the treatment of bacterial infection.
• Pharmacology: Sulfamoxole 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.
• Toxicity: Oral Rat LD50: > 12500 mg/kg; Intravenous Mouse LD50: 1 g/kg
• Affected Organisms: Enteric bacteria and other eubacteria
• References: DUGGER JA: Sulfamoxole (Nuprin), a new sulfonamide, in pediatric practice. J New Drugs. 1961 Sep-Oct;1:223-9. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - 46866

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

Toronto Research Chemicals - S689010

Silversulfadiazine and Sulfamoxol are common drugs in treatment of bacterial disease.

参考文献

• DUGGER JA: Sulfamoxole (Nuprin), a new sulfonamide, in pediatric practice. J New Drugs. 1961 Sep-Oct;1:223-9. Pubmed
• Jaiswal, P., et al.: Talanta, 17, 236 (1970)
• Saxena, A., et al.: Prog. Drugs Res., 30, 221 (1970)