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

• ChemBase编号: 888
• 分子式: C10H11N3O3S
• 平均质量: 253.27764
• 单一同位素质量: 253.05211223
• SMILES: S(=O)(=O)(Nc1noc(c1)C)c1ccc(N)cc1
• 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

名称和登记号

名称

• IUPAC标准名: 4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzene-1-sulfonamide
• IUPAC传统名: 4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzene-1-sulfonamide; sulfamethoxazole; trib
• 商标名: Apo-Sulfamethoxazole; Azo Gantanol; Azo-Gantanol; Bactrimel; Gamazole; Gantanol; Gantanol-DS; Metoxal; Radonil; SIM; Septran; Simsinomin; Sinomin; Sulfamethalazole; Sulfamethoxazol; Sulfamethoxizole; Sulfamethylisoxazole; Sulfisomezole; Sulpha-Methoxizole; Sulphamethalazole; Sulphamethoxazol; Sulphamethoxazole; Sulphamethoxazole BP 98; Sulphamethylisoxazole; Sulphisomezole; Trib; Urobak
• 别名: 4-氨基-N-(5-甲基-3-异噁唑基)苯磺酰胺; N1-(5-甲基异噁唑基-3-基)磺胺; 新诺明; Sulphamethoxazole; 4-[N-(5-Methylisoxazol-3-yl)sulphamoyl]aniline; 4-Amino-N-(5-methylisoxazol-3-yl)benzenesulphonamide; Gantanol; Gantanol DS; 4-Amino-N-(5-methyl-3-isoxazolyl)benzenesulfonamide; N1-(5-Methylisoxazol-3-yl)sulfanilamide; Sulfamethoxazole; 4-Amino-N-(5-methyl-3-isoxazolyl)-benzenesulfonamide; Sulfamethoxazole; 4-amino-N-(5-methylisoxazol-3-yl)benzenesulfonamide; 4-Amino-N-[5-methyl-3-isoxazolyl]benzenesulfonamide; N1-(5-methylisoxazol-3-yl)-4-aminobenzene-1-sulfonamide; 3-(p-Aminobenzenesulfonamido)-5-methylisoxazole; Sulfamethoxazole; 3-Sulfanilamido-5-methylisoxazole; 5-Methyl-3-sulfanilamidoisoxazole; MS 53; Radonil; Ro 4-2130; STX 608; Sinomin; Sulfamethalazole; Sulfamethoxazol; 4-amino-n-(5-methyl-3-isoxazolyl)benzenesulfonamide

登记号

• CAS号: 723-46-6
• EC号: 211-963-3
• MDL号: MFCD00010546
• Beilstein号: 6732984
• PubChem SID: 24870521; 160964351; 24899752; 46508111
• PubChem CID: 5329

理论计算性质

JChem

• Acid pKa: 6.1607323
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 0.71531755
• LogD (pH = 7.4): 9.2587294E-4
• Log P: 0.7905494
• 摩尔折射率: 64.4958 cm^3
• 极化性: 24.161753 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: 0.79
• LOG S: -2.74
• 溶解度: 4.59e-01 g/l

分子性质

理化性质

• 溶解度: 610 mg/L; DMSO; Methanol
• 外观: White Solid
• 熔点: 166-169°C; 168-170°C
• 疏水性(logP): 0.7

安全信息

• 保存条件: -20°C; Refrigerator, Under Inert Atmosphere; Room Temperature (15-30°C), Protect from light
• 保存注意事项: IRRITANT; Irritant/Light Sensitive
• RTECS编号: WP0700000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 2
• 危险公开号: 36/37/38-43
• 安全公开号: 26-36
• TSCA收录: false
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H317-H319-H335
• GHS警示性声明: P261-P280-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• 保存温度: room temp

药理学性质

• 作用靶点: DNA/RNA
• 相关基因信息: rat ... Ednra(24326)
• 生物活性机理: Folate antagonist; Folate synthesis inhibitor; Restrict folate synthesis through competitive antagonism of PABA

产品相关信息

• 纯度: 95+%; 97%; 98%
• 级别: certified reference material; TraceCERT®; VETRANAL™, analytical standard
• 成盐信息: Free Base
• 包装: pkg of 1 g
• 有效期: (limited shelf life, expiry date on the label)
• 应用领域: Sulfonamide bacteriostatic antibiotic; Used in treatment of respiratory and urinary tract infections
• Pharmacopeia Traceability: traceable to BP 314; traceable to PhEur S2100000; traceable to USP 1631001
• Empirical Formula (Hill Notation): C10H11N3O3S

详细说明

MP Biomedicals - 02156711

(4-Amino-N-[5-methyl-3-
isoxazolyl]benzenesulfonamide)

DrugBank - DB01015

• Drug Groups: approved
• Description: A bacteriostatic antibacterial agent that interferes with folic acid synthesis in susceptible bacteria. Its broad spectrum of activity has been limited by the development of resistance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p208)
• Indication: For the treatment bacterial infections causing bronchitis, prostatitis and urinary tract infections.
• Pharmacology: Sulfamethoxazole is a sulfonamide drug that inhibits bacterial synthesis of dihydrofolic acid by competing with para-aminobenzoic acid (PABA) for binding to dihydropteroate synthetase (dihydrofolate synthetase). Sulfamethoxazole is bacteriostatic in nature. Inhibition of dihydrofolic acid synthesis decreases the synthesis of bacterial nucleotides and DNA. Sulfamethoxazole is normally given in combination with Trimethoprim, a dihydrofolate reductase inhibitor, which inhibits the reduction of dihydrofolic acid to tetrahydrofolic acid. Studies have shown that bacterial resistance develops more slowly with the combination of the two drugs than with either Trimethoprim or Sulfamethoxazole alone.
• Toxicity: Sulfamethoxazole may cause nausea, vomiting, diarrhea and hypersensitivity reactions. Hematologic effects such as anemia, agranulocytosis, thrombocytopenia and hemolytic anemia in patients with glucose-6-phosphate dehydrogenase deficiency may also occur. Sulfamethoxazole may displace bilirubin from albumin binding sites causing jaundice or kernicterus in newborns.
• Affected Organisms: Gram negative and gram positive bacteria
• Biotransformation: Hepatic. The metabolism of sulfamethoxazole occurs predominately by N4-acetylation, although the glucuronide conjugate has been identified.
• Absorption: Rapidly absorbed following oral administration. Also well-absorbed topically.
• Half Life: 10 hours
• Protein Binding: 70%
• External Links: Wikipedia; RxList

Selleck Chemicals - S1915

Research Area: Infection
Biological Activity:
Sulfamethoxazole is a sulfonamide bacteriostatic antibiotic with an IC50 of 2.7 μM. Sulfamethoxazole is most often used as a part of synergistic combination with trimethoprim in a 5:1 ratio in co-trimoxazole. Sulfonamides are structural analogs and competitive antagonists of para-aminobenzoic acid (PABA). They inhibit normal bacterial utilization of PABA for the synthesis of folic acid, an important metabolite in DNA synthesis. [1][2]

Sigma Aldrich - 76177

General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
法律信息
TraceCERT 注册商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - S7507

Biochem/physiol Actions
通过抑制二氢叶酸合成酶阻断二氢叶酸合成的磺胺类抗生素。 作用方式：在原核生物中抑制叶酸合成。 抗菌谱：革兰氏阳性菌、革兰氏阴性菌、衣原体 抗性机理：二氢叶酸合成酶或叶酸合成替代路径的改变。

Sigma Aldrich - PHR1126

General description
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34.
Other Notes
Values of analytes vary lot to lot.

Sigma Aldrich - 31737

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

Toronto Research Chemicals - S699086

An antibacterial drug. Sulfonamide antibiotic that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase.

参考文献

• http://en.wikipedia.org/wiki/Sulfamethoxazole
• 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)
• U.K. Pat., 1959, 814276; CA, 55, 20091c, (synth)
• Fujimoto, M. et al., Chem. Pharm. Bull., 1962, 10, 572-575, (derivs)
• Iwai, I. et al., Chem. Pharm. Bull., 1966, 14, 1277, (synth)
• Rudy, B.C. et al., Anal. Profiles Drug Subst., 1973, 2, 467, (rev, synth, props)
• Brumfitt, W. et al., J. Infect. Dis., 1973, 128, 5778, (rev, pharmacol)
• Manzo, R.H. et al., J. Pharm. Sci., 1973, 62, 152, (uv)
• IARC Monog., 1980, 24, 285; Suppl. 7, 348; Suppl. 6, 502, (rev, tox)
• Bushby, S.R.M. et al., Handb. Exp. Pharmacol., 1983, 64, 75; 163; 185, (revs)
• Bult, A., Pharm. Weekbl., Sci. Ed., 1983, 5, 77, (cmr, tautom)
• Maury, L. et al., Can. J. Chem., 1985, 63, 3012, (cryst struct, ir, Raman)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 1514; 3212
• Kirk-Othmer Encycl. Chem. Technol., 4th edn., Wiley, 1991, 2, 876
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 208
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, SNK000