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

• ChemBase编号: 4415
• 分子式: C9H9N3O2S2
• 平均质量: 255.31666
• 单一同位素质量: 255.01361854
• SMILES: Nc1ccc(cc1)S(=O)(=O)Nc1nccs1
• Canonical SMILES: Nc1ccc(cc1)S(=O)(=O)Nc1nccs1
• InChI: InChI=1S/C9H9N3O2S2/c10-7-1-3-8(4-2-7)16(13,14)12-9-11-5-6-15-9/h1-6H,10H2,(H,11,12)
• InChIKey: JNMRHUJNCSQMMB-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 4-amino-N-(1,3-thiazol-2-yl)benzene-1-sulfonamide
• IUPAC传统名: 4-amino-N-(1,3-thiazol-2-yl)benzene-1-sulfonamide; sulfathiazole; thiazamide
• 商标名: Neo-Strepsan
• 别名: 4-氨基-N-(2-噻唑基)苯磺酰胺; N1-(2-噻唑基)磺胺; 磺胺噻唑; Sulfathiazole; 4-Amino-N-2-thiazolyl-benzenesulfonamide; N₁-(2-Thiazolyl)sulfanilamide; N(1)-(2-Thiazolyl)sulfanilamide; Sultrin; 4-Amino-N-2-thiazolylbenzenesulfonamide; N1-2-Thiazolylsulfanilamide; 2-(p-Aminobenzenesulfonamido)thiazole; 2-Sulfathiazole-d4; Azoquimiol; Azoseptale; Chemosept; Ciba 3714; Cibazol; Duatok; Dulana; Eleudron; Enterobiocine; Sulfathiazol; Sulfocerol; Thiozamide; 4-Amino-N-(thiazol-2-yl)benzenesulfonamide; Sulphathiazole; Sodium sulfathiazole; Sulfathiazole; 4-Amino-N-(2-thiazolyl)benzenesulfonamide; N1-(2-Thiazolyl)sulfanilamide

登记号

• CAS号: 72-14-0
• EC号: 200-771-5
• MDL号: MFCD00005319
• Beilstein号: 226178
• 默克索引号: 148943
• PubChem SID: 24870550; 24846323; 160967847; 24899859
• PubChem CID: 5340
• CHEBI ID: 9337
• ATC码: D06BA02; J01EB07; QJ01EQ07
• CHEMBL: 437
• Chemspider ID: 5148
• DrugBank ID: DB06147
• KEGG ID: D01047
• 美国药典/FDA物质标识码: Y7FKS2XWQH
• 维基百科标题: Sulfathiazole

理论计算性质

JChem

• Acid pKa: 6.9284616
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 0.96082556
• LogD (pH = 7.4): 0.50352055
• Log P: 0.9750279
• 摩尔折射率: 62.2723 cm^3
• 极化性: 24.194004 Å^3
• 极化表面积: 85.08 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: 0.88
• LOG S: -2.44
• 溶解度: 9.21e-01 g/l

分子性质

理化性质

• 溶解度: 0.373 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; DMSO Methanol
• 外观: WHite Solid
• 熔点: 196-198°C; 200- 202°C; 200-202 °C(lit.); 200-203°C; 201-204 °C
• 疏水性(logP): 0.05 [HANSCH,C ET AL. (1995)]

安全信息

• 保存条件: Refrigerator; Room Temperature (15-30°C)
• RTECS编号: WP2360000
• 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
• 安全公开号: 26-36; 26-37
• TSCA收录: 是
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

药理学性质

• 作用靶点: Others
• 相关基因信息: rat ... Ednra(24326)
• 生物活性机理: Dihydrofolate reductase inhibitor; Dihydrofolate synthesis inhibitor; Folate-antagonist

产品相关信息

• 纯度: ≥98.0%; ≥98.0% (N); 98%; 99%
• 级别: purum; VETRANAL™, analytical standard
• 成盐信息: Free Base
• 适用性: suitable for 1694 per US EPA
• 应用领域: Sulfonamide; Used in treatment of severe staphylococcal infections, but use restricted due to its systemic toxicity.
• Empirical Formula (Hill Notation): C9H9N3O2S2

详细说明

MP Biomedicals - 02102992

Free Acid
Crystalline

DrugBank - DB06147

• Drug Groups: approved
• Description: Sulfathiazole is a short-acting sulfa drug. It used to be a common oral and topical antimicrobial until less toxic alternatives were discovered. It is still occasionally used, sometimes in combination with sulfabenzamide and sulfacetamide.
• Indication: Sulfathiazole is effective against a wide range of gram positive and gram negative pathogenic microorganisms. Although no longer used in humans, it is used in cattle.
• Toxicity: Acute oral toxicity (LD50): 4500 mg/kg [Mouse].
• Biotransformation: Metabolism of sulfonamide drugs in animals includes conjugation at the N4-position (acetyl, sulfate, glucuronic acid, and glucose), conjugation at the N1-position (sulfate and glucuronic acid), removal of the p-amino group (formation of the desamino metabolite), ring hydroxylation, and conjugation of the ring hydroxylation products. Dietary nitrite enhances the production of the desamino metabolite of sulfathiazole. The intermediate leading to the desamino metabolite of sulfamethazine is weakly mutagenic in the Ames test (Nelson et al., 1987; Paulson et al., 1987).
• External Links: Wikipedia

Sigma Aldrich - 46902

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - S9876

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。
包装
100, 250 g in poly bottle

Toronto Research Chemicals - S699093

Antibacterial.

参考文献

• Kapoor, V.K., et al.: Anal. Profiles Drug Subs. Excip., 22, 389 (1993)
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• Hughes, D.S. et al., Acta Cryst. C, 1999, 55, 1831-1833, (cryst struct)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, TEX250; TEX500