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

• ChemBase编号: 458
• 分子式: C9H10N4O2S2
• 平均质量: 270.3313
• 单一同位素质量: 270.02451758
• SMILES: S(=O)(=O)(Nc1sc(nn1)C)c1ccc(N)cc1
• Canonical SMILES: Nc1ccc(cc1)S(=O)(=O)Nc1nnc(s1)C
• InChI: InChI=1S/C9H10N4O2S2/c1-6-11-12-9(16-6)13-17(14,15)8-4-2-7(10)3-5-8/h2-5H,10H2,1H3,(H,12,13)
• InChIKey: VACCAVUAMIDAGB-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 4-amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzene-1-sulfonamide
• IUPAC传统名: sulfamethizole
• 商标名: Sulfamethizole [Usan:Inn:Jan]; Sulfamethizolum [INN-Latin]; Sulfamethylthiadiazole; Sulfametizol [INN-Spanish]; Sulfapyelon; Sulfstat; Sulfurine; Sulphamethizole; Sulphamethyltiadiazole; Tetracid; Thidicur; Thiosulfil; Thiosulfil Forte; Ultrasul; Urocydal; Urodiaton; Urolucosil; Urosulfin; Uroz; Ayerlucil; Famet; Lucosil; Methazol; Microsul; Proklar; Renasul; Rufol; Sulfamethiazole; Salimol; Solfametizolo [Dcit]; Sulamethizole; Sulfa Gram; Sulfamethazole; Sulfamethizol
• 别名: 4-氨基-N-(5-甲基-1,3,4-噻二唑-2-基)苯磺酰胺; N1-(5-甲基-1,3,4-噻二唑-2-基)磺胺; 磺胺甲二唑; Sulfamethizole; Sulfamethizol; Sulfamethizole; 4-Amino-N-[5-methyl-1,3,4-thiadiazol-2-yl]benzenesulfonamide; 4-Amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzenesulfonamide; N1-(5-Methyl-1,3,4-thiadiazol-2-yl)sulfanilamide; Proklar; Sulfamethizole (Proklar)

登记号

• CAS号: 144-82-1
• EC号: 205-641-1
• MDL号: MFCD00053363
• Beilstein号: 255002
• PubChem SID: 24899662; 24870514; 160963921; 46508656
• PubChem CID: 5328

理论计算性质

JChem

• Acid pKa: 6.707642
• 质子受体: 5
• 质子供体: 2
• LogD (pH = 5.5): 0.19116575
• LogD (pH = 7.4): -0.364739
• Log P: 0.21434596
• 摩尔折射率: 66.8358 cm^3
• 极化性: 25.134037 Å^3
• 极化表面积: 97.97 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: 0.53
• LOG S: -2.65
• 溶解度: 6.11e-01 g/l

分子性质

理化性质

• 溶解度: 1050 mg/L
• 疏水性(logP): 0.9

安全信息

• 保存条件: 2-8°C
• RTECS编号: WP0875000
• 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
• 保存温度: 2-8°C

药理学性质

• 作用靶点: Others

产品相关信息

• 纯度: ≥99% (HPLC); 98%
• 级别: VETRANAL™, analytical standard
• 成盐信息: Free Base
• 适用性: suitable for 1694 per US EPA
• Empirical Formula (Hill Notation): C9H10N4O2S2

详细说明

MP Biomedicals - 02156710

Crystalline
Purity: 98%

DrugBank - DB00576

• Drug Groups: approved
• Description: A sulfathiazole antibacterial agent. [PubChem]
• Indication: For the treatment of urinary tract infection
• Pharmacology: Sulfamethizole 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: Enteric bacteria and other eubacteria
• Biotransformation: Hepatic.
• Absorption: Rapidly absorbed.
• Half Life: 3-8 hours
• Protein Binding: 98-99%
• References: Ratanajamit C, Skriver MV, Norgaard M, Jepsen P, Schonheyder HC, Sorensen HT: Adverse pregnancy outcome in users of sulfamethizole during pregnancy: a population-based observational study. J Antimicrob Chemother. 2003 Nov;52(5):837-41. Epub 2003 Sep 30. [Pubmed] ; Kerrn MB, Frimodt-Moller N, Espersen F: Effects of sulfamethizole and amdinocillin against Escherichia coli strains (with various susceptibilities) in an ascending urinary tract infection mouse model. Antimicrob Agents Chemother. 2003 Mar;47(3):1002-9. [Pubmed] ; Watanabe H, Hastings JW: Inhibition of bioluminescence in Photobacterium phosphoreum by sulfamethizole and its stimulation by thymine. Biochim Biophys Acta. 1990 Jun 26;1017(3):229-34. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - 46842

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

参考文献

• Ratanajamit C, Skriver MV, Norgaard M, Jepsen P, Schonheyder HC, Sorensen HT: Adverse pregnancy outcome in users of sulfamethizole during pregnancy: a population-based observational study. J Antimicrob Chemother. 2003 Nov;52(5):837-41. Epub 2003 Sep 30. Pubmed
• Kerrn MB, Frimodt-Moller N, Espersen F: Effects of sulfamethizole and amdinocillin against Escherichia coli strains (with various susceptibilities) in an ascending urinary tract infection mouse model. Antimicrob Agents Chemother. 2003 Mar;47(3):1002-9. Pubmed
• Watanabe H, Hastings JW: Inhibition of bioluminescence in Photobacterium phosphoreum by sulfamethizole and its stimulation by thymine. Biochim Biophys Acta. 1990 Jun 26;1017(3):229-34. Pubmed