4-amino-N-(5,6-dimethoxypyrimidin-4-yl)benzene-1-sulfonamide

• ChemBase编号: 1151
• 分子式: C12H14N4O4S
• 平均质量: 310.32896
• 单一同位素质量: 310.07357595
• SMILES: S(=O)(=O)(Nc1ncnc(OC)c1OC)c1ccc(N)cc1
• Canonical SMILES: COc1c(OC)ncnc1NS(=O)(=O)c1ccc(cc1)N
• InChI: InChI=1S/C12H14N4O4S/c1-19-10-11(14-7-15-12(10)20-2)16-21(17,18)9-5-3-8(13)4-6-9/h3-7H,13H2,1-2H3,(H,14,15,16)
• InChIKey: PJSFRIWCGOHTNF-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 4-amino-N-(5,6-dimethoxypyrimidin-4-yl)benzene-1-sulfonamide
• IUPAC传统名: sulfadoxine
• 别名: 磺胺多辛; Sulfadoxine; Sulphadoxine; Sulfadoxin; 4-Amino-N-(5,6-dimethoxy-4-pyrimidinyl)benzenesulfonamide; N1-(5,6-Dimethoxy-4-pyrimidinyl)sulfanilamide; 4,5-Dimethoxy-6-sulfanilamidopyrimidine; 4-Sulfanilamido-5,6-dimethoxypyrimidine; Fanasil; Fanasulf; Orthosulfin; Ro 4-4393; Sanasil; Sulfadoxin; Sulforthomidine; WR 4073

登记号

• CAS号: 2447-57-6
• EC号: 219-504-9
• MDL号: MFCD00792890
• Beilstein号: 625453
• PubChem SID: 46507915; 24899765; 24870487; 160964614
• PubChem CID: 17134
• ATC码: QJ01EQ13
• CHEMBL: 1539
• Chemspider ID: 16218
• DrugBank ID: DB01299
• KEGG ID: D00580
• 美国药典/FDA物质标识码: 88463U4SM5
• 维基百科标题: Sulfadoxine

理论计算性质

JChem

• Acid pKa: 6.1161876
• 质子受体: 7
• 质子供体: 2
• LogD (pH = 5.5): 0.499187
• LogD (pH = 7.4): -0.2197638
• Log P: 0.58204734
• 摩尔折射率: 77.8083 cm^3
• 极化性: 29.692802 Å^3
• 极化表面积: 116.43 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.72
• LOG S: -3.02
• 溶解度: 2.96e-01 g/l

分子性质

理化性质

• 溶解度: DMSO; Methanol
• 外观: White Solid
• 熔点: 196-198°C
• 疏水性(logP): 0.70 [SANGSTER (1994)]

安全信息

• 保存条件: -20°C; -20°C Freezer
• RTECS编号: DA9500000
• 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
• 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
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥95% (TLC)
• 级别: VETRANAL™, analytical standard
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C12H14N4O4S

详细说明

DrugBank - DB01299

• Drug Groups: approved
• Description: A long acting sulfonamide that is used, usually in combination with other drugs, for respiratory, urinary tract, and malarial infections. [PubChem]
• Indication: Sulfadoxine is used in combination with pyrimethamine for the treatment or prevention of malaria. It can also be used to treat various infections in livestock as well.; Sulfadoxine and pyrimethamine is indicated for the treatment of Plasmodium falciparum malaria in those patients in whom chloroquine resistance is suspected.
• Pharmacology: Sulfadoxine helps inhibit the enzyme dihydropteroate synthetase which is an enzyme necessary in the conversion of PABA to folic acid. As folic acid is vital to the synthesis, repair, and methylation of DNA which is vital to cell growth in Plasmodium falciparum. With this vital nutrient lacking, the parasite has difficulty in reproducing.

Selleck Chemicals - S2511

Research Area: Infection
Biological Activity:
Sulfadoxine(Sulphadoxine) is an ultra-long-lasting sulfonamide with an IC50 of 249 µg/ml for P. vivax. It is often used in combination with pyrimethamine to treat or prevent malaria. Both drugs are antifolates; they inhibit the production of enzymes involved in the synthesis of folic acid within the parasites. Either drug by itself is only moderately effective in treating malaria, because the parasite Plasmodium falciparum may be able to use exogenous folic acid, i.e. folic acid which is present in the parasite’s environment, while in combination, the two substances have a synergistic effect which outbalances that ability. [1][2]

Sigma Aldrich - S7821

Application
Sulfadoxine is a sulfonamide antibiotic used in combination with pyrimethamine for the treatment or prevention of malaria. It is also used to treat various infections in livestock. Sulfadoxine and pyrimethamine is indicated for the treatment of Plasmodium falciparum malaria in patients where chloroquine resistance is suspected1. It is used to study infections caused by Toxoplasma gondii2 and has been used to prevent infections after surgery during animal studies3.
Biochem/physiol Actions
Sulfadoxine is a sulfonamide antibacterial that inhibits dihydropteroate synthase (DHPS), an enzyme that transforms 4-aminobenzoic acid (PABA) in the synthesis of dihydropteroic acid. This enzyme is also a component of the folate metabolic pathway and is upstream of dihydrofolate reductase (DHFR).

Sigma Aldrich - 31736

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - 46810

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

Toronto Research Chemicals - S699070

Used as an antibacterial.

参考文献

• http://en.wikipedia.org/wiki/Sulfadoxine
• Kapoor, V.K., et al.: Anal. Profiles Drug Subs., 17, 571 (1988)