7-chloro-3-methyl-4H-1$l^{6},2,4-benzothiadiazine-1,1-dione

• ChemBase编号: 990
• 分子式: C8H7ClN2O2S
• 平均质量: 230.67138
• 单一同位素质量: 229.99167615
• SMILES: Clc1cc2S(=O)(=O)N=C(Nc2cc1)C
• Canonical SMILES: Clc1ccc2c(c1)S(=O)(=O)N=C(N2)C
• InChI: InChI=1S/C8H7ClN2O2S/c1-5-10-7-3-2-6(9)4-8(7)14(12,13)11-5/h2-4H,1H3,(H,10,11)
• InChIKey: GDLBFKVLRPITMI-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 7-chloro-3-methyl-4H-1$l^{6},2,4-benzothiadiazine-1,1-dione; 7-chloro-3-methyl-4H-1λ^6,2,4-benzothiadiazine-1,1-dione
• IUPAC传统名: diazoxide; hyperstat
• 商标名: Dizoxide; Eudemine; Hyperstat; Hypertonalum; Mutabase; Proglicem; Proglycem
• 别名: Diazoxide; 7-Chloro-3-methyl-2H-1,2,4-benzothiadiazine 1,1-Dioxide; 3-Methyl-7-chloro-1,2,4-benzothiadiazine 1,1-Dioxide; Dizoxide; Hyperstat; Hypertonalum; Mutabase; NSC 64198; NSC 76130; Proglicem; Proglycem; SRG 95213; Sch 6783

登记号

• CAS号: 364-98-7
• PubChem SID: 160964453; 46508027
• PubChem CID: 3019

理论计算性质

JChem

• Acid pKa: 10.483212
• 质子受体: 4
• 质子供体: 1
• LogD (pH = 5.5): 1.0004389
• LogD (pH = 7.4): 1.0001315
• Log P: 1.0004865
• 摩尔折射率: 54.8408 cm^3
• 极化性: 21.23918 Å^3
• 极化表面积: 58.53 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.09
• LOG S: -2.62
• 溶解度: 5.52e-01 g/l

分子性质

理化性质

• 溶解度: 2850 mg/L; DMSO
• 外观: White Solid
• 熔点: >310°C
• 疏水性(logP): 1.3

安全信息

• 保存条件: Refrigerator

详细说明

DrugBank - DB01119

• Drug Groups: approved
• Description: A benzothiadiazine derivative that is a peripheral vasodilator used for hypertensive emergencies. It lacks diuretic effect, apparently because it lacks a sulfonamide group. [PubChem]
• Indication: Used parentally to treat hypertensive emergencies. Also used to treat hypoglycemia secondary to insulinoma.
• Pharmacology: Diazoxide is a potassium channel activator, which causes local relaxation in smooth muscle by increasing membrane permeability to potassium ions. This switches off voltage-gated calcium ion channels which inhibits the generation of an action potential.
• Toxicity: Oral LD₅₀ in rat and mouse: 980 mg/kg and 444 mg/kg, respectively.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Readily absorbed following oral administration.
• Half Life: 28 ±8.3 hours in normal adults.
• Protein Binding: Very high (more than 90%) to serum proteins.
• Elimination: Proglycem is extensively bound (more than 90%) to serum proteins, and is excreted in the kidneys.
• External Links: Wikipedia; Drugs.com

Toronto Research Chemicals - D417305

Diazoxide reduces status epilepticus neuron damage in diabetes.

参考文献

• Baba, A., et al.: J. Neurosci., 23, 7737 (2003)
• Bancila, V., et al.: J. Neurochem., 90, 1243 (2003)
• Bancila, V., et al.: J. Biol. Chem., 280, 8793 (2003)