1-(azepan-1-yl)-3-(4-methylbenzenesulfonyl)urea

• ChemBase编号: 718
• 分子式: C14H21N3O3S
• 平均质量: 311.39984
• 单一同位素质量: 311.13036255
• SMILES: S(=O)(=O)(NC(=O)NN1CCCCCC1)c1ccc(cc1)C
• Canonical SMILES: O=C(NS(=O)(=O)c1ccc(cc1)C)NN1CCCCCC1
• InChI: InChI=1S/C14H21N3O3S/c1-12-6-8-13(9-7-12)21(19,20)16-14(18)15-17-10-4-2-3-5-11-17/h6-9H,2-5,10-11H2,1H3,(H2,15,16,18)
• InChIKey: OUDSBRTVNLOZBN-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1-(azepan-1-yl)-3-(4-methylbenzenesulfonyl)urea
• IUPAC传统名: tolazamide; 1-(azepan-1-yl)-3-(4-methylbenzenesulfonyl)urea
• 商标名: Norglycin; Tolanase; Tolinase
• 别名: 1-(Hexahydro-1H-azepin-1-yl)-3-(p-toluenesulfonyl)urea; Tolazamide; N-[[(Hexahydro-1H-azepin-1-yl)amino]carbonyl]-4-methylbenzenesulfonamide; 1-(4-Methylphenylsulfonyl)-3-(hexahydro-1H-azepin-1-yl)urea; 1-(Hexahydro-1-azepinyl)-3-p-tolylsulfonylurea; Diabewas; N-(p-Toluenesulfonyl)-N'-hexa-methyleniminourea; NSC 70762; Norglycin; Tolanase; Tolinase; U 17835; Tolazamide

登记号

• CAS号: 1156-19-0
• EC号: 214-588-3
• MDL号: MFCD00083504
• PubChem SID: 24277741; 46505642; 160964181
• PubChem CID: 5503

理论计算性质

JChem

• Acid pKa: 4.0720177
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 1.0754167
• LogD (pH = 7.4): 0.9706159
• Log P: 1.91199
• 摩尔折射率: 81.3361 cm^3
• 极化性: 32.191742 Å^3
• 极化表面积: 78.51 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: 1.4
• LOG S: -3.01
• 溶解度: 3.08e-01 g/l

分子性质

理化性质

• 溶解度: DMSO; Methanol; Solubility at pH 6.0 (mean urinary pH) is 27.8 mg/100 mL
• 外观: White Solid
• 熔点: 162-164°C
• 疏水性(logP): 2.5

安全信息

• 保存条件: Refrigerator
• RTECS编号: YT4400000
• 德国WGK号: 3
• 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: human ... ALB(213), KCNJ1(3758)

产品相关信息

• 成盐信息: Free Base

详细说明

DrugBank - DB00839

• Drug Groups: approved
• Description: A sulphonylurea hypoglycemic agent with actions and uses similar to those of chlorpropamide. [PubChem]
• Indication: For use as an adjunct to diet to lower the blood glucose in patients with non-insulin dependent diabetes mellitus (Type II) whose hyperglycemia cannot be satisfactorily controlled by diet alone.
• Pharmacology: Tolazamide is an oral blood glucose lowering drug of the sulfonylurea class. Tolazamide appears to lower the blood glucose acutely by stimulating the release of insulin from the pancreas, an effect dependent upon functioning beta cells in the pancreatic islets. The mechanism by which tolazamide lowers blood glucose during long-term administration has not been clearly established. With chronic administration in Type II diabetic patients, the blood glucose lowering effect persists despite a gradual decline in the insulin secretory response to the drug. Extrapancreatic effects may be involved in the mechanism of action of oral sulfonylurea hypoglycemic drugs. Some patients who are initially responsive to oral hypoglycemic drugs, including tolazamide, may become unresponsive or poorly responsive over time. Alternatively, tolazamide may be effective in some patients who have become unresponsive to one or more other sulfonylurea drugs. In addition to its blood glucose lowering actions, tolazamide produces a mild diuresis by enhancement of renal free water clearance.
• Toxicity: Overdosage of sulfonylureas can produce hypoglycemia. Severe hypoglycemic reactions with coma, seizure, or other neurological impairment occur infrequently, but constitute medical emergencies requiring immediate hospitalization.
• Affected Organisms: Humans and other mammals
• Biotransformation: Tolazamide is metabolized to five major metabolites ranging in hypoglycemic activity from 0 to 70%.
• Absorption: Rapidly and well absorbed from the gastrointestinal tract.
• Half Life: The average biological half-life of the drug is 7 hours.
• Elimination: Tolazamide is metabolized to five major metabolites ranging in hypoglycemic activity from 0% to 70%. They are excreted principally in the urine.
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - T2408

Biochem/physiol Actions
Stimulates pancreatic islet cells to secrete insulin; blocks ATP-sensitive K+ channels.

Toronto Research Chemicals - T534500

Tolazamide is an antidiabetic.

参考文献

• Welling, et al.: J. Pharma. Sci., 71, 1259 (1982)