3-butyl-1-(4-methylbenzenesulfonyl)urea

• ChemBase编号: 995
• 分子式: C12H18N2O3S
• 平均质量: 270.34792
• 单一同位素质量: 270.10381345
• SMILES: S(=O)(=O)(NC(=O)NCCCC)c1ccc(cc1)C
• Canonical SMILES: CCCCNC(=O)NS(=O)(=O)c1ccc(cc1)C
• InChI: InChI=1S/C12H18N2O3S/c1-3-4-9-13-12(15)14-18(16,17)11-7-5-10(2)6-8-11/h5-8H,3-4,9H2,1-2H3,(H2,13,14,15)
• InChIKey: JLRGJRBPOGGCBT-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 3-butyl-1-(4-methylbenzenesulfonyl)urea
• IUPAC传统名: 3-butyl-1-(4-methylbenzenesulfonyl)urea; tolbutamide
• 商标名: Aglicid; Apo-Tolbutamide; Arkozal; Artosin; Artozin; Butamid; Butamide; Diaben; Diabetamid; Diabetol; Diabuton; Diasulfon; Dirastan; Dolipol; Drabet; Glyconon; Ipoglicone; Mobenol; Novo-Butamide; Orabet; Oralin; Orezan; Orinase; Orinase Diagnostic; Orinaz; Oterben; Pramidex; Rastinon; Restinon; Sk-tolbutamide; Tol-Tab; Tolbusal; Tolbutamid; Toluina; Tolumid; Toluvan; Tolylsulfonylbutylurea; Willbutamide
• 别名: 1-丁基-3-(4-甲苯磺酰基)脲; 甲苯磺丁脲; Tolbutamide; 1-Butyl-3-(4-methylphenylsulfonyl)urea; N-[(Butylamino)carbonyl]-4-methyl-benzenesulfonamide; 1-Butyl-3-(p-tolylsulfonyl)urea; Tolylsulfonylbutylurea; 3-(p-Tolyl-4-sulfonyl)-1-butylurea; N-Butyl-N'-(4-methyl-phenylsulfonyl)urea; Artosin; Artozin; Mobenol; Diabetol; Orabet; Oralin; Orezan; Orinase; Orinaz; Oterben; Pramidex; Rastinon; NSC 23813; NSC 87833; 3-[p-Tolyl-4-sulfonyl]-1-butylurea; Tolbutamide; 1-n-Butyl-3-(p-tolylsulfonyl)urea; N-(Butylcarbamoyl)-4-methylbenzenesulfonamide

登记号

• CAS号: 64-77-7
• EC号: 200-594-3
• MDL号: MFCD00027169
• Beilstein号: 1984428
• 默克索引号: 149507
• PubChem SID: 24870476; 46508421; 24277742; 160964458
• PubChem CID: 5505

理论计算性质

JChem

• Acid pKa: 4.3339453
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 1.5273758
• LogD (pH = 7.4): 1.3552772
• Log P: 2.2953358
• 摩尔折射率: 70.27 cm^3
• 极化性: 27.809378 Å^3
• 极化表面积: 75.27 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: 2.04
• LOG S: -3.13
• 溶解度: 2.02e-01 g/l

分子性质

理化性质

• 溶解度: 109 mg/L; Chloroform
• 外观: White Solid
• 熔点: 125-127°C; 128-130°C
• 疏水性(logP): 2.2

安全信息

• 保存条件: Refrigerator; Room Temperature (15-30°C)
• RTECS编号: YS4550000
• 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: 24-37
• TSCA收录: 是
• GHS危险品标识: GHS07
• GHS危险声明: H302-H317
• GHS警示性声明: P261-P280-P302+P352-P321-P301+P312-P501A
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

药理学性质

• 作用靶点: Potassium Channel
• 相关基因信息: human ... ALB(213), CYP1A2(1544), CYP2C9(1559), EPHX2(2053), KCNJ1(3758)mouse ... Ephx2(13850)

产品相关信息

• 纯度: 95+%; 98%
• 级别: VETRANAL™, analytical standard
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C12H18N2O3S

详细说明

MP Biomedicals - 02190274

Crystalline

DrugBank - DB01124

• Drug Groups: approved
• Description: Tolbutamide is an oral antihyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). It is structurally similar to acetohexamide, chlorpropamide and tolazamide and belongs to the sulfonylurea class of insulin secretagogues, which act by stimulating β cells of the pancreas to release insulin. Sulfonylureas increase both basal insulin secretion and meal-stimulated insulin release. Medications in this class differ in their dose, rate of absorption, duration of action, route of elimination and binding site on their target pancreatic β cell receptor. Sulfonylureas also increase peripheral glucose utilization, decrease hepatic gluconeogenesis and may increase the number and sensitivity of insulin receptors. Sulfonylureas are associated with weight gain, though less so than insulin. Due to their mechanism of action, sulfonylureas may cause hypoglycemia and require consistent food intake to decrease this risk. The risk of hypoglycemia is increased in elderly, debilitated and malnourished individuals. Tolbutamide appears to be metabolized in the liver. Tolbutamide and its metabolites are excreted in urine (75-85%) and feces.
• Indication: For treatment of NIDDM (non-insulin-dependent diabetes mellitus) in conjunction with diet and exercise.
• Pharmacology: Tolbutamide, a first-generation sulfonylurea antidiabetic agent, is used with diet to lower blood glucose levels in patients with diabetes mellitus type II. Tolbutamide is twice as potent as the related second-generation agent glipizide. Tolbutamide lowers blood sugar by stimulating the pancreas to secrete insulin and helping the body use insulin efficiently. The pancreas must be able to produce insulin for this drug to work.
• Toxicity: Oral, mouse: LD₅₀ = 2600 mg/kg
• Affected Organisms: Humans and other mammals
• Biotransformation: Metabolized in the liver principally via oxidation of the p-methyl group producing the carboxyl metabolite, 1-butyl-3-p-carboxyphenylsulfonylurea. May also be metabolized to hydroxytolbutamide. Tolbutamide does not undergo acetylation like antibacterial sulfonamides as it does not have a p-amino group.
• Absorption: Readily absorbed following oral administration. Tolbutamide is detectable in plasma 30-60 minutes following oral administration of a single dose with peak plasma concentrations occurring within 3-5 hours. ; ; Absorption is unaltered if taken with food but is increased with high pH.
• Half Life: Approximately 7 hours with interindividual variations ranging from 4-25 hours. Tolbutamide has the shortest duration of action, 6-12 hours, of the antidiabetic sulfonylureas.
• Protein Binding: Approximately 95% bound to plasma proteins.
• Elimination: Unchanged drug and metabolites are eliminated in the urine and feces. Approximately 75-85% of a single orally administered dose is excreted in the urine principally as the 1-butyl-3-p-carboxyphenylsulfonylurea within 24 hours.
• External Links: Wikipedia; Drugs.com

Sigma Aldrich - T0891

Biochem/physiol Actions
Anti-diabetic agent. Metabolized by CYP2C9 (tolbutamide hydroxylase).

Sigma Aldrich - 46968

Biochem/physiol Actions
Anti-diabetic agent. Metabolized by CYP2C9 (tolbutamide hydroxylase).
法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

Toronto Research Chemicals - T535150

An antidiabetic, used as a hypoglycemic agent in veterinary medicine.

参考文献

• Mourad, N., et al.: Am. J. Physiol., 299, C389 (2010)
• Van Eerdenbrugh, B., et al.: J. Pharm. Sci., 99, 3826 (2010)
• Testai, L., et al.: J. Pharm. Pharmacol., 62, 924 (2010)