1-(4-chlorobenzenesulfonyl)-3-propylurea

• ChemBase编号: 554
• 分子式: C10H13ClN2O3S
• 平均质量: 276.73982
• 单一同位素质量: 276.03354097
• SMILES: Clc1ccc(S(=O)(=O)NC(=O)NCCC)cc1
• Canonical SMILES: CCCNC(=O)NS(=O)(=O)c1ccc(cc1)Cl
• InChI: InChI=1S/C10H13ClN2O3S/c1-2-7-12-10(14)13-17(15,16)9-5-3-8(11)4-6-9/h3-6H,2,7H2,1H3,(H2,12,13,14)
• InChIKey: RKWGIWYCVPQPMF-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 1-(4-chlorobenzenesulfonyl)-3-propylurea
• IUPAC传统名: 1-(4-chlorobenzenesulfonyl)-3-propylurea; chlorpropamide
• 商标名: Chlorpropamide Bp/ Usp; Clorpropamide; Diabaril; Diabechlor; Diabenal; Diabenese; Diabeneza; Diabet-Pages; Diabetoral; Diabinese; Diamel Ex; Dynalase; Glisema; Glucamide; Insulase; Meldian; Melitase; Mellinese; Millinese; Novo-Propamide; Oradian; Stabinol; Adiaben; Apo-Chlorpropamide; Asucrol; Catanil; Chlorodiabina; Chloronase; Chloropropamide; Chlorpropamid
• 别名: 对氯苯磺酰丙脲; 氯磺丙脲; Chlorporpamide; Chlorpropamide; 4-Chloro-N-[(propylamino)carbonyl]benzenesulfonamide; Adiaben; Asucrol; Catanil; Chlorodiabina; Chloronase; Chloropropamide; Chlorpropamid; Chlorpropamide; Diabaril; Diabechlor; Diabenal; Diabenese; Glisema; Meldian; Melitase; Millinese; N-(4-Chlorophenylsulfonyl)-N'-propylurea; NSC 44634; NSC 626720; P 607; Stabinol; U 9818; N-(p-Chlorobenzenesulfonyl)-N'-propylurea; N-Propyl-N'-(p-chlorobenzenesulfonyl)urea; Diabinese; 4-Chloro-N-(propylcarbamoyl)benzenesulfonamide; Chlorpropamide; 1-[p-Chlorobenzenesulfonyl]-3-propylurea

登记号

• CAS号: 94-20-2
• EC号: 202-314-5
• MDL号: MFCD00079004
• PubChem SID: 160964017; 24277701; 46506402
• PubChem CID: 2727

理论计算性质

JChem

• Acid pKa: 4.329167
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 1.1719515
• LogD (pH = 7.4): 1.0013003
• Log P: 1.9413904
• 摩尔折射率: 65.4326 cm^3
• 极化性: 26.156296 Å^3
• 极化表面积: 75.27 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.15
• LOG S: -3.25
• 溶解度: 1.57e-01 g/l

分子性质

理化性质

• 溶解度: Solubility at pH 6 is 2.2 mg/ml
• 疏水性(logP): 1.8

安全信息

• 保存条件: Room Temperature (15-30°C)
• RTECS编号: YS6650000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 20/21/22-40
• 安全公开号: 22-36
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Warning
• GHS危险声明: H312-H332-H351
• GHS警示性声明: P280
• 个人保护装置: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

药理学性质

• 作用靶点: Others
• 相关基因信息: human ... ALB(213), EPHX2(2053), KCNJ1(3758)mouse ... Ephx2(13850)
• 生物活性机理: Augmenting insulin secretion

产品相关信息

• 纯度: ≥97%; 95+%; 97%
• 成盐信息: Free Base
• 应用领域: Oral antihyperglycaemic drug; Used to treat non-insulin dependent diabetes mellitus

详细说明

MP Biomedicals - 02154978

(1-[p-Chlorobenzenesulfonyl]-3-propylurea) Purity: 97%

DrugBank - DB00672

• Drug Groups: approved
• Description: Chlorpropamide is an oral antihyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). It 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. Chlorpropamide is not recommended for the treatment of NIDDM as it increases blood pressure and the risk of retinopathy (UKPDS-33). Up to 80% of the single oral dose of chlorpropramide is metabolized, likely in the liver; 80-90% of the dose is excreted in urine as unchanged drug and metabolites. Renal and hepatic dysfunction may increase the risk of hypoglycemia.
• Indication: For treatment of NIDDM in conjunction with diet and exercise.
• Pharmacology: Chlorpropamide, a second-generation sulfonylurea antidiabetic agent, is used with diet to lower blood glucose levels in patients with diabetes mellitus type II. Chlorpropamide is twice as potent as the related second-generation agent glipizide.
• Toxicity: IPN-RAT LD₅₀ 580 mg/kg
• Affected Organisms: Humans and other mammals
• Biotransformation: Up to 80% of dose is metabolized likely through the liver to to 2-hydroxylchlorpropamide (2-OH CPA), p-chlorobenzenesulfonylurea (CBSU), 3-hydroxylchlorpropamide (3-OH CPA), and p-chlorobenzenesulfonamide (CBSA); CBSA may be produced by decomposition in urine. It is unknown whether chlorpropamide metabolites exert hypoglycemic effects.
• Absorption: Readily absorbed from the GI tract. Peak plasma concentrations occur within 2-4 hours and the onset of action occurs within one hour. The maximal effect of chlorpropamide is seen 3-6 hours following oral administration.
• Half Life: Approximately 36 hours with interindividual variation ranging from 25-60 hours. Duration of effect persists for at least 24 hours.
• Protein Binding: Highly bound to plasma proteins.
• Elimination: 80-90% of a single oral dose is excreted in the urine as unchaged drug and metabolites within 96 hours.
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - C424800

Chlorpropamide is a sulfonylurea derivative. Chlorpropamide is a long acting hyopglycemic agent. Chlorpropamide is used in the treatment of diabetes metilus type 2. Chlorpropamide acts to increase the secretion of insulin and is not effective in patients

参考文献

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