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135062-02-1 分子结构
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2-ethoxy-4-({[(1S)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]carbamoyl}methyl)benzoic acid

ChemBase编号:788
分子式:C27H36N2O4
平均质量:452.58574
单一同位素质量:452.26750764
SMILES和InChIs

SMILES:
O=C(N[C@H](c1c(N2CCCCC2)cccc1)CC(C)C)Cc1cc(OCC)c(cc1)C(=O)O
Canonical SMILES:
CCOc1cc(ccc1C(=O)O)CC(=O)N[C@H](c1ccccc1N1CCCCC1)CC(C)C
InChI:
InChI=1S/C27H36N2O4/c1-4-33-25-17-20(12-13-22(25)27(31)32)18-26(30)28-23(16-19(2)3)21-10-6-7-11-24(21)29-14-8-5-9-15-29/h6-7,10-13,17,19,23H,4-5,8-9,14-16,18H2,1-3H3,(H,28,30)(H,31,32)/t23-/m0/s1
InChIKey:
FAEKWTJYAYMJKF-QHCPKHFHSA-N

引用这个纪录

CBID:788 http://www.chembase.cn/molecule-788.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
2-ethoxy-4-({[(1S)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]carbamoyl}methyl)benzoic acid
IUPAC传统名
2-ethoxy-4-({[(1S)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]carbamoyl}methyl)benzoic acid
repaglinide
商标名
Prandin
GlucoNorm
别名
(S)-(+)-2-Ethoxy-4-[N-[1-(2-piperidinophenyl)-3-methyl-1-butyl]aminocarbonylmethyl]benzoic acid
Repaglinide
(S)-2-Ethoxy-4-[2-[[[(1S)-3-methyl-1-[2-(1-piperidinyl)phenyl]butyl]amino]-2-oxoethyl]benzoic Acid
AG-EE-623
Repaglinida [INN-Spanish]
Repaglinidum [INN-Latin]
AG-EE 388 ZW
AG-EE 623 ZW
repaglinide
Repaglinide
Prandin
GlucoNorm
NovoNorm
CAS号
135062-02-1
MDL号
MFCD00906179
PubChem SID
46508150
24724596
160964251
PubChem CID
65981

理论计算性质

理论计算性质

JChem ALOGPS 2.1
摩尔折射率 131.8281 cm3 极化性 50.317257 Å3
极化表面积 78.87 Å2 可自由旋转的化学键 10 
里宾斯基五规则 true  Acid pKa 3.6754997 
质子受体 质子供体
LogD (pH = 5.5) 3.3981318  LogD (pH = 7.4) 1.9463284 
Log P 3.9468045 
溶解度 2.94e-03 g/l  Log P 5.05 
LOG S -5.19 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
Chloroform expand 查看数据来源
DMSO: >20 mg/mL expand 查看数据来源
Methanol expand 查看数据来源
外观
white solid expand 查看数据来源
White Solid expand 查看数据来源
熔点
129-130.2 °C expand 查看数据来源
133-135°C expand 查看数据来源
疏水性(logP)
5.9 expand 查看数据来源
保存条件
-20°C expand 查看数据来源
-20°C Freezer expand 查看数据来源
RTECS编号
DI0876305 expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
2 expand 查看数据来源
个人保护装置
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand 查看数据来源
保存温度
2-8°C expand 查看数据来源
作用靶点
potassium channel expand 查看数据来源
相关基因信息
human ... KCNJ1(3758) expand 查看数据来源
生物活性机理
Stimulating the release of insulin from the pancreas by closing ATP-dependent potassium channels in the membrane of the beta cells expand 查看数据来源
纯度
≥98% (HPLC) expand 查看数据来源
成盐信息
Free Base expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
应用领域
Antihyperglycaemic agent used in the treatment of type II diabetes expand 查看数据来源
Empirical Formula (Hill Notation)
C27H36N2O4 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank -  DB00912 external link
Item Information
Drug Groups approved; investigational
Description Repaglinide is an oral antihyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). It belongs to the meglitinide class of short-acting insulin secretagogues, which act by binding to β cells of the pancreas to stimulate insulin release. Repaglinide induces an early insulin response to meals decreasing postprandial blood glucose levels. It should only be taken with meals and meal-time doses should be skipped with any skipped meal. Approximately one month of therapy is required before a decrease in fasting blood glucose is seen. Meglitnides may have a neutral effect on weight or cause a slight increase in weight. The average weight gain caused by meglitinides appears to be lower than that caused by sulfonylureas and insulin and appears to occur only in those na?ve to oral antidiabetic agents. Due to their mechanism of action, meglitinides may cause hypoglycemia although the risk is thought to be lower than that of sulfonylureas since their action is dependent on the presence of glucose. In addition to reducing postprandial and fasting blood glucose, meglitnides have been shown to decrease glycosylated hemoglobin (HbA1c) levels, which are reflective of the last 8-10 weeks of glucose control. Meglitinides appear to be more effective at lowering postprandial blood glucose than metformin, sulfonylureas and thiazolidinediones. Repaglinide is extensively metabolized in the liver and excreted in bile. Repaglinide metabolites do not possess appreciable hypoglycemic activity. Approximately 90% of a single orally administered dose is eliminated in feces and 8% in urine.
Indication For the treatment of non-insulin dependent-diabetes mellitus in conjunction with diet and exercise.
Pharmacology Insulin secretion by pancreatic β cells is partly controlled by cellular membrane potential. Membrane potential is regulated through an inverse relationship between the activity of cell membrane ATP-sensitive potassium channels (ABCC8) and extracellular glucose concentrations. Extracellular glucose enters the cell via GLUT2 (SLC2A2) transporters. Once inside the cell, glucose is metabolized to produce ATP. High concentrations of ATP inhibit ATP-sensitive potassium channels causing membrane depolarization. When extracellular glucose concentrations are low, ATP-sensitive potassium channels open causing membrane repolarization. High glucose concentrations cause ATP-sensitive potassium channels to close resulting in membrane depolarization and opening of L-type calcium channels. The influx of calcium ions stimulates calcium-dependent exocytosis of insulin granules. Repaglinide increases insulin release by inhibiting ATP-sensitive potassium channels in a glucose-dependent manner.
Toxicity LD50 >1 g/kg (rat) (W. Grell)
Affected Organisms
Humans and other mammals
Biotransformation Repaglinide is rapidly metabolized via oxidation and dealkylation by cytochrome P450 3A4 and 2C9 to form the major dicarboxylic acid derivative (M2). Further oxidation produces the aromatic amine derivative (M1). Glucuronidation of the carboxylic acid group of repaglinide yields an acyl glucuronide (M7). Several other unidentified metabolites have been detected. Repaglinide metabolites to not possess appreciable hypoglycemic activity.
Absorption Rapidly and completely absorbed following oral administration. Peak plasma concentrations are observed within 1 hour (range 0.5-1.4 hours). Absolutely bioavailability is approximately 56%. Maximal biological effect is observed within 3-3.5 hours and plasma insulin levels remain elevated for 4-6 hours
Half Life 1 hour
Protein Binding >98% (e.g. to to albumin and α1-acid glycoprotein)
Elimination 90% eliminated in feces (<2% as unchanged drug), 8% in urine (0.1% as unchanged drug)
Distribution 31 L following IV administration in healthy individuals
Clearance 33-38 L/hour following IV administration
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Selleck Chemicals -  S1426 external link
Research Area: Endocrinology
Biological Activity:
Repaglinide is for the treatment of type II diabetes. Repaglinide belongs to the meglitinide class of blood glucose-lowering drugs. Repaglinide lowers blood glucose by stimulating the release of insulin from the pancreas. It achieves this by closing ATP-dependent potassium channels in the membrane of the beta cells. [1]
Sigma Aldrich -  R9028 external link
Biochem/physiol Actions
Repaglinide is a potent short-acting insulin secretagogue that acts by closing ATP-sensitive potassium (KATP) channels in the plasma membrane of the pancreatic beta cell. It represents a new class of insulin secretagogues, structurally unrelated to sulphonylureas, which were developed for the treatment of type 2 diabetes.
Toronto Research Chemicals -  R144500 external link
Non-sulfonylurea oral hypoglycemic agent. Used as an antidiabetic.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • http://en.wikipedia.org/wiki/Repaglinide
  • Wolffenbuttel, B.H.R., et al.: Eur. J. Clin. Pharmacol., 45, 113 (1993)
  • Ampudia-Blasco, F.J., et al.: Diabetologia, 37, 703 (1993)
  • Ger. Pat., 1987, Thomae, 3 522 604; CA, 106, 196260j, (synth)
  • Eur. Pat., 1989, 147 850; CA, 104, 5651p
  • Verspohl, E.J. et al., J. Pharm. Pharmacol., 1990, 42, 230, (pharmacol)
  • Wolffenbuttel, B.H.R. et al., Eur. J. Clin. Pharmacol., 1993, 45, 113, (use)
  • Pat. Coop. Treaty (WIPO), 1993, Thomae, 93 00 337; CA, 118, 254759q, (synth, isomers)
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专利

专利

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