Ezetimibe has been reported to be a cholesterol transport inhibitor. Mechanistic studies show that this compound directly affects Niemann-Pick C1-like 1 (NPC1L1) and prevents it from incorporating into clathrin-coated vesicles. NPC1L1 is a polytopic transmembrane protein that facilitates absorption of cholesterol via clathrin/AP2-mediated endocytosis. By binding to NPC1L1, ezetimibe prevents endocytosis of this protein therefore blocking cholesterol transfer across membranes. Ezetimibe is used clinically to lower plasma cholesterol levels.A cholesterol transport inhibitor that binds to NPC1L1

Information

Ezetimibe (SCH-58235) Ezetimibe (SCH-58235) is a potent, selective, cholesterol absorption inhibitor, used to lower cholesterol.
In vitro

Ezetimibe produces a significant reduction in total cholesterol, LDL cholesterol, and triglycerides as well as a small but significant increase in HDL cholesterol. Ezetimibe reduces cholesterol transport by 31% in Caco-2 cells, but not retinol transport. Ezetimibe results in a significant decrease in mRNA expression for the surface receptors SR-BI, Niemann-Pick type C1 Like 1 protein (NPC1L1), and ATP-binding cassette transporter, subfamily A (ABCA1) and for the nuclear receptors retinoid acid receptor (RAR)gamma, sterol-regulatory element binding proteins (SREBP)-1 and -2, and liver X receptor (LXR)beta as assessed by real-time PCR analysis in Caco-2 cells.

In vivo

Ezetimibe reduces plasma cholesterol levels from 964 to 374 mg/dL, from 726 to 231 mg/dL, and from 516 to 178 mg/dL in the western, low-fat, and cholesterol-free diet mice, respectively. Ezetimibe reduces aortic atherosclerotic lesion surface area from 20.2% to 4.1% in the western diet group and from 24.1% to 7.0% in the low-fat cholesterol diet mice. Ezetimibe reduces carotid artery atherosclerotic lesion cross-sectional area by 97% in the western and low-fat cholesterol groups and by 91% in the cholesterol-free mice. Ezetimibe inhibits cholesterol absorption, reduces plasma cholesterol, increases high density lipoprotein levels, and inhibits the progression of atherosclerosis under western, low-fat, and cholesterol-free dietary conditions in apoE-/- mice. Ezetimibe potently inhibits the transport of cholesterol across the intestinal wall, thereby reducing plasma cholesterol in preclinical animal models of hypercholesterolemia. Ezetimibe eliminates exocrine pancreatic function from the intestine while maintaining bile flow, is established in the rat. Ezetimibe reduces plasma cholesterol and hepatic cholesterol accumulation in cholesterol-fed hamsters with an ED(50) of 0.04 mg /kg.
Cell Data

cell lines：

Concentrations：

Incubation Time：

Powder Purity:≥99%

规格

别名

依折麦布 (SCH-58235)

英文别名

(3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)-2-azetidinone

规格或纯度

Moligand™, 10mM in DMSO

英文名称

Ezetimibe (SCH-58235)

生化机理

依折麦布（SCH-58235）是一种强效、选择性胆固醇吸收抑制剂，用于降低胆固醇。

储存条件

-80℃储存

运输条件

特低温运输

作用类型

抑制剂

作用机制

尼曼-皮克 C1 样蛋白 1 抑制剂

名称和识别符

EC号

682-606-0

分子类型

小分子

Isomeric SMILES

C1=CC(=CC=C1[C@@H]2[C@H](C(=O)N2C3=CC=C(C=C3)F)CC[C@@H](C4=CC=C(C=C4)F)O)O

关联CAS

163222-33-1

MeSH Entry Terms

(1-(4-fluorophenyl)-(3R)-(3-(4-fluorophenyl)-(3S)-hydroxypropyl)-(4S)-(4-hydroxyphenyl)-2-azetidinone);58235, SCH;ezetimib;ezetimibe;Ezetrol;SCH 58235;SCH-58235;SCH58235;Zetia

分子量

409.43

Reaxy-Rn

11745669

Reaxys-RN link address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=11745669&ln=

技术文档

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高级数据

产品属性

ALogP	4

关联靶点（人）

NPC1L1 Tclin NPC1 类细胞内胆固醇转运体 1(NPC1-like intracellular cholesterol transporter 1) (1 活性数据)

点击查看靶蛋白信息： NPC1L1

活性类型	活性值-log(M)	作用机制	期刊	参考文献(PubMed IDs)

化学和物理性质

溶解性

Solubility (25°C) In vitro Ethanol: mg/mL

熔点

327.2 - 330.8 °C

安全和危险性（GHS）

象形图

GHS09

信号词

Warning

危险声明

H410: 对水生生物有剧毒并具有长期持续影响

预防措施声明

P273: 避免释放到环境中。

P501: 将内容物/容器处理到。。。

P391: 收集溢出物

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批号(Lot Number)	证书类型	货号
L2214620	分析证书	E408174

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