您当前所在的位置:首页 > 产品中心 > 产品详细信息
163222-33-1 分子结构
点击图片或这里关闭

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

ChemBase编号:848
分子式:C24H21F2NO3
平均质量:409.4252464
单一同位素质量:409.14894998
SMILES和InChIs

SMILES:
Fc1ccc(N2[C@@H]([C@@H](CC[C@H](O)c3ccc(F)cc3)C2=O)c2ccc(O)cc2)cc1
Canonical SMILES:
Oc1ccc(cc1)[C@@H]1[C@@H](CC[C@@H](c2ccc(cc2)F)O)C(=O)N1c1ccc(cc1)F
InChI:
InChI=1S/C24H21F2NO3/c25-17-5-1-15(2-6-17)22(29)14-13-21-23(16-3-11-20(28)12-4-16)27(24(21)30)19-9-7-18(26)8-10-19/h1-12,21-23,28-29H,13-14H2/t21-,22+,23-/m1/s1
InChIKey:
OLNTVTPDXPETLC-XPWALMASSA-N

引用这个纪录

CBID:848 http://www.chembase.cn/molecule-848.html

Collapse All Expand All

名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
(3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one
IUPAC传统名
ezetimibe
商标名
Ezedoc
Zetia
Ezetrol
别名
(3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one
Ezetimibe
Zetia
Ezetrol
CAS号
163222-33-1
MDL号
MFCD00937872
PubChem SID
160964311
46507625
PubChem CID
150311

数据来源

数据来源

所有数据来源 商品来源 非商品来源

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 9.484299  质子受体
质子供体 LogD (pH = 5.5) 4.559083 
LogD (pH = 7.4) 4.555587  Log P 4.559128 
摩尔折射率 108.8617 cm3 极化性 41.585533 Å3
极化表面积 60.77 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 4.14  LOG S -4.68 
溶解度 8.46e-03 g/l 

分子性质

分子性质

理化性质 安全信息 产品相关信息 生物活性(PubChem)
疏水性(logP)
3.958 expand 查看数据来源
4.5 expand 查看数据来源
保存条件
-20°C expand 查看数据来源
纯度
95% expand 查看数据来源
成盐信息
Free Base expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Selleck Chemicals Selleck Chemicals
DrugBank -  DB00973 external link
Item Information
Drug Groups approved
Description Ezetimibe is an anti-hyperlipidemic medication which is used to lower cholesterol levels. Specifically, it appears to bind to a critical mediator of cholesterol absorption, the Niemann-Pick C1-Like 1 (NPC1L1) protein on the gastrointestinal tract epithelial cells as well as in hepatocytes.
Indication For use as adjunctive therapy to diet for the reduction of elevated total-C, LDL-C, and Apo B in patients with primary (heterozygous familial and non-familial) hypercholesterolemia.
Pharmacology Ezetimibe is in a class of lipid-lowering compounds that selectively inhibits the intestinal absorption of cholesterol and related phytosterols. Ezetimibe, administered alone is indicated as adjunctive therapy to diet for the reduction of elevated total-C, LDL-C, and Apo B in patients with primary (heterozygous familial and non-familial) hypercholesterolemia. It is also used in combination therapy with HMG-CoA reductase inhibitors. Ezetimibe has a mechanism of action that differs from those of other classes of cholesterol-reducing compounds (HMG-CoA reductase inhibitors, bile acid sequestrants, fibric acid derivatives, and plant stanols). Ezetimibe does not inhibit cholesterol synthesis in the liver, or increase bile acid excretion but instead localizes and appears to act at the brush border of the small intestine and inhibits the absorption of cholesterol, leading to a decrease in the delivery of intestinal cholesterol to the liver. This causes a reduction of hepatic cholesterol stores and an increase in clearance of cholesterol from the blood; this distinct mechanism is complementary to that of HMG-CoA reductase inhibitors.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic, intestinal wall
Half Life 22 hours
Protein Binding >90%
Elimination Ezetimibe is primarily metabolized in the small intestine and liver via glucuronide conjugation (a phase II reaction) with subsequent biliary and renal excretion. In humans, ezetimibe is rapidly metabolized to ezetimibe-glucuronide.
References
Garcia-Calvo M, Lisnock J, Bull HG, Hawes BE, Burnett DA, Braun MP, Crona JH, Davis HR Jr, Dean DC, Detmers PA, Graziano MP, Hughes M, Macintyre DE, Ogawa A, O'neill KA, Iyer SP, Shevell DE, Smith MM, Tang YS, Makarewicz AM, Ujjainwalla F, Altmann SW, Chapman KT, Thornberry NA: The target of ezetimibe is Niemann-Pick C1-Like 1 (NPC1L1). Proc Natl Acad Sci U S A. 2005 Jun 7;102(23):8132-7. Epub 2005 May 31. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals -  S1655 external link
Research Area: Cardiovascular Disease
Biological Activity:
Ezetimibe (Zetia) is a compound that lowers cholesterol. Ezetimibe (Zetia) acts by decreasing cholesterol absorption in the intestine. Ezetimibe (Zetia) may be used alone, when other cholesterol-lowering medications are not tolerated, or together with statins when statins alone do not control cholesterol. Ezetimibe localises at the brush border of the small intestine, where ezetimibe (Zetia) inhibits the absorption of cholesterol from the intestine. Specifically, ezetimibe (Zetia) appears to bind to a critical mediator of cholesterol absorption, the Niemann-Pick C1-Like 1 (NPC1L1) protein on the gastrointestinal tract epithelial cells as well as in hepatocytes. [1]

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Garcia-Calvo M, Lisnock J, Bull HG, Hawes BE, Burnett DA, Braun MP, Crona JH, Davis HR Jr, Dean DC, Detmers PA, Graziano MP, Hughes M, Macintyre DE, Ogawa A, O'neill KA, Iyer SP, Shevell DE, Smith MM, Tang YS, Makarewicz AM, Ujjainwalla F, Altmann SW, Chapman KT, Thornberry NA: The target of ezetimibe is Niemann-Pick C1-Like 1 (NPC1L1). Proc Natl Acad Sci U S A. 2005 Jun 7;102(23):8132-7. Epub 2005 May 31. Pubmed
  • http://en.wikipedia.org/wiki/Ezetimibe
正在搜索,请耐心等待...(如果遇到网页错误或者长时间没有结果,请刷新页面[F5])

专利

专利

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

互联网资源

互联网资源

百度图标百度 google iconGoogle