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65277-42-1 分子结构
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1-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one

ChemBase编号:72632
分子式:C26H28Cl2N4O4
平均质量:531.43092
单一同位素质量:530.14876076
SMILES和InChIs

SMILES:
c1(ccc(cc1)OC[C@@H]1O[C@@](OC1)(Cn1ccnc1)c1ccc(cc1Cl)Cl)N1CCN(CC1)C(=O)C
Canonical SMILES:
Clc1ccc(c(c1)Cl)[C@]1(OC[C@@H](O1)COc1ccc(cc1)N1CCN(CC1)C(=O)C)Cn1cncc1
InChI:
InChI=1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3/t23-,26-/m0/s1
InChIKey:
XMAYWYJOQHXEEK-OZXSUGGESA-N

引用这个纪录

CBID:72632 http://www.chembase.cn/molecule-72632.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
1-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one
IUPAC传统名
(2R,4S)-ketoconazole
别名
Nizoral
Extina
Xolegel
Kuric
Ketoconazole
(±)-cis-1-Acetyl-4-(4-[(2-[2,4-dichlorophenyl]-2-[1H-imidazol-1-ylmethyl]-1,3-dioxolan-4-yl)-methoxy]phenyl)piperazine
Ketoconazole
rel-1-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]ethanone
cis-1-Acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine
(+/-)-Ketoconazole
Brizoral
Fungarest
Fungoral
Ketoderm
Ketoisdin
Ketozoral
Nizral
Onofin K
Orifungal M
Panfungol
R 41400
CAS号
65277-42-1
EC号
265-667-4
MDL号
MFCD00058579
PubChem SID
24278176
162037557
24724652
PubChem CID
456201

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID
PubChem 456201 external link

理论计算性质

理论计算性质

JChem
质子受体 质子供体
LogD (pH = 5.5) 3.6516862  LogD (pH = 7.4) 4.128518 
Log P 4.191598  摩尔折射率 138.0672 cm3
极化性 53.26531 Å3 极化表面积 69.06 Å2
可自由旋转的化学键 里宾斯基五规则 false 

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 expand 查看数据来源
外观
White Solid expand 查看数据来源
white to light yellow expand 查看数据来源
熔点
144-146°C 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
TK7912300 expand 查看数据来源
欧盟危险性物质标志
环境危害性(Nature polluting) 环境危害性(Nature polluting) (N) expand 查看数据来源
有毒(Toxic) 有毒(Toxic) (T) expand 查看数据来源
联合国危险货物编号
2811 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
3 expand 查看数据来源
联合国危险货物等级
6.1 expand 查看数据来源
联合国危险货物包装类别(PG)
3 expand 查看数据来源
危险公开号
60-25-48/22-50/53 expand 查看数据来源
安全公开号
53-45-60-61 expand 查看数据来源
GHS危险品标识
GHS06 expand 查看数据来源
GHS08 expand 查看数据来源
GHS09 expand 查看数据来源
GHS警示词
Danger expand 查看数据来源
GHS危险声明
H301-H360F-H373-H410 expand 查看数据来源
GHS警示性声明
P201-P273-P301 + P310-P308 + P313-P501 expand 查看数据来源
个人保护装置
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges expand 查看数据来源
RID/ADR
UN 2811 6.1/PG 3 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
P450 expand 查看数据来源
相关基因信息
human ... ABCB1(5243), CYP11B1(1584), CYP11B2(1585), CYP17A1(1586), CYP19A1(1588), CYP1A2(1544), CYP24A1(1591), CYP26A1(1592), CYP3A4(1576), CYP51A1(1595), KCNH1(3756)mouse ... Abcb1a(18671), Abcb1b(18669)rat ... Alox5(25290), Cyp17a1(25146), Cyp51(25427), Cyp7a1(25428) 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
产品质量级别
PREMIUM expand 查看数据来源
Empirical Formula (Hill Notation)
C26H28Cl2N4O4 expand 查看数据来源

详细说明

详细说明

Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
Selleck Chemicals -  S1353 external link
Research Area: Infection
Biological Activity:
Ketoconazole is a synthetic antifungal drug used to prevent and treat skin and fungal infections, especially in immunocompromised patients such as those with AIDS. ketoconazole is structurally similar to imidazole and interferes with the fungal synthesis of ergosterol, a constituent of fungal cell membranes, as well as certain enzymes. [1] 
Sigma Aldrich -  UC280 external link
Application
CYP3A4 inhibitor
Biochem/physiol Actions
Antifungal agent
Sigma Aldrich -  K1003 external link
Application
CYP3A4 inhibitor
Ketoconazole is a broad spectrum antifungal agent used to treat candidiasis, chronic mucocutaneous candidiasis, oral thrush, candiduria, blastomycosis, coccidioidomycosis, histoplasmosis, chromomycosis, and paracoccidioidomycosis. It is used to identify p-glycoprotein/CYP3A-limited bioavailability in the monkey model1, to study interleukin 1 mediated antitumor effects2, and drug interactions in vivo3
Biochem/physiol Actions
Antifungal agent
Ketoconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme that is necessary for the conversion of lanosterol to ergosterol. This interaction inhibits ergosterol synthesis and results in increased fungal cellular permeability. Other possible mechanisms of action are the inhibition of endogenous respiration, interaction with membrane phospholipids, inhibition of yeast transformation to mycelial forms, inhibition of purine uptake, and impairment of triglyceride and/or phospholipid biosynthesis. Ketoconazole inhibits the synthesis of thromboxane and sterols such as aldosterone, cortisol, and testosterone .
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information
Toronto Research Chemicals -  K186000 external link
Inhibits cytochrome P-450 dependent steps in the biosynthesis of steroid hormones in vivo. Antimetastatic and antineoplastic activity. Orally active 5-lipoxygenase and thromboxane synthase inhibitor.

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/Ketoconazole
  • Lambert, A., et al.: Biochem. Pharmacol., 35, 3999 (1986)
  • Van Wauwe, J.P. and Janssen, P.A.J., J. Med. Chem., 32, 2231 (1986)
  • Nardone, P.A., et al.: . Surg. Res., 44, 425 (1986)
  • Tucker, W.F.G., et al.: Br. Med. J., 293, 882 (1986)
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专利

专利

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