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23593-75-1 分子结构
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1-[(2-chlorophenyl)diphenylmethyl]-1H-imidazole

ChemBase编号:142
分子式:C22H17ClN2
平均质量:344.83678
单一同位素质量:344.10802623
SMILES和InChIs

SMILES:
Clc1c(C(n2ccnc2)(c2ccccc2)c2ccccc2)cccc1
Canonical SMILES:
Clc1ccccc1C(n1cncc1)(c1ccccc1)c1ccccc1
InChI:
InChI=1S/C22H17ClN2/c23-21-14-8-7-13-20(21)22(25-16-15-24-17-25,18-9-3-1-4-10-18)19-11-5-2-6-12-19/h1-17H
InChIKey:
VNFPBHJOKIVQEB-UHFFFAOYSA-N

引用这个纪录

CBID:142 http://www.chembase.cn/molecule-142.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-[(2-chlorophenyl)diphenylmethyl]-1H-imidazole
IUPAC传统名
clotrimazole
lotrimin
1-[(2-chlorophenyl)diphenylmethyl]-1H-imidazole
商标名
Canesten
Canesten 1-Day Cream Combi-Pak
Canesten 1-Day Therapy
Canesten 3-Day Therapy
Canesten 6-Day Therapy
Canesten Combi-Pak 1-Day Therapy
Canesten Combi-Pak 3-Day Therapy
Canesten Cream
Canesten Solution
Canestine
Canifug
Cimitidine
Clotrimaderm
Empecid
FemCare
Gyne lotrimin
Gyne-Lotrimin 3
Gyne-Lotrimin 3 Combination Pack
Gyne-Lotrimin Combination Pack
Gyne-lotrimin
Gynix
Lotrimin
Lotrimin AF Cream
Lotrimin AF Jock-Itch Cream
Lotrimin AF Lotion
Lotrimin AF Solution
Lotrimin Af
Lotrimin Cream
Lotrimin Lotion
Lotrimin Solution
Mono-baycuten
Mycelax
Mycelex
Mycelex 7
Mycelex Cream
Mycelex G
Mycelex Solution
Mycelex Troches
Mycelex Twin Pack
Mycelex-7
Mycelex-7 Combination Pack
Mycelex-G
Myclo Cream
Myclo Solution
Myclo Spray Solution
Myclo-Gyne
Mycosporin
Mykosporin
Neo-Zol Cream
Trimysten
Trivagizole 3
Veltrim
Lotrimin AF, Mycelex
别名
1-[(2-氯苯基)二苯甲基]-1H-咪唑
三苯氯甲咪唑
氯苯甲咪唑
克霉唑
Clotrimazol
Chlotrimazole
Clotrimazole
Lotrimin
Mycelex
Canesten
Clotrimazole
1-(o-Chlorotrityl)imidazole
1-(o-Chloro-α,α-diphenylbenzyl)imidazole
1-[(2-Chlorophenyl)diphenylmethyl]-1H-imidazole
Clotrimazole(Canesten)
1-[(2-Chlorophenyl)-diphenyl-methyl]-1H-imidazole
FB-5097
Bay b 5097
Canifug
Empecid
Mycofung
Desamix F
Diphenyl(2-chlorophenyl)(1-imidazolyl)methane
Femcare
Gyne-Lotrimin
Gyne-Lotrimin 7
Locasten
1-((2-chlorophenyl)diphenylmethyl)-1h-imidazole
CAS号
23593-75-1
EC号
245-764-8
MDL号
MFCD00057220
PubChem SID
24860592
46507927
160963605
24278327
PubChem CID
2812
CHEBI ID
3764
ATC码
D01AC01
G01AF02
QJ02AB90
A01AB18
CHEMBL
104
Chemspider ID
2710
DrugBank ID
DB00257
KEGG ID
D00282
美国药典/FDA物质标识码
G07GZ97H65
维基百科标题
Clotrimazole
Medline Plus
a682753

理论计算性质

理论计算性质

JChem ALOGPS 2.1
质子受体 质子供体
LogD (pH = 5.5) 5.3291874  LogD (pH = 7.4) 5.7905 
Log P 5.839452  摩尔折射率 103.7645 cm3
极化性 39.57285 Å3 极化表面积 17.82 Å2
可自由旋转的化学键 里宾斯基五规则 false 
Log P 5.48  LOG S -5.37 
溶解度 1.47e-03 g/l 

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
29.84 mg/mL expand 查看数据来源
Chloroform expand 查看数据来源
DMSO expand 查看数据来源
Ethyl Acetate expand 查看数据来源
外观
White Solid expand 查看数据来源
熔点
142-144°C expand 查看数据来源
疏水性(logP)
6.1 expand 查看数据来源
保存条件
-20°C expand 查看数据来源
Refrigerator expand 查看数据来源
Room Temperature (15-30°C) expand 查看数据来源
RTECS编号
NI4377000 expand 查看数据来源
欧盟危险性物质标志
有害性(Harmful) 有害性(Harmful) (Xn) 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
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
危险公开号
22-36/38 expand 查看数据来源
R:22 expand 查看数据来源
安全公开号
26-36 expand 查看数据来源
S:36/37/39 expand 查看数据来源
GHS危险品标识
GHS07 expand 查看数据来源
GHS警示词
Warning expand 查看数据来源
GHS危险声明
H302-H315-H319 expand 查看数据来源
GHS警示性声明
P305 + P351 + P338 expand 查看数据来源
个人保护装置
dust mask type N95 (US), Eyeshields, Gloves expand 查看数据来源
给药途径
topical expand 查看数据来源
生物利用度
Poorly and erratically absorbed orally expand 查看数据来源
半衰期
2 hours expand 查看数据来源
代谢
hepatic expand 查看数据来源
蛋白结合率
90% expand 查看数据来源
法定药品分级
P (UK) expand 查看数据来源
妊娠期药物分类
A (Australia) expand 查看数据来源
C (oral) and B (topical) (US) expand 查看数据来源
相关基因信息
human ... ABCB1(5243), CYP17A1(1586), CYP3A4(1576)mouse ... Abcb1a(18671), Abcb1b(18669) expand 查看数据来源
生物活性机理
Appears to increase permeability of fungal-cell-membrane causing leakage of intracellular components. expand 查看数据来源
Functions as Lanosterol C-14 demethylation inhibitor expand 查看数据来源
Induces K+ release from Trichophyton mentagrophytes mycelium expand 查看数据来源
Induces membrane disruption expand 查看数据来源
Potent cytochrome P-450b and P-450c inhibitor expand 查看数据来源
纯度
98% expand 查看数据来源
级别
VETRANAL™, analytical standard 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
下载链接 expand 查看数据来源
应用领域
Antifungal agent expand 查看数据来源
Pharmacopeia Traceability
traceable to BP 379 expand 查看数据来源
traceable to PhEur C2430000 expand 查看数据来源
traceable to USP 1141002 expand 查看数据来源
Empirical Formula (Hill Notation)
C22H17ClN2 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank TRC TRC Sigma Aldrich Sigma Aldrich MP Biomedicals MP Biomedicals Wikipedia Wikipedia Selleck Chemicals Selleck Chemicals
DrugBank -  DB00257 external link
Item Information
Drug Groups approved
Description An imidazole derivative with a broad spectrum of antimycotic activity. It inhibits biosynthesis of the sterol ergostol, an important component of fungal cell membranes. Its action leads to increased membrane permeability and apparent disruption of enzyme systems bound to the membrane. [PubChem]
Indication For the local treatment of oropharyngeal candidiasis and vaginal yeast infections, also used in fungal infections of the skin such as ringworm, athlete's foot, and jock itch.
Pharmacology Clotrimazole, an imidazole derivative with a broad spectrum of antimycotic activity, inhibits biosynthesis of the sterol ergostol, an important component of fungal cell membranes. Its action leads to increased membrane permeability and apparent disruption of enzyme systems bound to the membrane. Betamethasone and clotrimazole are used together to treat cutaneous tinea infections. In studies in fungal cultures, the minimum fungicidal concentration of clotrimazole caused leakage of intracellular phosphorous compounds into the ambient medium with concomitant breakdown of cellular nucleic acids, and accelerated potassium etflux. Both of these events began rapidly and extensively after addition of the drug to the cultures. The primary action of clotrimazole is against dividing and growing organisms.
Toxicity Symptoms of overdose include erythema, stinging, blistering, peeling, edema, pruritus, urticaria, burning, and general irritation of the skin, and cramps.
Affected Organisms
Yeast and other fungi
Biotransformation Hepatic (metabolized to inactive metabolites)
Absorption Poorly and erratically absorbed orally, minimal vaginal or topical absorption.
Half Life 2 hours
Protein Binding 90%
External Links
Wikipedia
RxList
Drugs.com
Toronto Research Chemicals -  C587400 external link
Clotrimazole is an antifungal agent.
Sigma Aldrich -  C6019 external link
Biochem/physiol Actions
Specific inhibitor of Ca2+-activated K+ channels. Antifungal azole. Antifungal mode of action: Inhibits cytochrome P450-dependent 14α-demethylase, which is critical to ergosterol biosynthesis. The accumulated 14α-methylated sterols change the membrane structure of sensitive fungi, altering cell membrane permeability.
Sigma Aldrich -  33894 external link
法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC
MP Biomedicals -  02198944 external link
Specific inhibitor of Ca2+ activated K+ channels.
Selleck Chemicals -  S1606 external link
Research Area: Infection
Biological Activity:
Clotrimazole(Canesten) is a synthetic, antifungal and broad-spectrum derivate of imidazole. Clotrimazole inhibits biosynthesis of sterols, particularly inhibiting ergosterol, which is an essential component of the fungal cell membrane, thereby damaging and affecting the permeability of the cell membrane. This results in the  leakage and the loss of essential intracellular compounds, and eventually causes the lysis of cell.  [1, 2]

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Buechel, K.H. et al., Arzneim.-Forsch., 1972, 22, 1260, (synth, pharmacol)
  • Kracmar, J. et al., Cesk. Farm., 1977, 26, 345, (uv)
  • Raab, W., Curr. Ther. Res., Clin. Exp., 1977, 22, 65, (pharmacol)
  • Ruppert, J.F., Diss. Abstr. Int., B, 1977, 38, 2681, (synth)
  • Hoogerheide, J.G. et al., Anal. Profiles Drug Subst., 1982, 11, 225, (rev)
  • Lewis, D.F.V. et al., J. Biochem. Toxicol., 1989, 4, 231, (pharmacol)
  • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 320
  • Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 8792
  • Song, H. et al., Acta Cryst. C, 1998, 54, 1675-1677, (cryst struct)
  • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, MRX500
  • http://en.wikipedia.org/wiki/Clotrimazole
  • Podust, L., et al.: J. Biol. Chem., 284, 25211 (2009)
  • Hollender, J., et al.: Environ. Sci. Technol., 43, 7862 (2009)
  • Marciniec, B., et al.: J. Pharm. Biomed. Anal., 50, 675 (2009)
  • McGinnity, D., et al.: Drug Metab. Disposition, 37, 1259 (2009)
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专利

专利

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