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: 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

名称和登记号

名称

• IUPAC标准名: 1-[(2-chlorophenyl)diphenylmethyl]-1H-imidazole
• IUPAC传统名: lotrimin; 1-[(2-chlorophenyl)diphenylmethyl]-1H-imidazole; clotrimazole
• 商标名: Lotrimin AF, Mycelex; 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
• 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; Clotrimazole; 1-(o-Chlorotrityl)imidazole; 1-(o-Chloro-α,α-diphenylbenzyl)imidazole; 1-[(2-Chlorophenyl)diphenylmethyl]-1H-imidazole; Clotrimazol; Chlotrimazole; Clotrimazole; Lotrimin; Mycelex; Canesten; 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

登记号

• CAS号: 23593-75-1
• EC号: 245-764-8
• MDL号: MFCD00057220
• PubChem SID: 46507927; 24860592; 160963605; 24278327
• PubChem CID: 2812
• CHEBI ID: 3764
• ATC码: D01AC01; QJ02AB90; A01AB18; G01AF02
• 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

JChem

• 质子受体: 1
• 质子供体: 0
• LogD (pH = 5.5): 5.3291874
• LogD (pH = 7.4): 5.7905
• Log P: 5.839452
• 摩尔折射率: 103.7645 cm^3
• 极化性: 39.57285 Å^3
• 极化表面积: 17.82 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 5.48
• LOG S: -5.37
• 溶解度: 1.47e-03 g/l

分子性质

理化性质

• 溶解度: 29.84 mg/mL; Chloroform; DMSO; Ethyl Acetate
• 外观: White Solid
• 熔点: 142-144°C
• 疏水性(logP): 6.1

安全信息

• 保存条件: -20°C; Refrigerator; Room Temperature (15-30°C)
• RTECS编号: NI4377000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22-36/38; R:22
• 安全公开号: 26-36; S:36/37/39
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H315-H319
• GHS警示性声明: P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

药理学性质

• 给药途径: topical
• 生物利用度: Poorly and erratically absorbed orally
• 半衰期: 2 hours
• 代谢: hepatic
• 蛋白结合率: 90%
• 法定药品分级: P (UK)
• 妊娠期药物分类: A (Australia); C (oral) and B (topical) (US)
• 相关基因信息: human ... ABCB1(5243), CYP17A1(1586), CYP3A4(1576)mouse ... Abcb1a(18671), Abcb1b(18669)
• 生物活性机理: Appears to increase permeability of fungal-cell-membrane causing leakage of intracellular components.; Functions as Lanosterol C-14 demethylation inhibitor; Induces K+ release from Trichophyton mentagrophytes mycelium; Induces membrane disruption; Potent cytochrome P-450b and P-450c inhibitor

产品相关信息

• 纯度: 98%
• 级别: VETRANAL™, analytical standard
• 成盐信息: Free Base
• 应用领域: Antifungal agent
• Pharmacopeia Traceability: traceable to BP 379; traceable to PhEur C2430000; traceable to USP 1141002
• Empirical Formula (Hill Notation): C22H17ClN2

详细说明

MP Biomedicals - 02198944

Specific inhibitor of Ca^2+ activated K^+ channels.

DrugBank - DB00257

• 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

Selleck Chemicals - S1606

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]

Sigma Aldrich - C6019

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

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

Toronto Research Chemicals - C587400

Clotrimazole is an antifungal agent.

参考文献

• 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)
• 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