ethyl 2-(4-chlorophenoxy)-2-methylpropanoate

• ChemBase编号: 518
• 分子式: C12H15ClO3
• 平均质量: 242.6987
• 单一同位素质量: 242.07097202
• SMILES: Clc1ccc(OC(C)(C)C(=O)OCC)cc1
• Canonical SMILES: CCOC(=O)C(Oc1ccc(cc1)Cl)(C)C
• InChI: InChI=1S/C12H15ClO3/c1-4-15-11(14)12(2,3)16-10-7-5-9(13)6-8-10/h5-8H,4H2,1-3H3
• InChIKey: KNHUKKLJHYUCFP-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: ethyl 2-(4-chlorophenoxy)-2-methylpropanoate
• IUPAC传统名: clofibrate
• 商标名: Amotril; Amotril S; Angiokapsul; Anparton; Antilipid; Antilipide; Apolan; Arterioflexin; Arterosol; Artes; Artevil; Ateculon; Ateriosan; Athebrate; Atheromide; Atheropront; Athranid-Wirkstoff; Atrolen; Atromid; Atromid S; Atromid-S; Atromida; Atromidin; Atrovis; Azionyl; Bioscleran; Bresit; Cartagyl; Citiflus; Claripex; Claripex CPIB; Cloberat; Clobrat; Clobren-5F; Clobren-SF; Clofar; Clofibram; Clofibrat; Clofinit; Clofipront; Delipid; Deliva; Dura clofibrat; ELPI; Fibralem; Gerastop; Hyclorate; Klofibrat; Klofiran; Levatrom; Lipamid; Lipavil; Lipavlon; Lipide 500; Lipidsenker; Lipofacton; Lipomid; Liponorm; Liporeduct; Liporil; Liposid; Liprin; Liprinal; Lobetrin; Miscleron; Negalip; Neo-Atromid; Normalip; Normat; Normolipol; Novofibrate; Oxan 600; Persantinat; Regardin; Regelan; Regelan N; Robigram; Scrobin; Serofinex; Serotinex; Skerolip; Sklerepmexe; Sklero; Sklero-Tablinen; Sklero-tablinene; Sklero-tabuls; Sklerolip; Skleromex; Skleromexe; Tetrasipton; Thillate; Thiosan; Ticlobran; Vincamin compositum; Xyduril; Yoclo; neo-Atomid
• 别名: 氯贝特; 氯贝丁酯; 2-(4-氯苯氧基)异丁酸乙酯; 2-甲基-2-(4-氯苯氧基)丙酸乙酯; 氯贝丁酯; 氯贝特; Chlorfenisate; Chlorphenisate; Clofibate; Clofibrato; Clofibratum; Ethyl chlorophenoxyisobutyrate; Ethyl clofibrate; EPIB; Ethyl p-chlorophenoxyisobutyrate; Ethyl para-chlorophenoxyisobutyrate; CPIB; Clofibrate; Clofibrate; Ethyl 2-(4-chlorophenoxy)-2-methylpropanoate; Atromid-S; Clofibrate; 2-(4-Chlorophenoxy)-2-methylpropanoic Acid Ethyl Ester; Ethyl Clofibrate-d4; Ethyl 2-(4-Chlorophenoxy-d4)-2-methylpropionate; Ethyl 2-(p-chlorophenoxy)isobutyrate; Ethyl 2-(4-chlorophenoxy)-2-methylpropionate; 2-(p-Chlorophenoxy)-2-methylpropionic acid ethyl ester; 2-(4-Chlorophenoxy)-2-methylpropionic acid ethyl ester; Ethyl 2-(4-chlorophenoxy)-2-methylpropionate; Ethyl 2-(4-chlorophenoxy)isobutyrate

登记号

• CAS号: 637-07-0
• EC号: 211-277-4
• MDL号: MFCD00000615
• Beilstein号: 1913459
• PubChem SID: 24278085; 160963981; 46504748
• PubChem CID: 2796
• CHEBI ID: 3750
• ATC码: C10AB01
• CHEMBL: 565
• Chemspider ID: 2694
• DrugBank ID: DB00636
• KEGG ID: D00279
• 美国药典/FDA物质标识码: HPN91K7FU3
• 维基百科标题: Clofibrate

理论计算性质

JChem

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 3.4018347
• LogD (pH = 7.4): 3.4018347
• Log P: 3.4018347
• 摩尔折射率: 62.1355 cm^3
• 极化性: 24.701744 Å^3
• 极化表面积: 35.53 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.99
• LOG S: -3.92
• 溶解度: 2.90e-02 g/l

分子性质

理化性质

• 溶解度: Chloroform; Insoluble
• 外观: Clear Colorless Oil; clear, colorless liquid
• 沸点: 148°C (298.4°F); 154-156 °C/20 mmHg(lit.)
• 闪点: 113 °C; 235.4 °F
• 密度: 1.137 g/mL at 20 °C; 1.14 g/mL at 25 °C(lit.)
• 折射率: n20/D 1.503
• 疏水性(logP): 3.3; 4.119

安全信息

• 保存条件: -20°C; Refrigerator; Room Temperature (15-30°C), Protect from light
• 保存注意事项: Harmful/Irritant
• RTECS编号: UE9480000
• 欧盟危险性物质标志: 环境危害性(Nature polluting) (N); 有害性(Harmful) (Xn)
• 联合国危险货物编号: 3082
• 德国WGK号: 3
• 联合国危险货物等级: 9
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 22-37/38-41-51/53; R:22
• 安全公开号: 26-36/37/39-61; S:36/37/39
• GHS危险品标识: GHS05; GHS07
• GHS警示词: Danger
• GHS危险声明: H302-H315-H318-H335
• GHS警示性声明: P261-P280-P305 + P351 + P338
• 个人保护装置: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3082 9/PG 3
• 保存温度: 2-8°C

药理学性质

• 给药途径: Oral
• 排泄: Renal, 95 to 99%
• 半衰期: Highly variable; average 18–22 hours. Prolonged in renal failure
• 代谢: Hydrolyzed to clofibric acid; hepatic glucuronidation
• 蛋白结合率: Variable, 92–97% at therapeutic concentrations
• 法定药品分级: Discontinued (US)
• 妊娠期药物分类: B1 (Australia); C (US)
• 相关基因信息: human ... PPARA(5465)mouse ... Ppara(19013)

产品相关信息

• 纯度: ≥98.0% (GC); 95%; 97%; 99%
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C12H15ClO3

详细说明

MP Biomedicals - 02190342

[2-(p-Chlorophenoxy)-2-methylpropionic acid ethyl ester]

DrugBank - DB00636

• Drug Groups: approved
• Description: A fibric acid derivative used in the treatment of hyperlipoproteinemia type III and severe hypertriglyceridemia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p986)
• Indication: For Primary Dysbetalipoproteinemia (Type III hyperlipidemia) that does not respond adequately to diet. This helps control high cholesterol and high triglyceride levels.
• Pharmacology: Clofibrate is an antilipidemic agent similar to gemfibrozil. It acts to lower elevated serum lipids by reducing the very low-density lipoprotein fraction (S_f 20-400) rich in triglycerides. Serum cholesterol may be decreased, particularly in those patients whose cholesterol elevation is due to the presence of IDL as a result of Type III hyperlipoproteinemia. Several investigators have observed in their studies that clofibrate may produce a decrease in cholesterol linoleate but an increase in palmitoleate and oleate, the latter being considered atherogenic in experimental animals. The significance of this finding is unknown at this time. Reduction of triglycerides in some patients treated with clofibrate or certain of its chemically and clinically similar analogs may be associated with an increase in LDL cholesterol. Increase in LDL cholesterol has been observed in patients whose cholesterol is initially normal. Animal studies suggest that clofibrate interrupts cholesterol biosynthesis prior to mevalonate formation.
• Toxicity: Oral, mouse: LD₅₀ = 1220 mg/kg; Oral, rabbit: LD₅₀ = 1370 mg/kg; Oral, rat: LD₅₀ = 940 mg/kg. No reported case of overdosage in humans.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic and gastrointestinal: rapid de-esterification occurs in the gastrointestinal tract and/or on first-pass metabolism to produce the active form, clofibric acid (chlorophenoxy isobutyric acid [CPIB]).
• Absorption: Completely but slowly absorbed from the intestine. Between 95% and 99% of an oral dose of clofibrate is excreted in the urine as free and conjugated clofibric acid; thus, the absorption of clofibrate is virtually complete.
• Half Life: Half-life in normal volunteers averages 18 to 22 hours (range 14 to 35 hours) but can vary by up to 7 hours in the same subject at different times.
• Protein Binding: Highly protein-bound (95% to 97%).
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1820

Research Area: Cardiovascular Disease
Biological Activity:
Clofibrate (Atromid-S), a fibric acid derivative used in the treatment of hyperlipoproteinemia type III and severe hypertriglyceridemia. Clofibrate increases the activity of extrahepatic lipoprotein lipase (LL), thereby increasing lipoprotein triglyceride lipolysis. Chylomicrons are degraded, VLDLs are converted to LDLs, and LDLs are converted to HDL. This is accompanied by a slight increase in secretion of lipids into the bile and ultimately the intestine. Clofibrate also inhibits the synthesis and increases the clearance of apolipoprotein B, a carrier molecule for VLDL. [1]

Sigma Aldrich - C6643

Biochem/physiol Actions
Peroxisome proliferator-activated receptor-α (PPARα) agonist. Antihyperlipoproteinemic believed to act by inhibiting cholesterol biosynthesis.
包装
1, 5, 10 g in glass bottle
250 mg in glass bottle

Toronto Research Chemicals - C586910

Antilipemic.

参考文献

• http://www.drugbank.ca/drugs/DB00636
• Metz, G., et al.: Arzneim.-Forsch., 27, 1173 (1977)
• Hassan, A.M., et al.: Anal. Profiles Drug Subs., 11, 197 (1977)