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

• ChemBase ID: 518
• Molecular Formular: C12H15ClO3
• Molecular Mass: 242.6987
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2-(4-chlorophenoxy)-2-methylpropanoate
• IUPAC Traditional name: clofibrate
• Brand Name: 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
• Synonyms: 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; 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

Database IDs

• CAS Number: 637-07-0
• EC Number: 211-277-4
• MDL Number: MFCD00000615
• Beilstein Number: 1913459
• PubChem SID: 46504748; 24278085; 160963981
• PubChem CID: 2796
• CHEBI ID: 3750
• ATC CODE: C10AB01
• CHEMBL: 565
• Chemspider ID: 2694
• DrugBank ID: DB00636
• KEGG ID: D00279
• Unique Ingredient Identifier: HPN91K7FU3
• Wikipedia Title: Clofibrate

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.4018347
• LogD (pH = 7.4): 3.4018347
• Log P: 3.4018347
• Molar Refractivity: 62.1355 cm^3
• Polarizability: 24.701744 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.99
• LOG S: -3.92
• Solubility (Water): 2.90e-02 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Insoluble
• Apperance: Clear Colorless Oil; clear, colorless liquid
• Boiling Point: 148°C (298.4°F); 154-156 °C/20 mmHg(lit.)
• Flash Point: 113 °C; 235.4 °F
• Density: 1.137 g/mL at 20 °C; 1.14 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.503
• Hydrophobicity(logP): 3.3; 4.119

Safety Information

• Storage Condition: -20°C; Refrigerator; Room Temperature (15-30°C), Protect from light
• Storage Warning: Harmful/Irritant
• RTECS: UE9480000
• European Hazard Symbols: Nature polluting (N); Harmful (Xn)
• UN Number: 3082
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 22-37/38-41-51/53; R:22
• Safety Statements: 26-36/37/39-61; S:36/37/39
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H315-H318-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: 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
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: Oral
• Excretion: Renal, 95 to 99%
• Half Life: Highly variable; average 18–22 hours. Prolonged in renal failure
• Metabolism: Hydrolyzed to clofibric acid; hepatic glucuronidation
• Protein Bound: Variable, 92–97% at therapeutic concentrations
• Legal Status: Discontinued (US)
• Pregnancy Category: B1 (Australia); C (US)
• Gene Information: human ... PPARA(5465)mouse ... Ppara(19013)

Product Information

• Purity: ≥98.0% (GC); 95%; 97%; 99%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C12H15ClO3

DETAILS

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.

REFERENCES

• 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)