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Record Information
Version1.0
Creation Date2014-09-11 05:16:26 UTC
Update Date2016-11-09 01:09:12 UTC
Accession NumberCHEM003741
Identification
Common NameClofibrate
ClassSmall Molecule
DescriptionA fibric acid derivative used in the treatment of hyperlipoproteinemia type III and severe hypertriglyceridemia.
Contaminant Sources
  • HMDB Contaminants - Urine
  • IARC Carcinogens Group 3
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Anticholesteremic Agent
  • Drug
  • Ester
  • Ether
  • Hypolipidemic Agent
  • Metabolite
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
2-(4-Chlorophenoxy)-2-methylpropanoic acid ethyl esterChEBI
2-(p-Chlorophenoxy)-2-methylpropionic acid ethyl esterChEBI
alpha-(p-Chlorophenoxy)isobutyric acid, ethyl esterChEBI
alpha-p-Chlorophenoxyisobutyryl ethyl esterChEBI
Atromid-SChEBI
ClofibratoChEBI
ClofibratumChEBI
ELPIChEBI
EPIBChEBI
Ethyl 2-(p-chlorophenoxy)isobutyrateChEBI
Ethyl chlorophenoxyisobutyrateChEBI
Ethyl clofibrateChEBI
LipofactonChEBI
LiprinChEBI
2-(4-Chlorophenoxy)-2-methylpropanoate ethyl esterGenerator
2-(p-Chlorophenoxy)-2-methylpropionate ethyl esterGenerator
a-(p-Chlorophenoxy)isobutyrate, ethyl esterGenerator
a-(p-Chlorophenoxy)isobutyric acid, ethyl esterGenerator
alpha-(p-Chlorophenoxy)isobutyrate, ethyl esterGenerator
Α-(p-chlorophenoxy)isobutyrate, ethyl esterGenerator
Α-(p-chlorophenoxy)isobutyric acid, ethyl esterGenerator
a-p-Chlorophenoxyisobutyryl ethyl esterGenerator
Α-p-chlorophenoxyisobutyryl ethyl esterGenerator
Ethyl 2-(p-chlorophenoxy)isobutyric acidGenerator
Ethyl chlorophenoxyisobutyric acidGenerator
Ethyl clofibric acidGenerator
Clofibric acidGenerator
ChlorfenisateHMDB
ChlorphenisateHMDB
ClofibateHMDB
CPIBHMDB
Ethyl p-chlorophenoxyisobutyrateHMDB
Ethyl para-chlorophenoxyisobutyrateHMDB
MiscleronHMDB
Clofibric acid, ethyl esterHMDB
AtromidHMDB
Atromid SHMDB
MiskleronHMDB
Chlorophenoxyisobutyrate, ethylHMDB
AthromidinHMDB
Chemical FormulaC12H15ClO3
Average Molecular Mass242.699 g/mol
Monoisotopic Mass242.071 g/mol
CAS Registry Number637-07-0
IUPAC Nameethyl 2-(4-chlorophenoxy)-2-methylpropanoate
Traditional Nameartes
SMILESCCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1
InChI IdentifierInChI=1S/C12H15ClO3/c1-4-15-11(14)12(2,3)16-10-7-5-9(13)6-8-10/h5-8H,4H2,1-3H3
InChI KeyKNHUKKLJHYUCFP-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenoxyacetic acid derivatives. Phenoxyacetic acid derivatives are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenoxyacetic acid derivatives
Direct ParentPhenoxyacetic acid derivatives
Alternative Parents
Substituents
  • Phenoxyacetate
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Ether
  • Monocarboxylic acid or derivatives
  • Organochloride
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organohalogen compound
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point118-119°C
Boiling Point149°C at 2.00E+01 mm Hg
SolubilityInsoluble
Predicted Properties
PropertyValueSource
Water Solubility0.029 g/LALOGPS
logP3.99ALOGPS
logP3.4ChemAxon
logS-3.9ALOGPS
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity62.14 m³·mol⁻¹ChemAxon
Polarizability24.7 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-00or-4900000000-b0f27a4473b7e59d68c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0390000000-a206c9f16b476083dcdbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1920000000-cdf7fd63fdcb1f2840cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-6900000000-bf1eef6ec7349495a9b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0290000000-f8e44478c85e8deb28e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-1960000000-5686cbdf03cff625cebcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-2900000000-de1ce5552c1bea344c1eView in MoNA
MSMass Spectrum (Electron Ionization)splash10-004i-3900000000-fc2f01df51d424557e9fView in MoNA
Toxicity Profile
Route of ExposureCompletely 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.
Mechanism of ToxicityClofibrate 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. Also, as a fibrate, Clofibrate is an agonist of the PPAR-‘± receptor[4] in muscle, liver, and other tissues. This agonism ultimately leads to modification in gene expression resulting in increased beta-oxidation, decreased triglyceride secretion, increased HDL, increased lipoprotein lipase activity.
MetabolismHepatic 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]). 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.
Toxicity ValuesOral, mouse: LD50 = 1220 mg/kg; Oral, rabbit: LD50 = 1370 mg/kg; Oral, rat: LD50 = 940 mg/kg.
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (1)
Uses/SourcesFor Primary Dysbetalipoproteinemia (Type III hyperlipidemia) that does not respond adequately to diet. This helps control high cholesterol and high triglyceride levels.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00636
HMDB IDHMDB0014774
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkClofibrate
Chemspider ID2694
ChEBI ID3750
PubChem Compound ID2796
Kegg Compound IDC06916
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Jones, W.G.M.,Thorp, J.M. and Waring, W.S.; U.S. Patent 3,262,850; July 26, 1966; assigned to Imperial Chemical Industries Limited, England.

MSDSLink
General ReferencesNot Available