ContaminantDB: Clofibrate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (2)XML

Record Information

Version

1.0

Creation Date

2014-09-11 05:16:26 UTC

Update Date

2016-11-09 01:09:12 UTC

Accession Number

CHEM003741

Identification

Common Name

Clofibrate

Class

Small Molecule

Description

A 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(4-Chlorophenoxy)-2-methylpropanoic acid ethyl ester	ChEBI
2-(p-Chlorophenoxy)-2-methylpropionic acid ethyl ester	ChEBI
alpha-(p-Chlorophenoxy)isobutyric acid, ethyl ester	ChEBI
alpha-p-Chlorophenoxyisobutyryl ethyl ester	ChEBI
Atromid-S	ChEBI
Clofibrato	ChEBI
Clofibratum	ChEBI
ELPI	ChEBI
EPIB	ChEBI
Ethyl 2-(p-chlorophenoxy)isobutyrate	ChEBI
Ethyl chlorophenoxyisobutyrate	ChEBI
Ethyl clofibrate	ChEBI
Lipofacton	ChEBI
Liprin	ChEBI
2-(4-Chlorophenoxy)-2-methylpropanoate ethyl ester	Generator
2-(p-Chlorophenoxy)-2-methylpropionate ethyl ester	Generator
a-(p-Chlorophenoxy)isobutyrate, ethyl ester	Generator
a-(p-Chlorophenoxy)isobutyric acid, ethyl ester	Generator
alpha-(p-Chlorophenoxy)isobutyrate, ethyl ester	Generator
Α-(p-chlorophenoxy)isobutyrate, ethyl ester	Generator
Α-(p-chlorophenoxy)isobutyric acid, ethyl ester	Generator
a-p-Chlorophenoxyisobutyryl ethyl ester	Generator
Α-p-chlorophenoxyisobutyryl ethyl ester	Generator
Ethyl 2-(p-chlorophenoxy)isobutyric acid	Generator
Ethyl chlorophenoxyisobutyric acid	Generator
Ethyl clofibric acid	Generator
Clofibric acid	Generator
Chlorfenisate	HMDB
Chlorphenisate	HMDB
Clofibate	HMDB
CPIB	HMDB
Ethyl p-chlorophenoxyisobutyrate	HMDB
Ethyl para-chlorophenoxyisobutyrate	HMDB
Miscleron	HMDB
Clofibric acid, ethyl ester	HMDB
Atromid	HMDB
Atromid S	HMDB
Miskleron	HMDB
Chlorophenoxyisobutyrate, ethyl	HMDB
Athromidin	HMDB

Chemical Formula

C₁₂H₁₅ClO₃

Average Molecular Mass

242.699 g/mol

Monoisotopic Mass

242.071 g/mol

CAS Registry Number

637-07-0

IUPAC Name

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

Traditional Name

artes

SMILES

CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1

InChI Identifier

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

InChI Key

KNHUKKLJHYUCFP-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenoxyacetic acid derivatives

Direct Parent

Phenoxyacetic 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

ethyl ester (CHEBI:3750 )
aromatic ether (CHEBI:3750 )
monochlorobenzenes (CHEBI:3750 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	118-119°C
Boiling Point	149°C at 2.00E+01 mm Hg
Solubility	Insoluble

Predicted Properties

Property	Value	Source
Water Solubility	0.029 g/L	ALOGPS
logP	3.99	ALOGPS
logP	3.4	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	62.14 m³·mol⁻¹	ChemAxon
Polarizability	24.7 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00or-4900000000-b0f27a4473b7e59d68c3	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014v-0930000000-829386905d164431d8d2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014r-0900000000-7d85ceb3a8f1381c7da6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-001l-0900000000-4a173dddc088d2ecd596	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-015c-0900000000-dcd68fabfcd01b516107	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014r-0900000000-409b5800e94ffbb11863	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-001l-0900000000-63251a4c6680c9389c2f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0290000000-f8e44478c85e8deb28e7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004l-1960000000-5686cbdf03cff625cebc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-2900000000-de1ce5552c1bea344c1e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0920000000-255926cbf0927bf8a9fa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-4910000000-64c9da59c5fb22afb366	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0059-7900000000-cd5c6706685e8cd7dbe1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0390000000-a206c9f16b476083dcdb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-1920000000-cdf7fd63fdcb1f2840cd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-6900000000-bf1eef6ec7349495a9b5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-6980000000-60ef91c08059dec83cfe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00p0-7910000000-106c9afa2a025a09891e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9200000000-710d7a203fef2cd8e30b	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004i-3900000000-fc2f01df51d424557e9f	Spectrum

Toxicity Profile

Route of Exposure

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.

Mechanism of Toxicity

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. 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.

Metabolism

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]). 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 Values

Oral, mouse: LD₅₀ = 1220 mg/kg; Oral, rabbit: LD₅₀ = 1370 mg/kg; Oral, rat: LD₅₀ = 940 mg/kg.

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (1)

Uses/Sources

For Primary Dysbetalipoproteinemia (Type III hyperlipidemia) that does not respond adequately to diet. This helps control high cholesterol and high triglyceride levels.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID