ChemFOnt: Showing chemical card for Clofibrate (CFc000009119)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:09 UTC

Chemfont ID

CFc000009119

Molecule Identification

Common Name

Clofibrate

Definition

Clofibrate is only found in individuals that have used or taken this drug. It is a fibric acid derivative used in the treatment of hyperlipoproteinemia type III and severe hypertriglyceridemia (from Martindale, The Extra Pharmacopoeia, 30th ed, p986). 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-α 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.

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 Weight

242.699

Monoisotopic Molecular Weight

242.070972053

IUPAC Name

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

Traditional Name

artes

CAS Registry Number

637-07-0

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 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014774)
Membrane (HMDB: HMDB0014774)

Source

Exogenous

Exogenous (HMDB: HMDB0014774)

Process

Not Available

Role

Not Available

Physical Properties

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon