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Details

Stereochemistry ACHIRAL
Molecular Formula C12H15ClO3
Molecular Weight 242.699
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLOFIBRATE

SMILES

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

InChI

InChIKey=KNHUKKLJHYUCFP-UHFFFAOYSA-N
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

HIDE SMILES / InChI
Clofibrate is a fibric acid derivative used to lower cholesterol and triglyceride (fat-like substances) levels in the blood. This may help prevent medical problems caused by such substances clogging the blood vessels. However, this treatment was discontinued in 2002 due to adverse effects. Clofibrate is an agonist of the PPAR-α receptor 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, and increased lipoprotein lipase activity. Clofibrate increased the activity of extrahepatic lipoprotein lipase (LL), thereby increasing lipoprotein triglyceride lipolysis, inhibited the synthesis, and increases the clearance of apolipoprotein B, a carrier molecule for VLDL. In addition, clofibrate was investigated as a novel therapy agent in multiple myeloma and it shown the promising results.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
50.0 µM [EC50]
Target ID: Q7RTX0
Gene ID: 83756.0
Gene Symbol: TAS1R3
Target Organism: Homo sapiens (Human)
28.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ATROMID-S

Approved Use

Unknown

Launch Date

1967
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
216 μg/mL
100 mg/kg single, oral
dose: 100 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
CLOFIBRIC ACID plasma
Homo sapiens
population: UNHEALTHY
age: NEWBORN
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
30649 μg × h/mL
100 mg/kg single, oral
dose: 100 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
CLOFIBRIC ACID plasma
Homo sapiens
population: UNHEALTHY
age: NEWBORN
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
103.1 h
100 mg/kg single, oral
dose: 100 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
CLOFIBRIC ACID plasma
Homo sapiens
population: UNHEALTHY
age: NEWBORN
sex: FEMALE / MALE
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​
PubMed

PubMed

TitleDatePubMed
Glucagon secretion in primary endogenous hypertriglyceridemia before and after clofibrate treatment.
1975 Aug
[A 50-year history of new drugs in Japan: the developments and trends of antihyperlipidemic drugs].
2001
[Fibrate influence on lipids and insulin resistance in patients with metabolic syndrome].
2001
The syrian hamster embryo (SHE) cell transformation assay: review of the methods and results.
2001
Neonatal mouse model: review of methods and results.
2001
How well tolerated are lipid-lowering drugs?
2001
[Necrotizing myopathies].
2001
Cytochrome P450 1A1 and 4A activities in isolated rat spleen lymphocytes.
2001 Apr
Stimulatory effect of clofibrate on the action of estradiol in the mammary gland but not in the uterus of rats.
2001 Apr
Characterization of clofibrate-induced retrograde Golgi membrane movement to the endoplasmic reticulum: clofibrate distinguishes the Golgi from the trans Golgi network.
2001 Aug
Binding constant determination of drugs toward subdomain IIIA of human serum albumin by near-infrared dye-displacement capillary electrophoresis.
2001 Aug
PPARalpha-dependent induction of liver microsomal esterification of estradiol and testosterone by a prototypical peroxisome proliferator.
2001 Aug
Peroxisome proliferator-activated receptor alpha (PPAR alpha) agonist, WY-14,643, increased transcription of myosin light chain-2 in cardiomyocytes.
2001 Dec
The use of fibrates and of statins in preventing atherosclerosis in diabetes.
2001 Dec
Detection of DNA adducts using a quantitative long PCR technique and the fluorogenic 5' nuclease assay (TaqMan).
2001 Dec 12
Major clofibrate effects on liver and plasma lipids are independent of changes in polyunsaturated fatty acid composition induced by dietary fat.
2001 Feb
Peroxisome proliferator-activated receptors (PPAR) and the mitochondrial aldehyde dehydrogenase (ALDH2) promoter in vitro and in vivo.
2001 Jul
Hormonal regulation of multiple promoters of the rat mitochondrial glycerol-3-phosphate dehydrogenase gene: identification of a complex hormone-response element in the ubiquitous promoter B.
2001 Jul
Tocopherols are metabolized in HepG2 cells by side chain omega-oxidation and consecutive beta-oxidation.
2001 Jul 15
Expression and characterization of recombinant rat Acyl-CoA synthetases 1, 4, and 5. Selective inhibition by triacsin C and thiazolidinediones.
2001 Jul 6
Localization of mRNAs encoding peroxisomal proteins in cell culture by non-radioactive in situ hybridization. Comparison of rat and human hepatoma cells and their responses to two divergent hypolipidemic drugs.
2001 Jun
Characterization of the promoter region of the human peroxisomal multifunctional enzyme type 2 gene.
2001 Jun 1
Combined interferon-alfa, 13-cis-retinoic acid, and alpha-tocopherol in locally advanced head and neck squamous cell carcinoma: novel bioadjuvant phase II trial.
2001 Jun 15
The expression of PPAR-associated genes is modulated through postnatal development of PPAR subtypes in the small intestine.
2001 Mar 30
Peroxisome-proliferator-activated receptors as physiological sensors of fatty acid metabolism: molecular regulation in peroxisomes.
2001 May
Modulation of cytosolic phospholipase A(2) by PPAR activators in human preadipocytes.
2001 May
Autoantibodies to lipids in bronchoalveolar lavage fluid of patients with acute respiratory distress syndrome.
2001 Oct
Mechanism of clofibrate hepatotoxicity: mitochondrial damage and oxidative stress in hepatocytes.
2001 Sep 1
Comparison of various characteristics of women who do and do not attend for breast cancer screening.
2002
Troglitazone suppresses the secretion of type I collagen by mesangial cells in vitro.
2002 Apr
Role of hypolipidemic drug clofibrate in altering iron regulatory proteins IRP1 and IRP2 activities and hepatic iron metabolism in rats fed a low-iron diet.
2002 Apr 15
Effects of fatty acids on mitochondrial beta-oxidation enzyme gene expression in renal cell lines.
2002 Aug
Do lipid-lowering drugs cause erectile dysfunction? A systematic review.
2002 Feb
Characterization of catechol glucuronidation in rat liver.
2002 Feb
Synergistic effect of 4-hydroxynonenal and PPAR ligands in controlling human leukemic cell growth and differentiation.
2002 Feb 1
In vitro induction of bilirubin conjugation in primary rat hepatocyte culture.
2002 Feb 15
Peroxisome proliferator-activated receptor ligands as antiatherogenic agents: panacea or another Pandora's box?
2002 Jan
Topical peroxisome proliferator activated receptor-alpha activators reduce inflammation in irritant and allergic contact dermatitis models.
2002 Jan
CYP1A-mediated metabolism of the Janus kinase-3 inhibitor 4-(4'-hydroxyphenyl)-amino-6,7-dimethoxyquinazoline: structural basis for inactivation by regioselective O-demethylation.
2002 Jan
Ligands of the peroxisome proliferator-activated receptors (PPAR-gamma and PPAR-alpha) reduce myocardial infarct size.
2002 Jul
Prediction of compound signature using high density gene expression profiling.
2002 Jun
Gene expression analysis reveals chemical-specific profiles.
2002 Jun
Presence and features of fatty acyl-CoA binding activity in rat hepatic peroxisomes.
2002 Mar
Potentiation of TNF-alpha-stimulated group IIA phospholipase A(2) expression by peroxisome proliferator-activated receptor alpha activators in rat mesangial cells.
2002 Mar
Effect of clofibrate administration on the esterification and deesterification of steroid hormones by liver and extrahepatic tissues in rats.
2002 Mar 1
Myopathy and rhabdomyolysis with lipid-lowering drugs.
2002 Mar 10
Clofibrate-induced relocation of phosphatidylcholine transfer protein to mitochondria in endothelial cells.
2002 Mar 10
Lipid-lowering drug use and cardiovascular events after myocardial infarction.
2002 May
Selective inhibition of cyclooxygenase-2 expression by 15-deoxy-Delta(12,14)(12,14)-prostaglandin J(2) in activated human astrocytes, but not in human brain macrophages.
2002 May 1
Exposure simulation for pharmaceuticals in European surface waters with GREAT-ER.
2002 May 10
Patents

Sample Use Guides

In Vivo Use Guide
For oral dosage form (capsules): for high cholesterol: adults—1.5 to 2 grams a day. This is divided into two to four doses. Children—Dose must be determined by doctor.
Route of Administration: Oral
The antitumor apoptotic effect of clofibrate at doses ranging from 0.1-600 μM was investigated on four human and one murine myeloma cell lines, as well as in two human lymphoma cell lines, using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium-bromide assay. Clofibrate significantly reduced cell viability in all tested myeloma and lymphoma cell lines in a dose-dependent manner, while healthy cells were hardly affected.
Name Type Language
CLOFIBRATE
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
PROPANOIC ACID, 2-(4-CHLOROPHENOXY)-2-METHYL-, ETHYL ESTER
Common Name English
PROPIONIC ACID, 2-(P-CHLOROPHENOXY)-2-METHYL-, ETHYL ESTER
Systematic Name English
ETHYL P-CHLOROPHENOXYISOBUTYRATE
Common Name English
CLOFIBRATE [ORANGE BOOK]
Common Name English
ICI 28257
Code English
CLOFIBRATE [MART.]
Common Name English
CLOFIBRATE [JAN]
Common Name English
ATROMID
Brand Name English
Clofibrate [WHO-DD]
Common Name English
CLOFIBRATE [USP IMPURITY]
Common Name English
AY-61123
Code English
NSC-79389
Code English
CLOFIBRATE [EP MONOGRAPH]
Common Name English
CLOFIBRATE [USAN]
Common Name English
CLOFIBRATE [IARC]
Common Name English
clofibrate [INN]
Common Name English
CLOFIBRATE [MI]
Common Name English
ICI-28257
Code English
CLOFIBRATE [VANDF]
Common Name English
ATROMID-S
Brand Name English
CLOFIBRATE [HSDB]
Common Name English
ETHYL 2-(P-CHLOROPHENOXY)-2-METHYLPROPIONATE
Common Name English
Classification Tree Code System Code
WHO-VATC QC10AB01
Created by admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
WHO-ATC C10AB01
Created by admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
NCI_THESAURUS C98150
Created by admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
LIVERTOX NBK548134
Created by admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
Code System Code Type Description
HSDB
3038
Created by admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
PRIMARY
SMS_ID
100000084334
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PRIMARY
MESH
D002994
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PRIMARY
IUPHAR
2667
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PRIMARY
WIKIPEDIA
CLOFIBRATE
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PRIMARY
MERCK INDEX
m3640
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PRIMARY Merck Index
DRUG BANK
DB00636
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PRIMARY
NCI_THESAURUS
C378
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PRIMARY
CAS
637-07-0
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PRIMARY
CHEBI
3750
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PRIMARY
ChEMBL
CHEMBL565
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PRIMARY
EPA CompTox
DTXSID3020336
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PRIMARY
NSC
79389
Created by admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
PRIMARY
PUBCHEM
2796
Created by admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
PRIMARY
FDA UNII
HPN91K7FU3
Created by admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
PRIMARY
EVMPD
SUB06706MIG
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PRIMARY
DRUG CENTRAL
694
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PRIMARY
ECHA (EC/EINECS)
211-277-4
Created by admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
PRIMARY
RXCUI
2594
Created by admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
PRIMARY RxNorm
INN
1530
Created by admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
PRIMARY