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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

Molecular Formula C12H15ClO3
Molecular Weight 242.699
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Effect of halofenate and clofibrate on lipid synthesis in rat adipocytes.
1975 Feb 20
The PPARs: from orphan receptors to drug discovery.
2000 Feb 24
Involvement of the peroxisome proliferator-activated receptor alpha in regulating long-chain acyl-CoA thioesterases.
2000 May
Evidence against the peroxisome proliferator-activated receptor alpha (PPARalpha) as the mediator for polyunsaturated fatty acid suppression of hepatic L-pyruvate kinase gene transcription.
2000 May
Peroxisome proliferator-activated receptor alpha-null mice lack resistance to acetaminophen hepatotoxicity following clofibrate exposure.
2000 Oct
Keratinocyte differentiation in hyperproliferative epidermis: topical application of PPARalpha activators restores tissue homeostasis.
2000 Sep
[Fibrate influence on lipids and insulin resistance in patients with metabolic syndrome].
2001
Neonatal mouse model: review of methods and results.
2001
How well tolerated are lipid-lowering drugs?
2001
[Necrotizing myopathies].
2001
Use of real-time gene-specific polymerase chain reaction to measure RNA expression of three family members of rat cytochrome P450 4A.
2001
WY-14,643 and other agonists of the peroxisome proliferator-activated receptor reveal a new mode of action for salicylic acid in soybean disease resistance.
2001 Apr
Cytochrome P450 1A1 and 4A activities in isolated rat spleen lymphocytes.
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
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
Effects of polyunsaturated fatty acids and clofibrate on chicken stearoyl-coA desaturase 1 gene expression.
2001 Jan 12
The transcriptional and DNA binding activity of peroxisome proliferator-activated receptor alpha is inhibited by ethanol metabolism. A novel mechanism for the development of ethanol-induced fatty liver.
2001 Jan 5
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
Peroxisome proliferator-activated receptors (PPARs): novel therapeutic targets in renal disease.
2001 Jul
The biochemistry of hypo- and hyperlipidemic fatty acid derivatives: metabolism and metabolic effects.
2001 Jul
Accumulation of medium chain acyl-CoAs during beta-oxidation of long chain fatty acid by isolated peroxisomes from rat liver.
2001 Jun
Unique gene expression patterns in liver and kidney associated with exposure to chemical toxicants.
2001 Jun
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
[Overviews of fibrate].
2001 Mar
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
Contribution of CYP1A2 in the hepatic metabolism of melatonin: studies with isolated microsomal preparations and liver slices.
2001 Nov
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
Eighth World Congress of Intensive and Critical Care Medicine, 28 October-1 November 2001, Sydney, Australia: Harm minimization and effective risk management.
2002 Feb
PPARgamma ligands suppress proliferation of human urothelial basal cells in vitro.
2002 Jun
Effects of peroxisome proliferator-activated receptor agonists on LPS-induced neuronal death in mixed cortical neurons: associated with iNOS and COX-2.
2002 Jun 21
Influence of peroxisome proliferator-activated receptor alpha agonists on the intracellular turnover and secretion of apolipoprotein (Apo) B-100 and ApoB-48.
2002 Jun 21
Presence and features of fatty acyl-CoA binding activity in rat hepatic peroxisomes.
2002 Mar
Effect of clofibrate administration on the esterification and deesterification of steroid hormones by liver and extrahepatic tissues in rats.
2002 Mar 1
Clofibrate-induced relocation of phosphatidylcholine transfer protein to mitochondria in endothelial cells.
2002 Mar 10
Getting a GRIP on liprins.
2002 Mar 28
Activation of the immune system and inflammatory activity in relation to markers of atherothrombotic disease and atherosclerosis in rheumatoid arthritis.
2002 May
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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:08:55 GMT 2023
Edited
by admin
on Fri Dec 15 15:08:55 GMT 2023
Record UNII
HPN91K7FU3
Record Status Validated (UNII)
Record Version
  • Download
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
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
MESH
D002994
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
IUPHAR
2667
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
WIKIPEDIA
CLOFIBRATE
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
MERCK INDEX
m3640
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 Merck Index
DRUG BANK
DB00636
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
NCI_THESAURUS
C378
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
CAS
637-07-0
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
CHEBI
3750
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
ChEMBL
CHEMBL565
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
EPA CompTox
DTXSID3020336
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
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
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
DRUG CENTRAL
694
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
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
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