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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

-9.1411202E10
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
Inhibition of transforming growth factor beta1-induced hepatoma cell apoptosis by liver tumor promoters: characterization of primary signaling events and effects on CPP32-like caspase activity.
1999 Feb
Stimulation by eicosapentaenoic acids of leptin mRNA expression and its secretion in mouse 3T3-L1 adipocytes in vitro.
2000 Apr 13
Peroxisome proliferator-activated receptor alpha-null mice lack resistance to acetaminophen hepatotoxicity following clofibrate exposure.
2000 Oct
[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
[Necrotizing myopathies].
2001
Binding constant determination of drugs toward subdomain IIIA of human serum albumin by near-infrared dye-displacement capillary electrophoresis.
2001 Aug
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
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
Three-dimensional high voltage electron microscopy of thick biological specimens.
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
Cytochrome p450-dependent metabolism of trichloroethylene in rat kidney.
2001 Mar
A systematic gene expression screen of Caenorhabditis elegans cytochrome P450 genes reveals CYP35 as strongly xenobiotic inducible.
2001 Nov 15
Comparison of various characteristics of women who do and do not attend for breast cancer screening.
2002
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
Characterization of catechol glucuronidation in rat liver.
2002 Feb
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
Ligands of the peroxisome proliferator-activated receptors (PPAR-gamma and PPAR-alpha) reduce myocardial infarct size.
2002 Jul
Effect of clofibrate administration on the esterification and deesterification of steroid hormones by liver and extrahepatic tissues in rats.
2002 Mar 1
Lipid-lowering drug use and cardiovascular events after myocardial infarction.
2002 May
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 UTC 2023 , Edited by admin on Fri Dec 15 15:08:55 UTC 2023
WHO-ATC C10AB01
Created by admin on Fri Dec 15 15:08:55 UTC 2023 , Edited by admin on Fri Dec 15 15:08:55 UTC 2023
NCI_THESAURUS C98150
Created by admin on Fri Dec 15 15:08:55 UTC 2023 , Edited by admin on Fri Dec 15 15:08:55 UTC 2023
LIVERTOX NBK548134
Created by admin on Fri Dec 15 15:08:55 UTC 2023 , Edited by admin on Fri Dec 15 15:08:55 UTC 2023
Code System Code Type Description
HSDB
3038
Created by admin on Fri Dec 15 15:08:55 UTC 2023 , Edited by admin on Fri Dec 15 15:08:55 UTC 2023
PRIMARY
SMS_ID
100000084334
Created by admin on Fri Dec 15 15:08:55 UTC 2023 , Edited by admin on Fri Dec 15 15:08:55 UTC 2023
PRIMARY
MESH
D002994
Created by admin on Fri Dec 15 15:08:55 UTC 2023 , Edited by admin on Fri Dec 15 15:08:55 UTC 2023
PRIMARY
IUPHAR
2667
Created by admin on Fri Dec 15 15:08:55 UTC 2023 , Edited by admin on Fri Dec 15 15:08:55 UTC 2023
PRIMARY
WIKIPEDIA
CLOFIBRATE
Created by admin on Fri Dec 15 15:08:55 UTC 2023 , Edited by admin on Fri Dec 15 15:08:55 UTC 2023
PRIMARY
MERCK INDEX
m3640
Created by admin on Fri Dec 15 15:08:55 UTC 2023 , Edited by admin on Fri Dec 15 15:08:55 UTC 2023
PRIMARY Merck Index
DRUG BANK
DB00636
Created by admin on Fri Dec 15 15:08:55 UTC 2023 , Edited by admin on Fri Dec 15 15:08:55 UTC 2023
PRIMARY
NCI_THESAURUS
C378
Created by admin on Fri Dec 15 15:08:55 UTC 2023 , Edited by admin on Fri Dec 15 15:08:55 UTC 2023
PRIMARY
CAS
637-07-0
Created by admin on Fri Dec 15 15:08:55 UTC 2023 , Edited by admin on Fri Dec 15 15:08:55 UTC 2023
PRIMARY
CHEBI
3750
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PRIMARY
ChEMBL
CHEMBL565
Created by admin on Fri Dec 15 15:08:55 UTC 2023 , Edited by admin on Fri Dec 15 15:08:55 UTC 2023
PRIMARY
EPA CompTox
DTXSID3020336
Created by admin on Fri Dec 15 15:08:55 UTC 2023 , Edited by admin on Fri Dec 15 15:08:55 UTC 2023
PRIMARY
NSC
79389
Created by admin on Fri Dec 15 15:08:55 UTC 2023 , Edited by admin on Fri Dec 15 15:08:55 UTC 2023
PRIMARY
PUBCHEM
2796
Created by admin on Fri Dec 15 15:08:55 UTC 2023 , Edited by admin on Fri Dec 15 15:08:55 UTC 2023
PRIMARY
FDA UNII
HPN91K7FU3
Created by admin on Fri Dec 15 15:08:55 UTC 2023 , Edited by admin on Fri Dec 15 15:08:55 UTC 2023
PRIMARY
EVMPD
SUB06706MIG
Created by admin on Fri Dec 15 15:08:55 UTC 2023 , Edited by admin on Fri Dec 15 15:08:55 UTC 2023
PRIMARY
DRUG CENTRAL
694
Created by admin on Fri Dec 15 15:08:55 UTC 2023 , Edited by admin on Fri Dec 15 15:08:55 UTC 2023
PRIMARY
ECHA (EC/EINECS)
211-277-4
Created by admin on Fri Dec 15 15:08:55 UTC 2023 , Edited by admin on Fri Dec 15 15:08:55 UTC 2023
PRIMARY
RXCUI
2594
Created by admin on Fri Dec 15 15:08:55 UTC 2023 , Edited by admin on Fri Dec 15 15:08:55 UTC 2023
PRIMARY RxNorm
INN
1530
Created by admin on Fri Dec 15 15:08:55 UTC 2023 , Edited by admin on Fri Dec 15 15:08:55 UTC 2023
PRIMARY