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Details

Stereochemistry ACHIRAL
Molecular Formula C10H11ClO3
Molecular Weight 214.646
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLOFIBRIC ACID

SMILES

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

InChI

InChIKey=TXCGAZHTZHNUAI-UHFFFAOYSA-N
InChI=1S/C10H11ClO3/c1-10(2,9(12)13)14-8-5-3-7(11)4-6-8/h3-6H,1-2H3,(H,12,13)

HIDE SMILES / InChI

Molecular Formula C10H11ClO3
Molecular Weight 214.646
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
Activators of peroxisome proliferator-activated receptor-alpha induce the expression of the uncoupling protein-3 gene in skeletal muscle: a potential mechanism for the lipid intake-dependent activation of uncoupling protein-3 gene expression at birth.
1999 Jun
Mitochondrial damage by the "pro-oxidant" peroxisomal proliferator clofibrate.
1999 Nov
Acyl-CoA thioesterases belong to a novel gene family of peroxisome proliferator-regulated enzymes involved in lipid metabolism.
2000
Involvement of the peroxisome proliferator-activated receptor alpha in regulating long-chain acyl-CoA thioesterases.
2000 May
Keratinocyte differentiation in hyperproliferative epidermis: topical application of PPARalpha activators restores tissue homeostasis.
2000 Sep
Tg.AC genetically altered mouse: assay working group overview of available data.
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
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
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
The use of fibrates and of statins in preventing atherosclerosis in diabetes.
2001 Dec
The transcription of the peroxisome proliferator-activated receptor alpha gene is regulated by protein kinase C.
2001 Dec 15
Molecular cloning and regulation of expression of two novel mouse CYP4F genes: expression in peroxisome proliferator-activated receptor alpha-deficient mice upon lipopolysaccharide and clofibrate challenges.
2001 Feb
Stimulatory effect of clofibrate and gemfibrozil administration on the formation of fatty acid esters of estradiol by rat liver microsomes.
2001 Jan
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
Peroxisome proliferator-activated receptors (PPAR) and the mitochondrial aldehyde dehydrogenase (ALDH2) promoter in vitro and in vivo.
2001 Jul
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
Allosteric modification of oxygen delivery by hemoglobin.
2001 Mar
Cytochrome p450-dependent metabolism of trichloroethylene in rat kidney.
2001 Mar
Differential induction of rat hepatic cytochromes P450 3A1, 3A2, 2B1, 2B2, and 2E1 in response to pyridine treatment.
2001 Mar
Peroxisome-proliferator-activated receptors as physiological sensors of fatty acid metabolism: molecular regulation in peroxisomes.
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
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
Synergistic effect of 4-hydroxynonenal and PPAR ligands in controlling human leukemic cell growth and differentiation.
2002 Feb 1
Topical peroxisome proliferator activated receptor-alpha activators reduce inflammation in irritant and allergic contact dermatitis models.
2002 Jan
PPARgamma ligands suppress proliferation of human urothelial basal cells in vitro.
2002 Jun
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
Clofibrate-induced relocation of phosphatidylcholine transfer protein to mitochondria in endothelial cells.
2002 Mar 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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:51:53 GMT 2023
Edited
by admin
on Sat Dec 16 17:51:53 GMT 2023
Record UNII
53PF01Q249
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CLOFIBRIC ACID
INN   MI   WHO-DD  
INN  
Official Name English
CLOFIBRIC ACID [MI]
Common Name English
NSC-1149
Code English
clofibric acid [INN]
Common Name English
2-(4-CHLOROPHENOXY)-2-METHYLPROPIONIC ACID
Systematic Name English
Clofibric acid [WHO-DD]
Common Name English
2-(P-CHLOROPHENOXY)-2-METHYLPROPIONIC ACID
Common Name English
2-(4-CHLOROPHENOXY)-2-METHYLPROPANOIC ACID
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C541
Created by admin on Sat Dec 16 17:51:55 GMT 2023 , Edited by admin on Sat Dec 16 17:51:55 GMT 2023
Code System Code Type Description
NSC
1149
Created by admin on Sat Dec 16 17:51:55 GMT 2023 , Edited by admin on Sat Dec 16 17:51:55 GMT 2023
PRIMARY
PUBCHEM
2797
Created by admin on Sat Dec 16 17:51:55 GMT 2023 , Edited by admin on Sat Dec 16 17:51:55 GMT 2023
PRIMARY
ECHA (EC/EINECS)
212-925-9
Created by admin on Sat Dec 16 17:51:55 GMT 2023 , Edited by admin on Sat Dec 16 17:51:55 GMT 2023
PRIMARY
DRUG CENTRAL
695
Created by admin on Sat Dec 16 17:51:55 GMT 2023 , Edited by admin on Sat Dec 16 17:51:55 GMT 2023
PRIMARY
EVMPD
SUB06707MIG
Created by admin on Sat Dec 16 17:51:55 GMT 2023 , Edited by admin on Sat Dec 16 17:51:55 GMT 2023
PRIMARY
FDA UNII
53PF01Q249
Created by admin on Sat Dec 16 17:51:55 GMT 2023 , Edited by admin on Sat Dec 16 17:51:55 GMT 2023
PRIMARY
MERCK INDEX
m3641
Created by admin on Sat Dec 16 17:51:55 GMT 2023 , Edited by admin on Sat Dec 16 17:51:55 GMT 2023
PRIMARY Merck Index
MESH
D002995
Created by admin on Sat Dec 16 17:51:55 GMT 2023 , Edited by admin on Sat Dec 16 17:51:55 GMT 2023
PRIMARY
NCI_THESAURUS
C81531
Created by admin on Sat Dec 16 17:51:55 GMT 2023 , Edited by admin on Sat Dec 16 17:51:55 GMT 2023
PRIMARY
WIKIPEDIA
CLOFIBRIC ACID
Created by admin on Sat Dec 16 17:51:55 GMT 2023 , Edited by admin on Sat Dec 16 17:51:55 GMT 2023
PRIMARY
INN
2439
Created by admin on Sat Dec 16 17:51:55 GMT 2023 , Edited by admin on Sat Dec 16 17:51:55 GMT 2023
PRIMARY
CHEBI
34648
Created by admin on Sat Dec 16 17:51:55 GMT 2023 , Edited by admin on Sat Dec 16 17:51:55 GMT 2023
PRIMARY
ALANWOOD
clofibric acid
Created by admin on Sat Dec 16 17:51:55 GMT 2023 , Edited by admin on Sat Dec 16 17:51:55 GMT 2023
PRIMARY
SMS_ID
100000084315
Created by admin on Sat Dec 16 17:51:55 GMT 2023 , Edited by admin on Sat Dec 16 17:51:55 GMT 2023
PRIMARY
EPA CompTox
DTXSID1040661
Created by admin on Sat Dec 16 17:51:55 GMT 2023 , Edited by admin on Sat Dec 16 17:51:55 GMT 2023
PRIMARY
ChEMBL
CHEMBL683
Created by admin on Sat Dec 16 17:51:55 GMT 2023 , Edited by admin on Sat Dec 16 17:51:55 GMT 2023
PRIMARY
CAS
882-09-7
Created by admin on Sat Dec 16 17:51:55 GMT 2023 , Edited by admin on Sat Dec 16 17:51:55 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TARGET -> ACTIVATOR
EC50
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
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PRODRUG -> METABOLITE ACTIVE
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ACTIVE MOIETY