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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
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
Effect of halofenate and clofibrate on lipid synthesis in rat adipocytes.
1975 Feb 20
Effects of clofibrate in primary biliary cirrhosis hypercholesterolemia and gallstones.
1975 Oct
[A 50-year history of new drugs in Japan: the developments and trends of antihyperlipidemic drugs].
2001
How well tolerated are lipid-lowering drugs?
2001
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
Peroxisome proliferator-activated receptor alpha (PPAR alpha) agonist, WY-14,643, increased transcription of myosin light chain-2 in cardiomyocytes.
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
Etofibrate but not controlled-release niacin decreases LDL cholesterol and lipoprotein (a) in type IIb dyslipidemic subjects.
2001 Feb
The peroxisomal proliferator clofibrate enhances the hepatic cytoplasmic movement of fatty acids in rats.
2001 Feb
Long-chain fatty acids regulate liver carnitine palmitoyltransferase I gene (L-CPT I) expression through a peroxisome-proliferator-activated receptor alpha (PPARalpha)-independent pathway.
2001 Feb 15
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 (PPARs): novel therapeutic targets in renal disease.
2001 Jul
The biochemistry of hypo- and hyperlipidemic fatty acid derivatives: metabolism and metabolic effects.
2001 Jul
Tocopherols are metabolized in HepG2 cells by side chain omega-oxidation and consecutive beta-oxidation.
2001 Jul 15
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
Characterization of the promoter region of the human peroxisomal multifunctional enzyme type 2 gene.
2001 Jun 1
[Overviews of fibrate].
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
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
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
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
PPARgamma ligands suppress proliferation of human urothelial basal cells in vitro.
2002 Jun
Prediction of compound signature using high density gene expression profiling.
2002 Jun
Gene expression analysis reveals chemical-specific profiles.
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
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
Blunted induction of hepatic CYP4A in TNF (p55-/-/p75-/-) double receptor knockout mice following clofibrate treatment.
2002 May
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
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
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
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PRIMARY
ECHA (EC/EINECS)
212-925-9
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PRIMARY
DRUG CENTRAL
695
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PRIMARY
EVMPD
SUB06707MIG
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PRIMARY
FDA UNII
53PF01Q249
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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
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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
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PRIMARY
INN
2439
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PRIMARY
CHEBI
34648
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PRIMARY
ALANWOOD
clofibric acid
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PRIMARY
SMS_ID
100000084315
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PRIMARY
EPA CompTox
DTXSID1040661
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PRIMARY
ChEMBL
CHEMBL683
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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