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
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)
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL239 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19817384 |
50.0 µM [EC50] | ||
Target ID: Q7RTX0 Gene ID: 83756.0 Gene Symbol: TAS1R3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/19817384 |
28.0 µM [IC50] | ||
Target ID: CHEMBL239 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10922459 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ATROMID-S Approved UseUnknown Launch Date1967 |
|||
Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
216 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7550835/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
30649 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7550835/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
103.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7550835/ |
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/16316932/ Page: 6.0 |
moderate [Inhibition 100 uM] | |||
no | ||||
not significant | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/7685601/ |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/7685601/ |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/11033061/ |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/cons/clofibrate.html
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27354598
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 | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |
ACTIVE MOIETY
PRODRUG (METABOLITE ACTIVE)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)