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
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
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 |
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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 |
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Primary | ATROMID-S Approved UseUnknown Launch Date1967 |
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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 |
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Glucagon secretion in primary endogenous hypertriglyceridemia before and after clofibrate treatment. | 1975 Aug |
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[A 50-year history of new drugs in Japan: the developments and trends of antihyperlipidemic drugs]. | 2001 |
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[Fibrate influence on lipids and insulin resistance in patients with metabolic syndrome]. | 2001 |
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The syrian hamster embryo (SHE) cell transformation assay: review of the methods and results. | 2001 |
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Neonatal mouse model: review of methods and results. | 2001 |
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How well tolerated are lipid-lowering drugs? | 2001 |
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[Necrotizing myopathies]. | 2001 |
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Cytochrome P450 1A1 and 4A activities in isolated rat spleen lymphocytes. | 2001 Apr |
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Stimulatory effect of clofibrate on the action of estradiol in the mammary gland but not in the uterus of rats. | 2001 Apr |
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Characterization of clofibrate-induced retrograde Golgi membrane movement to the endoplasmic reticulum: clofibrate distinguishes the Golgi from the trans Golgi network. | 2001 Aug |
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Binding constant determination of drugs toward subdomain IIIA of human serum albumin by near-infrared dye-displacement capillary electrophoresis. | 2001 Aug |
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PPARalpha-dependent induction of liver microsomal esterification of estradiol and testosterone by a prototypical peroxisome proliferator. | 2001 Aug |
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Peroxisome proliferator-activated receptor alpha (PPAR alpha) agonist, WY-14,643, increased transcription of myosin light chain-2 in cardiomyocytes. | 2001 Dec |
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The use of fibrates and of statins in preventing atherosclerosis in diabetes. | 2001 Dec |
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Detection of DNA adducts using a quantitative long PCR technique and the fluorogenic 5' nuclease assay (TaqMan). | 2001 Dec 12 |
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Major clofibrate effects on liver and plasma lipids are independent of changes in polyunsaturated fatty acid composition induced by dietary fat. | 2001 Feb |
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Peroxisome proliferator-activated receptors (PPAR) and the mitochondrial aldehyde dehydrogenase (ALDH2) promoter in vitro and in vivo. | 2001 Jul |
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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 |
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Tocopherols are metabolized in HepG2 cells by side chain omega-oxidation and consecutive beta-oxidation. | 2001 Jul 15 |
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Expression and characterization of recombinant rat Acyl-CoA synthetases 1, 4, and 5. Selective inhibition by triacsin C and thiazolidinediones. | 2001 Jul 6 |
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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 |
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Characterization of the promoter region of the human peroxisomal multifunctional enzyme type 2 gene. | 2001 Jun 1 |
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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 |
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The expression of PPAR-associated genes is modulated through postnatal development of PPAR subtypes in the small intestine. | 2001 Mar 30 |
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Peroxisome-proliferator-activated receptors as physiological sensors of fatty acid metabolism: molecular regulation in peroxisomes. | 2001 May |
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Modulation of cytosolic phospholipase A(2) by PPAR activators in human preadipocytes. | 2001 May |
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Autoantibodies to lipids in bronchoalveolar lavage fluid of patients with acute respiratory distress syndrome. | 2001 Oct |
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Mechanism of clofibrate hepatotoxicity: mitochondrial damage and oxidative stress in hepatocytes. | 2001 Sep 1 |
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Comparison of various characteristics of women who do and do not attend for breast cancer screening. | 2002 |
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Troglitazone suppresses the secretion of type I collagen by mesangial cells in vitro. | 2002 Apr |
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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 |
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Effects of fatty acids on mitochondrial beta-oxidation enzyme gene expression in renal cell lines. | 2002 Aug |
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Do lipid-lowering drugs cause erectile dysfunction? A systematic review. | 2002 Feb |
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Characterization of catechol glucuronidation in rat liver. | 2002 Feb |
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Synergistic effect of 4-hydroxynonenal and PPAR ligands in controlling human leukemic cell growth and differentiation. | 2002 Feb 1 |
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In vitro induction of bilirubin conjugation in primary rat hepatocyte culture. | 2002 Feb 15 |
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Peroxisome proliferator-activated receptor ligands as antiatherogenic agents: panacea or another Pandora's box? | 2002 Jan |
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Topical peroxisome proliferator activated receptor-alpha activators reduce inflammation in irritant and allergic contact dermatitis models. | 2002 Jan |
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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 |
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Ligands of the peroxisome proliferator-activated receptors (PPAR-gamma and PPAR-alpha) reduce myocardial infarct size. | 2002 Jul |
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Prediction of compound signature using high density gene expression profiling. | 2002 Jun |
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Gene expression analysis reveals chemical-specific profiles. | 2002 Jun |
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Presence and features of fatty acyl-CoA binding activity in rat hepatic peroxisomes. | 2002 Mar |
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Potentiation of TNF-alpha-stimulated group IIA phospholipase A(2) expression by peroxisome proliferator-activated receptor alpha activators in rat mesangial cells. | 2002 Mar |
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Effect of clofibrate administration on the esterification and deesterification of steroid hormones by liver and extrahepatic tissues in rats. | 2002 Mar 1 |
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Myopathy and rhabdomyolysis with lipid-lowering drugs. | 2002 Mar 10 |
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Clofibrate-induced relocation of phosphatidylcholine transfer protein to mitochondria in endothelial cells. | 2002 Mar 10 |
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Lipid-lowering drug use and cardiovascular events after myocardial infarction. | 2002 May |
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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 |
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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.
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LIVERTOX |
NBK548134
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ACTIVE MOIETY
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