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)
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
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 |
---|---|---|
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 |
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 17:51:53 GMT 2023
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Record UNII |
53PF01Q249
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Record Status |
Validated (UNII)
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Record Version |
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C541
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1149
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2797
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212-925-9
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SUB06707MIG
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53PF01Q249
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m3641
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D002995
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C81531
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CLOFIBRIC ACID
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2439
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34648
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clofibric acid
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100000084315
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DTXSID1040661
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CHEMBL683
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882-09-7
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> ACTIVATOR |
EC50
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METABOLIC ENZYME -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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PRODRUG -> METABOLITE ACTIVE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |