Details
Stereochemistry | ACHIRAL |
Molecular Formula | C10H11ClO3.C8H11NO3 |
Molecular Weight | 383.823 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=C(O)C(CO)=C(CO)C=N1.CC(C)(OC2=CC=C(Cl)C=C2)C(O)=O
InChI
InChIKey=XHNQLDLSWAXHBW-UHFFFAOYSA-N
InChI=1S/C10H11ClO3.C8H11NO3/c1-10(2,9(12)13)14-8-5-3-7(11)4-6-8;1-5-8(12)7(4-11)6(3-10)2-9-5/h3-6H,1-2H3,(H,12,13);2,10-12H,3-4H2,1H3
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 |
Molecular Formula | C8H11NO3 |
Molecular Weight | 169.1778 |
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 |
---|---|---|
Peroxisome proliferator-activated receptor alpha-null mice lack resistance to acetaminophen hepatotoxicity following clofibrate exposure. | 2000 Oct |
|
[A 50-year history of new drugs in Japan: the developments and trends of antihyperlipidemic drugs]. | 2001 |
|
[Fibrate influence on lipids and insulin resistance in patients with metabolic syndrome]. | 2001 |
|
Use of isotopes and LC-MS-ESI-TOF for mechanistic studies of tienilic acid metabolic activation. | 2001 |
|
The syrian hamster embryo (SHE) cell transformation assay: review of the methods and results. | 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 |
|
Characterization of clofibrate-induced retrograde Golgi membrane movement to the endoplasmic reticulum: clofibrate distinguishes the Golgi from the trans Golgi network. | 2001 Aug |
|
Peroxisome proliferator-activated receptor alpha (PPAR alpha) agonist, WY-14,643, increased transcription of myosin light chain-2 in cardiomyocytes. | 2001 Dec |
|
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 |
|
Unique gene expression patterns in liver and kidney associated with exposure to chemical toxicants. | 2001 Jun |
|
Three-dimensional high voltage electron microscopy of thick biological specimens. | 2001 Jun |
|
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 |
|
Troglitazone suppresses the secretion of type I collagen by mesangial cells in vitro. | 2002 Apr |
|
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 |
|
Eighth World Congress of Intensive and Critical Care Medicine, 28 October-1 November 2001, Sydney, Australia: Harm minimization and effective risk management. | 2002 Feb |
|
Topical peroxisome proliferator activated receptor-alpha activators reduce inflammation in irritant and allergic contact dermatitis models. | 2002 Jan |
|
Fibrate and statin synergistically increase the transcriptional activities of PPARalpha/RXRalpha and decrease the transactivation of NFkappaB. | 2002 Jan 11 |
|
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 |
|
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 |
|
Potentiation of TNF-alpha-stimulated group IIA phospholipase A(2) expression by peroxisome proliferator-activated receptor alpha activators in rat mesangial cells. | 2002 Mar |
|
Effect of clofibrate administration on the esterification and deesterification of steroid hormones by liver and extrahepatic tissues in rats. | 2002 Mar 1 |
|
Myopathy and rhabdomyolysis with lipid-lowering drugs. | 2002 Mar 10 |
|
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 |
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
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Record UNII |
097241263Y
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Record Status |
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Record Version |
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