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
Molecular Formula | C12H15ClO3 |
Molecular Weight | 242.699 |
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 |
---|---|---|
Glucagon secretion in primary endogenous hypertriglyceridemia before and after clofibrate treatment. | 1975 Aug |
|
Effect of halofenate and clofibrate on lipid synthesis in rat adipocytes. | 1975 Feb 20 |
|
The PPARs: from orphan receptors to drug discovery. | 2000 Feb 24 |
|
Involvement of the peroxisome proliferator-activated receptor alpha in regulating long-chain acyl-CoA thioesterases. | 2000 May |
|
Evidence against the peroxisome proliferator-activated receptor alpha (PPARalpha) as the mediator for polyunsaturated fatty acid suppression of hepatic L-pyruvate kinase gene transcription. | 2000 May |
|
Peroxisome proliferator-activated receptor alpha-null mice lack resistance to acetaminophen hepatotoxicity following clofibrate exposure. | 2000 Oct |
|
Keratinocyte differentiation in hyperproliferative epidermis: topical application of PPARalpha activators restores tissue homeostasis. | 2000 Sep |
|
[Fibrate influence on lipids and insulin resistance in patients with metabolic syndrome]. | 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 |
|
PPARalpha-dependent induction of liver microsomal esterification of estradiol and testosterone by a prototypical peroxisome proliferator. | 2001 Aug |
|
Peroxisome proliferator-activated receptor alpha (PPAR alpha) agonist, WY-14,643, increased transcription of myosin light chain-2 in cardiomyocytes. | 2001 Dec |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
[Overviews of fibrate]. | 2001 Mar |
|
Peroxisome-proliferator-activated receptors as physiological sensors of fatty acid metabolism: molecular regulation in peroxisomes. | 2001 May |
|
Modulation of cytosolic phospholipase A(2) by PPAR activators in human preadipocytes. | 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 |
|
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 |
|
PPARgamma ligands suppress proliferation of human urothelial basal cells in vitro. | 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 |
|
Presence and features of fatty acyl-CoA binding activity in rat hepatic peroxisomes. | 2002 Mar |
|
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 |
|
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 |
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
Fri Dec 15 15:08:55 GMT 2023
by
admin
on
Fri Dec 15 15:08:55 GMT 2023
|
Record UNII |
HPN91K7FU3
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
WHO-VATC |
QC10AB01
Created by
admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
|
||
|
WHO-ATC |
C10AB01
Created by
admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
|
||
|
NCI_THESAURUS |
C98150
Created by
admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
|
||
|
LIVERTOX |
NBK548134
Created by
admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
3038
Created by
admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
|
PRIMARY | |||
|
100000084334
Created by
admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
|
PRIMARY | |||
|
D002994
Created by
admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
|
PRIMARY | |||
|
2667
Created by
admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
|
PRIMARY | |||
|
CLOFIBRATE
Created by
admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
|
PRIMARY | |||
|
m3640
Created by
admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
|
PRIMARY | Merck Index | ||
|
DB00636
Created by
admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
|
PRIMARY | |||
|
C378
Created by
admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
|
PRIMARY | |||
|
637-07-0
Created by
admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
|
PRIMARY | |||
|
3750
Created by
admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
|
PRIMARY | |||
|
CHEMBL565
Created by
admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
|
PRIMARY | |||
|
DTXSID3020336
Created by
admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
|
PRIMARY | |||
|
79389
Created by
admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
|
PRIMARY | |||
|
2796
Created by
admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
|
PRIMARY | |||
|
HPN91K7FU3
Created by
admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
|
PRIMARY | |||
|
SUB06706MIG
Created by
admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
|
PRIMARY | |||
|
694
Created by
admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
|
PRIMARY | |||
|
211-277-4
Created by
admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
|
PRIMARY | |||
|
2594
Created by
admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
|
PRIMARY | RxNorm | ||
|
1530
Created by
admin on Fri Dec 15 15:08:55 GMT 2023 , Edited by admin on Fri Dec 15 15:08:55 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE ACTIVE -> PRODRUG |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |