U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C19H20ClNO4
Molecular Weight 361.819
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BEZAFIBRATE

SMILES

CC(C)(OC1=CC=C(CCNC(=O)C2=CC=C(Cl)C=C2)C=C1)C(O)=O

InChI

InChIKey=IIBYAHWJQTYFKB-UHFFFAOYSA-N
InChI=1S/C19H20ClNO4/c1-19(2,18(23)24)25-16-9-3-13(4-10-16)11-12-21-17(22)14-5-7-15(20)8-6-14/h3-10H,11-12H2,1-2H3,(H,21,22)(H,23,24)

HIDE SMILES / InChI

Description

Bezafibrate is a lipid-lowering fibric acid derivative. Bezafibrate directly bound to and activated all three peroxisome proliferator-activated receptor (PPAR) subtypes respectively in PPAR binding and transactivation assays. However, from a biochemical point of view, bezafibrate is a PPAR ligand with a relatively low potency. Bezafibrate leads to considerable raising of HDL cholesterol and reduces triglycerides, improves insulin sensitivity and reduces blood glucose level, significantly lowering the incidence of cardiovascular events and new diabetes in patients with features of metabolic syndrome. It is the only pan-PPAR activator with more than a quarter of a century of therapeutic experience with a good safety profile.

CNS Activity

PMID

PMID

TitleDatePMID
[Clinical, epidemiologic, and biochemical findings on the reverse cholesterol transport (cholesterol-HDL)].
2001
Effects of diet, drugs, and genes on plasma fibrinogen levels.
2001
Bezafibrate-induced anaphylactic shock: unusual clinical presentation.
2001
Disorders of lipid metabolism in patients with HIV disease treated with antiretroviral agents: frequency, relationship with administered drugs, and role of hypolipidaemic therapy with bezafibrate.
2001 Apr
Effect of bezafibrate and clofibrate on the heme-iron geometry of ferrous nitrosylated heme-human serum albumin: an EPR study.
2001 Apr
Rhabdomyolysis and acute renal failure following a switchover of therapy between two fibric acid derivatives.
2001 Aug
Improvement in endothelial dysfunction in patients with hypoalphalipoproteinemia and coronary artery disease treated with bezafibrate.
2001 Aug
Bezafibrate reduces mRNA levels of adipocyte markers and increases fatty acid oxidation in primary culture of adipocytes.
2001 Aug
Concurrent administration of sustained-release bezafibrate may counteract the increased thrombotic risk associated with oral estrogen therapy.
2001 Aug
Effects of bezafibrate on beta-cell function of rat pancreatic islets.
2001 Aug 31
Alternations in hepatic expression of fatty-acid metabolizing enzymes in ArKO mice and their reversal by the treatment with 17beta-estradiol or a peroxisome proliferator.
2001 Dec
Lipid-lowering trials in diabetes.
2001 Dec
Alterations in the extrinsic pathway in hypertriglyceridemia do not cause a 'procoagulant state': effects of bezafibrate therapy.
2001 Dec
Blood lipids and first-ever ischemic stroke/transient ischemic attack in the Bezafibrate Infarction Prevention (BIP) Registry: high triglycerides constitute an independent risk factor.
2001 Dec 11
Influence of low high-density lipoprotein cholesterol and elevated triglyceride on coronary heart disease events and response to simvastatin therapy in 4S.
2001 Dec 18
15-Deoxy-delta 12,14-prostaglandin J2 and thiazolidinediones activate the MEK/ERK pathway through phosphatidylinositol 3-kinase in vascular smooth muscle cells.
2001 Dec 28
Oral antidiabetic treatment in patients with coronary disease: time-related increased mortality on combined glyburide/metformin therapy over a 7.7-year follow-up.
2001 Feb
[Fibrates in the secondary prevention of ischemic cardiopathy].
2001 Jan-Mar
Fibrate-induced increase in blood urea and creatinine.
2001 Jul
Peroxisome proliferator-activated receptors (PPARs): novel therapeutic targets in renal disease.
2001 Jul
Is pseudocholinesterase activity related to markers of triacylglycerol synthesis in Type II diabetes mellitus?
2001 Jul
Treating dyslipidaemia in non-insulin-dependent diabetes mellitus -- a special reference to statins.
2001 Jul-Aug
Long-term diuretic therapy in patients with coronary disease: increased colon cancer-related mortality over a 5-year follow-up.
2001 Jun
Effect of bezafibrate in primary biliary cirrhosis: a pilot study.
2001 Jun
Normocholesterolaemic dysslipidaemia: is there a role for fibrates?
2001 Jun 4
Effect of a pharmacological activation of PPAR on the expression of RAR and TR in rat liver.
2001 Mar
Effect of a pharmacological activation of PPAR on the expression of RAR and TR in rat liver.
2001 Mar
How is the liver primed or sensitized for alcoholic liver disease?
2001 May
Study of effectiveness of bezafibrate in the treatment of chronic hepatitis C.
2001 May
[Rhabdomyolysis and acute renal failure secondary to statins].
2001 May-Jun
Are high density lipoprotein (HDL) and triglyceride levels relevant in stroke prevention?
2001 Nov
Antecedent hyperglycemia, not hyperlipidemia, is associated with increased islet triacylglycerol content and decreased insulin gene mRNA level in Zucker diabetic fatty rats.
2001 Nov
High and low oxygen affinity conformations of T state hemoglobin.
2001 Nov
Squalene synthase inhibitors reduce plasma triglyceride through a low-density lipoprotein receptor-independent mechanism.
2001 Nov 23
Variation at position 162 of peroxisome proliferator-activated receptor alpha does not influence the effect of fibrates on cholesterol or triacylglycerol concentrations in hyperlipidaemic subjects.
2001 Oct
Antineoplastic and anti-inflammatory effects of PPAR ligands in colitis.
2001 Oct
A prospective study of plasma fibrinogen levels and the risk of stroke among participants in the bezafibrate infarction prevention study.
2001 Oct 15
Changes in matrix proteoglycans induced by insulin and fatty acids in hepatic cells may contribute to dyslipidemia of insulin resistance.
2001 Sep
Aromatase-deficient (ArKO) mice are retrieved from severe hepatic steatosis by peroxisome proliferator administration.
2002 Apr
Marked removal of bezafibrate-induced high-density lipoprotein-cholesterol by low-density lipoprotein apheresis.
2002 Apr
Soluble intercellular adhesion molecule-1 and long-term risk of acute coronary events in patients with chronic coronary heart disease. Data from the Bezafibrate Infarction Prevention (BIP) Study.
2002 Apr 3
[A case of primary sclerosing cholangitis presenting transient hypoperfusion and treated with bezafibrate beneficially].
2002 Feb
Use of fibrates in the management of hyperlipidemia in HIV-infected patients receiving HAART.
2002 Jan
Investigation into the efficacy of bezafibrate against primary biliary cirrhosis, with histological references from cases receiving long term monotherapy.
2002 Jan
Severity of angina pectoris and risk of ischemic stroke.
2002 Jan
Prevention of radiation-induced mammary tumors.
2002 Jan 1
Fibrate and statin synergistically increase the transcriptional activities of PPARalpha/RXRalpha and decrease the transactivation of NFkappaB.
2002 Jan 11
Evaluation of myopathy risk for HMG-CoA reductase inhibitors by urethane infusion method.
2002 Mar
Are high-density lipoprotein and triglyceride levels important in secondary prevention: impressions from the BIP and VA-HIT trials.
2002 Mar
Severe hypertriglyceridemia with insulin resistance is associated with systemic inflammation: reversal with bezafibrate therapy in a randomized controlled trial.
2002 Mar
Patent

Sample Use Guides

In Vivo Use Guide
Bezafibrate recommended dosage is 200 mg 3 times daily, or alternatively 400 mg once daily as a sustained-release preparation.
Route of Administration: Oral
In Vitro Use Guide
400 uM bezafibrate increases in the levels of carnitine palmitoyltransferase II activity, mitochondrial fatty acid β-oxidation, intracellular ATP, and mitochondrial membrane potential in human fibroblasts
Name Type Language
BEZAFIBRATE
EP   INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
BM 15.075
Code English
2-(P-(2-(P-CHLOROBENZAMIDO)ETHYL)PHENOXY)-2-METHYLPROPIONIC ACID
Common Name English
BEZAFIBRATE [JAN]
Common Name English
BEZAFIBRATE [WHO-DD]
Common Name English
BEZAFIBRATE [USAN]
Common Name English
BEZAFIBRATE [INN]
Common Name English
PROPANOIC ACID, 2-(4-(2-((4-CHLOROBENZOYL)AMINO)ETHYL)PHENOXY)-2-METHYL-
Common Name English
BM-15075
Code English
BM-15.075
Code English
BEZATOL SR
Brand Name English
BEZAFIBRATE [EP]
Common Name English
BEZAFIBRATE [MI]
Common Name English
BEZAFIBRATE [MART.]
Common Name English
Classification Tree Code System Code
WHO-VATC QC10AB02
Created by admin on Tue Mar 06 12:04:53 UTC 2018 , Edited by admin on Tue Mar 06 12:04:53 UTC 2018
WHO-ATC C10AB02
Created by admin on Tue Mar 06 12:04:53 UTC 2018 , Edited by admin on Tue Mar 06 12:04:53 UTC 2018
Code System Code Type Description
INN
3968
Created by admin on Tue Mar 06 12:04:53 UTC 2018 , Edited by admin on Tue Mar 06 12:04:53 UTC 2018
PRIMARY
PUBCHEM
39042
Created by admin on Tue Mar 06 12:04:53 UTC 2018 , Edited by admin on Tue Mar 06 12:04:53 UTC 2018
PRIMARY SWITZERF
DRUG BANK
DB01393
Created by admin on Tue Mar 06 12:04:53 UTC 2018 , Edited by admin on Tue Mar 06 12:04:53 UTC 2018
PRIMARY
MESH
D001629
Created by admin on Tue Mar 06 12:04:53 UTC 2018 , Edited by admin on Tue Mar 06 12:04:53 UTC 2018
PRIMARY
ECHA (EC/EINECS)
255-567-9
Created by admin on Tue Mar 06 12:04:53 UTC 2018 , Edited by admin on Tue Mar 06 12:04:53 UTC 2018
PRIMARY
WIKIPEDIA
BEZAFIBRATE
Created by admin on Tue Mar 06 12:04:53 UTC 2018 , Edited by admin on Tue Mar 06 12:04:53 UTC 2018
PRIMARY
EPA CompTox
41859-67-0
Created by admin on Tue Mar 06 12:04:53 UTC 2018 , Edited by admin on Tue Mar 06 12:04:53 UTC 2018
PRIMARY
NCI_THESAURUS
C87449
Created by admin on Tue Mar 06 12:04:53 UTC 2018 , Edited by admin on Tue Mar 06 12:04:53 UTC 2018
PRIMARY
CAS
41859-67-0
Created by admin on Tue Mar 06 12:04:53 UTC 2018 , Edited by admin on Tue Mar 06 12:04:53 UTC 2018
PRIMARY
MERCK INDEX
M2469
Created by admin on Tue Mar 06 12:04:53 UTC 2018 , Edited by admin on Tue Mar 06 12:04:53 UTC 2018
PRIMARY Merck Index
RXCUI
1525
Created by admin on Tue Mar 06 12:04:53 UTC 2018 , Edited by admin on Tue Mar 06 12:04:53 UTC 2018
PRIMARY RxNorm
IUPHAR
2668
Created by admin on Tue Mar 06 12:04:53 UTC 2018 , Edited by admin on Tue Mar 06 12:04:53 UTC 2018
PRIMARY
ChEMBL
CHEMBL264374
Created by admin on Tue Mar 06 12:04:53 UTC 2018 , Edited by admin on Tue Mar 06 12:04:53 UTC 2018
PRIMARY
EVMPD
SUB05810MIG
Created by admin on Tue Mar 06 12:04:53 UTC 2018 , Edited by admin on Tue Mar 06 12:04:53 UTC 2018
PRIMARY