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

Details

Stereochemistry ACHIRAL
Molecular Formula C19H20ClNO4
Molecular Weight 361.8201
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BEZAFIBRATE

SMILES

CC(C)(C(=O)O)Oc1ccc(cc1)CCNC(=O)c2ccc(cc2)Cl

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

Molecular Formula C19H20ClNO4
Molecular Weight 361.8201
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/9171241 | https://www.ncbi.nlm.nih.gov/pubmed/24759758

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

Curator's Comment:: Bezafibrate is CNS active in rodents. No human data available.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
BEZALIP

Approved Use

Bezafibrate belongs to a group of medicines known as lipid-lowering substances.
PubMed

PubMed

TitleDatePubMed
Uncoupling protein-3 mRNA levels are increased in white adipose tissue and skeletal muscle of bezafibrate-treated rats.
1999 Jul 5
Peroxisome proliferator-activated receptor alpha (PPARalpha) activators, bezafibrate and Wy-14,643, increase uncoupling protein-3 mRNA levels without modifying the mitochondrial membrane potential in primary culture of rat preadipocytes.
2000 Aug 15
Fibrate-induced increase in blood urea and creatinine: is gemfibrozil the only innocuous agent?
2000 Dec
Impaired expression of the uncoupling protein-3 gene in skeletal muscle during lactation: fibrates and troglitazone reverse lactation-induced downregulation of the uncoupling protein-3 gene.
2000 Jul
A paradoxical severe decrease in serum HDL-cholesterol after treatment with a fibrate.
2000 Oct
Down-regulation of uncoupling protein-3 and -2 by thiazolidinediones in C2C12 myotubes.
2000 Oct 27
[Marked creatine-phosphokinase elevation in myopathy after treatment with bezafibrate].
2000 Sep
Effects of diet, drugs, and genes on plasma fibrinogen levels.
2001
Homocysteine elevation with fibrates: is it a class effect?
2001 Apr
Bezafibrate reduces heart rate and blood pressure in patients with hypertriglyceridemia.
2001 Apr
Antihypertensive mechanisms of lipid-lowering drugs: decoding the Rosetta stone's inscriptions'.
2001 Apr
Effect of bezafibrate on soluble adhesion molecules and platelet activation markers in patients with connective tissue diseases and secondary hyperlipidemia.
2001 Apr
Concurrent administration of sustained-release bezafibrate may counteract the increased thrombotic risk associated with oral estrogen therapy.
2001 Aug
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
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
Determination of drug residues in water by the combination of liquid chromatography or capillary electrophoresis with electrospray mass spectrometry.
2001 Feb 23
Bezafibrate induces acyl-CoA oxidase mRNA levels and fatty acid peroxisomal beta-oxidation in rat white adipose tissue.
2001 Jan
Effects of fluvastatin and bezafibrate combination on plasma fibrinogen, t-plasminogen activator inhibitor and C reactive protein levels in coronary artery disease patients with mixed hyperlipidaemia (FACT Study)--a rebuttal.
2001 Jan
Treating dyslipidaemia in non-insulin-dependent diabetes mellitus -- a special reference to statins.
2001 Jul-Aug
Three-dimensional high voltage electron microscopy of thick biological specimens.
2001 Jun
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
[Drug combination therapies for patients with hyperlipidemia and its significance].
2001 Mar
Plasma concentrations of active lovastatin acid are markedly increased by gemfibrozil but not by bezafibrate.
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
Squalene synthase inhibitors reduce plasma triglyceride through a low-density lipoprotein receptor-independent mechanism.
2001 Nov 23
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
Investigation into the efficacy of bezafibrate against primary biliary cirrhosis, with histological references from cases receiving long term monotherapy.
2002 Jan
Patents

Sample Use Guides

Bezafibrate recommended dosage is 200 mg 3 times daily, or alternatively 400 mg once daily as a sustained-release preparation.
Route of Administration: Oral
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
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:17:10 UTC 2021
Edited
by admin
on Fri Jun 25 21:17:10 UTC 2021
Record UNII
Y9449Q51XH
Record Status Validated (UNII)
Record Version
  • Download
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 [EP MONOGRAPH]
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
NSC-758174
Code English
BEZATOL SR
Brand Name English
BEZAFIBRATE [MI]
Common Name English
BEZAFIBRATE [MART.]
Common Name English
Classification Tree Code System Code
WHO-VATC QC10AB02
Created by admin on Fri Jun 25 21:17:10 UTC 2021 , Edited by admin on Fri Jun 25 21:17:10 UTC 2021
FDA ORPHAN DRUG 400013
Created by admin on Fri Jun 25 21:17:10 UTC 2021 , Edited by admin on Fri Jun 25 21:17:10 UTC 2021
WHO-ATC C10AB02
Created by admin on Fri Jun 25 21:17:10 UTC 2021 , Edited by admin on Fri Jun 25 21:17:10 UTC 2021
NCI_THESAURUS C98150
Created by admin on Fri Jun 25 21:17:10 UTC 2021 , Edited by admin on Fri Jun 25 21:17:10 UTC 2021
Code System Code Type Description
INN
3968
Created by admin on Fri Jun 25 21:17:10 UTC 2021 , Edited by admin on Fri Jun 25 21:17:10 UTC 2021
PRIMARY
FDA UNII
Y9449Q51XH
Created by admin on Fri Jun 25 21:17:10 UTC 2021 , Edited by admin on Fri Jun 25 21:17:10 UTC 2021
PRIMARY
PUBCHEM
39042
Created by admin on Fri Jun 25 21:17:10 UTC 2021 , Edited by admin on Fri Jun 25 21:17:10 UTC 2021
PRIMARY
DRUG BANK
DB01393
Created by admin on Fri Jun 25 21:17:10 UTC 2021 , Edited by admin on Fri Jun 25 21:17:10 UTC 2021
PRIMARY
MESH
D001629
Created by admin on Fri Jun 25 21:17:10 UTC 2021 , Edited by admin on Fri Jun 25 21:17:10 UTC 2021
PRIMARY
ECHA (EC/EINECS)
255-567-9
Created by admin on Fri Jun 25 21:17:10 UTC 2021 , Edited by admin on Fri Jun 25 21:17:10 UTC 2021
PRIMARY
WIKIPEDIA
BEZAFIBRATE
Created by admin on Fri Jun 25 21:17:10 UTC 2021 , Edited by admin on Fri Jun 25 21:17:10 UTC 2021
PRIMARY
EPA CompTox
41859-67-0
Created by admin on Fri Jun 25 21:17:10 UTC 2021 , Edited by admin on Fri Jun 25 21:17:10 UTC 2021
PRIMARY
NCI_THESAURUS
C87449
Created by admin on Fri Jun 25 21:17:10 UTC 2021 , Edited by admin on Fri Jun 25 21:17:10 UTC 2021
PRIMARY
CAS
41859-67-0
Created by admin on Fri Jun 25 21:17:10 UTC 2021 , Edited by admin on Fri Jun 25 21:17:10 UTC 2021
PRIMARY
DRUG CENTRAL
362
Created by admin on Fri Jun 25 21:17:10 UTC 2021 , Edited by admin on Fri Jun 25 21:17:10 UTC 2021
PRIMARY
MERCK INDEX
M2469
Created by admin on Fri Jun 25 21:17:10 UTC 2021 , Edited by admin on Fri Jun 25 21:17:10 UTC 2021
PRIMARY Merck Index
RXCUI
1525
Created by admin on Fri Jun 25 21:17:10 UTC 2021 , Edited by admin on Fri Jun 25 21:17:10 UTC 2021
PRIMARY RxNorm
IUPHAR
2668
Created by admin on Fri Jun 25 21:17:10 UTC 2021 , Edited by admin on Fri Jun 25 21:17:10 UTC 2021
PRIMARY
ChEMBL
CHEMBL264374
Created by admin on Fri Jun 25 21:17:10 UTC 2021 , Edited by admin on Fri Jun 25 21:17:10 UTC 2021
PRIMARY
EVMPD
SUB05810MIG
Created by admin on Fri Jun 25 21:17:10 UTC 2021 , Edited by admin on Fri Jun 25 21:17:10 UTC 2021
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY