BEZAFIBRATE

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16168052
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Peroxisome proliferator-activated receptor alpha 60 Target ID: CHEMBL239 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9171241 \| https://www.ncbi.nlm.nih.gov/pubmed/24759758	Agonist 2458	37.37 µM [EC50]
Peroxisome proliferator-activated receptor delta 22 Target ID: CHEMBL3979 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9171241 \| https://www.ncbi.nlm.nih.gov/pubmed/24759758	Agonist 2458	40.3 µM [EC50]
Peroxisome proliferator-activated receptor gamma 100 Target ID: CHEMBL235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9171241 \| https://www.ncbi.nlm.nih.gov/pubmed/24759758	Agonist 2458	64.76 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hyperlipidemia 74 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3301301 https://www.ncbi.nlm.nih.gov/pubmed/18629356	Primary		Approved 8003	BEZALIP Approved Use Bezafibrate belongs to a group of medicines known as lipid-lowering substances.

PubMed

Title	Date	PubMed
Uncoupling protein-3 mRNA levels are increased in white adipose tissue and skeletal muscle of bezafibrate-treated rats.	1999 Jul 5	10403804
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	10933891
Fibrate-induced increase in blood urea and creatinine: is gemfibrozil the only innocuous agent?	2000 Dec	11096145
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	10909982
A paradoxical severe decrease in serum HDL-cholesterol after treatment with a fibrate.	2000 Oct	11064678
Down-regulation of uncoupling protein-3 and -2 by thiazolidinediones in C2C12 myotubes.	2000 Oct 27	11056218
[Marked creatine-phosphokinase elevation in myopathy after treatment with bezafibrate].	2000 Sep	11062950
Effects of diet, drugs, and genes on plasma fibrinogen levels.	2001	11460508
Homocysteine elevation with fibrates: is it a class effect?	2001 Apr	11344833
Bezafibrate reduces heart rate and blood pressure in patients with hypertriglyceridemia.	2001 Apr	11330878
Antihypertensive mechanisms of lipid-lowering drugs: decoding the Rosetta stone's inscriptions'.	2001 Apr	11330868
Effect of bezafibrate on soluble adhesion molecules and platelet activation markers in patients with connective tissue diseases and secondary hyperlipidemia.	2001 Apr	11292194
Concurrent administration of sustained-release bezafibrate may counteract the increased thrombotic risk associated with oral estrogen therapy.	2001 Aug	11461176
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	11739302
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	11748098
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	11460818
Determination of drug residues in water by the combination of liquid chromatography or capillary electrophoresis with electrospray mass spectrometry.	2001 Feb 23	11263577
Bezafibrate induces acyl-CoA oxidase mRNA levels and fatty acid peroxisomal beta-oxidation in rat white adipose tissue.	2001 Jan	11216866
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	11204580
Treating dyslipidaemia in non-insulin-dependent diabetes mellitus -- a special reference to statins.	2001 Jul-Aug	11457674
Three-dimensional high voltage electron microscopy of thick biological specimens.	2001 Jun	11070359
Effect of a pharmacological activation of PPAR on the expression of RAR and TR in rat liver.	2001 Mar	11579993
Effect of a pharmacological activation of PPAR on the expression of RAR and TR in rat liver.	2001 Mar	11519881
[Drug combination therapies for patients with hyperlipidemia and its significance].	2001 Mar	11347133
Plasma concentrations of active lovastatin acid are markedly increased by gemfibrozil but not by bezafibrate.	2001 May	11372002
[Rhabdomyolysis and acute renal failure secondary to statins].	2001 May-Jun	11471312
Are high density lipoprotein (HDL) and triglyceride levels relevant in stroke prevention?	2001 Nov	11684067
Squalene synthase inhibitors reduce plasma triglyceride through a low-density lipoprotein receptor-independent mechanism.	2001 Nov 23	11730728
Aromatase-deficient (ArKO) mice are retrieved from severe hepatic steatosis by peroxisome proliferator administration.	2002 Apr	11929713
Marked removal of bezafibrate-induced high-density lipoprotein-cholesterol by low-density lipoprotein apheresis.	2002 Apr	11880117
Investigation into the efficacy of bezafibrate against primary biliary cirrhosis, with histological references from cases receiving long term monotherapy.	2002 Jan	11808959

Patents

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

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

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Name

Type

Language

BEZAFIBRATE

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