BEZAFIBRATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H20ClNO4
Molecular Weight	361.819
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

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

Molecular Formula	C19H20ClNO4
Molecular Weight	361.819
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 62 Target ID: CHEMBL239 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9171241 \| https://www.ncbi.nlm.nih.gov/pubmed/24759758	Agonist 2678	37.37 µM [EC50]
Peroxisome proliferator-activated receptor delta 29 Target ID: CHEMBL3979 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9171241 \| https://www.ncbi.nlm.nih.gov/pubmed/24759758	Agonist 2678	40.3 µM [EC50]
Peroxisome proliferator-activated receptor gamma 111 Target ID: CHEMBL235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9171241 \| https://www.ncbi.nlm.nih.gov/pubmed/24759758	Agonist 2678	64.76 µM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hyperlipidemia 80 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3301301 https://www.ncbi.nlm.nih.gov/pubmed/18629356	Primary		Approved 8429	BEZALIP Approved Use Bezafibrate belongs to a group of medicines known as lipid-lowering substances.

PubMed

Title	Date	PubMed
Peroxisome proliferator-activated receptor beta regulates acyl-CoA synthetase 2 in reaggregated rat brain cell cultures.	1999 Dec 10	10585473
Uncoupling protein-3 mRNA levels are increased in white adipose tissue and skeletal muscle of bezafibrate-treated rats.	1999 Jul 5	10403804
Combined effects of probucol and benzafibrate on lipoprotein metabolism and liver cholesteryl ester transfer protein mRNA in cholesterol-fed rabbits.	1999 Jun	10406588
Effects of fibrate compounds on expression of plasminogen activator inhibitor-1 by cultured endothelial cells.	1999 Jun	10364093
Statin + fibrate combination therapy fluvastatin with bezafibrate or ciprofibrate in high risk patients with vascular disease.	1999 Jun 1	10402106
Effect of lipoprotein lipase activators bezafibrate and NO-1886, on B16 melanoma-induced cachexia in mice.	1999 Sep-Oct	10628360
Stimulation by eicosapentaenoic acids of leptin mRNA expression and its secretion in mouse 3T3-L1 adipocytes in vitro.	2000 Apr 13	10753628
Fibrate-induced increase in blood urea and creatinine: is gemfibrozil the only innocuous agent?	2000 Dec	11096145
Secondary prevention by raising HDL cholesterol and reducing triglycerides in patients with coronary artery disease.	2000 Jul 4	10880410
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
[Clinical, epidemiologic, and biochemical findings on the reverse cholesterol transport (cholesterol-HDL)].	2001	11474568
Effects of diet, drugs, and genes on plasma fibrinogen levels.	2001	11460508
Effect of bezafibrate and clofibrate on the heme-iron geometry of ferrous nitrosylated heme-human serum albumin: an EPR study.	2001 Apr	11374593
Effect of bezafibrate on soluble adhesion molecules and platelet activation markers in patients with connective tissue diseases and secondary hyperlipidemia.	2001 Apr	11292194
Differential involvement of peroxisome-proliferator-activated receptors alpha and delta in fibrate and fatty-acid-mediated inductions of the gene encoding liver fatty-acid-binding protein in the liver and the small intestine.	2001 Apr 15	11284737
Rhabdomyolysis and acute renal failure following a switchover of therapy between two fibric acid derivatives.	2001 Aug	11764054
Bezafibrate reduces mRNA levels of adipocyte markers and increases fatty acid oxidation in primary culture of adipocytes.	2001 Aug	11473052
Concurrent administration of sustained-release bezafibrate may counteract the increased thrombotic risk associated with oral estrogen therapy.	2001 Aug	11461176
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	11850202
Lipid-lowering trials in diabetes.	2001 Dec	11801861
Alterations in the extrinsic pathway in hypertriglyceridemia do not cause a 'procoagulant state': effects of bezafibrate therapy.	2001 Dec	11734672
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
Differential induction of stearoyl-CoA desaturase and acyl-CoA oxidase genes by fibrates in HepG2 cells.	2001 Feb 1	11172741
Determination of drug residues in water by the combination of liquid chromatography or capillary electrophoresis with electrospray mass spectrometry.	2001 Feb 23	11263577
Statins in children: what do we know and what do we need to do?	2001 Jan	11123845
Normocholesterolaemic dyslipidaemia: is there a role for fibrates?	2001 Jan 15	11245504
[Fibrates in the secondary prevention of ischemic cardiopathy].	2001 Jan-Mar	11565320
Peroxisome proliferator-activated receptors (PPARs): novel therapeutic targets in renal disease.	2001 Jul	11422732
Is pseudocholinesterase activity related to markers of triacylglycerol synthesis in Type II diabetes mellitus?	2001 Jul	11410111
Treating dyslipidaemia in non-insulin-dependent diabetes mellitus -- a special reference to statins.	2001 Jul-Aug	11457674
Normocholesterolaemic dysslipidaemia: is there a role for fibrates?	2001 Jun 4	11453341
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
Coronary artery reactivity after treatment with simvastatin.	2001 Mar	11177653
How is the liver primed or sensitized for alcoholic liver disease?	2001 May	11391068
Study of effectiveness of bezafibrate in the treatment of chronic hepatitis C.	2001 May	11374732
Effects of bezafibrate and simvastatin on plasma lipoproteins in hypercholesterolemia resistant to hormone replacement therapy.	2001 May 30	11358645
[Rhabdomyolysis and acute renal failure secondary to statins].	2001 May-Jun	11471312
Antineoplastic and anti-inflammatory effects of PPAR ligands in colitis.	2001 Oct	11606520
Changes in matrix proteoglycans induced by insulin and fatty acids in hepatic cells may contribute to dyslipidemia of insulin resistance.	2001 Sep	11522680
Aromatase-deficient (ArKO) mice are retrieved from severe hepatic steatosis by peroxisome proliferator administration.	2002 Apr	11929713
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	11923036
[A case of primary sclerosing cholangitis presenting transient hypoperfusion and treated with bezafibrate beneficially].	2002 Feb	11877955
Use of fibrates in the management of hyperlipidemia in HIV-infected patients receiving HAART.	2002 Jan	11876511
Investigation into the efficacy of bezafibrate against primary biliary cirrhosis, with histological references from cases receiving long term monotherapy.	2002 Jan	11808959
Prevention of radiation-induced mammary tumors.	2002 Jan 1	11777641
Evaluation of myopathy risk for HMG-CoA reductase inhibitors by urethane infusion method.	2002 Mar	11913531

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 Dec 15 15:15:52 GMT 2023` Edited by `admin` on `Fri Dec 15 15:15:52 GMT 2023`
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 [USAN]

Common Name

English

BEZAFIBRATE [EP MONOGRAPH]

Common Name

English

Bezafibrate [WHO-DD]

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