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B7273

Sigma-Aldrich

Bezafibrate

≥98%, solid

Synonym(s):

2-[4-[2-(4-Chlorobenzamido)ethyl]phenoxy]-2-methylpropanoic acid

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About This Item

Empirical Formula (Hill Notation):
C19H20ClNO4
CAS Number:
41859-67-0
Molecular Weight:
361.82
EC Number:
255-567-9
MDL number:
MFCD00078970
UNSPSC Code:
12352200
PubChem Substance ID:
24891983
NACRES:
NA.77

Quality Level

200

assay

≥98%

form

solid

solubility

DMF: soluble
deionized water: insoluble
methanol: soluble

originator

Roche

SMILES string

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

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)

InChI key

IIBYAHWJQTYFKB-UHFFFAOYSA-N

Gene Information

human ... HBA2(3040) , PPARA(5465) , PPARD(5467) , PPARG(5468)
mouse ... Ppara(19013) , Ppard(19015) , Pparg(19016)

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Application

Bezafibrate has been used:
  • a supplement in the standard diet (SD) for mice to study its effect on diabetes
  • to evaluate its effect on hepatitis C virus (HCV) assembly and secretion
  • to evaluate its effect on gonadal steroidogenesis and spermatogenesis of zebrafish and also used as standard for HPLC

Biochem/physiol Actions

Bezafibrate has the ability to repress HCV assembly and secretion. It is used to treat dyslipidemia.
The peroxisome proliferator-activated receptor (PPAR) is a member of the steroid nuclear receptor superfamily. Bezafibrate is a peroxisome proliferator-activated receptor agonist for PPARα, PPARδ, and PPARγ. Lipoprotein lipase (LPL) activator.
PPARgamma agonists, including Bezafibrate, have beneficial effects in the suppression of the inflammatory response during RSV infection and therefore might have clinical efficacy in the course of severe RSV-infection.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Roche. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Bezafibrate improves insulin sensitivity and metabolic flexibility in STZ-induced diabetic mice
Franko A, et al.
Diabetes, 65(9), 2540-2552 (2016)
Akira Honda et al.
Hepatology (Baltimore, Md.), 57(5), 1931-1941 (2012-08-23)
Bezafibrate is a widely used hypolipidemic agent and is known as a ligand of the peroxisome proliferator-activated receptors (PPARs). Recently this agent has come to be recognized as a potential anticholestatic medicine for the treatment of primary biliary cirrhosis (PBC)
Bezafibrate ameliorates diabetes via reduced steatosis and improved hepatic insulin sensitivity in diabetic TallyHo mice
Franko A, et al.
Molecular Metabolism, 6(3), 256-266 (2017)
Marc Engelen et al.
PloS one, 7(7), e41013-e41013 (2012-08-23)
X-linked adrenoleukodystrophy (X-ALD) is caused by mutations in the ABCD1 gene and is characterized by impaired beta-oxidation of very-long-chain fatty acids (VLCFA) and subsequent VLCFA accumulation in tissues. In adulthood X-ALD most commonly manifests as a gradually progressive myelopathy, (adrenomyeloneuropathy;
Magali Dumont et al.
Human molecular genetics, 21(23), 5091-5105 (2012-08-28)
Peroxisome proliferator-activated receptors (PPARs) are ligand-mediated transcription factors, which control both lipid and energy metabolism and inflammation pathways. PPARγ agonists are effective in the treatment of metabolic diseases and, more recently, neurodegenerative diseases, in which they show promising neuroprotective effects.
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