Bezafibrate | CAS#41859-67-0 | PPARα Agonist

MedKoo Cat#: 317323 | Name: Bezafibrate

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Bezafibrate is an agonist of peroxisome proliferator-activated receptor alpha (PPARalpha) with antilipidemic activity. Bezafibrate is a fibrate drug used for the treatment of hyperlipidaemia. Bezafibrate decreases triglyceride levels, increases high density lipoprotein cholesterol levels, and decreases total and low density lipoprotein cholesterol levels. It is commonly marketed as Bezalip.

Chemical Structure

Bezafibrate

CAS#41859-67-0

Theoretical Analysis

MedKoo Cat#: 317323

Name: Bezafibrate

CAS#: 41859-67-0

Chemical Formula: C19H20ClNO4

Exact Mass: 361.1081

Molecular Weight: 361.82

Elemental Analysis: C, 63.07; H, 5.57; Cl, 9.80; N, 3.87; O, 17.69

Price and Availability

Size	Price	Availability
1g	USD 250.00	2 Weeks
5g	USD 450.00	2 Weeks
10g	USD 650.00	2 Weeks

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Synonym

Bezafibrate; Benzofibrate; BM 15075; Bezalip; Bezatrol; Difaterol; Cedur; Bezafibratum

IUPAC/Chemical Name

2-[4-[2-[(4-chlorobenzoyl)amino]ethyl]phenoxy]-2-methyl-propanoic acid

InChi Key

IIBYAHWJQTYFKB-UHFFFAOYSA-N

InChi Code

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)

SMILES Code

ClC1=CC=C(C(NCCC2=CC=C(OC(C)(C)C(O)=O)C=C2)=O)C=C1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Bezafibrate is an agonist of PPAR, with EC50s of 50 μM, 60 μM, 20 μM for human PPARα, PPARγ and PPARδ, and 90 μM, 55 μM, 110 μM for murine PPARα, PPARγ and PPARδ, respectively.

In vitro activity:

Whether bezafibrate treatment could rescue the inhibition of FSH (follicle-stimulating hormone) induced follicle development and steroidogenesis by TNF (tumor necrosis factor-alpha) was evaluated. Bezafibrate treatment rescued inhibition of follicle development, secretion of E2, and ovulation rate by TNF. As the protein expression of only PPARG was observed in mouse preantral follicles, it was examined whether bezafibrate could affect follicle development and steroidogenesis through PPARG pathways. Treatment with GW1929, a selective PPARG agonist, restored inhibition of FSH-induced follicle development and steroidogenesis by TNF, whereas treatment with GW9662, a selective PPARG antagonist, canceled the restorative effects of bezafibrate. Collectively, the results suggest that bezafibrate may directly exhibit a restorative effect on the inhibition of ovarian follicle development and steroidogenesis by TNF through the PPARG pathway. Reference: Biol Reprod. 2011 Nov;85(5):895-906. https://academic.oup.com/biolreprod/article/85/5/895/2530504

In vivo activity:

Whether a pre-treatment with the pan-peroxisome proliferator-activated receptor (PPAR) agonist bezafibrate could prevent the alterations caused by MGA (3-Methylglutaric acid) was evaluated. MGA provoked lipid peroxidation, increased heme oxygenase-1 content, and altered the activities of antioxidant enzymes, strongly suggestive of oxidative stress. MGA also impaired mitochondrial function and biogenesis by decreasing the activities of succinate dehydrogenase and various respiratory chain complexes, as well as the nuclear levels of PGC-1α and NT-PGC-1α, and cell content of Sirt1. AMPKα1 was further increased by MGA. Neural cell damage was also observed following the MGA administration, as verified by decreased Akt and synaptophysin content and reduced ERK phosphorylation, and by the increase of active caspase-3 and p38 and Tau phosphorylation. Importantly, bezafibrate prevented MGA-elicited toxic effects towards mitochondrial function, redox homeostasis, and neural cell injury, implying that this compound may be potentially used as an adjunct therapy for MGTA and HMGA and other disorders with mitochondrial dysfunction. Reference: Neurotox Res. 2019 May;35(4):809-822. https://link.springer.com/article/10.1007%2Fs12640-019-00019-9

	Solvent	mg/mL	mM
Solubility
	DMSO:PBS (pH 7.2)(1:1)	0.5	1.38
	DMF	30.0	82.91
	Ethanol	31.5	87.06

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 361.82 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Hara S, Takahashi T, Amita M, Igarashi H, Tsutsumi S, Kurachi H. Bezafibrate restores the inhibition of FSH-induced follicular development and steroidogenesis by tumor necrosis factor-alpha through peroxisome proliferator-activated receptor-gamma pathway in an in vitro mouse preantral follicle culture. Biol Reprod. 2011 Nov;85(5):895-906. doi: 10.1095/biolreprod.111.090738. Epub 2011 Jul 6. PMID: 21734263. 2. da Rosa-Junior NT, Parmeggiani B, da Rosa MS, Glänzel NM, de Moura Alvorcem L, Wajner M, Leipnitz G. Bezafibrate In Vivo Administration Prevents 3-Methylglutaric Acid-Induced Impairment of Redox Status, Mitochondrial Biogenesis, and Neural Injury in Brain of Developing Rats. Neurotox Res. 2019 May;35(4):809-822. doi: 10.1007/s12640-019-00019-9. Epub 2019 Mar 9. PMID: 30850947.

In vitro protocol:

In vivo protocol:

1. da Rosa-Junior NT, Parmeggiani B, da Rosa MS, Glänzel NM, de Moura Alvorcem L, Wajner M, Leipnitz G. Bezafibrate In Vivo Administration Prevents 3-Methylglutaric Acid-Induced Impairment of Redox Status, Mitochondrial Biogenesis, and Neural Injury in Brain of Developing Rats. Neurotox Res. 2019 May;35(4):809-822. doi: 10.1007/s12640-019-00019-9. Epub 2019 Mar 9. PMID: 30850947.

1: Erratum: Systematic review and meta-analysis: bezafibrate in patients with primary biliary cirrhosis [Erratum]. Drug Des Devel Ther. 2015 Nov 6;9:5947. eCollection 2015. PubMed PMID: 26604692; PubMed Central PMCID: PMC4642802. 2: Liu X, Yang X, Chen X, Zhang Y, Pan X, Wang G, Ye Y. Expression Profiling Identifies Bezafibrate as Potential Therapeutic Drug for Lung Adenocarcinoma. J Cancer. 2015 Sep 20;6(12):1214-21. doi: 10.7150/jca.12191. eCollection 2015. PubMed PMID: 26535062; PubMed Central PMCID: PMC4622851. 3: Yin Q, Li J, Xia Y, Zhang R, Wang J, Lu W, Zhou Y, Zheng Y, Abudumijiti H, Chen R, Chen K, Li S, Liu T, Wang F, Lu J, Zhou Y, Guo C. Systematic review and meta-analysis: bezafibrate in patients with primary biliary cirrhosis. Drug Des Devel Ther. 2015 Sep 30;9:5407-19. doi: 10.2147/DDDT.S92041. eCollection 2015. PubMed PMID: 26491252; PubMed Central PMCID: PMC4599574. 4: Feng Y, Wang C, Liu Q, Meng Q, Huo X, Liu Z, Sun P, Yang X, Sun H, Qin J, Liu K. Bezafibrate-mizoribine interaction: Involvement of organic anion transporters OAT1 and OAT3 in rats. Eur J Pharm Sci. 2016 Jan 1;81:119-28. doi: 10.1016/j.ejps.2015.10.008. Epub 2015 Oct 22. PubMed PMID: 26474691. 5: Courchesne-Loyer A, St-Pierre V, Hennebelle M, Castellano CA, Fortier M, Tessier D, Cunnane SC. Ketogenic response to cotreatment with bezafibrate and medium chain triacylglycerols in healthy humans. Nutrition. 2015 Oct;31(10):1255-9. doi: 10.1016/j.nut.2015.05.015. Epub 2015 Jun 6. PubMed PMID: 26333891. 6: Honda A, Ikegami T, Matsuzaki Y. Anti-gp210 and anti-centromere antibodies for the prediction of PBC patients with an incomplete biochemical response to UDCA and bezafibrate. Hepatol Res. 2015 Aug;45(8):827-8. doi: 10.1111/hepr.12461. PubMed PMID: 26205698. 7: Mizuno S, Hirano K, Isayama H, Watanabe T, Yamamoto N, Nakai Y, Sasahira N, Tada M, Omata M, Koike K. Prospective study of bezafibrate for the treatment of primary sclerosing cholangitis. J Hepatobiliary Pancreat Sci. 2015 Oct;22(10):766-70. doi: 10.1002/jhbp.281. Epub 2015 Aug 21. PubMed PMID: 26173026. 8: Licinio R, Facciorusso A, Castellaneta NM, Di Leo A. Combination Therapy of Ursodeoxycholic Acid and Bezafibrate in Patients With Primary Biliary Cirrhosis: The End of the Steroid Era in Autoimmune Liver Diseases? Am J Gastroenterol. 2015 Jul;110(7):1086. doi: 10.1038/ajg.2015.163. PubMed PMID: 26148263. 9: Djouadi F, Habarou F, Le Bachelier C, Ferdinandusse S, Schlemmer D, Benoist JF, Boutron A, Andresen BS, Visser G, de Lonlay P, Olpin S, Fukao T, Yamaguchi S, Strauss AW, Wanders RJ, Bastin J. Mitochondrial trifunctional protein deficiency in human cultured fibroblasts: effects of bezafibrate. J Inherit Metab Dis. 2015 Jun 25. [Epub ahead of print] PubMed PMID: 26109258. 10: Kobayashi J. How Does Bezafibrate Affect the Plasma LDL Cholesterol Levels? J Atheroscler Thromb. 2015 Jul 23;22(7):658-9. doi: 10.5551/jat.ED007. Epub 2015 Mar 6. PubMed PMID: 25752495. 11: Hirose T, Teramoto T, Abe K, Taneyama T; J-BENEFIT study group. Determinants of Bezafibrate-induced Improvements in LDL Cholesterol in Dyslipidemic Patients with Diabetes. J Atheroscler Thromb. 2015 Jul 23;22(7):676-84. doi: 10.5551/jat.27425. Epub 2015 Mar 6. PubMed PMID: 25752494. 12: Hosonuma K, Sato K, Yamazaki Y, Yanagisawa M, Hashizume H, Horiguchi N, Kakizaki S, Kusano M, Yamada M. A prospective randomized controlled study of long-term combination therapy using ursodeoxycholic acid and bezafibrate in patients with primary biliary cirrhosis and dyslipidemia. Am J Gastroenterol. 2015 Mar;110(3):423-31. doi: 10.1038/ajg.2015.20. Epub 2015 Mar 3. PubMed PMID: 25732417. 13: Saha L, Bhandari S, Bhatia A, Banerjee D, Chakrabarti A. Anti-kindling Effect of Bezafibrate, a Peroxisome Proliferator-activated Receptors Alpha Agonist, in Pentylenetetrazole Induced Kindling Seizure Model. J Epilepsy Res. 2014 Dec 31;4(2):45-54. eCollection 2014 Dec. PubMed PMID: 25625088; PubMed Central PMCID: PMC4295053. 14: Vatanavicharn N, Yamada K, Aoyama Y, Fukao T, Densupsoontorn N, Jirapinyo P, Sathienkijkanchai A, Yamaguchi S, Wasant P. Carnitine-acylcarnitine translocase deficiency: Two neonatal cases with common splicing mutation and in vitro bezafibrate response. Brain Dev. 2015 Aug;37(7):698-703. doi: 10.1016/j.braindev.2014.10.005. Epub 2014 Nov 1. PubMed PMID: 25459972. 15: Shiochi H, Ohkura T, Fujioka Y, Sumi K, Yamamoto N, Nakanishi R, Matsuzawa K, Izawa S, Ohkura H, Inoue K, Ueta E, Kato M, Taniguchi S, Yamamoto K. Bezafibrate improves insulin resistance evaluated using the glucose clamp technique in patients with type 2 diabetes mellitus: a small-scale clinical study. Diabetol Metab Syndr. 2014 Oct 17;6(1):113. doi: 10.1186/1758-5996-6-113. eCollection 2014. PubMed PMID: 25360162; PubMed Central PMCID: PMC4213459. 16: Ørngreen MC, Vissing J, Laforét P. No effect of bezafibrate in patients with CPTII and VLCAD deficiencies. J Inherit Metab Dis. 2015 Mar;38(2):373-4. doi: 10.1007/s10545-014-9779-3. Epub 2014 Oct 21. PubMed PMID: 25331908. 17: Bastin J, Bonnefont JP, Djouadi F, Bresson JL. Should the beneficial impact of bezafibrate on fatty acid oxidation disorders be questioned? J Inherit Metab Dis. 2015 Mar;38(2):371-2. doi: 10.1007/s10545-014-9775-7. Epub 2014 Oct 14. PubMed PMID: 25310995. 18: Tanaka A, Hirohara J, Nakanuma Y, Tsubouchi H, Takikawa H. Biochemical responses to bezafibrate improve long-term outcome in asymptomatic patients with primary biliary cirrhosis refractory to UDCA. J Gastroenterol. 2015 Jun;50(6):675-82. doi: 10.1007/s00535-014-0998-z. Epub 2014 Sep 20. PubMed PMID: 25239675. 19: Shioya A, Takuma H, Yamaguchi S, Ishii A, Hiroki M, Fukuda T, Sugie H, Shigematsu Y, Tamaoka A. Amelioration of acylcarnitine profile using bezafibrate and riboflavin in a case of adult-onset glutaric acidemia type 2 with novel mutations of the electron transfer flavoprotein dehydrogenase (ETFDH) gene. J Neurol Sci. 2014 Nov 15;346(1-2):350-2. doi: 10.1016/j.jns.2014.08.040. Epub 2014 Aug 30. PubMed PMID: 25216552. 20: Gonçalves AG, Órfão JJ, Pereira MF. Ozonation of bezafibrate over ceria and ceria supported on carbon materials. Environ Technol. 2015 Mar-Apr;36(5-8):776-85. doi: 10.1080/09593330.2014.961563. Epub 2014 Oct 3. PubMed PMID: 25189707.