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C6643 Sigma

Clofibrate

liquid

Synonym: 2-(4-Chlorophenoxy)-2-methylpropionic acid ethyl ester, Ethyl 2-(4-chlorophenoxy)-2-methylpropionate, Ethyl 2-(4-chlorophenoxy)isobutyrate

  • CAS Number 637-07-0

  • Empirical Formula (Hill Notation) C12H15ClO3

  • Molecular Weight 242.70

  •  Beilstein Registry Number 1913459

  •  EC Number 211-277-4

  •  MDL number MFCD00000615

  •  PubChem Substance ID 24278085

  • Popular Documents:  FTNMR (PDF)  

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Properties

Related Categories Approved Therapeutics/Drug Candidates, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, CI-CZ, Cell Biology,
form   liquid
color   clear, colorless
density   1.14 g/mL at 25 °C(lit.)
originator   Wyeth
storage temp.   2-8°C
Gene Information   human ... PPARA(5465)
mouse ... Ppara(19013)

Description

Biochem/physiol Actions

Peroxisome proliferator-activated receptor-α (PPARα) agonist. Antihyperlipoproteinemic believed to act by inhibiting cholesterol biosynthesis.

Packaging

1, 5, 10 g in glass bottle

250 mg in glass bottle

Bottomless glass bottle. Contents are inside inserted fused cone.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®,1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

This compound is featured on the Nuclear Receptors (PPARs) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

This compound was developed by Wyeth. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Price and Availability


DISCOVER Bioactive Small Molecules

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Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
Hazard Codes (Europe) 
Risk Statements (Europe) 
Safety Statements (Europe) 
26-36/37/39-61
RIDADR 
UN 3082 9 / PGIII
WGK Germany 
3
RTECS 
UE9480000
Flash Point(F) 
235.4 °F
Flash Point(C) 
113 °C

Protocols & Articles

Articles

Antilipemic Agents

Download BioFiles v7 n5 (3.18 Mb PDF) Back to Pharmaceutical Drugs and Drug Candidates homepage
Sami Barghshoon
BioFiles v7 n5, 2012, 21–24
Keywords: Anti-inflammatory agents, Biofiles, Cardiovascular, Chemical vapor deposition, Clinical, Diabetes, Events, Inflammation, Oxidations, Pharmaceutical, Transcription

Cholesterol Biosynthesis Regulation

The amount of cholesterol that is synthesized in the liver is tightly regulated by dietary cholesterol levels. When dietary intake of cholesterol is high, synthesis is decreased and when dietary inta...
BioFiles 2007, 2.7, 6.
Keywords: Gene expression, Transcription

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Peer-Reviewed Papers

References

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Drug treatment of lipid disorders. Knopp, R.H., et al. N. Engl. J. Med. 341, 498, (1999)

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Inhibition of transforming growth factor beta1-induced hepatoma cell apoptosis by liver tumor promoters: characterization of primary signaling events and effects on CPP32-like caspase activity. Buchmann, A., et al. Cell Death Differ. 6, 190, (1999)

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Tissue-specific effect of clofibrate on rat lipogenic enzyme gene expression. Karbowska, J. Eur. J. Pharmacol. 370, 329, (1999)

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Chemical genetics reveals a complex functional ground state of neural stem cells Diamandis, P., et. al. Nat. Chem. Biol. 3(5), 268-273, (2007)

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Identifying off-target effects and hidden phenotypes of drugs in human cells. Marnie L MacDonald et al Nat. Chem. Biol. 2, 329-37, (2006)

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Characterization of the drug binding specificity of rat liver fatty acid binding protein. Sara Chuang et al J. Med. Chem. 51, 3755-64, (2008)

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Probing the fibrate binding specificity of rat liver fatty acid binding protein. Sara Chuang et al J. Med. Chem. 52, 5344-55, (2009)

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Clofibrate. IARC Monogr. Eval. Carcinog. Risks Hum. 66, 391-426, (1996)

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[Clofibrate treatment of hyperlipoproteinemia]. Oikawa S and Midorikawa H Nihon Rinsho. 52(12), 3285-91, (1994)

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Clofibrate. IARC Monogr. Eval. Carcinog. Risk Chem. Hum. 24, 39-58, (1980)

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[The treatment of essential hyperlipidemia with clofibrate]. Reuter W and Seifert A Z. Gesamte Inn. Med. 24(1), Suppl:184-7, (1969)

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[Currently used therapeutic agents for arteriosclerosis--with special reference ro a protein anabolic hormone, clofibrate (C.P.I.B.)]. Yasugi T and Sasa E Nihon Rinsho. 28(5), 1470-4, (1970)

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Severe hypoalphalipoproteinemia induced by a combination of probucol and clofibrate. Davignon J, Nestruck AC, Alaupovic P, et al. Adv. Exp. Med. Biol. 201, 111-25, (1986)

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The effect of clofibrate on hyperbilirubinemia of term neonates. Habibi M, Mahyar A, Ayazi P, et al. Acta Med. Iran. 50(1), 21-5, (2012)

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[Clofibrate in coronary diseases]. Erikssen J Tidsskr. Nor. Laegeforen. 95(34-36), 1987-8, (1975)

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Spectrophotometric determination of drugs with iodine. Karuna T, et al. J. Sci. Ind. Res. 65(10), 808, (2006)

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The Japanese toxicogenomics project: application of toxicogenomics. Takeki Uehara et al Mol. Nutr. Food. Res. 54, 218-27, (2010)

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Hologram QSAR model for the prediction of human oral bioavailability. Tiago L Moda et al Bioorg. Med. Chem. 15, 7738-45, (2007)

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FDA-approved drug labeling for the study of drug-induced liver injury. Minjun Chen et al Drug Discov. Today 16, 697-703, (2011)

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Novel use of a lipid-lowering fibrate medication to prevent nicotine reward and relapse: preclinical findings. Panlilio LV, Justinova Z, Mascia P, et al. Biol. Psychiatry 37(8), 1838-47, (2012)

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Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species. Denis Fourches et al Chem. Res. Toxicol. 23, 171-83, (2010)

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Evaluation of a published in silico model and construction of a novel Bayesian model for predicting phospholipidosis inducing potential. Dennis J Pelletier et al J. Chem. Inf. Model. 47, 1196-205, (2007)

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Importance of sphingosine kinase (SphK) as a target in developing cancer therapeutics and recent developments in the synthesis of novel SphK inhibitors. Plano D, Amin S, and Sharma AK J. Med. Chem. 57(13), 5509-24, (2014)

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Floratheasaponins A-C, acylated oleanane-type triterpene oligoglycosides with anti-hyperlipidemic activities from flowers of the tea plant (Camellia sinensis). Masayuki Yoshikawa et al J. Nat. Prod. 68, 1360-5, (2005)

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Developing structure-activity relationships for the prediction of hepatotoxicity. Nigel Greene et al Chem. Res. Toxicol. 23, 1215-22, (2010)

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Multi-target spectral moment QSAR versus ANN for antiparasitic drugs against different parasite species. Francisco J Prado-Prado et al Bioorg. Med. Chem. 18, 2225-31, (2010)

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PPAR-alpha: a key to the mechanism of hepatoprotection by clofibrate. Mehendale HM Toxicol. Sci. 57(2), 187-90, (2000)

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Perennisosides I-VII, acylated triterpene saponins with antihyperlipidemic activities from the flowers of Bellis perennis. Toshio Morikawa et al J. Nat. Prod. 71, 828-35, (2008)

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Identification, organ expression and ligand-dependent expression levels of peroxisome proliferator activated receptors in grass carp (Ctenopharyngodon idella). He S, Liang XF, Qu CM, et al. Comp. Biochem. Physiol. C. Toxicol. Pharmacol. 155(2), 381-8, (2012)

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Clofibrate myopathy: a case report and a review of the literature. Rush P, Baron M, and Kapusta M Semin. Arthritis Rheum. 15(3), 226-9, (1986)

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Prediction of drug intestinal absorption by new linear and non-linear QSPR. Alan Talevi et al Eur. J. Med. Chem. 46, 218-28, (2011)

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Can pharmaceuticals interfere with the synthesis of active androgens in male fish? An in vitro study. Fernandes D, Schnell S, and Porte C Mar. Pollut. Bull. 62(10), 2250-3, (2011)

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Tissue-specific differential induction of duplicated fatty acid-binding protein genes by the peroxisome proliferator, clofibrate, in zebrafish (Danio rerio). Venkatachalam AB, Lall SP, Denovan-Wright EM, et al. BMC Evol. Biol. 12, 112, (2012)

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A predictive ligand-based Bayesian model for human drug-induced liver injury. Sean Ekins et al Drug Metab. Dispos. 38, 2302-8, (2010)

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Stereospecific synthesis and bio-activity of novel beta(3)-adrenoceptor agonists and inverse agonists. Maria Grazia Perrone et al Bioorg. Med. Chem. 16, 2473-88, (2008)

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Cytotoxic properties of clofibrate and other peroxisome proliferators: relevance to cancer progression. Penna F, Bonelli G, Baccino FM, et al. Curr. Med. Chem. 17(4), 309-20, (2010)

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Clofibrate-induced reduction of plasma branched-chain amino acid concentrations impairs glucose tolerance in rats. Kadota Y, Kazama S, Bajotto G, et al. J. Parenter. Enteral Nutr. 36(3), 337-43, (2012)

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Treatment with pharmacological PPARα agonists stimulates the ubiquitin proteasome pathway and myofibrillar protein breakdown in skeletal muscle of rodents. Ringseis R, Keller J, Lukas I, et al. Biochim. Biophys. Acta 1830(1), 2105-17, (2013)

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Clofibrate and related compounds in hyperlipoproteinaemia. A review. Gustafson A Postgrad. Med. J. 51(8), 66-71, (1975)

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Organotypic modeling of human keratinocyte response to peroxisome proliferators. Zhang C, Gurevich I, and Aneskievich BJ Cells Tissues Organs 196(5), 431-41, (2012)

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Caspase 2 activation and ER stress drive rapid Jurkat cell apoptosis by clofibrate. Penna F, Pin F, Costamagna D, et al. PLoS ONE 7(9), e45327, (2012)

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Conservation and divergence of chemical defense system in the tunicate Oikopleura dioica revealed by genome wide response to two xenobiotics. Yadetie F, Butcher S, Førde HE, et al. BMC Genomics 13, 55, (2012)

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Changes in lipid content and fatty acid composition along the reproductive cycle of the freshwater mussel Dreissena polymorpha: its modulation by clofibrate exposure. Lazzara R, Fernandes D, Faria M, et al. Sci. Total Environ. 432, 195-201, (2012)

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In situ tumour radiosensitization induced by clofibrate administration: single dose and fractionated studies. Calais G and Hirst DG Radiother. Oncol. 22(2), 99-103, (1991)

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Synthesis and biological evaluation of some novel cyclic-imides as hypoglycaemic, anti-hyperlipidemic agents. Alaa A-M Abdel-Aziz et al Eur. J. Med. Chem. 46, 4324-9, (2011)

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Neural computational prediction of oral drug absorption based on CODES 2D descriptors. A Guerra et al Eur. J. Med. Chem. 45, 930-40, (2010)

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Clofibrate PPARα activation reduces oxidative stress and improves ultrastructure and ventricular hemodynamics in no-flow myocardial ischemia. Ibarra-Lara L, Hong E, Soria-Castro E, et al. J. Cardiovasc. Pharmacol. 60(4), 323-34, (2012)

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Tissue-specific transcriptional modulation of fatty acid-binding protein genes, fabp2, fabp3 and fabp6, by fatty acids and the peroxisome proliferator, clofibrate, in zebrafish (Danio rerio). Venkatachalam AB, Sawler DL, and Wright JM Gene 520(1), 14-21, (2013)

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Biomolecular chemistry of isopropyl fibrates. Balendiran GK, Rath N, Kotheimer A, et al. J. Pharm. Sci. 101(4), 1555-69, (2012)

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Synthesis of highly water-soluble fibrate derivatives via BGLation. Nemoto H, Kamiya M, Nakamoto A, et al. Bioorg. Med. Chem. Lett. 22(20), 6425-8, (2012)

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The clofibrate saga: a retrospective commentary. Oliver M Br. J. Clin. Pharmacol. 74(6), 907-10, (2012)

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Design, synthesis and hypolipidemic activity of novel 2-(m-tolyloxy) isobutyric acid derivatives. Gamal A Idrees et al Eur. J. Med. Chem. 44, 2679-84, (2009)

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Synthesis and structure-activity relationships of fibrate-based analogues inside PPARs. Giampietro L, D'Angelo A, Giancristofaro A, et al. Bioorg. Med. Chem. Lett. 22(24), 7662-6, (2012)

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Attenuation of kidney injuries maintains serum sulfatide levels dependent on hepatic synthetic ability: a possible involvement of oxidative stress. Sheng X, Nakajima T, Wang L, et al. Tohoku J. Exp. Med. 227(1), 1-12, (2012)

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PPARα-mediated responses in human adult liver stem cells: In vivo/in vitro and cross-species comparisons. Kim S, Kiyosawa N, Burgoon LD, et al. J. Steroid Biochem. Mol. Biol. 138, 236-47, (2013)

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Endothelial nitric oxide synthase impairment is restored by clofibrate treatment in an animal model of hypertension. Cervantes-Pérez LG, Ibarra-Lara Mde L, Escalante B, et al. Eur. J. Pharmacol. 685(1-3), 108-15, (2012)

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Clofibrate relaxes the longitudinal smooth muscle of the mouse distal colon through calcium-mediated desensitisation of contractile machinery. Azuma YT, Nishiyama K, Morioka A, et al. Pharmacology 88(1-2), 65-71, (2011)

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Super-induced gene expression of the N-methyl-D-aspartate receptor 2C subunit in chemical-induced hypertrophic liver in rats. Nemoto K, Tanaka T, Ikeda A, et al. J. Toxicol. Sci. 36(5), 507-14, (2011)

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Clofibrate for unconjugated hyperbilirubinemia in neonates: a systematic review. Xiong T, Chen D, Duan Z, et al. Indian Pediatr. 49(1), 35-41, (2012)

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Estrogen and androgen receptor status in hepatocellular hypertrophy induced by phenobarbital, clofibrate, and piperonyl butoxide in F344 rats. Fujimoto N, Inoue K, Yoshida M, et al. J. Toxicol. Sci. 37(2), 281-6, (2012)

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Altered expression of GADD45 genes during the development of chemical-mediated liver hypertrophy and liver tumor promotion in rats. Ozawa S, Gamou T, Habano W, et al. J. Toxicol. Sci. 36(5), 613-23, (2011)

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[Fibrates: mechanism of action, effect on levels of lipids and lipoproteins, risk of coronary events. Part 1. Clofibrate, gemfibrosil, besafibrate]. Dobordzhginidze LM and Gratsianskiĭ NA Kardiologiia 44(2), 96-103, (2004)

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[Pharmacological basis for the therapeutic utilisation of hypolipedmic effects of clofibrate (author's transl)]. Chevais M Therapie. 35(1), 5-22, (1980)

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A review of studies on the mode of action of clofibrate and betabenzalbutyrate. Fallon HJ, Adams LL, and Lamb RG Lipids 7(2), 106-9, (1972)

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Hypolipidemic effect of clofibrate and fatty acid oxidation in peroxisomes. Nutr. Rev. 35(4), 74-5, (1977)

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Clofibrate in combination with phototherapy for unconjugated neonatal hyperbilirubinaemia. Gholitabar M, McGuire H, Rennie J, et al. Cochrane Database Syst. Rev. 12, CD009017, (2012)

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Clofibrate and related compounds in hyperlipoproteinaemia. A review. Gustafson A Postgrad. Med. J. 51(8), suppl 66-71, (1975)

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Beil. 6,IV,851

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