Drugbank Logo

Showing drug card for Fenofibrate (DB01039)

Legend: drug field target field enzyme field

for drugs
Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:06:43
Primary Accession Number DB01039
Secondary Accession Number
  • APRD00405
Name Fenofibrate
Drug Type
  • Approved
  • Small Molecule
Description An antilipemic agent which reduces both cholesterol and triglycerides in the blood. [PubChem]
Synonyms
  1. FNF
  2. Fenofibrato [INN-Spanish]
  3. Fenofibratum [INN-Latin]
  4. Finofibrate
Brand Names
  1. Ankebin
  2. Antara
  3. Elasterate
  4. Elasterin
  5. Fenobrate
  6. Fenogal
  7. Fenotard
  8. Lipanthyl
  9. Lipantil
  10. Lipidex
  11. Lipidil
  12. Lipidil Micro
  13. Lipidil Supra
  14. Lipifen
  15. Lipirex
  16. Lipoclar
  17. Lipofene
  18. Liposit
  19. Lipsin
  20. Lofibra
  21. Luxacor
  22. Nolipax
  23. Procetofen
  24. Proctofene
  25. Protolipan
  26. Secalip
  27. Sedufen
  28. Tricor
  29. Triglide
Brand Mixtures Not Available
Chemical IUPAC Name propan-2-yl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoate
Chemical Formula C20H21ClO4
Chemical Structure Structure
CAS Registry Number 49562-28-9
InChI Identifier InChI=1/C20H21ClO4/c1-13(2)24-19(23)20(3,4)25-17-11-7-15(8-12-17)18(22)14-5-9-16(21)10-6-14/h5-13H,1-4H3
InChI Key YMTINGFKWWXKFG-UHFFFAOYAW
KEGG Drug D00565 Link Image
KEGG Compound C07586 Link Image
PubChem Compound 3339 Link Image
PubChem Substance 180502 Link Image
ChEBI ID 5001 Link Image
PharmGKB ID PA449594 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 02250039 Link Image
RxList Link http://www.rxlist.com/cgi/generic3/fenofibrate.htm Link Image
PDRhealth Link http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/cx1550.shtml Link Image
Wikipedia Link http://en.wikipedia.org/wiki/Fenofibrate Link Image
FDA Label
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 360.8310
Monoisotopic Molecular Weight 360.1128
State Solid
Melting Point 80.5 oC
Experimental Water Solubility 0.25mg/ml at 25 oC Source: PhysProp
Predicted Water Solubility 7.07e-04 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 5.3 Source: PhysProp
Predicted LogP 4.86 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -5.71 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CC(C)OC(=O)C(C)(C)OC1=CC=C(C=C1)C(=O)C1=CC=C(Cl)C=C1
Canonical SMILES CC(C)OC(=O)C(C)(C)OC1=CC=C(C=C1)C(=O)C1=CC=C(Cl)C=C1
Drug Category
  • Antilipemic Agents
  • Fribic Acid Derivatives
ATC Codes
AHFS Codes
  • 24:06.06
Indication For use as adjunctive therapy to diet to reduce elevated LDL-C, Total-C,Triglycerides and Apo B, and to increase HDL-C in adult patients with primary hypercholesterolemia or mixed dyslipidemia (Fredrickson Types IIa and IIb)
Pharmacology Fenofibrate is a lipid regulating agent indicated as adjunctive therapy to diet to reduce elevated LDL-C, Total-C,Triglycerides and Apo B, and to increase HDL-C in adult patients with primary hypercholesterolemia or mixed dyslipidemia (Fredrickson Types IIa and IIb). Fenofibrate is also indicated as adjunctive therapy to diet for treatment of adult patients with hypertriglyceridemia (Fredrickson Types IV and V hyperlipidemia). Fenofibric acid, the active metabolite of Fenofibrate, produces reductions in total cholesterol, LDL cholesterol, apolipoprotein B, total triglycerides and triglyceride rich lipoprotein (VLDL) in treated patients. In addition, treatment with fenofibrate results in increases in high density lipoprotein (HDL) and apoproteins apoAI and apoAII.
Mechanism of Action Fenofibrate exerts its therapeutic effects through activation of peroxisome proliferator activated receptor a (PPARa). This increases lipolysis and elimination of triglyceride-rich particles from plasma by activating lipoprotein lipase and reducing production of apoprotein C-III. The resulting fall in triglycerides produces an alteration in the size and composition of LDL from small, dense particles, to large buoyant particles. These larger particles have a greater affinity for cholesterol receptors and are catabolized rapidly.
Absorption Fenofibrate is well absorbed from the gastrointestinal tract. After absorption, fenofibrate is mainly excreted in the urine in the form of metabolites, primarily fenofibric acid and fenofibric acid glucuronide
Toxicity LD50=1600 mg/kg (Oral, in mice); Investigated as a teratogen and reproductive hazard.
Protein Binding ~99% (Serum protein binding)
Biotransformation Not Available
Half Life 20 hours
Dosage Forms
Form Route
Capsule Oral
Tablet Oral
Patient Information Not Available
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Acenocoumarol The fibrate increases the anticoagulant effect
Anisindione The fibrate increases the anticoagulant effect
Atorvastatin Increased risk of myopathy/rhabdomyolysis
Cerivastatin Increased risk of myopathy/rhabdomyolysis
Dicumarol The fibrate increases the anticoagulant effect
Fluvastatin Increased risk of myopathy/rhabdomyolysis
Lovastatin Increased risk of myopathy/rhabdomyolysis
Pravastatin Increased risk of myopathy/rhabdomyolysis
Rosuvastatin Rosuvastatin possibly increases the effect of the fibrate
Simvastatin Increased risk of myopathy/rhabdomyolysis
Ursodeoxycholic acid The fibric acid derivative decreases the effect of ursodiol
Warfarin The fibrate increases the anticoagulant effect
Food Interactions
  • Increased absorption- take with meals.
Pathways Not Available
General References
  1. Wysocki J, Belowski D, Kalina M, Kochanski L, Okopien B, Kalina Z: Effects of micronized fenofibrate on insulin resistance in patients with metabolic syndrome. Int J Clin Pharmacol Ther. 2004 Apr;42(4):212-7. [PubMed Link Image]
  2. Keech A, Simes RJ, Barter P, Best J, Scott R, Taskinen MR, Forder P, Pillai A, Davis T, Glasziou P, Drury P, Kesaniemi YA, Sullivan D, Hunt D, Colman P, d'Emden M, Whiting M, Ehnholm C, Laakso M: Effects of long-term fenofibrate therapy on cardiovascular events in 9795 people with type 2 diabetes mellitus (the FIELD study): randomised controlled trial. Lancet. 2005 Nov 26;366(9500):1849-61. [PubMed Link Image]
  3. Drugs.com Link Image
  4. Wikipedia Link Image
  5. RxList Link Image
  6. PDRhealth Link Image
Organisms Affected
  • Humans and other mammals
Targets
  1. Peroxisome proliferator-activated receptor alpha
  2. Metalloproteinase
Drug Target 1 [top]
Target 1 ID 80
Target 1 Name Peroxisome proliferator-activated receptor alpha
Target 1 Synonyms
  1. PPAR-alpha
Target 1 Gene Name PPARA
Target 1 Protein Sequence >Peroxisome proliferator-activated receptor alpha 
MVDTESPLCPLSPLEAGDLESPLSEEFLQEMGNIQEISQSIGEDSSGSFGFTEYQYLGSC
PGSDGSVITDTLSPASSPSSVTYPVVPGSVDESPSGALNIECRICGDKASGYHYGVHACE
GCKGFFRRTIRLKLVYDKCDRSCKIQKKNRNKCQYCRFHKCLSVGMSHNAIRFGRMPRSE
KAKLKAEILTCEHDIEDSETADLKSLAKRIYEAYLKNFNMNKVKARVILSGKASNNPPFV
IHDMETLCMAEKTLVAKLVANGIQNKEAEVRIFHCCQCTSVETVTELTEFAKAIPGFANL
DLNDQVTLLKYGVYEAIFAMLSSVMNKDGMLVAYGNGFITREFLKSLRKPFCDIMEPKFD
FAMKFNALELDDSDISLFVAAIICCGDRPGLLNVGHIEKMQEGIVHVLRLHLQSNHPDDI
FLFPKLLQKMADLRQLVTEHAQLVQIIKKTESDAALHPLLQEIYRDMY
Target 1 Number of Residues 475
Target 1 Molecular Weight 52226
Target 1 Theoretical pI 6.20
Target 1 GO Classification
Function
steroid hormone receptor activity
transcription factor activity
signal transducer activity
receptor activity
ligand-dependent nuclear receptor activity
binding
nucleic acid binding
DNA binding
Process
regulation of biological process
regulation of physiological process
regulation of metabolism
regulation of cellular metabolism
regulation of nucleobase, nucleoside, nucleotide and nucleic acid metabolism
regulation of transcription
regulation of transcription, DNA-dependent
Component
organelle
membrane-bound organelle
intracellular membrane-bound organelle
nucleus
Target 1 General Function Involved in DNA binding
Target 1 Specific Function Receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the receptor binds to a promoter element in the gene for acyl-CoA oxidase and activates its transcription. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 307341 Link Image
Target 1 UniProtKB/Swiss-Prot ID Q07869 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name PPARA_HUMAN Link Image
Target 1 PDB ID 1K7L Link Image
Target 1 PDB File Show
Target 1 3D Structure
Target 1 Cellular Location
  • Nucleus
Target 1 Gene Sequence >1407 bp 
ATGGTGGACACGGAAAGCCCACTCTGCCCCCTCTCCCCACTCGAGGCCGGCGATCTAGAG
AGCCCGTTATCTGAAGAGTTCCTGCAAGAAATGGGAAACATCCAAGAGATTTCGCAATCC
ATCGGCGAGGATAGTTCTGGAAGCTTTGGCTTTACGGAATACCAGTATTTAGGAAGCTGT
CCTGGCTCAGATGGCTCGGTCATCACGGACACGCTTTCACCAGCTTCGAGCCCCTCCTCG
GTGACTTATCCTGTGGTCCCCGGCAGCGTGGACGAGTCTCCCAGTGGAGCATTGAACATC
GAATGTAGAATCTGCGGGGACAAGGCCTCAGGCTATCATTACGGAGTCCACGCGTGTGAA
GGCTGCAAGGGCTTCTTTCGGCGAACGATTCGACTCAAGCTGGTGTATGACAAGTGCGAC
CGCAGCTGCAAGATCCAGAAAAAGAACAGAAACAAATGCCAGTATTGTCGATTTCACAAG
TGCCTTTCTGTCGGGATGTCACACAACGCGATTCGTTTTGGACGAATGCCAAGATCTGAG
AAAGCAAAACTGAAAGCAGAAATTCTTACCTGTGAACATGACATAGAAGATTCTGAAACT
GCAGATCTCAAATCTCTGGCCAAGAGAATCTACGAGGCCTACTTGAAGAACTTCAACATG
AACAAGGTCAAAGCCCGGGTCATCCTCTCAGGAAAGGCCAGTAACAATCCACCTTTTGTC
ATACATGATATGGAGACACTGTGTATGGCTGAGAAGACGCTGGTGGCCAAGCTGGTGGCC
AATGGCATCCAGAACAAGGAGGTGGAGGTCCGCATCTTTCACTGCTGCCAGTGCACGTCA
GTGGAGACCGTCACGGAGCTCACGGAATTCGCCAAGGCCATCCCAGCGTTCGCAAACTTG
GACCTGAACGATCAAGTGACATTGCTAAAATACGGAGTTTATGAGGCCATATTCGCCATG
CTGTCTTCTGTGATGAACAAAGACGGGATGCTGGTAGCGTATGGAAATGGGTTTATAACT
CGTGAATTCCTAAAAAGCCTAAGGAAACCGTTCTGTGATATCATGGAACCCAAGTTTGAT
TTTGCCATGAAGTTCAATGCACTGGAACTGGATGACAGTGATATCTCCCTTTTTGTGGCT
GCTATCATTTGCTGTGGAGATCGTCCTGGCCTTCTAAACGTAGGACACATTGAAAAAATG
CAGGAGGGTATTGTACATGTGCTCAGACTCCACCTGCAGAGCAACCACCCGGACGATATC
TTTCTCTTCCCAAAACTTCTTCAAAAAATGGCAGACCTCCGGCAGCTGGTGACGGAGCAT
GCGCAGCTGGTGCAGATCATCAAGAAGACGGAGTCGGATGCTGCGCTGCACCCGCTACTG
CAGGAGATCTACAGGGACATGTACTGA
Target 1 GenBank Gene ID
Target 1 GeneCard ID PPARA Link Image
Target 1 GenAtlas ID PPARA Link Image
Target 1 HGNC ID HGNC:9232 Link Image
Target 1 Chromosome Location 22
Target 1 Locus 22q12-q13.1|22q13.31
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Dunham I, Shimizu N, Roe BA, Chissoe S, Hunt AR, Collins JE, Bruskiewich R, Beare DM, Clamp M, Smink LJ, Ainscough R, Almeida JP, Babbage A, Bagguley C, Bailey J, Barlow K, Bates KN, Beasley O, Bird CP, Blakey S, Bridgeman AM, Buck D, Burgess J, Burrill WD, O'Brien KP, et al.: The DNA sequence of human chromosome 22. Nature. 1999 Dec 2;402(6761):489-95. [PubMed Link Image]
  2. Caira F, Antonson P, Pelto-Huikko M, Treuter E, Gustafsson JA: Cloning and characterization of RAP250, a novel nuclear receptor coactivator. J Biol Chem. 2000 Feb 25;275(8):5308-17. [PubMed Link Image]
  3. Sher T, Yi HF, McBride OW, Gonzalez FJ: cDNA cloning, chromosomal mapping, and functional characterization of the human peroxisome proliferator activated receptor. Biochemistry. 1993 Jun 1;32(21):5598-604. [PubMed Link Image]
  4. Mukherjee R, Jow L, Noonan D, McDonnell DP: Human and rat peroxisome proliferator activated receptors (PPARs) demonstrate similar tissue distribution but different responsiveness to PPAR activators. J Steroid Biochem Mol Biol. 1994 Nov;51(3-4):157-66. [PubMed Link Image]
  5. Tugwood JD, Aldridge TC, Lambe KG, Macdonald N, Woodyatt NJ: Peroxisome proliferator-activated receptors: structures and function. Ann N Y Acad Sci. 1996 Dec 27;804:252-65. [PubMed Link Image]
  6. Li H, Gomes PJ, Chen JD: RAC3, a steroid/nuclear receptor-associated coactivator that is related to SRC-1 and TIF2. Proc Natl Acad Sci U S A. 1997 Aug 5;94(16):8479-84. [PubMed Link Image]
Target 1 Drug References
  1. Clavey V, Copin C, Mariotte MC, Bauge E, Chinetti G, Fruchart J, Fruchart JC, Dallongeville J, Staels B: Cell culture conditions determine apolipoprotein CIII secretion and regulation by fibrates in human hepatoma HepG2 cells. Cell Physiol Biochem. 1999;9(3):139-49. [PubMed Link Image]
  2. Chaput E, Saladin R, Silvestre M, Edgar AD: Fenofibrate and rosiglitazone lower serum triglycerides with opposing effects on body weight. Biochem Biophys Res Commun. 2000 May 10;271(2):445-50. [PubMed Link Image]
  3. Casas F, Pineau T, Rochard P, Rodier A, Daury L, Dauca M, Cabello G, Wrutniak-Cabello C: New molecular aspects of regulation of mitochondrial activity by fenofibrate and fasting. FEBS Lett. 2000 Sep 29;482(1-2):71-4. [PubMed Link Image]
  4. Bouly M, Masson D, Gross B, Jiang XC, Fievet C, Castro G, Tall AR, Fruchart JC, Staels B, Lagrost L, Luc G: Induction of the phospholipid transfer protein gene accounts for the high density lipoprotein enlargement in mice treated with fenofibrate. J Biol Chem. 2001 Jul 13;276(28):25841-7. Epub 2001 May 7. [PubMed Link Image]
  5. Dana SL, Hoener PA, Bilakovics JM, Crombie DL, Ogilvie KM, Kauffman RF, Mukherjee R, Paterniti JR Jr: Peroxisome proliferator-activated receptor subtype-specific regulation of hepatic and peripheral gene expression in the Zucker diabetic fatty rat. Metabolism. 2001 Aug;50(8):963-71. [PubMed Link Image]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed Link Image]
Drug Target 2 [top]
Target 2 ID 1541
Target 2 Name Metalloproteinase
Target 2 Synonyms Not Available
Target 2 Gene Name mmp20
Target 2 Protein Sequence >Metalloproteinase 
MDPGTVATMRKPRCSLPDVLGVAGLVRRRRRYALSGSVWKKRTLTWRVRSFPQSSQLSQE
TVRVLMSYALMAWGMESGLTFHEVDSPQGQEPDILIDFARAFHQDSYPFDGLGGTLAHAF
FPGEHPISGDTHFDDEETWTFGSKASQQLEQELAGGSPVDEELGFSRGWRVNPLGPGSPE
RLS
Target 2 Number of Residues 186
Target 2 Molecular Weight 20354
Target 2 Theoretical pI 6.01
Target 2 GO Classification
Function
metallopeptidase activity
catalytic activity
hydrolase activity
peptidase activity
endopeptidase activity
metalloendopeptidase activity
Process
physiological process
metabolism
macromolecule metabolism
protein metabolism
cellular protein metabolism
proteolysis
Component
extracellular matrix
extracellular matrix (sensu Metazoa)
Target 2 General Function Involved in metalloendopeptidase activity
Target 2 Specific Function Not Available
Target 2 Pathways Not Available
Target 2 Reactions Not Available
Target 2 Pfam Domain Function
Target 2 Signals
  • None
Target 2 Transmembrane Regions
  • None
Target 2 Essentiality Non-Essential
Target 2 GenBank ID Protein 2808657 Link Image
Target 2 UniProtKB/Swiss-Prot ID O43923 Link Image
Target 2 UniProtKB/Swiss-Prot Entry Name O43923_HUMAN Link Image
Target 2 PDB ID Not Available
Target 2 Cellular Location
  • Cytoplasmic
Target 2 Gene Sequence >552 bp 
ATGGACCCAGGGACAGTGGCCACCATGCGTAAGCCCCGCTGCTCCCTGCCTGACGTGCTG
GGGGTGGCGGGGCTGGTCAGGCGGCGTCGCCGGTACGCTCTGAGCGGCAGCGTGTGGAAG
AAGCGAACCCTGACATGGAGGGTACGTTCCTTCCCCCAGAGCTCCCAGCTGAGCCAGGAG
ACCGTGCGGGTCCTCATGAGCTATGCCCTGATGGCCTGGGGCATGGAGTCAGGCCTCACA
TTTCATGAGGTGGATTCCCCCCAGGGCCAGGAGCCCGACATCCTCATCGACTTTGCCCGC
GCCTTCCACCAGGACAGCTACCCCTTCGACGGGTTGGGGGGCACCCTAGCCCATGCCTTC
TTCCCTGGGGAGCACCCCATCTCCGGGGACACTCACTTTGACGATGAGGAGACCTGGACT
TTTGGGTCAAAAGCCTCTCAGCAGCTGGAGCAGGAGCTGGCAGGCGGCTCACCGGTTGAT
GAGGAGCTGGGCTTCAGCCGGGGCTGGCGTGTGAATCCTCTGGGTCCTGGCAGTCCTGAG
CGCCTGAGCTGA
Target 2 GenBank Gene ID
Target 2 GeneCard ID mmp20 Link Image
Target 2 GenAtlas ID mmp20 Link Image
Target 2 HGNC ID HGNC:14246 Link Image
Target 2 Chromosome Location Not Available
Target 2 Locus Not Available
Target 2 SNPs SNPJam Report Link Image
Target 2 General References
  1. Bernot A, Heilig R, Clepet C, Smaoui N, Da Silva C, Petit JL, Devaud C, Chiannilkulchai N, Fizames C, Samson D, Cruaud C, Caloustian C, Gyapay G, Delpech M, Weissenbach J: A transcriptional Map of the FMF region. Genomics. 1998 Jun 1;50(2):147-60. [PubMed Link Image]
Target 2 Drug References
  1. Duhaney TA, Cui L, Rude MK, Lebrasseur NK, Ngoy S, De Silva DS, Siwik DA, Liao R, Sam F: Peroxisome proliferator-activated receptor alpha-independent actions of fenofibrate exacerbates left ventricular dilation and fibrosis in chronic pressure overload. Hypertension. 2007 May;49(5):1084-94. Epub 2007 Mar 12. [PubMed Link Image]
  2. Lebrasseur NK, Duhaney TA, De Silva DS, Cui L, Ip PC, Joseph L, Sam F: Effects of fenofibrate on cardiac remodeling in aldosterone-induced hypertension. Hypertension. 2007 Sep;50(3):489-96. Epub 2007 Jul 2. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.