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Record Information
Version3.6
Creation Date2012-09-06 15:16:51 UTC
Update Date2017-09-14 04:28:10 UTC
HMDB IDHMDB0015173
Secondary Accession Numbers
  • HMDB15173
Metabolite Identification
Common NameFenofibrate
DescriptionFenofibrate is only found in individuals that have used or taken this drug. It is an antilipemic agent which reduces both cholesterol and triglycerides in the blood. [PubChem]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.
Structure
Thumb
Synonyms
ValueSource
2-(4-(4-Chlorobenzoyl)phenoxy)-2-methylpropanoic acid 1-methylethyl esterChEBI
FinofibrateChEBI
FNFChEBI
Isopropyl (4'-(P-chlorobenzoyl)-2-phenoxy-2-methyl)propionateChEBI
Isopropyl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropionateChEBI
LipantilChEBI
ProcetofenChEBI
TricorChEBI
2-(4-(4-Chlorobenzoyl)phenoxy)-2-methylpropanoate 1-methylethyl esterGenerator
Fenofibric acidGenerator
Finofibric acidGenerator
Isopropyl (4'-(P-chlorobenzoyl)-2-phenoxy-2-methyl)propionic acidGenerator
Isopropyl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropionic acidGenerator
AZU, fenofibratMeSH
Abbott brand OF procetofenMeSH
Antara micronized procetofenMeSH
anto Brand OF procetofenMeSH
apo FenofibrateMeSH
Fenofibrat heumannMeSH
Gen fenofibrateMeSH
Genpharm brand OF procetofenMeSH
Heumann brand OF procetofenMeSH
Heumann, fenofibratMeSH
Hexal brand OF procetofenMeSH
Lichtenstein brand OF procetofenMeSH
LipanthylMeSH
LivesanMeSH
LofibraMeSH
MTW FenofibratMeSH
MTW-FenofibratMeSH
NormalipMeSH
Pharmascience brand OF procetofenMeSH
ProcetofeneMeSH
Stada, fenofibratMeSH
SupralipMeSH
DurafenatMeSH
apo feno MicroMeSH
apo-FenofibrateMeSH
Bouchara brand OF procetofenMeSH
CiLMeSH
FenobetaMeSH
Fenofibrat hexalMeSH
Fenofibrat stadaMeSH
Fenofibrat-ratiopharmMeSH
GNR Pharma brand OF procetofenMeSH
gate Brand OF procetofenMeSH
Gen-fenofibrateMeSH
Knoll brand OF procetofenMeSH
Lipidil terMeSH
MTW Brand OF procetofenMeSH
Micronized procetofen, antaraMeSH
Novartis brand OF procetofenMeSH
Nu fenofibrateMeSH
Procetofen reliant brandMeSH
Q-Pharm brand OF procetofenMeSH
Reliant brand OF procetofenMeSH
Schering plough brand OF procetofenMeSH
Ratiopharm brand OF procetofenMeSH
apo-feno-MicroMeSH
Azupharma brand OF procetofenMeSH
Fenofibrat azuMeSH
Fenofibrat abzMeSH
Fenofibrat FPHMeSH
Fenofibrat ratiopharmMeSH
Fénofibrate MSDMeSH
Hexal, fenofibratMeSH
Merck dura brand OF procetofenMeSH
novo-FenofibrateMeSH
Novopharm brand OF procetofenMeSH
Nu pharm brand OF procetofenMeSH
Nu-fenofibrateMeSH
Nu-pharm brand OF procetofenMeSH
PMS-Fenofibrate microMeSH
PhenofibrateMeSH
Schering-plough brand OF procetofenMeSH
United drug brand OF procetofenMeSH
Betapharm brand OF procetofenMeSH
CT Arzneimittel brand OF procetofenMeSH
CT-Arzneimittel brand OF procetofenMeSH
AbZ brand OF procetofenMeSH
Aliud brand OF procetofenMeSH
Apotex brand OF procetofenMeSH
ControlipMeSH
Debat, fénofibrateMeSH
FenofantonMeSH
Fenofibrat alMeSH
Fournier brand OF procetofenMeSH
Fénofibrate debatMeSH
GNR-Pharma brand OF procetofenMeSH
LiparisonMeSH
LipidilMeSH
Lipidil-terMeSH
novo FenofibrateMeSH
PMS Fenofibrate microMeSH
Procetofen, antara micronizedMeSH
Q Pharm brand OF procetofenMeSH
SecalipMeSH
Stadapharm brand OF procetofenMeSH
Fenofibrat von CTMeSH
Chemical FormulaC20H21ClO4
Average Molecular Weight360.831
Monoisotopic Molecular Weight360.112836867
IUPAC Namepropan-2-yl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methylpropanoate
Traditional Nameantara
CAS Registry Number49562-28-9
SMILES
CC(C)OC(=O)C(C)(C)OC1=CC=C(C=C1)C(=O)C1=CC=C(Cl)C=C1
InChI Identifier
InChI=1S/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 KeyYMTINGFKWWXKFG-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentBenzophenones
Alternative Parents
Substituents
  • Benzophenone
  • Aryl-phenylketone
  • Diphenylmethane
  • Phenoxyacetate
  • Phenoxy compound
  • Aryl ketone
  • Phenol ether
  • Benzoyl
  • Alkyl aryl ether
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Carboxylic acid ester
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Ether
  • Organohalogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organochloride
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Antilipemic Agents
  • Fribic Acid Derivatives
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point80.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility7.07e-04 g/LNot Available
LogP5.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000707 mg/mLALOGPS
logP4.86ALOGPS
logP5.28ChemAxon
logS-5.7ALOGPS
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity97.13 m3·mol-1ChemAxon
Polarizability38.15 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , PositiveNot Available
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0090000000-f4e7816cd30c8701cce3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0029000000-60bbd2de375b9b56ec55View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0190000000-6e83f7c906eaeb363cafView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0019-0930000000-fccf28abf1a426a6949bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-07739caadc1c26a7baaaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-5045a0039b18e3d7dd9aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-1900000000-25a145c2138d34aa4b52View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0029000000-a98245ce05ccb6a6707eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0190000000-4e9b3e71fc7960db389eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0019-0930000000-9d3908b5ee8b5f59218dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-1090af5e239a872654d9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-5dcab26837d06f9756f8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-1900000000-2663fed5f3ba78d3c7a5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0090000000-4933bea6ce44715c6172View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-01qi-0595000000-d3c4c1cce3b5e1fbb33fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-01qi-1594000000-9756f301ee5d44577654View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-3920000000-91103d7fd9d1063bae9aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0019-0941000000-27e0cd2c4e952b499a9aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01039 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01039 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-3 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-1 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01039
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3222
KEGG Compound IDC07586
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFenofibrate
NuGOwiki LinkHMDB0015173
METLIN IDNot Available
PubChem Compound3339
PDB IDNot Available
ChEBI ID5001
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)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:15124979 ]
  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:16310551 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular weight:
55824.275
References
  1. Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. [PubMed:15601807 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in DNA binding
Specific function:
Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl- 2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleylethanolamide, a naturally occurring lipid that regulates satiety. Receptor for peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the receptor binds to promoter elements of target genes. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as transcription activator for the acyl-CoA oxidase gene
Gene Name:
PPARA
Uniprot ID:
Q07869
Molecular weight:
52224.6
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:10494028 ]
  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:10799317 ]
  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:11018525 ]
  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:11342537 ]
  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:11474486 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  7. Guerre-Millo M, Gervois P, Raspe E, Madsen L, Poulain P, Derudas B, Herbert JM, Winegar DA, Willson TM, Fruchart JC, Berge RK, Staels B: Peroxisome proliferator-activated receptor alpha activators improve insulin sensitivity and reduce adiposity. J Biol Chem. 2000 Jun 2;275(22):16638-42. [PubMed:10828060 ]
General function:
Not Available
Specific function:
Not Available
Gene Name:
mmp20
Uniprot ID:
O43923
Molecular weight:
20354.0
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:17353509 ]
  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:17606858 ]