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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:41:07 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
Data?1582753266
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
AntaraKegg
LipofenKegg
TriglideKegg
2-(4-(4-Chlorobenzoyl)phenoxy)-2-methylpropanoate 1-methylethyl esterGenerator
Finofibric acidGenerator
Isopropyl (4'-(p-chlorobenzoyl)-2-phenoxy-2-methyl)propionic acidGenerator
Isopropyl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropionic acidGenerator
Fenofibric acidGenerator
AZU, fenofibratHMDB
Abbott brand OF procetofenHMDB
Antara micronized procetofenHMDB
Anto brand OF procetofenHMDB
Apo fenofibrateHMDB
Fenofibrat heumannHMDB
Gen fenofibrateHMDB
Genpharm brand OF procetofenHMDB
Heumann brand OF procetofenHMDB
Heumann, fenofibratHMDB
Hexal brand OF procetofenHMDB
Lichtenstein brand OF procetofenHMDB
LipanthylHMDB
LivesanHMDB
LofibraHMDB
MTW FenofibratHMDB
MTW-FenofibratHMDB
NormalipHMDB
Pharmascience brand OF procetofenHMDB
ProcetofeneHMDB
Stada, fenofibratHMDB
SupralipHMDB
DurafenatHMDB
Apo feno microHMDB
Apo-fenofibrateHMDB
Bouchara brand OF procetofenHMDB
CiLHMDB
FenobetaHMDB
Fenofibrat hexalHMDB
Fenofibrat stadaHMDB
Fenofibrat-ratiopharmHMDB
GNR Pharma brand OF procetofenHMDB
gate Brand OF procetofenHMDB
Gen-fenofibrateHMDB
Knoll brand OF procetofenHMDB
Lipidil terHMDB
MTW Brand OF procetofenHMDB
Micronized procetofen, antaraHMDB
Novartis brand OF procetofenHMDB
Nu fenofibrateHMDB
Procetofen reliant brandHMDB
Q-Pharm brand OF procetofenHMDB
Reliant brand OF procetofenHMDB
Schering plough brand OF procetofenHMDB
Ratiopharm brand OF procetofenHMDB
Apo-feno-microHMDB
Azupharma brand OF procetofenHMDB
Fenofibrat azuHMDB
Fenofibrat abzHMDB
Fenofibrat FPHHMDB
Fenofibrat ratiopharmHMDB
Fénofibrate MSDHMDB
Hexal, fenofibratHMDB
Merck dura brand OF procetofenHMDB
Novo-fenofibrateHMDB
Novopharm brand OF procetofenHMDB
Nu pharm brand OF procetofenHMDB
Nu-fenofibrateHMDB
Nu-pharm brand OF procetofenHMDB
PMS-Fenofibrate microHMDB
PhenofibrateHMDB
Schering-plough brand OF procetofenHMDB
United drug brand OF procetofenHMDB
Betapharm brand OF procetofenHMDB
CT Arzneimittel brand OF procetofenHMDB
CT-Arzneimittel brand OF procetofenHMDB
AbZ brand OF procetofenHMDB
Aliud brand OF procetofenHMDB
Apotex brand OF procetofenHMDB
ControlipHMDB
Debat, fénofibrateHMDB
FenofantonHMDB
Fenofibrat alHMDB
Fournier brand OF procetofenHMDB
Fénofibrate debatHMDB
GNR-Pharma brand OF procetofenHMDB
LiparisonHMDB
LipidilHMDB
Lipidil-terHMDB
Novo fenofibrateHMDB
PMS Fenofibrate microHMDB
Procetofen, antara micronizedHMDB
Q Pharm brand OF procetofenHMDB
SecalipHMDB
Stadapharm brand OF procetofenHMDB
Fenofibrat von CTHMDB
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
Description belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzophenones
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
Disposition

Source:

Route of exposure:

Biological location:

Role

Environmental role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point80.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00071 g/LNot Available
LogP5.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00071 g/LALOGPS
logP4.86ALOGPS
logP5.28ChemAxon
logS-5.7ALOGPS
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity97.13 m³·mol⁻¹ChemAxon
Polarizability38.15 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-6390000000-5464dc4b809f70f9340dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-000i-0122900000-4e3cc64221a0b278b61eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0090000000-f4e7816cd30c8701cce3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0029000000-60bbd2de375b9b56ec55Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0190000000-6e83f7c906eaeb363cafSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0019-0930000000-fccf28abf1a426a6949bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-07739caadc1c26a7baaaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-5045a0039b18e3d7dd9aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-1900000000-25a145c2138d34aa4b52Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0029000000-a98245ce05ccb6a6707eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0190000000-4e9b3e71fc7960db389eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0019-0930000000-9d3908b5ee8b5f59218dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-1090af5e239a872654d9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-5dcab26837d06f9756f8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-1900000000-2663fed5f3ba78d3c7a5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0090000000-4933bea6ce44715c6172Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-01qi-0595000000-d3c4c1cce3b5e1fbb33fSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-01qi-1594000000-9756f301ee5d44577654Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-3920000000-91103d7fd9d1063bae9aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0019-0941000000-27e0cd2c4e952b499a9aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0039000000-944af46f336da55a8475Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-2293000000-4801131855d2da97d5eeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ec-5970000000-1378e4f4b3a07ef9697dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0119000000-2b2235f5a6097ea83d1eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-053r-1297000000-e56c9f467ebb0930e34aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-0970000000-abe9ec8d570cd8856680Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01039 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01039 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01039
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3222
KEGG Compound IDC07586
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFenofibrate
METLIN IDNot Available
PubChem Compound3339
PDB IDNot Available
ChEBI ID5001
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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 ]