You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2020-02-26 21:41:40 UTC
HMDB IDHMDB0015465
Secondary Accession Numbers
  • HMDB15465
Metabolite Identification
Common NameBezafibrate
DescriptionBezafibrate, also known as bezalip or bezatol SR, belongs to the class of organic compounds known as phenoxyacetic acid derivatives. Phenoxyacetic acid derivatives are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative. Bezafibrate is a drug which is used for the treatment of primary hyperlipidaemia types iia, iib, iii, iv and v (fredrickson classification) corresponding to groups i, ii and iii of the european atherosclerosis society guidelines - when diet alone or improvements in lifestyle such as increased exercise or weight reduction do not lead to an adequate response. also for the treatment of secondary hyperlipidaemias, e.g. severe hypertriglyceridemias, when sufficient improvement does not occur after correction of the underlying disorder (e.g. diabetes mellitus). Bezafibrate is an extremely weak basic (essentially neutral) compound (based on its pKa). Bezafibrate exerts an effect on thrombogenic factors. In the same patients, the concentration of fasting and postprandial free fatty acids was reduced by bezafibrate. Furthermore, cholesterol biosynthesis is reduced by bezafibrate, which is accompanied by a stimulation of the LDL-receptor-mediated lipoprotein catabolism. It decreases low density lipoproteins and increases high density lipoproteins. The activity of triglyceride lipases (lipoprotein lipase and hepatic lipoproteinlipase) involved in the catabolism of triglyceride-rich lipoproteins is increased by bezafibrate.
Structure
Data?1582753300
Synonyms
ValueSource
2-(p-(2-(p-Chlorobenzamido)ethyl)phenoxy)-2-methylpropionic acidChEBI
BefizalChEBI
BezafibratoChEBI
BezafibratumChEBI
BezalipChEBI
Bezatol SRChEBI
CedurChEBI
2-(p-(2-(p-Chlorobenzamido)ethyl)phenoxy)-2-methylpropionateGenerator
Bezafibric acidGenerator
BezafibratHMDB
BefibratHMDB
Beza purenHMDB
Bezafibrat PBHMDB
Bezafibrate elfar brandHMDB
Bezafibrate isis brandHMDB
Bezafibrate tad brandHMDB
EulitopHMDB
Hennig brand OF bezafibrateHMDB
LipoxHMDB
SklerofibratHMDB
Teva brand OF bezafibrateHMDB
DurabezurHMDB
Azupharma brand OF bezafibrateHMDB
Beza landeHMDB
BezacurHMDB
Bezafibrate berlin-chemie brandHMDB
Bezafibrate hennig brandHMDB
Bezafibrate hexal brandHMDB
Bezafibrate merckle brandHMDB
Bezafibrate teva brandHMDB
Hexal brand OF bezafibrateHMDB
Isis brand OF bezafibrateHMDB
Lakeside brand OF bezafibrateHMDB
PB, BezafibratHMDB
SolibayHMDB
Synthelabo brand OF bezafibrateHMDB
Bayer brand OF bezafibrateHMDB
Berlin chemie brand OF bezafibrateHMDB
Berlin-chemie brand OF bezafibrateHMDB
Beza-landeHMDB
Beza-purenHMDB
Bezafibrate synthelabo brandHMDB
BezafisalHMDB
BezamerckHMDB
BéfizalHMDB
Cryopharma brand OF bezafibrateHMDB
DifaterolHMDB
Elfar brand OF bezafibrateHMDB
Merckle brand OF bezafibrateHMDB
Roche brand OF bezafibrateHMDB
AzufibratHMDB
Betapharm brand OF bezafibrateHMDB
BezaLandeHMDB
BezaPurenHMDB
BezabetaHMDB
Bezafibrate azupharma brandHMDB
Bezafibrate bayer brandHMDB
Bezafibrate betapharm brandHMDB
Bezafibrate cryopharma brandHMDB
Bezafibrate lakeside brandHMDB
Bezafibrate roche brandHMDB
Boehringer mannheim brand OF bezafibrateHMDB
ReducterolHMDB
Regadrin bHMDB
TAD brand OF bezafibrateHMDB
Chemical FormulaC19H20ClNO4
Average Molecular Weight361.819
Monoisotopic Molecular Weight361.10808584
IUPAC Name2-(4-{2-[(4-chlorophenyl)formamido]ethyl}phenoxy)-2-methylpropanoic acid
Traditional Namebezafibrate
CAS Registry Number41859-67-0
SMILES
CC(C)(OC1=CC=C(CCNC(=O)C2=CC=C(Cl)C=C2)C=C1)C(O)=O
InChI Identifier
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)
InChI KeyIIBYAHWJQTYFKB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenoxyacetic acid derivatives. Phenoxyacetic acid derivatives are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenoxyacetic acid derivatives
Direct ParentPhenoxyacetic acid derivatives
Alternative Parents
Substituents
  • Phenoxyacetate
  • 4-halobenzoic acid or derivatives
  • Halobenzoic acid or derivatives
  • Benzoic acid or derivatives
  • Benzamide
  • Phenoxy compound
  • Phenol ether
  • Benzoyl
  • Chlorobenzene
  • Alkyl aryl ether
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Ether
  • Organic nitrogen compound
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point186 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0016 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0016 g/LALOGPS
logP3.97ALOGPS
logP3.99ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)3.83ChemAxon
pKa (Strongest Basic)-0.84ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.63 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity95.96 m³·mol⁻¹ChemAxon
Polarizability37.53 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000l-1921000000-ed1d61965cb5663ba976Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-000i-4921000000-cf3ec530f82c5fef8a3aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00di-0090000000-ad4511ba17ddb3a6b528Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-03k9-0049000000-319540ed864d05b5a9e8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00di-0090000000-65fad146d0a2b8cc3aebSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0uk9-1980000000-f98f5d510895c2946e24Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-1900000000-58a247b2b13eaf401a8aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-3900000000-82a7a949824b1efdbd18Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-03k9-0049000000-e56612834951c9281537Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00di-0090000000-54280ef14ba8e69fb8fbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0fk9-1890000000-81049839e6d37ddb476aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0900000000-3ff4da4d943e21e1f3a1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-2900000000-d499986dc5288dfff06cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00di-0090000000-62a3f94f91039648ffe1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00di-0390000000-52f95c54ab1946e7c69fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00di-0190000000-5257df29ed69050f426dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00di-0090000000-ced0d5dcc71914483b64Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00di-0090000000-849460edc8b9e96e9749Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-2392000000-f4f98f4b89b6ae9a88d1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-016r-0049000000-03924d783ef40666f558Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0019000000-58ff2df39e2672d16d49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0139000000-610de57b431b6eaccb80Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07fu-3975000000-315ebcbd95638a3d3b0eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08g0-2910000000-2d6abee2d54effe38335Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0219000000-13daa1136c7e69d084a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ir0-0955000000-59d63587ef6ff82c5b8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0w29-1910000000-7005220edef11728283cSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01393 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01393 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01393
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID35728
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBezafibrate
METLIN IDNot Available
PubChem Compound39042
PDB IDPEM
ChEBI ID47612
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Authors unspecified: Secondary prevention by raising HDL cholesterol and reducing triglycerides in patients with coronary artery disease. Circulation. 2000 Jul 4;102(1):21-7. [PubMed:10880410 ]
  2. Tenenbaum A, Motro M, Fisman EZ, Schwammenthal E, Adler Y, Goldenberg I, Leor J, Boyko V, Mandelzweig L, Behar S: Peroxisome proliferator-activated receptor ligand bezafibrate for prevention of type 2 diabetes mellitus in patients with coronary artery disease. Circulation. 2004 May 11;109(18):2197-202. Epub 2004 May 3. [PubMed:15123532 ]
  3. Tenenbaum A, Motro M, Fisman EZ, Tanne D, Boyko V, Behar S: Bezafibrate for the secondary prevention of myocardial infarction in patients with metabolic syndrome. Arch Intern Med. 2005 May 23;165(10):1154-60. [PubMed:15911729 ]
  4. Tenenbaum A, Fisman EZ, Boyko V, Benderly M, Tanne D, Haim M, Matas Z, Motro M, Behar S: Attenuation of progression of insulin resistance in patients with coronary artery disease by bezafibrate. Arch Intern Med. 2006 Apr 10;166(7):737-41. [PubMed:16606809 ]
  5. MEDSAFE [Link]

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.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Molecular weight:
58164.815
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. 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:
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. Key regulator of adipocyte differentiation and glucose homeostasis
Gene Name:
PPARG
Uniprot ID:
P37231
Molecular weight:
57619.6
References
  1. Tenenbaum A, Motro M, Fisman EZ: Dual and pan-peroxisome proliferator-activated receptors (PPAR) co-agonism: the bezafibrate lessons. Cardiovasc Diabetol. 2005 Sep 16;4:14. [PubMed:16168052 ]
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. Pedraza N, Solanes G, Carmona MC, Iglesias R, Vinas O, Mampel T, Vazquez M, Giralt M, Villarroya F: Impaired expression of the uncoupling protein-3 gene in skeletal muscle during lactation: fibrates and troglitazone reverse lactation-induced downregulation of the uncoupling protein-3 gene. Diabetes. 2000 Jul;49(7):1224-30. [PubMed:10909982 ]
  2. Cabrero A, Alegret M, Sanchez R, Adzet T, Laguna JC, Vazquez M: Peroxisome proliferator-activated receptor alpha (PPARalpha) activators, bezafibrate and Wy-14,643, increase uncoupling protein-3 mRNA levels without modifying the mitochondrial membrane potential in primary culture of rat preadipocytes. Arch Biochem Biophys. 2000 Aug 15;380(2):353-9. [PubMed:10933891 ]
  3. Inoue I, Goto S, Matsunaga T, Nakajima T, Awata T, Hokari S, Komoda T, Katayama S: The ligands/activators for peroxisome proliferator-activated receptor alpha (PPARalpha) and PPARgamma increase Cu2+,Zn2+-superoxide dismutase and decrease p22phox message expressions in primary endothelial cells. Metabolism. 2001 Jan;50(1):3-11. [PubMed:11172467 ]
  4. Guan Y, Breyer MD: Peroxisome proliferator-activated receptors (PPARs): novel therapeutic targets in renal disease. Kidney Int. 2001 Jul;60(1):14-30. [PubMed:11422732 ]
  5. Bonilla S, Redonnet A, Noel-Suberville C, Groubet R, Pallet V, Higueret P: Effect of a pharmacological activation of PPAR on the expression of RAR and TR in rat liver. J Physiol Biochem. 2001 Mar;57(1):1-8. [PubMed:11519881 ]
  6. Goldenberg I, Benderly M, Goldbourt U: Update on the use of fibrates: focus on bezafibrate. Vasc Health Risk Manag. 2008;4(1):131-41. [PubMed:18629356 ]
  7. Fruchart JC, Duriez P: Mode of action of fibrates in the regulation of triglyceride and HDL-cholesterol metabolism. Drugs Today (Barc). 2006 Jan;42(1):39-64. [PubMed:16511610 ]
  8. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in DNA binding
Specific function:
Ligand-activated transcription factor. Receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Has a preference for poly-unsaturated fatty acids, such as gamma-linoleic acid and eicosapentanoic acid. 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. Decreases expression of NPC1L1 once activated by a ligand
Gene Name:
PPARD
Uniprot ID:
Q03181
Molecular weight:
49903.0
References
  1. Tenenbaum A, Motro M, Fisman EZ: Dual and pan-peroxisome proliferator-activated receptors (PPAR) co-agonism: the bezafibrate lessons. Cardiovasc Diabetol. 2005 Sep 16;4:14. [PubMed:16168052 ]

Transporters

General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:
SLCO1B1
Uniprot ID:
Q9Y6L6
Molecular weight:
76448.0
References
  1. Sharma P, Holmes VE, Elsby R, Lambert C, Surry D: Validation of cell-based OATP1B1 assays to assess drug transport and the potential for drug-drug interaction to support regulatory submissions. Xenobiotica. 2010 Jan;40(1):24-37. doi: 10.3109/00498250903351013. [PubMed:19919292 ]