Record Information
Version1.0
Creation Date2014-09-11 05:17:33 UTC
Update Date2016-11-09 01:09:13 UTC
Accession NumberCHEM003766
Identification
Common NameGemfibrozil
ClassSmall Molecule
DescriptionA lipid-regulating agent that lowers elevated serum lipids primarily by decreasing serum triglycerides with a variable reduction in total cholesterol. These decreases occur primarily in the VLDL fraction and less frequently in the LDL fraction. Gemfibrozil increases HDL subfractions HDL2 and HDL3 as well as apolipoproteins A-I and A-II. Its mechanism of action has not been definitely established.
Contaminant Sources
  • HMDB Contaminants - Urine
  • IARC Carcinogens Group 3
  • STOFF IDENT Compounds
  • Suspected Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Drug
  • Ether
  • Hypolipidemic Agent
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
2,2-Dimethyl-5-(2,5-dimethylphenoxy)valeriansaeureChEBI
2,2-Dimethyl-5-(2,5-xylyloxy)valeriansaeureChEBI
2,2-Dimethyl-5-(2,5-xylyloxy)valeric acidChEBI
GemfibroziloChEBI
GemfibrozilumChEBI
LopidChEBI
2,2-Dimethyl-5-(2,5-xylyloxy)valerateGenerator
1a Brand OF gemfibrozilHMDB
Alphapharm brand OF gemfibrozilHMDB
Bayvit, gemfibroziloHMDB
Bexal brand OF gemfibrozilHMDB
Biochemie brand OF gemfibrozilHMDB
BolutolHMDB
Chem mart gemfibrozilHMDB
Farmasierra brand OF gemfibrozilHMDB
Faulding brand OF gemfibrozilHMDB
Gemfibrozil, healthsenseHMDB
GenRX gemfibrozilHMDB
Genpharm brand OF gemfibrozilHMDB
Ipsen brand OF gemfibrozilHMDB
JezilHMDB
Lipox gemfiHMDB
Menarini brand OF gemfibrozilHMDB
Nu-gemfibrozilHMDB
Nu-pharm brand OF gemfibrozilHMDB
PMS-GemfibrozilHMDB
SBPA gemfibrozilHMDB
Sigma brand OF gemfibrozilHMDB
Warner lambert brand OF gemfibrozilHMDB
ApoGemfibrozilHMDB
AusgemHMDB
Bayvit brand OF gemfibrozilHMDB
DBL GemfibrozilHMDB
Douglas brand OF gemfibrozilHMDB
Gemfibrozil, sbpaHMDB
Gemfibrozilo urHMDB
GenGemfibrozilHMDB
LipazilHMDB
Novo-gemfibrozilHMDB
Nu pharm brand OF gemfibrozilHMDB
NuGemfibrozilHMDB
Pharmascience brand OF gemfibrozilHMDB
Apo-gemfibrozilHMDB
Cantabria brand OF gemfibrozilHMDB
Chem mart brand OF gemfibrozilHMDB
GemfibrosilHMDB
Gemfibrozilo bayvitHMDB
Gemfibrozilo bexalHMDB
GemhexalHMDB
Gen gemfibrozilHMDB
Gen-gemfibrozilHMDB
LipurHMDB
Lopid RHMDB
Nu gemfibrozilHMDB
Parke davis brand OF gemfibrozilHMDB
PilderHMDB
Terry white chemists brand OF gemfibrozilHMDB
United drug brand OF gemfibrozilHMDB
Warner-lambert brand OF gemfibrozilHMDB
Apo gemfibrozilHMDB
Apotex brand OF gemfibrozilHMDB
Bull brand OF gemfibrozilHMDB
DecrelipHMDB
Ferrer brand OF gemfibrozilHMDB
Gemfi 1a pharmaHMDB
Gemfibrozil, genrxHMDB
Healthsense brand OF gemfibrozilHMDB
Healthsense gemfibrozilHMDB
Hexal brand OF gemfibrozilHMDB
LitarekHMDB
Novo gemfibrozilHMDB
Novopharm brand OF gemfibrozilHMDB
PMS GemfibrozilHMDB
Pfizer brand OF gemfibrozilHMDB
Quimifar brand OF gemfibrozilHMDB
TAD brand OF gemfibrozilHMDB
Terry white chemists gemfibrozilHMDB
TrialminHMDB
Chemical FormulaC15H22O3
Average Molecular Mass250.333 g/mol
Monoisotopic Mass250.157 g/mol
CAS Registry Number25812-30-0
IUPAC Name5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid
Traditional Namegemfibrozil
SMILESCC1=CC(OCCCC(C)(C)C(O)=O)=C(C)C=C1
InChI IdentifierInChI=1S/C15H22O3/c1-11-6-7-12(2)13(10-11)18-9-5-8-15(3,4)14(16)17/h6-7,10H,5,8-9H2,1-4H3,(H,16,17)
InChI KeyHEMJJKBWTPKOJG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassNot Available
Direct ParentPhenol ethers
Alternative Parents
Substituents
  • Phenoxy compound
  • P-xylene
  • Xylene
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point62°C
Boiling Point158.5°C at 2.00E-02 mm Hg
Solubility10 mg/mL (in base)
Predicted Properties
PropertyValueSource
Water Solubility0.028 g/LALOGPS
logP3.61ALOGPS
logP4.39ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)4.42ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity71.82 m³·mol⁻¹ChemAxon
Polarizability28.9 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0076-6950000000-ea8e6e101df62d80313aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05g0-9721000000-e7c61af259566e389d95Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-0900000000-24b892a8bd68bdf9cef6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-0900000000-7a9eaaae65f0e1efcbc4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-0900000000-12b36ea4be2a1b876c61Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-0900000000-647692900acca2ec2441Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-0900000000-41c8e4e08162dfaf1fc4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-0900000000-28d25da91cc1d391cc84Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00di-0900000000-a08267bdc97edb1a2601Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-00di-0900000000-a133a90a69b988c45ffbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0059-6910000000-0ad597adcb83e9f4e4baSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0059-8900000000-8684ba342d3eb0a7f602Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-05cr-9400000000-008385b887cc6ac6d748Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0ac0-9300000000-74e1b5c007dd49af6a01Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0ab9-9200000000-cc36aaee7c70d8e92f96Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4i-9100000000-ce28ed926945c33079d6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-052g-9400000000-7df8d3b3c3d528585b24Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0ab9-9200000000-a29f6ecb2573b0a72463Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0a4i-9100000000-ce28ed926945c33079d6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0970000000-b6b747ddc80c5e277857Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0002-0390000000-b42eee5672459e8cc06bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zfr-0290000000-ed946d5de4de22b6bf20Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-4970000000-01a0d2adb215feef78ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-9500000000-f971c24cd2f474fea5a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0490000000-2ba2ea9e2ef949ad859bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1950000000-865193b239a02078f9b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-4900000000-adb1ff2509f9361f33feSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureWell absorbed from gastrointestinal tract (within 1-2 hours).
Mechanism of ToxicityGemfibrozil increases the activity of extrahepatic lipoprotein lipase (LL), thereby increasing lipoprotein triglyceride lipolysis. It does so by activating Peroxisome proliferator-activated receptor-alpha (PPAR‘±) 'transcription factor ligand', a receptor that is involved in metabolism of carbohydrates and fats, as well as adipose tissue differentiation. This increase in the synthesis of lipoprotein lipase thereby increases the clearance of triglycerides. Chylomicrons are degraded, VLDLs are converted to LDLs, and LDLs are converted to HDL. This is accompanied by a slight increase in secretion of lipids into the bile and ultimately the intestine. Gemfibrozil also inhibits the synthesis and increases the clearance of apolipoprotein B, a carrier molecule for VLDL.
MetabolismHepatic. Gemfibrozil mainly undergoes oxidation of a ring methyl group to successively form a hydroxymethyl and a carboxyl metabolite. Route of Elimination: Approximately seventy percent of the administered human dose is excreted in the urine, mostly as the glucuronide conjugate, with less than 2% excreted as unchanged gemfibrozil. Half Life: 1.5 hours
Toxicity ValuesOral, mouse: LD50 = 3162 mg/kg.
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (1)
Uses/SourcesFor treatment of adult patients with very high elevations of serum triglyceride levels (types IV and V hyperlipidemia) who are at risk of developing pancreatitis (inflammation of the pancreas) and who do not respond adequately to a strict diet.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms of overdose include abdominal cramps, diarrhea, joint and muscle pain, nausea, and vomiting.
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01241
HMDB IDHMDB0015371
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkGemfibrozil
Chemspider ID3345
ChEBI ID5296
PubChem Compound ID3463
Kegg Compound IDC07020
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Gianfranco Piccoli, Antonio Tarquini, Giovanni Frare, “Process for the preparation of gemfibrozil.” U.S. Patent US5654476, issued May, 1980.

MSDSLink
General ReferencesNot Available