ContaminantDB: Gemfibrozil

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (2)XML

Record Information

Version

1.0

Creation Date

2014-09-11 05:17:33 UTC

Update Date

2016-11-09 01:09:13 UTC

Accession Number

CHEM003766

Identification

Common Name

Gemfibrozil

Class

Small Molecule

Description

A 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2,2-Dimethyl-5-(2,5-dimethylphenoxy)valeriansaeure	ChEBI
2,2-Dimethyl-5-(2,5-xylyloxy)valeriansaeure	ChEBI
2,2-Dimethyl-5-(2,5-xylyloxy)valeric acid	ChEBI
Gemfibrozilo	ChEBI
Gemfibrozilum	ChEBI
Lopid	ChEBI
2,2-Dimethyl-5-(2,5-xylyloxy)valerate	Generator
1a Brand OF gemfibrozil	HMDB
Alphapharm brand OF gemfibrozil	HMDB
Bayvit, gemfibrozilo	HMDB
Bexal brand OF gemfibrozil	HMDB
Biochemie brand OF gemfibrozil	HMDB
Bolutol	HMDB
Chem mart gemfibrozil	HMDB
Farmasierra brand OF gemfibrozil	HMDB
Faulding brand OF gemfibrozil	HMDB
Gemfibrozil, healthsense	HMDB
GenRX gemfibrozil	HMDB
Genpharm brand OF gemfibrozil	HMDB
Ipsen brand OF gemfibrozil	HMDB
Jezil	HMDB
Lipox gemfi	HMDB
Menarini brand OF gemfibrozil	HMDB
Nu-gemfibrozil	HMDB
Nu-pharm brand OF gemfibrozil	HMDB
PMS-Gemfibrozil	HMDB
SBPA gemfibrozil	HMDB
Sigma brand OF gemfibrozil	HMDB
Warner lambert brand OF gemfibrozil	HMDB
ApoGemfibrozil	HMDB
Ausgem	HMDB
Bayvit brand OF gemfibrozil	HMDB
DBL Gemfibrozil	HMDB
Douglas brand OF gemfibrozil	HMDB
Gemfibrozil, sbpa	HMDB
Gemfibrozilo ur	HMDB
GenGemfibrozil	HMDB
Lipazil	HMDB
Novo-gemfibrozil	HMDB
Nu pharm brand OF gemfibrozil	HMDB
NuGemfibrozil	HMDB
Pharmascience brand OF gemfibrozil	HMDB
Apo-gemfibrozil	HMDB
Cantabria brand OF gemfibrozil	HMDB
Chem mart brand OF gemfibrozil	HMDB
Gemfibrosil	HMDB
Gemfibrozilo bayvit	HMDB
Gemfibrozilo bexal	HMDB
Gemhexal	HMDB
Gen gemfibrozil	HMDB
Gen-gemfibrozil	HMDB
Lipur	HMDB
Lopid R	HMDB
Nu gemfibrozil	HMDB
Parke davis brand OF gemfibrozil	HMDB
Pilder	HMDB
Terry white chemists brand OF gemfibrozil	HMDB
United drug brand OF gemfibrozil	HMDB
Warner-lambert brand OF gemfibrozil	HMDB
Apo gemfibrozil	HMDB
Apotex brand OF gemfibrozil	HMDB
Bull brand OF gemfibrozil	HMDB
Decrelip	HMDB
Ferrer brand OF gemfibrozil	HMDB
Gemfi 1a pharma	HMDB
Gemfibrozil, genrx	HMDB
Healthsense brand OF gemfibrozil	HMDB
Healthsense gemfibrozil	HMDB
Hexal brand OF gemfibrozil	HMDB
Litarek	HMDB
Novo gemfibrozil	HMDB
Novopharm brand OF gemfibrozil	HMDB
PMS Gemfibrozil	HMDB
Pfizer brand OF gemfibrozil	HMDB
Quimifar brand OF gemfibrozil	HMDB
TAD brand OF gemfibrozil	HMDB
Terry white chemists gemfibrozil	HMDB
Trialmin	HMDB

Chemical Formula

C₁₅H₂₂O₃

Average Molecular Mass

250.333 g/mol

Monoisotopic Mass

250.157 g/mol

CAS Registry Number

25812-30-0

IUPAC Name

5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid

Traditional Name

gemfibrozil

SMILES

CC1=CC(OCCCC(C)(C)C(O)=O)=C(C)C=C1

InChI Identifier

InChI=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 Key

HEMJJKBWTPKOJG-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol ethers

Sub Class

Not Available

Direct Parent

Phenol 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:5296 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	62°C
Boiling Point	158.5°C at 2.00E-02 mm Hg
Solubility	10 mg/mL (in base)

Predicted Properties

Property	Value	Source
Water Solubility	0.028 g/L	ALOGPS
logP	3.61	ALOGPS
logP	4.39	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	4.42	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	71.82 m³·mol⁻¹	ChemAxon
Polarizability	28.9 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0076-6950000000-ea8e6e101df62d80313a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05g0-9721000000-e7c61af259566e389d95	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00di-0900000000-24b892a8bd68bdf9cef6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00di-0900000000-7a9eaaae65f0e1efcbc4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00di-0900000000-12b36ea4be2a1b876c61	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00di-0900000000-647692900acca2ec2441	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00di-0900000000-41c8e4e08162dfaf1fc4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00di-0900000000-28d25da91cc1d391cc84	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-00di-0900000000-a08267bdc97edb1a2601	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-00di-0900000000-a133a90a69b988c45ffb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0059-6910000000-0ad597adcb83e9f4e4ba	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0059-8900000000-8684ba342d3eb0a7f602	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-05cr-9400000000-008385b887cc6ac6d748	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0ac0-9300000000-74e1b5c007dd49af6a01	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0ab9-9200000000-cc36aaee7c70d8e92f96	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0a4i-9100000000-ce28ed926945c33079d6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-052g-9400000000-7df8d3b3c3d528585b24	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-0ab9-9200000000-a29f6ecb2573b0a72463	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-0a4i-9100000000-ce28ed926945c33079d6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0970000000-b6b747ddc80c5e277857	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0002-0390000000-b42eee5672459e8cc06b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0zfr-0290000000-ed946d5de4de22b6bf20	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a59-4970000000-01a0d2adb215feef78cc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-053r-9500000000-f971c24cd2f474fea5a3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0490000000-2ba2ea9e2ef949ad859b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-1950000000-865193b239a02078f9b6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-4900000000-adb1ff2509f9361f33fe	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Well absorbed from gastrointestinal tract (within 1-2 hours).

Mechanism of Toxicity

Gemfibrozil 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.

Metabolism

Hepatic. 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 Values

Oral, mouse: LD₅₀ = 3162 mg/kg.

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (1)

Uses/Sources

For 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 Level

Not Available

Health Effects

Not Available

Symptoms

Symptoms of overdose include abdominal cramps, diarrhea, joint and muscle pain, nausea, and vomiting.

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID