GEMFIBROZIL

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC C10AB04
UNII Q8X02027X3
EPA CompTox DTXSID0020652

Structure

InChI Key HEMJJKBWTPKOJG-UHFFFAOYSA-N
Smiles Cc1ccc(C)c(OCCCC(C)(C)C(=O)O)c1
InChI
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)

Physicochemical Descriptors

Property Name Value
Molecular Formula C15H22O3
Molecular Weight 250.34
AlogP 3.57
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 6.0
Polar Surface Area 46.53
Molecular species ACID
Aromatic Rings 1.0
Heavy Atoms 18.0

Bioactivity

Mechanism of Action Action Reference
Peroxisome proliferator-activated receptor alpha agonist AGONIST DailyMed Wikipedia Wikipedia
Protein: Peroxisome proliferator-activated receptor alpha
Description: Peroxisome proliferator-activated receptor alpha
Organism : Homo sapiens
Q07869 ENSG00000186951
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Auxiliary transport protein Fatty acid binding protein family
- - - 1860 -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C8
- 4100-95000 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- 9600 - - -
Enzyme Oxidoreductase
- - - - 14
Secreted protein
- - 100 - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group C Nuclear hormone receptor subfamily 1 group C member 1
59000-59000 - - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- 4074-38000 - - 14-71
Unclassified protein
- - - 7291 -
Assay Description Organism Bioactivity Reference
Inhibition of beta-lactamase at 100 uM None 5.0 %
Inhibition of chymotrypsin at 250 uM unidentified 5.0 %
Compound was evaluated for the inhibitory activity against human platelet aggregation by COL/ADP cartridges at a concentration of 1 x 10 e-3 M Homo sapiens 0.0 %
Compound was evaluated for the inhibitory activity against human platelet aggregation by COL/ADP cartridges at a concentration of 2 x 10 e-3 M Homo sapiens 2.5 %
Compound was evaluated for the inhibitory activity against human platelet aggregation by COL/ADP cartridges at a concentration of 3 x 10 e-3 M Homo sapiens 17.0 %
Compound was evaluated for the inhibitory activity against human platelet aggregation by COL/ADP cartridges at a concentration of 4 x 10 e-3 M Homo sapiens 100.0 %
Compound was evaluated for the inhibitory activity against human platelet aggregation by COL/ADP cartridges at a concentration of 5 x 10 e-3 M Homo sapiens 100.0 %
Compound was tested for the inhibition of malate dehydrogenase (MDH) at 200 uM None 14.0 %
In vitro inhibitory activity against rat microsomal lipid peroxidation (m-LPO) Rattus norvegicus 0.1 ug.mL-1
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens 59.3 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 14.4 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 15.1 %
Antidyslipidemic activity in high fat diet fed Rattus norvegicus Charles Foster (rat) assessed as inhibition of cholesterol-induced phospholipid level in liver at 100 mg/kg, po administered QD for 30 days relative to control Rattus norvegicus -32.0 %
Antidyslipidemic activity in high fat diet fed Rattus norvegicus Charles Foster (rat) assessed as inhibition of cholesterol-induced triglyceride level in liver at 100 mg/kg, po administered QD for 30 days relative to control Rattus norvegicus -31.0 %
Antidyslipidemic activity in high fat diet fed Rattus norvegicus Charles Foster (rat) assessed as inhibition of cholesterol-induced total cholesterol level in liver at 100 mg/kg, po administered QD for 30 days relative to control Rattus norvegicus -28.0 %
Antidyslipidemic activity in high fat diet fed Rattus norvegicus Charles Foster (rat) assessed as inhibition of cholesterol-induced protein level in plasma at 100 mg/kg, po administered QD for 30 days relative to control Rattus norvegicus -31.0 %
Antidyslipidemic activity in high fat diet fed Rattus norvegicus Charles Foster (rat) assessed as inhibition of cholesterol-induced phospholipid level in plasma at 100 mg/kg, po administered QD for 30 days relative to control Rattus norvegicus -31.0 %
Antidyslipidemic activity in high fat diet fed Rattus norvegicus Charles Foster (rat) assessed as inhibition of cholesterol-induced triglyceride level in plasma at 100 mg/kg, po administered QD for 30 days relative to control Rattus norvegicus -34.0 %
Antidyslipidemic activity in high fat diet fed Rattus norvegicus Charles Foster (rat) assessed as inhibition of cholesterol-induced total cholesterol level in plasma at 100 mg/kg, po administered QD for 30 days relative to control Rattus norvegicus -34.0 %
Antidyslipidemic activity in Rattus norvegicus Charles Foster (rat) assessed as inhibition of triton WR1339-induced protein level in plasma at 100 mg/kg, po after 18 hr relative to control Rattus norvegicus -30.0 %
Antidyslipidemic activity in Rattus norvegicus Charles Foster (rat) assessed as inhibition of triton WR1339-induced phospholipid in plasma at 100 mg/kg, po after 18 hr relative to control Rattus norvegicus -34.0 %
Antidyslipidemic activity in Rattus norvegicus Charles Foster (rat) assessed as inhibition of triton WR1339-induced triglyceride in plasma at 100 mg/kg, po after 18 hr relative to control Rattus norvegicus 36.0 %
Antidyslipidemic activity in Rattus norvegicus Charles Foster (rat) assessed as inhibition of triton WR1339-induced total cholesterol in plasma at 100 mg/kg, po after 18 hr relative to control Rattus norvegicus -36.0 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 56.21 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 71.16 %
Binding affinity to TTR (unknown origin) by isothermal titration calorimetric analysis Homo sapiens 100.0 nM
Inhibition of human recombinant COX1 expressed in Sf9 cell microsomes assessed as reduction in conversion of arachidonic acid to PGE2 at 250 uM incubated for 5 mins by HTRF assay Homo sapiens 18.0 %
In vivo inhibition of CYP2C8 in human assessed as reduction in gemfibrozil-1-O-glucuronide metabolite formation in plasma at 30 mg/kg, po administered as single dose measured after 10 hrs by LC-MS/MS analysis Homo sapiens 50.0 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 11.1 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli 2.56 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 7.25 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 4.27 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 19.84 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 8.15 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans -1.55 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 3.12 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 7.55 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 31.76 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.38 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.17 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.38 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.17 %

Environmental Exposure

Environmental Exposure Map
Countries
Croatia
Slovenia

Cross References

Resources Reference
ChEBI 5296
ChEMBL CHEMBL457
DrugBank DB01241
DrugCentral 1285
FDA SRS Q8X02027X3
Human Metabolome Database HMDB0015371
Guide to Pharmacology 3439
KEGG C07020
PDB 4TX
PharmGKB PA449750
PubChem 3463
SureChEMBL SCHEMBL4813
ZINC ZINC000001530641
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