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Compound Detail

CHEMBL457

GEMFIBROZIL
💊 Approved Drug
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💊 Approved Drug
Cc1ccc(C)c(OCCCC(C)(C)C(=O)O)c1

Basic Information

ChEMBL ID CHEMBL457
Name GEMFIBROZIL
Phase Approved
Structure Type MOL
InChI Key HEMJJKBWTPKOJG-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

CI-719 Emfib Gemfibrozil Gemfibrozilo Lopid NSC-757024
11
Targets
29
Activities
4
Assay Types
30
PK Parameters
20
Publications
6
Known Names
15
Indications
1
Mechanisms

Molecular Properties

250.3
MW (Da)
3.57
ALogP
2
HBA
1
HBD
46.5
PSA (Ų)
0.78
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1981
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product
USAN Year 1980

Extended Properties

Molecular Formula C15H22O3
MW 250.34
Aromatic Rings 1
Heavy Atoms 18
NP-Likeness -0.36

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Peroxisome proliferator-activated receptor alpha agonist AGONIST Peroxisome proliferator-activated receptor alpha

Indications

Abdominal Pain Cardiovascular Diseases Coronary Disease Alcoholism Myocardial Ischemia Parkinson Disease Smoking Cessation Tobacco Use Disorder Anemia Diabetes Mellitus, Type 2 HIV Infections Hypertriglyceridemia Multiple Sclerosis Neoplasms Alzheimer Disease

ATC Classification

C10AB04
gemfibrozil
Level 1: CARDIOVASCULAR SYSTEM
Level 2: LIPID MODIFYING AGENTS

Activity Summary

IC50 14 meas. best 5.39
EC50 11 meas. best 4.93
Ki 3 meas. best 5.73
Kd 1 meas. best 7.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Transthyretin
CHEMBL3194
Kd 7.0 7.0 100.0 1
Fatty acid-binding protein, liver
CHEMBL5738
Ki 5.73 5.73 1860.0 1
Solute carrier organic anion transporter family member 1B1
CHEMBL1697668
IC50 5.39 4.9233 4073.8 3
Cytochrome P450 2C8
CHEMBL3721
IC50 5.39 4.4767 4100.0 3
Solute carrier organic anion transporter family member 1B3
CHEMBL1743121
IC50 5.15 5.15 7079.5 1
CDGSH iron-sulfur domain-containing protein 1
CHEMBL1795168
Ki 5.14 5.14 7291.0 1
Cytochrome P450 2C9
CHEMBL3397
IC50 5.02 5.02 9600.0 1
Peroxisome proliferator-activated receptor alpha
CHEMBL239
EC50 4.93 4.4633 11800.0 3
Peroxisome proliferator-activated receptor gamma
CHEMBL235
EC50 4.17 4.17 68400.0 1
Unchecked
CHEMBL612545
IC50 4.16 4.16 69000.0 1
Bovine viral diarrhea virus 1
CHEMBL612571
EC50 4.05 4.05 90000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 3.09 mL.min-1.kg-1 Homo sapiens
CL 29.51 mL.min-1.g-1 Homo sapiens
CL 66.07 uL.min-1.(10^6cells)-1 Homo sapiens
CL 150.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL - mL.min-1.kg-1 Homo sapiens
CL 1.7 mL.min-1.kg-1 Homo sapiens
CL 17.0 mL.min-1.g-1 Homo sapiens
CL 17.5 mL.min-1.g-1 Homo sapiens
CL - - Homo sapiens
CL 1.73 mL.min-1.kg-1 Homo sapiens
CL 1.7 mL.min-1.kg-1 Homo sapiens
CL 1.93 mL.min-1.kg-1 Homo sapiens
CL 1.78 mL.min-1.kg-1 Homo sapiens
CL 0.02 mL.min-1.kg-1 Homo sapiens
CL 1.7 mL.min-1.kg-1 Homo sapiens
CL 0.824 mL.min-1.g-1 Homo sapiens
CL 24.4 mL.min-1.g-1 Homo sapiens
CL 73.6 mL.min-1.g-1 Homo sapiens
CL 0.492 mL.min-1.g-1 Homo sapiens
CL 3.39 mL.min-1.g-1 Homo sapiens
CL 10.4 mL.min-1.g-1 Homo sapiens
CL 40.0 mL.min-1.g-1 Homo sapiens
CL 23.9 mL.min-1.g-1 Homo sapiens
CL 1910.0 mL.min-1.g-1 Homo sapiens
CL 265.0 mL.min-1.g-1 Homo sapiens
CL 1840.0 mL.min-1.g-1 Homo sapiens
CL 259.0 mL.min-1.g-1 Homo sapiens
F 80.0 % Homo sapiens
F 100.0 % Homo sapiens
Fu 0.97 - Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Transthyretin Kd = 100.0 nM 7.0 Binding affinity to TTR (unknown origin) by isothermal titration calorimetric an... 26214366
Fatty acid-binding protein, liver Ki = 1860.0 nM 5.73 Displacement of 1-anilinonaphthalene-8-sulphonic acid from rat recombinant L-FAB... 18533710
Cytochrome P450 2C8 IC50 = 4100.0 nM 5.39 Inhibition of CYP2C8 22409598
Solute carrier organic anion transporter family member 1B1 IC50 = 4073.8 nM 5.39 pIC50 values for sodium fluorescein (10 uM) uptake in OATP1B1-transfected CHO ce... 23571415
Solute carrier organic anion transporter family member 1B3 IC50 = 7079.46 nM 5.15 pIC50 values for sodium fluorescein (10 uM) uptake in OATP1B3-transfected CHO ce... 23571415
CDGSH iron-sulfur domain-containing protein 1 Ki = 7291.0 nM 5.14 Displacement of [3H]rosiglitazone from recombinant human C-terminal His-tagged M... 27687671
Cytochrome P450 2C9 IC50 = 9600.0 nM 5.02 Reversible inhibition of CYP2C9 in human liver microsomes 22409598
Solute carrier organic anion transporter family member 1B1 IC50 = 11000.0 nM 4.96 Inhibition of OATP1B1 (unknown origin) expressed in HEK293 cells using estradiol... 22587986
Peroxisome proliferator-activated receptor alpha EC50 = 11800.0 nM 4.93 Agonist activity at human PPARalpha transfected in COS-7 cells assessed lucifera... 33988379
Solute carrier organic anion transporter family member 1B1 IC50 = 38000.0 nM 4.42 Inhibition of OATP1B1 (unknown origin) expressed in HEK293 cells using pitavasta... 22587986
Peroxisome proliferator-activated receptor alpha EC50 = 59000.0 nM 4.23 Transactivation of human PPARalpha expressed in HEK293 cells incubated for 18 hr... -
Peroxisome proliferator-activated receptor alpha EC50 = 59000.0 nM 4.23 Agonist activity at Gal4-fused PPARalpha expressed in HEK293 cells after 18 hrs ... 21889235
Peroxisome proliferator-activated receptor gamma EC50 = 68400.0 nM 4.17 Agonist activity at human PPARgamma transfected in COS-7 cells assessed lucifera... 33988379
Unchecked IC50 = 69000.0 nM 4.16 Antagonist activity at human T1R2/T1R3 receptor expressed in HEK293E cells asses... 19817384
Bovine viral diarrhea virus 1 EC50 = 90000.0 nM 4.05 Antiviral activity against BVDV infected in MDBK cells assessed as inhibition of... 26443549
Cytochrome P450 2C8 IC50 = 95000.0 nM 4.02 Reversible inhibition of CYP2C8 in human liver microsomes 22409598
Cytochrome P450 2C8 IC50 = 95000.0 nM 4.02 Inhibition of CYP2C8 in human liver microsomes after 15 mins 28653847

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1434
- 10.6019/CHEMBL3885881 Rattus norvegicus 1041
6864730 10.1021/jm00361a015 Rattus norvegicus 77
- 10.1007/s00044-007-9058-z Syrian golden hamster 34
17562808 10.1128/aac.00219-07 H2N2 subtype 18
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
- 10.1007/s00044-009-9280-y Rattus norvegicus 14
32206235 10.1039/C9MD00286C No relevant target 13
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
22275465 10.1124/dmd.111.043984 UDP-glucuronosyltransferase 2B7 11
23954239 10.1016/j.ejmech.2013.07.009 Rattus norvegicus 9
22275465 10.1124/dmd.111.043984 Liver microsome 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
2913302 10.1021/jm00122a022 Mus musculus 7
16216504 10.1016/j.bmcl.2005.09.034 Rattus norvegicus 7
22275465 10.1124/dmd.111.043984 ADMET 7
11859010 10.1016/s0960-894x(02)00021-5 Homo sapiens 6
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 6
6747995 10.1021/jm00374a006 ADMET 6

Data from ChEMBL 36 via Core Engine