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Compound Detail

CHEMBL565

CLOFIBRATE
💊 Approved Drug
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💊 Approved Drug
CCOC(=O)C(C)(C)Oc1ccc(Cl)cc1

Basic Information

ChEMBL ID CHEMBL565
Name CLOFIBRATE
Phase Approved
Structure Type MOL
InChI Key KNHUKKLJHYUCFP-UHFFFAOYSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL683

Known Names

Atromid Atromid-s AY-61123 Chlorfenisate Clofibrate Clofibrato Ethyl p-chlorophenoxyisobutyrate ICI 28257 ICI-28257 NSC-79389
4
Targets
18
Activities
4
Assay Types
2
PK Parameters
20
Publications
10
Known Names
5
Indications
1
Mechanisms

Molecular Properties

242.7
MW (Da)
3.06
ALogP
3
HBA
0
HBD
35.5
PSA (Ų)
0.76
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1967
Availability Withdrawn
Chirality Achiral

Routes of Administration

Oral

Flags

Withdrawn Natural Product Prodrug
USAN Stem -fibrate
USAN Year 1963

Extended Properties

Molecular Formula C12H15ClO3
MW 242.70
Aromatic Rings 1
Heavy Atoms 16
NP-Likeness -0.79

Mechanism of Action

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

Indications

Cardiovascular Diseases Coronary Disease Heart Diseases Myocardial Infarction Myocardial Ischemia

ATC Classification

C10AB01
clofibrate
Level 1: CARDIOVASCULAR SYSTEM
Level 2: LIPID MODIFYING AGENTS

Drug Warnings

Withdrawn
vascular toxicity
Increases the incidence of gallstones and cholecystitis, drug-induced cardiac arrhythmias, cardiomegaly, angina, claudication and thromboembolic phenomena. It also enhances the effects and toxicity of...
Country: Israel; Norway; Bangladesh   Year: 1979
Withdrawn
carcinogenicity
Increases the incidence of gallstones and cholecystitis, drug-induced cardiac arrhythmias, cardiomegaly, angina, claudication and thromboembolic phenomena. It also enhances the effects and toxicity of...
Country: Israel; Norway; Bangladesh   Year: 1979
Withdrawn
General Warning
Increases the incidence of gallstones and cholecystitis, drug-induced cardiac arrhythmias, cardiomegaly, angina, claudication and thromboembolic phenomena. It also enhances the effects and toxicity of...
Country: Israel; Norway; Bangladesh   Year: 1979
Withdrawn
General Warning
Increased mortality associated with use
Country: Israel; Norway; Bangladesh   Year: 1979
Withdrawn
cardiotoxicity
Increases the incidence of gallstones and cholecystitis, drug-induced cardiac arrhythmias, cardiomegaly, angina, claudication and thromboembolic phenomena. It also enhances the effects and toxicity of...
Country: Israel; Norway; Bangladesh   Year: 1979
Withdrawn
General Warning
Increases the incidence of gallstones and cholecystitis, drug-induced cardiac arrhythmias, cardiomegaly, angina, claudication and thromboembolic phenomena. It also enhances the effects and toxicity of...
Country: Israel; Norway; Bangladesh   Year: 1979
Withdrawn
cardiotoxicity
Increases the incidence of gallstones and cholecystitis, drug-induced cardiac arrhythmias, cardiomegaly, angina, claudication and thromboembolic phenomena. It also enhances the effects and toxicity of...
Country: Israel; Norway; Bangladesh   Year: 1979
Withdrawn
General Warning
Increases the incidence of gallstones and cholecystitis, drug-induced cardiac arrhythmias, cardiomegaly, angina, claudication and thromboembolic phenomena. It also enhances the effects and toxicity of...
Country: Israel; Norway; Bangladesh   Year: 1979
Withdrawn
General Warning
Increases the incidence of gallstones and cholecystitis, drug-induced cardiac arrhythmias, cardiomegaly, angina, claudication and thromboembolic phenomena. It also enhances the effects and toxicity of...
Country: Israel; Norway; Bangladesh   Year: 1979

Activity Summary

Kd 8 meas. best 5.22
EC50 7 meas. best 4.3
IC50 2 meas. best 4.22
Ki 1 meas. best 5.16

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Fatty acid-binding protein, liver
CHEMBL5738
Kd 5.22 5.0738 6000.0 8
Fatty acid-binding protein, liver
CHEMBL5738
Ki 5.16 5.16 6920.0 1
Peroxisome proliferator-activated receptor alpha
CHEMBL2128
EC50 4.3 4.3 50000.0 1
Peroxisome proliferator-activated receptor alpha
CHEMBL239
EC50 4.26 4.26 55000.0 3
Bile salt export pump
CHEMBL6020
IC50 4.22 4.185 60000.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 157597.24 ng.hr.mL-1 Homo sapiens
F 95.0 % Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Fatty acid-binding protein, liver Kd = 6000.0 nM 5.22 Binding affinity to rat recombinant L-FABP high affinity site expressed in Esche... 19663428
Fatty acid-binding protein, liver Kd = 6700.0 nM 5.17 Binding affinity to rat recombinant L-FABP high affinity site expressed in Esche... 19663428
Fatty acid-binding protein, liver Ki = 6920.0 nM 5.16 Displacement of 1-anilinonaphthalene-8-sulphonic acid from rat recombinant L-FAB... 18533710
Fatty acid-binding protein, liver Kd = 7300.0 nM 5.14 Binding affinity to rat recombinant L-FABP high affinity site expressed in Esche... 19663428
Fatty acid-binding protein, liver Kd = 7800.0 nM 5.11 Binding affinity to rat recombinant L-FABP high affinity site expressed in Esche... 19663428
Fatty acid-binding protein, liver Kd = 8900.0 nM 5.05 Binding affinity to rat recombinant L-FABP high affinity site expressed in Esche... 19663428
Fatty acid-binding protein, liver Kd = 9600.0 nM 5.02 Binding affinity to rat recombinant L-FABP high affinity site expressed in Esche... 19663428
Fatty acid-binding protein, liver Kd = 11000.0 nM 4.96 Binding affinity to rat recombinant L-FABP high affinity site expressed in Esche... 19663428
Fatty acid-binding protein, liver Kd = 12000.0 nM 4.92 Binding affinity to rat recombinant L-FABP high affinity site expressed in Esche... 19663428
Peroxisome proliferator-activated receptor alpha EC50 = 50000.0 nM 4.3 Agonist activity for murine PPAR alpha receptor in transcriptional activation as... 10691680
Peroxisome proliferator-activated receptor alpha EC50 = 55000.0 nM 4.26 Agonist activity for Human PPAR alpha receptor in transcriptional activation ass... 10691680
Peroxisome proliferator-activated receptor alpha EC50 = 55000.0 nM 4.26 Effective concentration against human peroxisome proliferator activated receptor... 15293980
Peroxisome proliferator-activated receptor alpha EC50 = 55000.0 nM 4.26 Agonist activity at PPARalpha 22260081
Bile salt export pump IC50 = 60000.0 nM 4.22 Inhibition of human BSEP expressed in fall armyworm sf9 cell plasma membrane ves... 20829430
Bile salt export pump IC50 = 71000.0 nM 4.15 Inhibition of human BSEP overexpressed in Sf9 cell membrane vesicles assessed as... 23956101

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1443
- 10.6019/CHEMBL3885881 Rattus norvegicus 1041
30119959 10.1016/j.bmcl.2018.06.010 Mus musculus 20
722728 10.1021/jm00210a005 Rattus norvegicus 19
7086828 10.1021/jm00343a019 Rattus norvegicus 17
99517 10.1021/jm00206a026 Rattus norvegicus 17
406395 10.1021/jm00216a009 Rattus norvegicus 16
34015506 10.1016/j.bmcl.2021.128121 ADMET 15
35697180 10.1016/j.bmcl.2022.128844 ADMET 12
7143351 10.1021/jm00352a011 Rattus norvegicus 11
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
4009605 10.1021/jm00383a021 Rattus norvegicus 11
2913302 10.1021/jm00122a022 Mus musculus 10
19663428 10.1021/jm801349e Fatty acid-binding protein, liver 10
16180814 10.1021/np0580614 Mus musculus 9
18363378 10.1021/np8000333 Mus musculus 9
110933 10.1021/jm00192a017 Rattus norvegicus 9
31204228 10.1016/j.bmc.2019.06.012 RAW264.7 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
2299623 10.1021/jm00164a013 Rattus norvegicus 6

Data from ChEMBL 36 via Core Engine