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Compound Detail

CHEMBL608

PROBUCOL
💊 Approved Drug
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💊 Approved Drug
CC(C)(Sc1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1)Sc1cc(C(C)(C)C)c(O)c(C(C)(C)C)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL608
Name PROBUCOL
Phase Approved
Structure Type MOL
InChI Key FYPMFJGVHOHGLL-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Bisbid DH-581 Lorelco Lurselle NSC-652160 NSC-86225 Probucol Sinlestal
13
Targets
25
Activities
1
Assay Types
1
PK Parameters
20
Publications
8
Known Names
4
Indications
1
Mechanisms

Molecular Properties

516.9
MW (Da)
9.91
ALogP
4
HBA
2
HBD
40.5
PSA (Ų)
0.31
QED
2
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1977
Availability Withdrawn
Chirality Achiral

Routes of Administration

Oral

Flags

Withdrawn Natural Product
USAN Year 1970

Extended Properties

Molecular Formula C31H48O2S2
MW 516.86
Aromatic Rings 2
Heavy Atoms 35
NP-Likeness 0.17

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
ATP-binding cassette sub-family A member 1 inhibitor INHIBITOR Phospholipid-transporting ATPase ABCA1 ✓ ✓

Indications

Cardiovascular Diseases Hyperlipidemias Diabetic Nephropathies Peripheral Arterial Disease

ATC Classification

C10AX02
probucol
Level 1: CARDIOVASCULAR SYSTEM
Level 2: LIPID MODIFYING AGENTS

Drug Warnings

Withdrawn
metabolic toxicity
Reduction in serum HDL-C levels and partly because of possible QT interval prolongation or ventricular arrhythmias
Country: United States   Year: 1995
Withdrawn
cardiotoxicity
Reduction in serum HDL-C levels and partly because of possible QT interval prolongation or ventricular arrhythmias
Country: United States   Year: 1995
Withdrawn
cardiotoxicity
Reduction in serum HDL-C levels and partly because of possible QT interval prolongation or ventricular arrhythmias
Country: United States   Year: 1995

Activity Summary

IC50 25 meas. best 6.37

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Serine protease hepsin
CHEMBL2079849
 IC50 6.37 6.37 430.0 1
Sus scrofa
CHEMBL613488
 IC50 6.3 6.3 500.0 1
Unchecked
CHEMBL612545
 IC50 6.22 5.3967 600.0 3
THP-1
CHEMBL614245
 IC50 6.22 6.22 600.0 1
Plasma
CHEMBL613424
 IC50 5.89 5.89 1300.0 1
NAD-dependent protein deacylase sirtuin-5, mitochondrial
CHEMBL2163183
 IC50 5.8 5.8 1600.0 1
Cell line
CHEMBL614840
 IC50 5.55 5.55 2800.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.52 5.2817 3000.0 6
Plasma
CHEMBL613652
 IC50 5.44 5.44 3600.0 1
Homo sapiens
CHEMBL372
 IC50 5.28 5.28 5300.0 1
Polyunsaturated fatty acid lipoxygenase ALOX15
CHEMBL2903
 IC50 4.85 4.85 14000.0 1
Trypsin
CHEMBL2366
 IC50 4.47 4.47 33500.0 1
Radical scavenging activity
CHEMBL613712
 IC50 4.44 4.36 36110.0 2

Pharmacokinetic Data

Parameter Value Units Species
F 20.0 % Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Serine protease hepsin IC50 = 430.0 nM 6.37 High-Throughput Screening Assay: To identify novel inhibitors of hepsin, the Che... -
Sus scrofa IC50 = 500.0 nM 6.3 In vitro inhibition of Cu2+ catalyzed LDL oxidation 1656041
Unchecked IC50 = 600.0 nM 6.22 In vitro ability to protect human LDL against Cu2+-induced peroxidation. (concen... 15125921
THP-1 IC50 = 600.0 nM 6.22 Antioxidant activity in human THP1 cells assessed as inhibition of macrophage-me... 30015075
Plasma IC50 = 1300.0 nM 5.89 Antioxidant activity assessed as inhibition of LDL oxidation in human plasma 11754613
NAD-dependent protein deacylase sirtuin-5, mitochondrial IC50 = 1600.0 nM 5.8 Inhibition of SIRT5 (unknown origin) 32858418
Cell line IC50 = 2800.0 nM 5.55 Concentration required for inhibition of Cu+2-induced peroxidation in low-densit... 15482936
NON-PROTEIN TARGET IC50 = 3000.0 nM 5.52 Antioxidant activity assessed as inhibition of copper-induced human LDL oxidatio... 8691205
NON-PROTEIN TARGET IC50 = 3100.0 nM 5.51 Antioxidant activity against LDL-oxidation by TBARS assay 17998162
Plasma IC50 = 3600.0 nM 5.44 Antioxidant activity against human plasma LDL oxidation by TBARS assay 16919944
NON-PROTEIN TARGET IC50 = 4000.0 nM 5.4 Antioxidant activity assessed as inhibition of endothelial cell-induced human LD... 8691205
NON-PROTEIN TARGET IC50 = 4300.0 nM 5.37 Antioxidant activity against Cu2+-induced lipid peroxidation in human plasma LDL... 12027757
NON-PROTEIN TARGET IC50 = 4300.0 nM 5.37 Antioxidant activity assessed as inhibition of LDL oxidation 16724860
Unchecked IC50 = 5000.0 nM 5.3 Tested for inhibition of copper induced lipid peroxidation in human low density ... 9111294
Homo sapiens IC50 = 5300.0 nM 5.28 Compound was evaluated for the inhibition of human LDL oxidation mediated by cop... -
Polyunsaturated fatty acid lipoxygenase ALOX15 IC50 = 14000.0 nM 4.85 Inhibition of 15-lipoxygenase by LMB assay 15566311
Unchecked IC50 = 21600.0 nM 4.67 Inhibition of lipid peroxidation in genetically hypercholesterolemic KHC rabbit ... 18620381
NON-PROTEIN TARGET IC50 = 30000.0 nM 4.52 Antioxidant activity assessed as inhibition of copper-mediated LDL oxidation by ... -
Trypsin IC50 = 33500.0 nM 4.47 High-Throughput Screening Assay: To identify novel inhibitors of hepsin, the Che... -
Radical scavenging activity IC50 = 36110.0 nM 4.44 Antioxidant activity assessed as DPPH radical scavenging activity after 30 mins ... 12027755

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 346
11325231 10.1021/np000421u NON-PROTEIN TARGET 111
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
2913302 10.1021/jm00122a022 Mus musculus 9
1992130 10.1021/jm00105a046 Oryctolagus cuniculus 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
27777006 10.1016/j.bmcl.2016.10.033 NON-PROTEIN TARGET 5
1656041 10.1021/jm00114a004 Rattus norvegicus 5
12825946 10.1021/jm030062a Oryctolagus cuniculus 4
15482936 10.1016/j.bmcl.2004.08.054 Cell line 4
15566311 10.1021/jm049685u Unchecked 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
- 10.1007/s00044-008-9143-y NON-PROTEIN TARGET 3
20014752 10.1021/tx900326k Hepatotoxicity 3
12825946 10.1021/jm030062a Unchecked 3
24568631 10.1021/jm401842e Rattus norvegicus 3
15125921 10.1016/j.bmcl.2004.03.072 NON-PROTEIN TARGET 3
12431068 10.1021/jm011062i Rattus norvegicus 3
20888243 10.1016/j.bmc.2010.09.008 Rattus norvegicus 3
- 10.1016/S0960-894X(97)00046-2 ADMET 3

Data from ChEMBL 36 via Core Engine