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Details

Stereochemistry ACHIRAL
Molecular Formula C31H48O2S2
Molecular Weight 516.842
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROBUCOL

SMILES

CC(C)(SC1=CC(=C(O)C(=C1)C(C)(C)C)C(C)(C)C)SC2=CC(=C(O)C(=C2)C(C)(C)C)C(C)(C)C

InChI

InChIKey=FYPMFJGVHOHGLL-UHFFFAOYSA-N
InChI=1S/C31H48O2S2/c1-27(2,3)21-15-19(16-22(25(21)32)28(4,5)6)34-31(13,14)35-20-17-23(29(7,8)9)26(33)24(18-20)30(10,11)12/h15-18,32-33H,1-14H3

HIDE SMILES / InChI
Molecular Formula C31H48O2S2
Molecular Weight 516.842
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.drugs.com/cons/probucol.html

Probucol is used to lower levels of cholesterol (a fat-like substance) in the blood. Probucol is a drug used to lower LDL and HDL cholesterol yet has little effect on serum-triglyceride or VLDL cholesterol. This may help prevent medical problems caused by cholesterol clogging the blood vessels. Probucol was voluntarily removed from the market in the United States during 1995. The withdrawal from the market was due to safety concern. robucol lowers serum cholesterol by increasing the fractional rate of low-density lipoprotein (LDL) catabolism in the final metabolic pathway for cholesterol elimination from the body. Additionally, probucol may inhibit early stages of cholesterol biosynthesis and slightly inhibit dietary cholesterol absorption. Recent information suggests that probucol may inhibit the oxidation and tissue deposition of LDL cholesterol, thereby inhibiting atherogenesis. It appears to inhibits ABCA1-mediated cellular lipid efflux.

Approval Year

1977
76
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
LORELCO

Approved Use

Probucol is used to lower levels of cholesterol (a fat-like substance) in the blood. This may help prevent medical problems caused by cholesterol clogging the blood vessels.

Launch Date

1977
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1706 ng/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/19922880
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PROBUCOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
139400 ng × h/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/19922880
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PROBUCOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
177.5 h
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/19922880
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PROBUCOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
Doses

Doses

DosePopulationAdverse events​
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/4605082
unhealthy, 34 - 81 years
Health Status: unhealthy
Age Group: 34 - 81 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/4605082
Disc. AE: Blurred vision...
AEs leading to
discontinuation/dose reduction:
Blurred vision (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/4605082
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8022053
unhealthy, 64 years
Health Status: unhealthy
Age Group: 64 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/8022053
Disc. AE: QT interval prolonged...
AEs leading to
discontinuation/dose reduction:
QT interval prolonged (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/8022053
AEs

AEs

AESignificanceDosePopulation
Blurred vision 1 patient
Disc. AE
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/4605082
unhealthy, 34 - 81 years
Health Status: unhealthy
Age Group: 34 - 81 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/4605082
QT interval prolonged 1 patient
Disc. AE
500 mg 2 times / day multiple, oral
Recommended
Dose: 500 mg, 2 times / day
Route: oral
Route: multiple
Dose: 500 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8022053
unhealthy, 64 years
Health Status: unhealthy
Age Group: 64 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/8022053
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2252
inhibitor
2507
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A
70

CYP2A6
879

CYP2B6
926

CYP2C8/9
42

CYP2C19
2057

CYP2E1
1060
UGT
32
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A
122
 no
CYP2A6
911
 no
CYP2B6
1160
 no
CYP2C19
2141
 no
CYP2C8/9
42
 no
CYP2D6
2546
 no
CYP2E1
1146
 no
CYP3A4
2633
 no
UGT
70
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:8427
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8427
ChemicalBook
CB5244083
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5244083
eMolecules
593939
https://www.emolecules.com/cgi-bin/more?vid=593939
MolPort
MolPort-002-042-265
https://www.molport.com/shop/molecule-link/MolPort-002-042-265
Selleck Chemicals
probucol
http://www.selleckchem.com/products/probucol.html
ZINC
ZINC000001530755
http://zinc15.docking.org/substances/ZINC000001530755
PubMed

PubMed

TitleDatePubMed
Comparison of the effects of alpha-tocopherol, ubiquinone-10 and probucol at therapeutic doses on atherosclerosis in WHHL rabbits.
2002-08
Potential emerging therapeutic strategies to prevent restenosis in the peripheral vasculature.
2002-07
DNA damage and the effect of antioxidants in streptozotocin-treated mice.
2002-07
Probucol preserves pancreatic beta-cell function through reduction of oxidative stress in type 2 diabetes.
2002-07
Antioxidative activity of green tea polyphenol in cholesterol-fed rats.
2002-06-05
Probucol inhibits oxidized-low density lipoprotein-induced adhesion of monocytes to endothelial cells in vitro.
2002-06
Beneficial effects of long-term use of the antioxidant probucol in heart failure in the rat.
2002-05-28
Probucol and liver efficiency during chemically-induced hepatocarcinogenesis.
2002-05-17
Importance of NAD(P)H oxidase-mediated oxidative stress and contractile type smooth muscle myosin heavy chain SM2 at the early stage of atherosclerosis.
2002-05-14
Stilbazulenyl nitrone (STAZN): a nitronyl-substituted hydrocarbon with the potency of classical phenolic chain-breaking antioxidants.
2002-05-01
[Anti-hyperlipidemic agents].
2002-05
Anti-lipid-peroxidative principles from Tournefortia sarmentosa.
2002-05
Immunomodulation with DiNAC-- a new approach to the treatment of atherosclerosis?
2002-05
Inhibitory effect of a novel water-soluble vitamin E derivative on atherosclerosis in rabbits.
2002-05
Effects of antioxidants on kidney disease.
2002-04-30
The effect of antioxidants on glycated albumin-induced cytotoxicity in bovine retinal pericytes.
2002-04-12
Effect of BO-653 and probucol on c-MYC and PDGF-A messenger RNA of the iliac artery after balloon denudation in cholesterol-fed rabbits.
2002-04
Evaluation of alpha-tocopherol, probucol and ascorbic acid as suppressors of digoxin induced lipid peroxidation.
2002-03-06
Effects of plaque composition on vascular remodelling after angioplasty in the MultiVitamins and Probucol (MVP) trial.
2002-03
Probucol preserves endothelial function by reduction of the endogenous nitric oxide synthase inhibitor level.
2002-03
Comparison of antioxidant effects of naringin and probucol in cholesterol-fed rabbits.
2002-03
Antioxidant treatment of therapy-resistant idiopathic membranous nephropathy with probucol: a pilot study.
2002-02-28
Effects of probucol and pravastatin on common carotid atherosclerosis in patients with asymptomatic hypercholesterolemia. Fukuoka Atherosclerosis Trial (FAST).
2002-02-20
[Antioxidant effect of novel probucol analogs and their combinations with alpha-tocopherol].
2002-01-05
Improved post-myocardial infarction survival with probucol in rats: effects on left ventricular function, morphology, cardiac oxidative stress and cytokine expression.
2002-01-02
Drug reverses coronary atherosclerosis.
2002-01-01
Effects of pravastatin on exercise electrocardiography test performance and cardiovascular mortality and morbidity in patients with hypercholesterolemia: Lipid Intervention Study in Kyoto.
2002-01
Esophageal cancer and the esophagus: challenges and potential strategies for selective cytoprotection of the tumor-bearing organ during cancer treatment.
2002-01
Effects of Ginkgo biloba extract on the proliferation of vascular smooth muscle cells in vitro and on intimal thickening and interleukin-1beta expression after balloon injury in cholesterol-fed rabbits in vivo.
2002
Macrophages take up triacylglycerol-rich emulsions at a faster rate upon co-incubation with native and modified LDL: An investigation on the role of natural chylomicrons in atherosclerosis.
2002
Fluvastatin depresses the enhanced lipid peroxidation in vitamin E-deficient hamsters.
2001-12
Antioxidative effects of fluvastatin and its metabolites against oxidative DNA damage in mammalian cultured cells.
2001-12
[Lipid-lowering drugs].
2001-12
Abnormal lipoprotein metabolism and reversible female infertility in HDL receptor (SR-BI)-deficient mice.
2001-12
Effects of insulin and antioxidant on plasma 8-hydroxyguanine and tissue 8-hydroxydeoxyguanosine in streptozotocin-induced diabetic rats.
2001-12
Cyclodextrins in the treatment of a mouse model of Niemann-Pick C disease.
2001-11-30
Comparison of the antioxidant effects of equine estrogens, red wine components, vitamin E, and probucol on low-density lipoprotein oxidation in postmenopausal women.
2001-11-28
A novel series of 2,6,7-substituted 2,3-dihydro-1,4-benzodioxin and 2,6,7-substituted 1,4-benzodioxin derivatives as lipid peroxidation inhibitors. Structure-activity relationships for high inhibition of human low-density lipoprotein peroxidation.
2001-11-08
Allergic reactions at repeat femoral angiography with ioxaglate.
2001-11
Dietary hematein ameliorates fatty streak lesions in the rabbit by the possible mechanism of reducing VCAM-1 and MCP-1 expression.
2001-11
Probucol decreases total body fat loss in VX2-carcinoma-induced cachectic rabbits.
2001-10-18
Antioxidant compounds and Ca(2+) pathway blockers differentially protect against methylmercury and mercuric chloride neurotoxicity.
2001-10-01
Retinal glial cell immunoreactivity and neuronal cell changes in rats with STZ-induced diabetes.
2001-10
[Effect of probucol on the concentration of cyclosporin A in patients with nephrotic syndrome].
2001-10
A dynamic in vitro lipolysis model. II: Evaluation of the model.
2001-10
Restenosis drug discovery--a formidable task.
2001-09
Apheresis technology for prevention and regression of atherosclerosis.
2001-08
[A 50-year history of new drugs in Japan: the developments and trends of antihyperlipidemic drugs].
2001
Type 2 diabetes: pharmacological intervention in an animal model.
2001
Oxidative stress and functional deficit in diabetic cardiomyopathy.
2001
Patents

Patents

06602914
1
JP2002543194A
3
JP2005531585A
20
JP2006232848A
1
JP2007529285A
16
JP2008539832A
84
JP2011510067A
60
JPH0215027A
1

Sample Use Guides

In Vivo Use Guide
Adults: 500 milligrams two times a day taken with the morning and evening meals. Children: Up to 2 years of age—Use is not recommended. 2 years of age and over—Dose must be determined by your doctor.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: The study was designed to examine the effect of probucol on cultured (HUVECs) injured by hypoxia/reoxygenation (H/R) and the potential mechanisms involving endoplasmic reticulum stress (ERS).
Injured human umbilical vein endothelial cells (HUVECs) induced by Na2S2O4 served as an H/R model in vitro. The concentration of probucol in this study ranged from 3 to 27 μM. The results showed that the cell viability increased significantly with probucol, while the LDH leakage rate was significantly lower as analyzed by the LDH assay. Furthermore, the expression levels of GRP78, XBP-1, and CHOP were significantly downregulated.
Substance Class Chemical
Created
by admin
on Wed Apr 02 09:16:44 GMT 2025
Edited
by admin
on Wed Apr 02 09:16:44 GMT 2025
Record UNII
P3CTH044XJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LORELCO
Preferred Name English
PROBUCOL
INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
probucol [INN]
Common Name English
PHENOL, 4,4'-((1-METHYLETHYLIDENE)BIS(THIO))BIS(2,6-BIS(1,1-DIMETHYLETHYL)-
Systematic Name English
DH-581
Code English
PROBUCOL [JAN]
Common Name English
PROBUCOL [VANDF]
Common Name English
NSC-652160
Code English
NSC-86225
Code English
PROBUCOL [ORANGE BOOK]
Common Name English
Probucol [WHO-DD]
Common Name English
PROBUCOL [MI]
Common Name English
PROBUCOL [USP IMPURITY]
Common Name English
PROBUCOL [MART.]
Common Name English
PROBUCOL [USAN]
Common Name English
Acetone bis(3,5-di-tert-butyl-4-hydroxyphenyl) mercaptole
Common Name English
PROBUCOL [USP-RS]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29703
Created by admin on Wed Apr 02 09:16:44 GMT 2025 , Edited by admin on Wed Apr 02 09:16:44 GMT 2025
WHO-ATC C10AX02
Created by admin on Wed Apr 02 09:16:44 GMT 2025 , Edited by admin on Wed Apr 02 09:16:44 GMT 2025
WHO-VATC QC10AX02
Created by admin on Wed Apr 02 09:16:44 GMT 2025 , Edited by admin on Wed Apr 02 09:16:44 GMT 2025
Code System Code Type Description
RXCUI
8699
Created by admin on Wed Apr 02 09:16:44 GMT 2025 , Edited by admin on Wed Apr 02 09:16:44 GMT 2025
PRIMARY RxNorm
NSC
86225
Created by admin on Wed Apr 02 09:16:44 GMT 2025 , Edited by admin on Wed Apr 02 09:16:44 GMT 2025
PRIMARY
PUBCHEM
4912
Created by admin on Wed Apr 02 09:16:44 GMT 2025 , Edited by admin on Wed Apr 02 09:16:44 GMT 2025
PRIMARY
ECHA (EC/EINECS)
245-560-9
Created by admin on Wed Apr 02 09:16:44 GMT 2025 , Edited by admin on Wed Apr 02 09:16:44 GMT 2025
PRIMARY
ChEMBL
CHEMBL608
Created by admin on Wed Apr 02 09:16:44 GMT 2025 , Edited by admin on Wed Apr 02 09:16:44 GMT 2025
PRIMARY
DRUG BANK
DB01599
Created by admin on Wed Apr 02 09:16:44 GMT 2025 , Edited by admin on Wed Apr 02 09:16:44 GMT 2025
PRIMARY
SMS_ID
100000081111
Created by admin on Wed Apr 02 09:16:44 GMT 2025 , Edited by admin on Wed Apr 02 09:16:44 GMT 2025
PRIMARY
CHEBI
8427
Created by admin on Wed Apr 02 09:16:44 GMT 2025 , Edited by admin on Wed Apr 02 09:16:44 GMT 2025
PRIMARY
WIKIPEDIA
Probucol
Created by admin on Wed Apr 02 09:16:44 GMT 2025 , Edited by admin on Wed Apr 02 09:16:44 GMT 2025
PRIMARY
IUPHAR
7277
Created by admin on Wed Apr 02 09:16:44 GMT 2025 , Edited by admin on Wed Apr 02 09:16:44 GMT 2025
PRIMARY
FDA UNII
P3CTH044XJ
Created by admin on Wed Apr 02 09:16:44 GMT 2025 , Edited by admin on Wed Apr 02 09:16:44 GMT 2025
PRIMARY
INN
2928
Created by admin on Wed Apr 02 09:16:44 GMT 2025 , Edited by admin on Wed Apr 02 09:16:44 GMT 2025
PRIMARY
MESH
D011341
Created by admin on Wed Apr 02 09:16:44 GMT 2025 , Edited by admin on Wed Apr 02 09:16:44 GMT 2025
PRIMARY
EVMPD
SUB10054MIG
Created by admin on Wed Apr 02 09:16:44 GMT 2025 , Edited by admin on Wed Apr 02 09:16:44 GMT 2025
PRIMARY
CAS
23288-49-5
Created by admin on Wed Apr 02 09:16:44 GMT 2025 , Edited by admin on Wed Apr 02 09:16:44 GMT 2025
PRIMARY
RS_ITEM_NUM
1563309
Created by admin on Wed Apr 02 09:16:44 GMT 2025 , Edited by admin on Wed Apr 02 09:16:44 GMT 2025
PRIMARY
NCI_THESAURUS
C66470
Created by admin on Wed Apr 02 09:16:44 GMT 2025 , Edited by admin on Wed Apr 02 09:16:44 GMT 2025
PRIMARY
EPA CompTox
DTXSID2045440
Created by admin on Wed Apr 02 09:16:44 GMT 2025 , Edited by admin on Wed Apr 02 09:16:44 GMT 2025
PRIMARY
NSC
652160
Created by admin on Wed Apr 02 09:16:44 GMT 2025 , Edited by admin on Wed Apr 02 09:16:44 GMT 2025
PRIMARY
MERCK INDEX
m9143
Created by admin on Wed Apr 02 09:16:44 GMT 2025 , Edited by admin on Wed Apr 02 09:16:44 GMT 2025
PRIMARY Merck Index
DRUG CENTRAL
2269
Created by admin on Wed Apr 02 09:16:44 GMT 2025 , Edited by admin on Wed Apr 02 09:16:44 GMT 2025
PRIMARY
Related Record Type Details
Structure of SUCCINOBUCOL
DERIVATIVE -> PARENT
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Structure of 4,4'-(DISULFANEDIYL)BIS(2,6-DI-TERT-BUTYLPHENOL
IMPURITY -> PARENT
Structure of 4-((3,5-DI-TERT-BUTYL-2-HYDROXYPHENYLTHIO)ISOPROPYLIDENETHIO)-2,6-DI-TERT-BUTYLPHENOL
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 3,3',5,5'-TETRA-TERT-BUTYL-4,4'-DIPHENOQUINONE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
Structure of PROBUCOL
ACTIVE MOIETY
NIH
NCATS
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