CAS 23288-49-5 Probucol (HCID 4912)

Overview

Probucol is a dithioketal that is propane-2,2-dithiol in which the hydrogens attached to both sulfur atoms are replaced by 3,5-di-tert-butyl-4-hydroxyphenyl groups. An anticholesteremic drug with antioxidant and anti-inflammatory properties, it is used to treat high levels of cholesterol in blood. It has a role as an antioxidant, an anti-inflammatory drug, a cardiovascular drug, an antilipemic drug and an anticholesteremic drug. It is a polyphenol and a dithioketal.

Names & identifiers

Preferred name: Probucol
IUPAC: 2,6-ditert-butyl-4-[2-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanylpropan-2-ylsulfanyl]phenol
English name: Probucol
Molecular formula: C31H48O2S2
Molecular weight: 516.84

Names & synonyms

probucol23288-49-5LorelcoBiphenabidBisphenabidBisbidLurselleDH-581SinlestalProbucolumDH 581Acetone bis(3,5-di-tert-butyl-4-hydroxyphenyl) mercaptole

Show more names

Probucol-d6LorelcLipoMalProbuco.PHENBUTOL

4,4'-(Isopropylidenedithio)bis(2,6-di-tert-butylphenol)DTXSID20454402,6-ditert-butyl-4-[2-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanylpropan-2-ylsulfanyl]phenolDH581P3CTH044XJNSC-86225Phenol, 4,4'-[(1-methylethylidene)bis(thio)]bis[2,6-bis(1,1-dimethylethyl)-NSC-652160

Database identifiers

CAS: 23288-49-5
PubChem CID: 4912
DTXSID: DTXSID2045440
ChEMBL: CHEMBL608
ChEBI: CHEBI:8427
UNII: P3CTH044XJ
EC Number: 245-560-9
Nikkaji: J20.410B

Properties

Computed structural properties

XLogP: 11.3
Topological polar surface area: 91.1 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 4
Rotatable bonds: 8
Heavy atoms: 35
Formal charge: 0
Complexity: 583

Experimental & physicochemical properties

Drugs · 2 items

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Antilipidemics

Solubility4.18e-05 g/L

Human Drugs · 2 items

FDA approved drugs -> Active ingredient

Endocrine DisruptorsPotential endocrine disrupting compound

Melting Point125 °C

Physical DescriptionSolid

Physicochemical properties

Melting point: 126 · 126-128°C
Boiling point: 571.58 °C · 571.58°C (rough estimate)
Density: 1.0008 · 1.0008 (rough estimate)
refractive index: 1.5341 · 1.5341 (estimate)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
form: Solid
pka: 10.27 · 10.27±0.70(Predicted)
color: White to Off-White
Merck: 14 · 14,7755
Major Application: forensics and toxicologypharmaceutical (small molecule)
InChI: 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
InChIKey: FYPMFJGVHOHGLL-UHFFFAOYSA-N
SMILES: C(SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1)(SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1)(C)C
CAS DataBase Reference: 23288 · 23288-49-5(CAS DataBase Reference)
FDA UNII: 3 CTH044XJ · P3CTH044XJ
ATC code: 10 AX02 · C10AX02
UNSPSC Code: 41116107 · 41116107
NACRES: 24 · NA.24
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302
Precautionary statements: 280 · P280-P305+P351+P338
PPE: 95 · Eyeshields, Gloves, type N95 (US)
WGK Germany: 2 · 2
RTECS: 3705000 · AL3705000
HS Code: 2930902000 · 2930902000
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Other Safety InformationIMAP assessments - Phenol, 4,4'-[(1-methylethylidene)bis(thio)]bis[2,6-bis(1,1-dimethylethyl)-: Environment tier I assessment

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Toxicology

Drug Induced Liver Injury · 5 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

probucol

DILI Negative

Oral

DOI:10.1016/j.drudis.2019.09.022

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 2
rtecs: AL3705000
hs_code: 2930902000
Signal word: Warning
Symbol(GHS): GHS07
Storage Class: 11 - Combustible Solids
Hazard statements: H302
Precautionary statements: P280-P305+P351+P338

Chemistry & industry

Pharmacology

ATC Code · 2 items

C - Cardiovascular system

QC - Cardiovascular system

Pharmacodynamics · 1 item

Probucol lowers cholesterol levels by increasing LDL (low-density lipoprotein) breakdown. Additionally, probucol may inhibit cholesterol synthesis and delay cholesterol absorption. Probucol is a powerful antioxidant drug normally used to prevent vascular disease caused by the free radicals in the body.

Mechanism of Action · 1 item

Probucol 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. This drug may also act to inhibit the initial stages of cholesterol synthesis and act to inhibit the absorption of cholesterol from the diet. 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.

Biological Half-LifeRanges from 12 hours to more than 500 hours, the longest half-life probably being in adipose tissue.

MeSH Pharmacological Classification · 2 items

Substances used to lower plasma CHOLESTEROL levels.

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.

Absorption, Distribution and ExcretionAbsorption from the gastrointestinal tract is limited and variable (about 7%).

Applications · 6 items

DescriptionProbucol is a kind of bis-phenol antioxidant with anti-hyperlipidemic activity. It had been initially developed for the treatment of coronary artery disease. However, its clinical trials were stopped after people found that it could lower the HDL and LDL cholesterol in patients of a history of heart disease. Probucol exerts its effect through accelerating the fractional rate of low-density (LDL) catabolism which is in the final pathway of cholesterol elimination inside the body. It may also inhibit the early stage of cholesterol biosynthesis and dietary cholesterol absorption.

Usesantihyperlipidemic

UsesProbucol is an antilipemic.

Usesanti-hyperlipoproteinemic

UsesAn antioxidant, anti-inflammatory, and hypocholesterolemic agent which inhibits atherogenesis in murine models.

General DescriptionProbucol, 4,4＇ -[(1-methylethylidene)bis(thio)]bis[2,6-bis(1,1-dimethylethyl)phenol], DH-581(Lorelco), is a chemical agent that was developed for the plasticsand rubber industry in the 1960s. The probucol moleculehas two tertiary butylphenol groups linked by a dithiopropylidenebridge, giving it a high lipophilic character with strongantioxidant properties. In humans, it causes reduction of bothliver and serum cholesterol levels, but it does not alter plasmatriglycerides. It reduces LDL and (to a lesser extent) HDLlevels by a unique mechanism that is still not clearly delineated.The reduction of HDL may be caused by the ability ofprobucol to inhibit the synthesis of apoprotein A-1, a majorprotein component of HDL. It is effective at reducing levelsof LDL and is used in hyperlipoproteinemias characterized byelevated LDL levels.

Upstream & downstream products

Upstream raw materials

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

成都彼样生物科技有限公司18108052721 · [email protected]

合肥翰刚医药科技有限公司+8618062405514 · [email protected]

Additional notes · 1 item

DefinitionChEBI: A dithioketal that is propane-2,2-dithiol in which the hydrogens attached to both sulfur atoms are replaced by 3,5-di-tert-butyl-4-hydroxyphenyl groups. An anticholesteremic drug with antioxidant and anti-inflammatory properties, it is used to treat high l vels of cholesterol in blood.