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HomeProduct name listProbucol

Probucol

Synonym(s):Probucol

  • CAS NO.:23288-49-5
  • Empirical Formula: C31H48O2S2
  • Molecular Weight: 516.84
  • MDL number: MFCD00079281
  • EINECS: 245-560-9
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-10-31 13:32:20
Probucol Structural

What is Probucol?

Absorption

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

Chemical properties

White Solid

The Uses of Probucol

Probucol is an antilipemic.

The Uses of Probucol

antihyperlipidemic

The Uses of Probucol

anti-hyperlipoproteinemic

The Uses of Probucol

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

Background

A drug used to lower LDL and HDL cholesterol yet has little effect on serum-triglyceride or VLDL cholesterol. (From Martindale, The Extra Pharmacopoeia, 30th ed, p993).

Indications

Used to lower LDL and HDL cholesterol.

What are the applications of Application

Probucol is an antioxidant, anti-inflammatory, and hypocholesterolemic agent which inhibits atherogenesis in murine models

Definition

ChEBI: 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.

brand name

Lorelco (Sanofi Aventis).

Biological Functions

Probucol (Lorelco) is a hypocholesterolemic drug with few side effects that modestly (15–30%) decreases elevated plasma LDL cholesterol levels. The marginal LDL-lowering action plus reports that it can lower HDL cholesterol resulted in its discontinuation as a hypocholesterolemic drug. However, it still may reduce the risk of CHD because it is a powerful antioxidant.
The oxidation hypothesis of atherosclerosis states that oxidation of lipids in LDL is required for LDL uptake by macrophages and smooth muscle cells in the intima of arteries, leading to their transformation to foam cells, an early event in atherogenesis. A recent clinical trial reported that use of probucol decreased the rate of restenosis of coronary arteries by 50% in patients who underwent angioplasty. Fluvastatin also has potent antioxidant properties that may contribute to its antiatherosclerotic effects.These findings suggest that reducing high plasma lipids may not be the only approach to retarding the progression of atherosclerosis and decreasing the risk of coronary heart disease.

General Description

Probucol, 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.

Biological Activity

Antioxidant, anti-inflammatory and hypocholesterolemic agent. Inhibits atherogenesis in genetically hypercholesterolemic rabbits (Watanabe) and attenuates ischemia/reperfusion-induced cardiomyocyte apoptosis.

Mechanism of action

Probucol reduces the overall level of cholesterol—primarily low-density lipoproteins— without having an effect on triglycerides and very low-density lipoproteins. It has been suggested that it inhibits synthesis of cholesterol itself and increases removal of bile salts. Upon using this drug, a fraction of low-density proteins is reduced; however, even more significant is the reduction of high-density proteins. From the epidemiological point of view, this is dangerous, because lowering the concentration of high-density proteins means less cholesterol is removed from tissues. However, in any case, probucol lowers the level of cholesterol in the plasma by 10–15%. Moreover, it has been shown that probucol facilitates reduction of necrotic zones in myocardial ischemia.

Pharmacokinetics

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.

Pharmacology

Being a lipophilic compound, it is easily distributed into fatty tissue and, as a result, approximately 20% of its maximum concentration in the blood is still maintained for 6 months.

Synthesis

Probucol, bis(3,5-tert-butyl-4-hydroxyphenyl)mercaptol acetone (20.2.6), is synthesized by thioketalizing acetone with 2,6-di-tert-butyl-4-mercaptophenol in the presence of hydrogen chloride.

Synthesis_23288-49-5

Metabolism

Not Available

Properties of Probucol

Melting point: 126-128°C
Boiling point: 571.58°C (rough estimate)
Density  1.0008 (rough estimate)
refractive index  1.5341 (estimate)
storage temp.  Keep in dark place,Sealed in dry,Room Temperature
solubility  Chloroform (Slightly), Ethyl Acetate (Slightly)
form  neat
pka 10.27±0.70(Predicted)
form  Solid
color  White to Off-White
Merck  14,7755
CAS DataBase Reference 23288-49-5(CAS DataBase Reference)

Safety information for Probucol

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
Precautionary Statement Codes P280:Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Probucol

InChIKey FYPMFJGVHOHGLL-UHFFFAOYSA-N

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