プロブコール

Probucol

HCID 4912CAS 23288-49-5
部分構造検索類似構造を探す

基本情報

標準SMILES
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
InChIKey
FYPMFJGVHOHGLL-UHFFFAOYSA-N
分子式
C31H48O2S2
平均分子量
516.8 g/mol
単同位体質量
516.30957278

概要

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.

名称と識別子

優先名称
Probucol
IUPAC
2,6-ditert-butyl-4-[2-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanylpropan-2-ylsulfanyl]phenol
現地名
プロブコール
英語名
Probucol
分子式
C31H48O2S2
分子量
516.84

名称と別名

probucol23288-49-5LorelcoBiphenabidBisphenabidBisbidLurselleDH-581SinlestalProbucolumDH 581Acetone bis(3,5-di-tert-butyl-4-hydroxyphenyl) mercaptole
名称をさらに表示
4,4'-[(1-メチルエチリデン)ビスチオ]ビス[2,6-ビス(1,1-ジメチルエチル)フェノール]フッコラート4,4'-[イソプロピリデンビス(チオ)]ビス(2,6-ジ-tert-ブチルフェノール)ダウンオイールプロブコリンエバチコールクラフェデンロレルコワニール2,2-ビス(3,5-ジ-tert-ブチル-4-ヒドロキシフェニルチオ)プロパンイエスタミンスイムタールリポブコールエタクレートプロスエードピヨコール4,4'-[(1-メチルエチリデン)ビス(チオ)]ビス[2,6-ビス(1,1-ジメチルエチル)フェノール]プロブコールコバクス4,4'-(プロパン-2,2-ジイルビスチオ)ビス(2,6-ジ-tert-ブチルフェノール)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

データベース識別子

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

物性

構造計算による物性

XLogP
11.3
極性表面積
91.1 Ų
水素結合供与体数
2
水素結合受容体数
4
回転可能結合数
8
重原子数
35

実験および物理化学的性質

Drugs · 2 件

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Antilipidemics

Solubility4.18e-05 g/L
Human Drugs · 2 件

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point125 °C
Physical DescriptionSolid

物理化学的性質

融点
126 · 126-128°C
沸点
571.58 °C · 571.58°C (rough estimate)
比重(密度)
1.0008 · 1.0008 (rough estimate)
屈折率
1.5341 · 1.5341 (estimate)
貯蔵温度
Keep in dark place,Sealed in dry,Room Temperature
溶解性
クロロホルム（微量）、酢酸エチル（微量）

化学的性質

化学的特性White Solid

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

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%)

毒性情報

Drug Induced Liver Injury · 5 件

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

probucol

DILI Negative

Oral

DOI:10.1016/j.drudis.2019.09.022

安全データ

wgk
2
rtecs
AL3705000
hs_code
2930902000
ストレージクラス
11 - Combustible Solids

化学と産業

薬理情報

ATC Code · 2 件

C - Cardiovascular system

QC - Cardiovascular system

Pharmacodynamics · 1 件

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 件

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 件

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%).
応用分野 · 4 件

用途コレステロール生合成阻害作 用を示します。

用途コレステロール生合成阻害作 用を示します。

使用Probucol is an antilipemic.

一般的な説明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.

上流・下流製品情報

サプライヤー50 社

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]
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合肥翰刚医药科技有限公司+8618062405514 · [email protected]
補足説明 · 1 件

定義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.

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