Probucol

HCID 4912CAS 23288-49-5
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Grundinformationen

Standard-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
Summenformel
C31H48O2S2
Durchschnittliche Molmasse
516,8 g/mol
Monoisotopische Masse
516,30957278

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
Probucol
IUPAC
2,6-ditert-butyl-4-[2-(3,5-ditert-butyl-4-hydroxyphenyl)sulfanylpropan-2-ylsulfanyl]phenol
Lokaler Name
Probucol
Englischer Name
Probucol
Summenformel
C31H48O2S2
Molmasse
516.84

Namen und Synonyme

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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP
11,3
Polarare Oberfläche (TPSA)
91,1 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
8
Schwere Atome
35

Experimentelle und physikochemische Eigenschaften

Drugs · 2 Einträge

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Antilipidemics

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

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point125 °C
Physical DescriptionSolid

Physikochemische Eigenschaften

Schmelzpunkt
126 · 126-128°C
Siedepunkt
571.58 °C · 571.58°C (rough estimate)
Dichte
1.0008 · 1.0008 (rough estimate)
Brechungsindex
1.5341 · 1.5341 (estimate)
storage temp.
Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit
Chloroform (Slightly), Ethyl Acetate (Slightly)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

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%)

Toxikologische Informationen

Drug Induced Liver Injury · 5 Einträge

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

probucol

DILI Negative

Oral

DOI:10.1016/j.drudis.2019.09.022

Sicherheitsdaten

wgk
2
hs_code
2930902000
RTECS-Nr.
AL3705000
Speicherklasse
11 - Combustible Solids

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

C - Cardiovascular system

QC - Cardiovascular system

Pharmacodynamics · 1 Eintrag

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 Eintrag

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 Einträge

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%).

Anwendungen

VerwendenProbucol is an antilipemic.

Vor- und nachgelagerte Produkte

Anbieter50 Anbieter

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]
Ergänzende Hinweise · 1 Eintrag

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.

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