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Bezafibrate

HCID 178877415
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Grundinformationen

CAS
1189452-53-6
Standard-SMILES
CC(C)(Oc1ccc(CCNC(=O)c2ccc(Cl)cc2)cc1)C(=O)O
InChIKey
IIBYAHWJQTYFKB-UHFFFAOYSA-N
Summenformel
C19H20ClNO4
Durchschnittliche Molmasse
361,8 g/mol

Überblick

Bezafibrate is a monocarboxylic acid amide obtained by the formal condensation of the carboxy group of 4-chlorobenzoic acid with the amino group of 2-[4-(2-aminoethyl)phenoxy]-2-methylpropanoic acid. Benafibrate is used for the treatment of hyperlipidaemia. It has a role as a geroprotector, an antilipemic drug, a xenobiotic and an environmental contaminant. It is a monocarboxylic acid, a monocarboxylic acid amide, an aromatic ether and a member of monochlorobenzenes. It is functionally related to a propionic acid.

Namen und Bezeichner

Bevorzugter Name
Bezafibrate
IUPAC
2-[4-[2-[(4-chlorobenzoyl)amino]ethyl]phenoxy]-2-methylpropanoic acid
Englischer Name
BEZAFIBRATE-D4
Summenformel
C19H20ClNO4
Molmasse
361.8194

Namen und Synonyme

bezafibrate41859-67-0BezalipBezafibratoBezatol SRBezafibratumBM-15075BM-15.075DTXSID3029869BM 15.075NSC-758174Y9449Q51XH
Weitere Namen anzeigen
BEZAFIBRATE-D4[2H4]-Bezafibrate2-{4-[2-(4-Chlorobenzamido-d4)ethyl]phenozy}-2-methylpropanoic AcidBezafibrate d4Q: What is Bezafibrate d4 Q: What is the CAS Number of Bezafibrate d4 Q: What is the storage condition of Bezafibrate d4 Q: What are the applications of Bezafibrate d4
Propanoic acid, 2-(4-(2-((4-chlorobenzoyl)amino)ethyl)phenoxy)-2-methyl-DTXCID909869CHEBI:47612Propanoic acid, 2-[4-[2-[(4-chlorobenzoyl)amino]ethyl]phenoxy]-2-methyl-Beza LandeBeza PurenBM15.075Bezalip-mono

Datenbank-Bezeichner

CAS
1189452-53-6
ChEMBL
CHEMBL264374
ChEBI

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,8
Polarare Oberfläche (TPSA)
75,6 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
7
Schwere Atome
25
Formalladung
0
Komplexität
452

Experimentelle und physikochemische Eigenschaften

Drugs · 4 Einträge

Pharmaceuticals -> Antilipidemics

Pharmaceuticals

Pharmaceuticals -> Used in Switzerland

Pharmaceuticals -> Listed in ZINC15

Solubility · 2 Einträge

1.55e-03 g/L

>54.3 [ug/mL] (The mean of the results at pH 7.4)

Melting Point186 °C
Physical DescriptionSolid
Collision Cross Section · 4 Einträge

189.0 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID3029869]

177.3 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

180.44 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

183.8 Ų [M-H]-

Physikochemische Eigenschaften

Schmelzpunkt
181 · 181-184°C
storage temp.
-20 °C · Hygroscopic, -20°C Freezer, Under Inert Atmosphere

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

Warning

H302 (50.9%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 106 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

Gefahrenhinweise

Other Safety InformationIMAP assessments - Propanoic acid, 2-[4-[2-[(4-chlorobenzoyl)amino]ethyl]phenoxy]-2-methyl-: Environment tier I assessment
Hazard Classes and Categories · 2 Einträge

Acute Tox. 4 (50.9%)

Acute Tox. 4 (100%)

Toxikologische Informationen

Drug Induced Liver Injury · 5 Einträge

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

bezafibrate

DILI Negative

oral

DOI:10.1016/j.drudis.2019.09.022

Sicherheitsdaten

Alarmwort
Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H302

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 4 Einträge

C10AB02

C10AB02

C - Cardiovascular system

QC - Cardiovascular system

Protein Binding94-96% of bezafibrate is bound to protein in human serum.
Pharmacodynamics · 1 Eintrag

Bezafibrate is an antilipemic agent that lowers cholesterol and triglycerides. It decreases low density lipoproteins and increases high density lipoproteins. Bezafibrate lowers elevated blood lipids (triglycerides and cholesterol). Elevated VLDL and LDL are reduced by treatment with bezafibrate, whilst HDL-levels are increased. The activity of triglyceride lipases (lipoprotein lipase and hepatic lipoproteinlipase) involved in the catabolism of triglyceride-rich lipoproteins is increased by bezafibrate. In the course of the intensified degradation of triglyceride-rich lipoproteins (chylomicrons, VLDL) precursors for the formation of HDL are formed which explains an increase in HDL. Furthermore, cholesterol biosynthesis is reduced by bezafibrate, which is accompanied by a stimulation of the LDL-receptor-mediated lipoprotein catabolism. Elevated fibrinogen appears to be an important risk-factor, alongside the lipids, smoking and hypertension, in the development of atheroma. Fibrinogen plays an important role in viscosity, and therefore blood flow, and also appears to play an important role in thrombus development and lysability. Bezafibrate exerts an effect on thrombogenic factors. A significant decrease in elevated plasma fibrinogen levels can be achieved. This may lead, amongst other things, to a reduction in both blood and plasma viscosity. Inhibition of platelet aggregation has also been observed. A reduction in blood glucose concentration due to an increase in glucose tolerance has been reported in diabetic patients. In the same patients, the concentration of fasting and postprandial free fatty acids was reduced by bezafibrate.

Mechanism of ActionIt is generally accepted that bezafibrate is likely an agonist of PPAR-alpha. However, certain other investigations have also suggested that the substance might also elicit some effects on PPAR-gamma and PPAR-delta too.
Biological Half-Life1-2 hours

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CHEBI:47612
UNII
Y9449Q51XH
EC Number
255-567-9、941-659-2
Nikkaji
J16.626J
Löslichkeit
Acetone, DMSO (Slightly), Methanol
Aggregatzustand
Solid
Farbe
White to Off-White
Stabilität
Hygroscopic
Metabolism/Metabolites
Hepatic.
MeSH Pharmacological ClassificationSubstances that lower the levels of certain LIPIDS in the BLOOD. They are used to treat HYPERLIPIDEMIAS.
Absorption, Distribution and ExcretionBezafibrate is almost completely absorbed after oral administration. The relative bioavailability of bezafibrate retard compared to the standard form is about 70%.
Cellular LocationsCytoplasm

Verwendung und Herstellung

UsesUse (kg) in Switzerland (2009): >500
Use ClassificationPharmaceuticals -> Cardiovascular system -> Lipid modifying agents -> Lipid modifying agents, plain -> Fibrates -> Antilipemics