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Fludeoxyglucose (18F)

HCID 450503
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Grundinformationen

CAS
105851-17-0
Standard-SMILES
OC[C@H]1O[C@H](O)[C@H]([18F])[C@@H](O)[C@@H]1O
InChIKey
ZCXUVYAZINUVJD-AHXZWLDOSA-N
Summenformel
C6H11FO5
Durchschnittliche Molmasse
181,15 g/mol
Monoisotopische Masse
181,061586

Überblick

2-deoxy-2-((18)F)fluoro-alpha-D-glucose is a 2-deoxy-2-((18)F)fluoro-D-glucopyranose and a 2-deoxy-2-fluoro-alpha-D-glucose.

Namen und Bezeichner

Bevorzugter Name
Fludeoxyglucose (18F)
IUPAC
(2S,3R,4S,5S,6R)-3-(18F)fluoro-6-(hydroxymethyl)oxane-2,4,5-triol
Englischer Name
Fludeoxyglucose F 18
Summenformel
C6H11FO5
Molmasse
181.148

Namen und Synonyme

105851-17-0Fludeoxyglucose (18F)SBT3GBX27WF-18 FDGFludeoxyglucose (18F) [INN]UNII-SBT3GBX27W2-(Fluoro-18F)-2-deoxy-alpha-glucopyranosealpha-D-Glucopyranose, 2-deoxy-2-(fluoro-18F)-Fludeoxyglucose f 18 [USAN:USP](2S,3R,4S,5S,6R)-3-(18F)fluoranyl-6-(hydroxymethyl)oxane-2,4,5-triol2-Deoxy-2-fluoro-(sup 18)F-alpha-D-glucopyranosealpha-D-Glucopyranose, 2-deoxy-2-(fluoro-(sup 18)F)-
Weitere Namen anzeigen
Fludeoxyglucose F 18Fluorodeoxyglucose F18Fludeoxyglucose (18F)-2-deoxy-2-((18)F)fluoro-alpha-D-glucose2-Deoxy-2-(18F)fluoro-α-D-glucopyranose2-(18F)Fluoro-2-deoxy-α-D-glucopyranose2-Deoxy-2-(fluoro-18F)-α-D-glucopyranose (ACI)2-(Fluoro-18F)-alpha-D-glucopyranose, Fludeoxyglucose (18F)
Fluorodeoxyglucose F 18[18F]FDGFlucisFludeoxyglucose-18FSCHEMBL135994Fludeoxyglucose F 18 (USP)(18)FDGFludeoxyglucose (18F); Fludeoxyglucose F 18; Fluorine F 18 Fluorodeoxyglucose

Datenbank-Bezeichner

CAS
105851-17-0、63503-12-8
PubChem CID
450503
DTXSID
DTXSID50894178
ChEBI
CHEBI:31617
UNII
SBT3GBX27W
Nikkaji
J227.716F

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
-1,6
Polarare Oberfläche (TPSA)
90,2 Ų
H-Brücken-Donoren
4
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
1
Schwere Atome
12
Formalladung
0
Komplexität
155

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Various

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

V - Various

QV - Various

Protein BindingThe extent of binding of Fludeoxyglucose F 18 to plasma proteins is not known.
Pharmacodynamics · 1 Eintrag

Fludeoxyglucose F 18 Injection is rapidly distributed to all organs of the body after intravenous administration. After background clearance of Fludeoxyglucose F 18 Injection, optimal PET imaging is generally achieved between 30 to 40 minutes after administration. In cancer, the cells are generally characterized by enhanced glucose metabolism partially due to (1) an increase in the activity of glucose transporters, (2) an increased rate of phosphorylation activity, (3) a reduction of phosphatase activity or, (4) a dynamic alteration in the balance among all these processes. However, glucose metabolism of cancer as reflected by Fludeoxyglucose F 18 accumulation shows considerable variability. Depending on tumor type, stage, and location, Fludeoxyglucose F 18 accumulation may be increased, normal, or decreased. Also, inflammatory cells can have the same variability of uptake of Fludeoxyglucose F 18. In the heart, under normal aerobic conditions, the myocardium meets the bulk of its energy requirements by oxidizing free fatty acids. Most of the exogenous glucose taken up by the myocyte is converted into glycogen. However, under ischemic conditions, the oxidation of free fatty acids decreases, exogenous glucose becomes the preferred myocardial substrate, glycolysis is stimulated, and glucose taken up by the myocyte is metabolized immediately instead of being converted into glycogen. Under these conditions, phosphorylated Fludeoxyglucose F 18 accumulates in the myocyte and can be detected with PET imaging. Normally, the brain relies on anaerobic metabolism. In epilepsy, the glucose metabolism varies. Generally, during a seizure glucose metabolism increases. Interictally, the seizure focus tends to be hypometabolic.

Mechanism of Action · 1 Eintrag

Fludeoxyglucose F 18 is a glucose analog that concentrates in cells that rely upon glucose as an energy source, or in cells whose dependence on glucose increases under pathophysiological conditions. Fludeoxyglucose F 18 is transported through the cell membrane by facilitative glucose transporter proteins and is phosphorylated within the cell to [18F] FDG-6- phosphate by the enzyme hexokinase. Once phosphorylated it cannot exit until it is dephosphorylated by glucose-6-phosphatase. Therefore, within a given tissue or pathophysiological process, the retention and clearance of Fludeoxyglucose F 18 reflect a balance involving glucose transporter, hexokinase and glucose-6- phosphatase activities. When allowance is made for the kinetic differences between glucose and Fludeoxyglucose F 18 transport and phosphorylation (expressed as the “lumped constant” ratio), Fludeoxyglucose F 18 is used to assess glucose metabolism. In comparison to background activity of the specific organ or tissue type, regions of decreased or absent uptake of Fludeoxyglucose F 18 reflect the decrease or absence of glucose metabolism. Regions of increased uptake of Fludeoxyglucose F 18 reflect greater than normal rates of glucose metabolism.

Biological Half-Life10-13 minutes
Metabolism/Metabolites · 1 Eintrag

Fludeoxyglucose F 18 is transported into cells and phosphorylated to [18F]-FDG-6-phosphate at a rate proportional to the rate of glucose utilization within that tissue. [18F]-FDG-6-phosphate presumably is metabolized to 2-deoxy-2-[18F] fluoro-6-phospho-Dmannose ([18F]FDM-6-phosphate). Fludeoxyglucose F 18 Injection may contain several impurities (e.g., 2-deoxy-2-chloro-D-glucose (ClDG)). Biodistribution and metabolism of C1DG are presumed to be similar to Fludeoxyglucose F 18 and would be expected to result in intracellular formation of 2-deoxy-2-chloro-6-phospho-D-glucose (C1DG-6-phosphate) and 2-deoxy-2-chloro-6-phospho-D-mannose (ClDM-6-phosphate). The phosphorylated deoxyglucose compounds are dephosphorylated and the resulting compounds (FDG, FDM, C1DG, and ClDM) presumably leave cells by passive diffusion.

Absorption, Distribution and Excretion · 4 Einträge

Fludeoxyglucose F 18 Injection is rapidly distributed to all organs of the body after intravenous administration.

Fludeoxyglucose F 18 is cleared from most tissues within 24 hours and can be eliminated from the body unchanged in the urine.

Fludeoxyglucose F 18 Injection is rapidly distributed to all organs of the body after intravenous administration.

Fludeoxyglucose F 18 and related compounds are cleared from non-cardiac tissues within 3 to 24 hours after administration. Clearance from the cardiac tissue may require more than 96 hours

Anwendungen

VerwendenDiagnostic aid; radioactive agent.

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