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Fludeoxyglucose (18F)

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Fluorodeoxyglucose (18F)

Stereo skeletal formula of fluorodeoxyglucose (18F) ((2S,6R)-6-meth,-2-ol)

IUPAC name[hide]

2-Deoxy-2-[18F]fluoroglucose

Identifiers

Abbreviations [18F]FDG

CAS number 105851-17-0 (2S,6R)-6-meth,-2-ol

ChemSpider 396785 Yes, 8096174 (2R,6R)-6-meth,-2-ol Yes, 9644274 (6R)-6-meth Yes

KEGG D01843

ChEBI CHEBI:49130

ChEMBL CHEMBL497613

ATC code V09IX04

Beilstein Reference 2047723

Jmol-3D images Image 1

SMILES

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InChI

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Properties

Molecular formula C6H1118FO5

Molar mass 181.1495 g mol-1

Melting point 170 to 176 °C (338 to 349 °F; 443 to 449 K)

Pharmacology

Routes of

administration Intravenous

Metabolism 6-Phosphorylation

Glycolysis

Elimination

half-life 110 min (at 70%)

16 min (at 20%)

Excretion 20% Radioactivity renally excreted in 2 hours

Pregnancy

category X(AU)

Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)

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Infobox references

Fludeoxyglucose (18F) (INN), or fludeoxyglucose F 18 (USAN and USP), also commonly called fluorodeoxyglucose and abbreviated [18F]FDG, 18F-FDG or FDG, is a radiopharmaceutical used in the medical imaging modality positron emission tomography (PET). Chemically, it is 2-deoxy-2-(18F)fluoro-D-glucose, a glucose analog, with the positron-emitting radioactive isotope fluorine-18 substituted for the normal hydroxyl group at the 2' position in the glucose molecule.

The uptake of 18F-FDG by tissues is a marker for the tissue uptake of glucose, which in turn is closely correlated with certain types of tissue metabolism. After 18F-FDG is injected into a patient, a PET scanner can form two-dimensional or three-dimensional images of the distribution of 18F-FDG within the body.

Since its development in 1976, 18F-FDG had a profound influence on research in the neurosciences.[1] The subsequent discovery 1980 that 18F-FDG accumulates in tumors underpins the evolution of PET as a major clinical tool in cancer diagnosis.[2] 18F-FDG is now the standard radiotracer used for PET neuroimaging and cancer patient management.[3]

The images can be assessed by a nuclear medicine physician or radiologist to provide diagnoses of various medical conditions.

Contents [hide]

1 History

2 Synthesis

3 Mechanism of action, metabolic end-products, and metabolic rate

4 Distribution

5 Applications

6 References

History[edit]

In 1968, Dr. Josef Pacak, Zdenek Tocik and Miloslav Cerny at the Department of Organic Chemistry, Charles University, Czechoslovakia were the first to describe the synthesis of FDG.[4] Later, in the 1970s, Tatsuo Ido and Al Wolf at the Brookhaven National Laboratory were the first to describe the synthesis of FDG labeled with 18F.[5] The compound was first administered to two normal human volunteers by Abass Alavi in August, 1976 at the University of Pennsylvania. Brain images obtained with an ordinary (non-PET) nuclear scanner demonstrated the concentration of 18F-FDG in that organ (see history reference below).

Synthesis[edit]

18F-FDG was first synthesized via electrophilic fluorination with 18F2. Subsequently, a "nucleophilic synthesis" was devised with the same radioisotope.

As with all

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