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F5006

Sigma-Aldrich

2-Fluoro-2-deoxy-D-glucose

glycosylation inhibitor, glucose analog

Synonym(s):

2-Deoxy-2-fluoro-D-glucose, FDG, 2-Deoxy-2-fluoro-D-glucose

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About This Item

Empirical Formula (Hill Notation):
C6H11FO5
CAS Number:
29702-43-0
Molecular Weight:
182.15
MDL number:
MFCD00077527
UNSPSC Code:
41116107
PubChem Substance ID:
24894876
NACRES:
NA.32

Quality Level

300

storage temp.

2-8°C

SMILES string

OCC1OC(O)C(F)C(O)C1O

InChI

1S/C6H11FO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1H2

InChI key

ZCXUVYAZINUVJD-UHFFFAOYSA-N

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General description

2-Fluoro-2-deoxy-D-glucose is non-toxic and a structural analog of glucose, significantly inhibiting glycosylation. As a glucose analog, uptake of 2-Fluoro-2-deoxy-D-glucose is rapid in brain and heart cells.

2-Fluoro-2-deoxy-D-glucose can be taken up by cells but does not undergo metabolic glycolysis.

Application

2-Fluoro-2-deoxy-D-glucose is used as a tracer for rapid tumor detection. It is used as a glucose analog to study glucose uptake in mice with radiation and burn injuries. Oncology therapy studies use FDG in combination with PET (Positron Emission Topography)

Biochem/physiol Actions

Glucose analog that inhibits cellular glycosylation.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Dennis Vriens et al.
Cancer, 117(20), 4582-4594 (2011-03-25)
Indeterminate results at fine-needle aspiration biopsy (FNAB) of thyroid nodules pose a clinical dilemma, because only 20% to 30% of patients suffer from malignancy. Previous studies suggested that the false-negative ratio of [(18)F]-2-fluoro-2-deoxy-D-glucose-positron emission tomography (FDG-PET) is very low; therefore
Maarten J Vosselman et al.
The American journal of clinical nutrition, 98(1), 57-64 (2013-05-31)
Studies in rodents have shown that brown adipose tissue (BAT) is activated on food intake, thereby reducing metabolic efficiency. The current study investigated whether a single high-calorie, carbohydrate-rich meal activates BAT in lean human adults. BAT activity was studied in
P Som et al.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine, 21(7), 670-675 (1980-07-01)
Rapid uptake of F-18 FDG was observed in a variety of transplanted and spontaneous tumors in animals. The tumor uptake reached a peak by 30 min and remained relatively constant up to 60 min, with a very slow wash-out of
Frank J Brooks et al.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine, 55(1), 37-42 (2013-11-23)
The number of studies in the literature involving quantification of the metabolic heterogeneity seen in (18)F-FDG PET images has increased sharply over recent years. We hypothesized that inclusion of very small regions of interest as unique data points will have
G J Bosman et al.
Biochimica et biophysica acta, 696(3), 285-289 (1982-03-29)
Tunicamycin, 2-deoxy-D-glucose and 2-deoxy-2-fluoro-D-glucose inhibit dimethyl sulfoxide-induced differentiation of Friend cells. This inhibition, characterized by inhibition of hemoglobin synthesis, is accompanied by a specific inhibition of protein glycosylation. The results of cloning experiments indicate that this inhibition specifically affects cells
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