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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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
C J Hoekstra et al.
European journal of nuclear medicine, 27(6), 731-743 (2000-07-20)
[18F]-2-fluoro-2-deoxy-D-glucose positron emission tomography (FDG PET) is considered a valuable tool in the diagnosis and staging of cancer. In addition, it seems promising as a technique to monitor response to therapy. Progress is hampered, however, by the fact that various
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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