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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:
Molecular Weight:
182.15
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.32

Quality Level

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

Signal Word

Warning

Hazard Statements

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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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
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
Imke Schatka et al.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine, 55(1), 99-106 (2013-11-16)
Sarcoidosis is a systemic granulomatous disease of unknown etiology. Cardiac involvement may occur, leading to an adverse outcome. Although early treatment to improve morbidity and mortality is desirable, sensitive and accurate detection of cardiac sarcoidosis remains a challenge. Accordingly, interest
Johan Stender et al.
Lancet (London, England), 384(9942), 514-522 (2014-04-22)
Bedside clinical examinations can have high rates of misdiagnosis of unresponsive wakefulness syndrome (vegetative state) or minimally conscious state. The diagnostic and prognostic usefulness of neuroimaging-based approaches has not been established in a clinical setting. We did a validation study

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