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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

Certificates of Analysis (COA)

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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
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
Edward A Carter et al.
Journal of burn care & research : official publication of the American Burn Association, 33(6), 723-730 (2012-11-13)
Radiation exposure and burn injury have both been shown to alter glucose utilization in vivo. The present study was designed to study the effect of burn injury combined with radiation exposure on glucose metabolism in mice using [¹⁸F] 2-fluoro-2-deoxy-D-glucose (¹⁸FDG).
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