Fluorodeoxyglucose (18F)

Fluorodeoxyglucose (¹⁸F)
Names
	IUPAC name 2-Deoxy-2-[18F]fluoroglucose
Identifiers
CAS Number	63503-12-8 (2S,6R)-6-meth,-2-ol ;
3D model (JSmol)	Interactive image;
Abbreviations	[18F]FDG
Beilstein Reference	2047723
ChEBI	CHEBI:49130 ;
ChEMBL	ChEMBL497613 ;
ChemSpider	396785 ; 8096174 (2R,6R)-6-meth,-2-ol ; 9644274 (6R)-6-meth ;
KEGG	D01843 ;
PubChem CID	11469444 (6R)-6-meth; 9920539 (2R,6R)-6-meth,-2-ol; 450503 (2S,6R)-6-meth,-2-ol; 25173432 (2S)-2-ol;
UNII	0Z5B2CJX4D ;
CompTox Dashboard (EPA)	DTXSID50894178 DTXSID40212908, DTXSID50894178 ;
	InChI InChI=1S/C6H11FO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1H2/t2-,3-,4-,5-,6+/m1/s1/i7-1 Key: ZCXUVYAZINUVJD-AHXZWLDOSA-N ;
	SMILES OCC1OC(O)[C@H]([18F])[C@@H](O)[C@@H]1O;
Properties
Chemical formula	C6H1118FO5
Molar mass	181.1495 g mol−1
Melting point	170 to 176 °C (338 to 349 °F; 443 to 449 K)
Pharmacology
ATC code	V09IX04 (WHO)
Pregnancy; category	AU: X (High risk); ;
Routes of; administration	Intravenous
	Pharmacokinetics:
Metabolism	6-Phosphorylation; Glycolysis
Biological half-life	110 min (at 70%); 16 min (at 20%)
Excretion	20% Radioactivity renally excreted in two hours
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

[¹⁸F]Fluorodeoxyglucose (INN), or fluorodeoxyglucose F 18 (USAN and USP), also commonly called fluorodeoxyglucose and abbreviated [¹⁸F]FDG, 2-[¹⁸F]FDG or FDG, is a radiopharmaceutical, specifically a radiotracer, 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 radionuclide fluorine-18 substituted for the normal hydroxyl group at the C-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.^[2] The subsequent discovery in 1980 that [¹⁸F]FDG accumulates in tumors underpins the evolution of PET as a major clinical tool in cancer diagnosis.^[3] [¹⁸F]FDG is now the standard radiotracer used for PET neuroimaging and cancer patient management.^[4]

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

^ Pacák J, Točík Z, Černý M (1969). "Synthesis of 2-Deoxy-2-fluoro-D-glucose". Journal of the Chemical Society D: Chemical Communications. 1969 (2): 77. doi:10.1039/C29690000077.
^ Newberg A, Alavi A, Reivich M (January 2002). "Determination of regional cerebral function with FDG-PET imaging in neuropsychiatric disorders". Seminars in Nuclear Medicine. 32 (1): 13–34. doi:10.1053/snuc.2002.29276. PMID 11839066.
^ Som P, Atkins HL, Bandoypadhyay D, Fowler JS, MacGregor RR, Matsui K, et al. (July 1980). "A fluorinated glucose analog, 2-fluoro-2-deoxy-D-glucose (F-18): nontoxic tracer for rapid tumor detection". Journal of Nuclear Medicine. 21 (7): 670–5. PMID 7391842.
^ Kelloff GJ, Hoffman JM, Johnson B, Scher HI, Siegel BA, Cheng EY, et al. (April 2005). "Progress and promise of FDG-PET imaging for cancer patient management and oncologic drug development". Clinical Cancer Research. 11 (8): 2785–808. doi:10.1158/1078-0432.CCR-04-2626. PMID 15837727.

[JCS_1969-1] Pacák J, Točík Z, Černý M (1969). "Synthesis of 2-Deoxy-2-fluoro-D-glucose". Journal of the Chemical Society D: Chemical Communications. 1969 (2): 77. doi:10.1039/C29690000077.

[2] Newberg A, Alavi A, Reivich M (January 2002). "Determination of regional cerebral function with FDG-PET imaging in neuropsychiatric disorders". Seminars in Nuclear Medicine. 32 (1): 13–34. doi:10.1053/snuc.2002.29276. PMID 11839066.

[3] Som P, Atkins HL, Bandoypadhyay D, Fowler JS, MacGregor RR, Matsui K, et al. (July 1980). "A fluorinated glucose analog, 2-fluoro-2-deoxy-D-glucose (F-18): nontoxic tracer for rapid tumor detection". Journal of Nuclear Medicine. 21 (7): 670–5. PMID 7391842.

[4] Kelloff GJ, Hoffman JM, Johnson B, Scher HI, Siegel BA, Cheng EY, et al. (April 2005). "Progress and promise of FDG-PET imaging for cancer patient management and oncologic drug development". Clinical Cancer Research. 11 (8): 2785–808. doi:10.1158/1078-0432.CCR-04-2626. PMID 15837727.

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Names

IUPAC name 2-Deoxy-2-[¹⁸F]fluoroglucose
Identifiers
CAS Number	63503-12-8 (2S,6R)-6-meth,-2-ol^Y
3D model (JSmol)	Interactive image
Abbreviations	[¹⁸F]FDG
Beilstein Reference	2047723
ChEBI	CHEBI:49130^N
ChEMBL	ChEMBL497613^N
ChemSpider	396785^Y 8096174 (2R,6R)-6-meth,-2-ol^Y 9644274 (6R)-6-meth^Y
KEGG	D01843^N
PubChem CID	11469444 (6R)-6-meth 9920539 (2R,6R)-6-meth,-2-ol 450503 (2S,6R)-6-meth,-2-ol 25173432 (2S)-2-ol
UNII	0Z5B2CJX4D^Y
CompTox Dashboard (EPA)	DTXSID50894178 DTXSID40212908, DTXSID50894178
InChI InChI=1S/C6H11FO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1H2/t2-,3-,4-,5-,6+/m1/s1/i7-1^Y Key: ZCXUVYAZINUVJD-AHXZWLDOSA-N^Y
SMILES OCC1OC(O)[C@H]([18F])[C@@H](O)[C@@H]1O
Properties
Chemical formula	C₆H₁₁¹⁸FO₅
Molar mass	181.1495 g mol⁻¹
Melting point	170 to 176^[1] °C (338 to 349 °F; 443 to 449 K)
Pharmacology
ATC code	V09IX04 (WHO)
Pregnancy category	AU: X (High risk)
Routes of administration	Intravenous
Pharmacokinetics:
Metabolism	6-Phosphorylation Glycolysis
Biological half-life	110 min (at 70%) 16 min (at 20%)
Excretion	20% Radioactivity renally excreted in two hours
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references