105851-17-0 , 2-(Fluoro-18F)-a-D-glucopyranose,
Fludeoxyglucose (18F),
CAS:105851-17-0
C6H11FO5 / 181.149
MFCD00867250
2-(Fluoro-18F)-a-D-glucopyranose, Fludeoxyglucose (18F)
Fluorodeoxyglucose F 18 (18F-FDG) is a glucose analog that is used in nuclear medicine as a radioactive tracer to produce images of the distribution of glucose in the body. This agent is used for diagnosis and treatment of cancer, including tumors and cancers that have metastasized. 18F-FDG is taken up by cells with high levels of the P-glycoprotein (P-gp) protein, which transports drugs out of cells. In these cells, 18F-FDG accumulates and emits positrons that are detected by a PET scanner. The uptake rate constant and analytical method for 18F-FDG have been determined experimentally and are known to be independent of tumor type or location.
Fludeoxyglucose F18 (FDG-F18) is a radiopharmaceutical and a type of positron emission tomography (PET) imaging agent used to obtain images of the brain, heart, and other organs. Its unique properties allow for visualization of metabolic activity within cells, which makes it a valuable tool for scientific research and medical diagnosis. This paper will explore FDG-F18's definition and background, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, applications in scientific experiments, current state of research, potential implications in various fields of research and industry, limitations, and future directions.
Definition and Background
FDG-F18 is a radiopharmaceutical used to obtain images of metabolic activity within cells. Radiopharmaceuticals are substances that contain a radioactive atom; in the case of FDG-F18, the radioisotope is fluorine-18. The radiotracer is taken up by the body's cells and the radiation emitted by the fluorine-18 is detected by PET scanners to form an image of the metabolic activity of the tissue being imaged. FDG-F18 was first approved by the Food and Drug Administration (FDA) in 1997 for the imaging of glucose metabolism in the brain, but its use has since expanded to other organs and tissues.
Physical and Chemical Properties
FDG-F18 has a white crystalline appearance and is a soluble solid at room temperature. Its chemical formula is C6H11FO5 and its molecular weight is 181 g/mol. The radioactive half-life of F18 is 110 minutes, which limits its usefulness as a radiotracer. Due to its short half-life, FDG-F18 must be prepared in small quantities and used immediately after synthesis.
Synthesis and Characterization
FDG-F18 is synthesized using a multistep process that involves the nucleophilic substitution of a protected precursor with fluorine-18. The precursor is protected to prevent reaction with water and other nucleophiles. The reaction is then deprotected to produce FDG-F18. The radiopharmaceutical is characterized by high-performance liquid chromatography and mass spectrometry to ensure purity and identify any potential impurities.
Analytical Methods
FDG-F18 can be detected using PET scanners, which use detectors to capture the radiation emitted by the fluorine-18. The signals are then used to create images of the metabolic activity of the tissue being imaged. The images can be analyzed quantitatively to provide insight into the uptake of FDG-F18 within cells.
Biological Properties
FDG-F18 is a glucose analogue and is taken up by cells in a manner similar to glucose. It is transported into cells by glucose transporters and phosphorylated by hexokinase to form FDG-6-phosphate. Once inside the cell, FDG-6-phosphate cannot be metabolized further and accumulates within the cell, allowing for visualization of the metabolic activity of the tissue being imaged.
Toxicity and Safety in Scientific Experiments
The short half-life of FDG-F18 limits its toxicity and safety concerns. The radiation exposure from an FDG-F18 PET scan is minimal and the radiotracer is eliminated from the body quickly after imaging. However, safety precautions must still be taken in the handling and administration of the radiotracer to prevent exposure to ionizing radiation.
Applications in Scientific Experiments
FDG-F18 has numerous applications in scientific experiments, including the imaging of glucose metabolism in the brain, heart, and other organs. PET imaging using FDG-F18 has been used to study the metabolic alterations associated with neurodegenerative diseases, such as Alzheimer's and Parkinson's disease. It has also been used to assess the response to chemotherapy in cancer patients and to study the effects of exercise on glucose uptake in skeletal muscle.
Current State of Research
Current research is focused on further understanding the metabolic changes associated with various diseases, such as cancer and neurodegenerative diseases. FDG-F18 PET imaging is being used to study the metabolic alterations associated with cancer and to develop new therapies that target glucose metabolism in cancer cells.
Potential Implications in Various Fields of Research and Industry
The unique properties of FDG-F18 have potential implications in various fields of research and industry, including drug development, personalized medicine, and nuclear medicine. FDG-F18 can be used to develop new therapies that target glucose metabolism in cancer cells and can be used to monitor the response to therapy. It also has potential applications in the diagnosis and management of metabolic disorders.
Limitations and Future Directions
The short half-life of FDG-F18 limits its use as a radiotracer. Future research is focused on developing new radiotracers that can be used to study other aspects of metabolism and disease. There is also a need for new imaging techniques that can provide a clearer picture of metabolic activity at the cellular and molecular level.
Future Directions:
- Development of new radiotracers with longer half-lives for imaging metabolic activity
- Development of new imaging techniques that provide a clearer picture of metabolic activity at the cellular and molecular level
- Investigation of the role of glucose metabolism in other diseases, such as diabetes and obesity
- Evaluation of the potential of FDG-F18 in combination therapies for cancer
- Exploration of the use of FDG-F18 in personalized medicine and precision medicine
- Investigation of the potential of FDG-F18 in the diagnosis and management of metabolic disorders
- Development of novel methods of synthesis and purification of FDG-F18
- Investigation of the effects of different imaging protocols on the sensitivity and specificity of FDG-F18 imaging
- Evaluation of the safety and efficacy of FDG-F18 in preclinical studies and clinical trials
- Investigation of the potential of FDG-F18 in the imaging of metabolic changes associated with aging and diseases of aging
- Exploration of the use of FDG-F18 in the assessment of the efficacy of new therapies for metabolic disorders and cancer.
Title: Fludeoxyglucose F18
CAS Registry Number: 105851-17-0
CAS Name: 2-Deoxy-2-(fluoro-18F)-a-D-glucopyranose
Additional Names: 2-[18F]fluoro-2-deoxy-D-glucose; 18FDG
Molecular Formula: C6H1118FO5
Literature References: Radioactive glucose analog used clinically to evaluate glucose metabolism by PET. Prepn: T. Ido et al., J. Labelled Compd. Radiopharm. 14, 175 (1978). Review of syntheses: T. J. Tewson, Nucl. Med. Biol. 16, 533-551 (1989). Biodistribution: B. M. Gallagher et al., J. Nucl. Med. 19, 1154 (1978). Cerebral glucose measurement in man: M. Reivich et al., Circ. Res. 44, 127 (1979). Clinical evaluation of metabolic imaging in myocardium: R. J. Gropler et al., J. Nucl. Med. 31, 1749 (1990); in tumors: J. Okada et al., ibid. 33, 325 (1992); N. Y. Tse et al., Ann. Surg. 216, 27 (1992). Reviews of imaging in cerebrovascular disease: K. Herholz, W. D. Heiss, Semin. Neurol. 9, 293-300 (1989); Alzheimer's disease: J. M. Hoffman et al., Eur. Neurol. 29, Suppl. 3, 16-24 (1989); brain tumors: R. E. Coleman et al., J. Nucl. Med. 32, 616-622 (1991); pancreatic cancer: M. Zimny, U. Buell, Ann. Oncol. 10, Suppl. 4, S28-S32 (1999).
Therap-Cat: Diagnostic aid (radioactive imaging agent).
Keywords: Diagnostic Aid (Radioactive Imaging Agent).
CAS Number | 105851-17-0 |
Product Name | Fludeoxyglucose F18 |
IUPAC Name | (2S,3R,4S,5S,6R)-3-(18F)fluoranyl-6-(hydroxymethyl)oxane-2,4,5-triol |
Molecular Formula | C6H11FO5 |
Molecular Weight | 181.15 g/mol |
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 |
InChI Key | ZCXUVYAZINUVJD-AHXZWLDOSA-N |
SMILES | C(C1C(C(C(C(O1)O)F)O)O)O |
Synonyms | 18F Fluorodeoxyglucose, 18F-FDG, 18FDG, 2 Fluoro 2 deoxy D glucose, 2 Fluoro 2 deoxyglucose, 2-Fluoro-2-deoxy-D-glucose, 2-Fluoro-2-deoxyglucose, F 18, Fludeoxyglucose, F 18, Fluorodeoxyglucose, F18, Fluorodeoxyglucose, Fludeoxyglucose F 18, Fluorine 18 fluorodeoxyglucose, Fluorine-18-fluorodeoxyglucose, Fluorodeoxyglucose F 18, Fluorodeoxyglucose F18, Fluorodeoxyglucose, 18F |
Canonical SMILES | C(C1C(C(C(C(O1)O)F)O)O)O |
Isomeric SMILES | C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O)[18F])O)O)O |
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