2-Deoxy-D-glucose

Chemical Information
2-deoxyglucose is predominantly used as a diagnostic agent in its radiolabelled form (fluorine-18 is used as the radiolabel). By using positron emission tomography (PET), radiolabelled 2-deoxyglucose can determine glucose metabolism, which is altered in diseases such as cardiovascular disease, tumors, and Alzheimer's disease. Therapeutically, 2-deoxyglucose is an investigational drug that is being studied as an anticancer and antiviral agent. Concerning the former, 2- deoxyglucose was used as an adjunct to chemotherapy and radiotherapy in the treatment of solid tumors (lung, breast, pancreas, head, neck, and gastric tumors). The exact mechanisms of action of 2-deoxyglucose is still being investigated, but it is known that in hypoxic cancer cells, 2-deoxyglucose is a glycolysis inhibitor that prevents ATP production and, ultimately, cell survival. With respect to antiviral therapy, 2-deoxyglucose was shown to be effective against herpes simplex virus by affecting the virus' ability to penetrate cells. As an experimental drug, 2-deoxyglucose was demonstrated to work as an anticonvulsant in temporal lobe epilepsy. In this condition, 2-deoxyglucose represses the expression of certain proteins that are at high levels after a seizure. Although there are several possible therapeutic indications for 2-deoxyglucose, presently there is no approved indication for 2-deoxyglucose as a therapeutic agent.
| CAS Number | 154-17-6 |
| PubChem CID | 108223 |
| IUPAC Name | (3R,4S,5R)-3,4,5,6-tetrahydroxyhexanal |
| Molecular Formula | C6H12O5 |
| Molecular Weight | 164.16 |
| XLogP | -2.9 |
| Topological Polar Surface Area | 98 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 5 |
| Heavy Atom Count | 11 |
| Formal Charge | 0 |
| Complexity | 116 |
| Property | Value |
|---|---|
| Molecular Weight | 164.16 |
| XLogP3 | -2.9 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 5 |
| Exact Mass | 164.06847348 |
| Monoisotopic Mass | 164.06847348 |
| Topological Polar Surface Area | 98 Ų |
| Heavy Atom Count | 11 |
| Formal Charge | 0 |
| Complexity | 116 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 3 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
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