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Details

Stereochemistry ABSOLUTE
Molecular Formula C6H12O5
Molecular Weight 164.1565
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2-DEOXYGLUCOSE

SMILES

OC[C@@H](O)[C@@H](O)[C@H](O)CC=O

InChI

InChIKey=VRYALKFFQXWPIH-PBXRRBTRSA-N
InChI=1S/C6H12O5/c7-2-1-4(9)6(11)5(10)3-8/h2,4-6,8-11H,1,3H2/t4-,5-,6+/m1/s1

HIDE SMILES / InChI

Molecular Formula C6H12O5
Molecular Weight 164.1565
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

2-deoxyglucose is predominantly used as a diagnostic agent in its radiolabelled form (fluorine-18 is used as the radiolabel). Therapeutically, 2-deoxyglucose is an investigational drug that is being studied as an anticancer and antiviral agent. 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.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
The recommended dose of 2DG in combination with weekly docetaxel is 63 mg/kg/day.
Route of Administration: Oral
In Vitro Use Guide
LKB1-null non-small-cell lung carcinoma cell lines showed a significant decrease in cell viability for all doses tested, even at the lowest dose of 2-deoxyglucose (2.5 mmol/L) compared with LKB1-positive cells.
Substance Class Chemical
Record UNII
9G2MP84A8W
Record Status Validated (UNII)
Record Version