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Details

Stereochemistry ABSOLUTE
Molecular Formula C6H12O5
Molecular Weight 164.1567
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

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

Cmax

ValueDoseCo-administeredAnalytePopulation
449.2 μM
45 mg/kg single, oral
2-DEOXYGLUCOSE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1107.7 μM × h
45 mg/kg single, oral
2-DEOXYGLUCOSE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
7.3 h
45 mg/kg single, oral
2-DEOXYGLUCOSE plasma
Homo sapiens

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.