Identification
Name2-deoxyglucose
Accession NumberDB08831
TypeSmall Molecule
GroupsExperimental, Investigational
Description

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.

Structure
Thumb
Synonyms
2-Deoxy-D-arabino-hexose
2-deoxy-D-glucose
2-DG
D-arabino-2-desoxyhexose
External IDs BA 2758 / BA-2758 / NSC-15193
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNII9G2MP84A8W
CAS number154-17-6
WeightAverage: 164.1565
Monoisotopic: 164.068473494
Chemical FormulaC6H12O5
InChI KeyVRYALKFFQXWPIH-PBXRRBTRSA-N
InChI
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
IUPAC Name
(3R,4S,5R)-3,4,5,6-tetrahydroxyhexanal
SMILES
[H]C([H])(C=O)[C@@]([H])(O)[C@]([H])(O)[C@]([H])(O)CO
Pharmacology
Indication

As of July 2013, there is no approved therapeutic indication for 2-deoxyglucose. 2-deoxyglucose may have several potential indications as an adjunct to chemotherapy and radiotherapy in the treatment of solid tumors, as an antiviral treatment in herpes simplex patients, and as an antiepileptic in temporal lobe epilepsy patients.

Structured Indications Not Available
Pharmacodynamics

Physiologically 2-deoxyglucose is an inhibitor of glycolysis, certain viruses, and seizures.

Mechanism of action

Solid tumors have hypoxic areas with slow growing cells that are resistant to chemotherapy, which attacks rapidly dividing cells. In the hypoxic area of the tumor, the cells rely on anaerobic glycolysis to produce energy in the form of ATP while non-tumor cells can rely on additional pathways such as fatty acid and amino acid metabolism to produce ATP. 2-deoxyglucose is an inhibitor of glycolysis because as a modified glucose molecule (it has a hydrogen at the carbon 2 position instead of a hydroxyl group), it is unable to complete the glycolysis process, and as such will hinder the survival of slow growing cancer cells. Regarding 2-deoxyglucose's antiviral activity, it prevents the glycosylation of specific proteins and lipids as well as prevents proper penetration of the virus into the target cells. In temporal lobe epilepsy, 2-deoxyglucose represses the overactive brain-derived neurotrophic factor (BDNF) promoter and prevents the increased expression of BDNF protein and TrkB receptor (BDNF's receptor) that is observed in epileptic patients.

Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General References
  1. Korcok J, Dixon SJ, Lo TC, Wilson JX: Differential effects of glucose on dehydroascorbic acid transport and intracellular ascorbate accumulation in astrocytes and skeletal myocytes. Brain Res. 2003 Dec 12;993(1-2):201-7. [PubMed:14642847 ]
  2. Raez LE, Papadopoulos K, Ricart AD, Chiorean EG, Dipaola RS, Stein MN, Rocha Lima CM, Schlesselman JJ, Tolba K, Langmuir VK, Kroll S, Jung DT, Kurtoglu M, Rosenblatt J, Lampidis TJ: A phase I dose-escalation trial of 2-deoxy-D-glucose alone or combined with docetaxel in patients with advanced solid tumors. Cancer Chemother Pharmacol. 2013 Feb;71(2):523-30. doi: 10.1007/s00280-012-2045-1. Epub 2012 Dec 11. [PubMed:23228990 ]
  3. Garriga-Canut M, Schoenike B, Qazi R, Bergendahl K, Daley TJ, Pfender RM, Morrison JF, Ockuly J, Stafstrom C, Sutula T, Roopra A: 2-Deoxy-D-glucose reduces epilepsy progression by NRSF-CtBP-dependent metabolic regulation of chromatin structure. Nat Neurosci. 2006 Nov;9(11):1382-7. Epub 2006 Oct 15. [PubMed:17041593 ]
  4. Spivack JG, Prusoff WH, Tritton TR: A study of the antiviral mechanism of action of 2-deoxy-D-glucose: normally glycosylated proteins are not strictly required for herpes simplex virus attachment but increase viral penetration and infectivity. Virology. 1982 Nov;123(1):123-38. [PubMed:6293188 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (46.6 KB)
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentCancer, Breast / Head and Neck Carcinoma / Lung Cancers / Malignant Neoplasm of Pancreas / Malignant Neoplasm of Stomach1
1WithdrawnTreatmentNeoplasms Metastasis / Neoplasms, Intracranial1
1, 2TerminatedTreatmentMalignant Neoplasm of Prostate1
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)147°C (296.6°F)From MSDS.
boiling point (°C)DecomposesFrom MSDS.
Predicted Properties
PropertyValueSource
Water Solubility379.0 mg/mLALOGPS
logP-1.9ALOGPS
logP-2.9ChemAxon
logS0.36ALOGPS
pKa (Strongest Acidic)12.84ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity36.01 m3·mol-1ChemAxon
Polarizability15.47 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.6922
Blood Brain Barrier+0.5304
Caco-2 permeable-0.8684
P-glycoprotein substrateNon-substrate0.6448
P-glycoprotein inhibitor INon-inhibitor0.9436
P-glycoprotein inhibitor IINon-inhibitor0.9738
Renal organic cation transporterNon-inhibitor0.8973
CYP450 2C9 substrateNon-substrate0.8591
CYP450 2D6 substrateNon-substrate0.8744
CYP450 3A4 substrateNon-substrate0.6865
CYP450 1A2 substrateNon-inhibitor0.9823
CYP450 2C9 inhibitorNon-inhibitor0.976
CYP450 2D6 inhibitorNon-inhibitor0.9613
CYP450 2C19 inhibitorNon-inhibitor0.9644
CYP450 3A4 inhibitorNon-inhibitor0.9776
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9888
Ames testNon AMES toxic0.8531
CarcinogenicityNon-carcinogens0.9609
BiodegradationReady biodegradable0.9092
Rat acute toxicity1.0409 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9482
hERG inhibition (predictor II)Non-inhibitor0.9383
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 4 TMS)splash10-0q29-1951000000-06cc16a9680628545167View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 4 TMS)splash10-0lkc-0951000000-39e56efe41d6473040e4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0fr5-0920000000-5f7dfef22a1b59cae284View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0ktb-0920000000-6f9638179f688d51022eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0ktb-0920000000-6f9638179f688d51022eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-3900000000-45865b9816a45604d811View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ow-9200000000-7b5a5cbd361ec11efbbfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0707-9000000000-c9e6d3430eb1073f0d79View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0w29-5900000000-90300437f9ab1170e562View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0k96-9400000000-a11cb0518964ee7a83ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-b4574a9d519fced6b332View in MoNA
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohols
Direct ParentFatty alcohols
Alternative ParentsMedium-chain aldehydes / Carbohydrates and carbohydrate conjugates / Beta-hydroxy aldehydes / Alpha-hydrogen aldehydes / Secondary alcohols / 1,2-diols / Primary alcohols / Hydrocarbon derivatives
SubstituentsFatty alcohol / Medium-chain aldehyde / Saccharide / Beta-hydroxy aldehyde / Alpha-hydrogen aldehyde / Secondary alcohol / Polyol / 1,2-diol / Hydrocarbon derivative / Primary alcohol
Molecular FrameworkAliphatic acyclic compounds
External Descriptorsdeoxyglucose (CHEBI:15866 )

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Xenobiotic transporter activity
Specific Function:
Facilitative glucose transporter. This isoform may be responsible for constitutive or basal glucose uptake. Has a very broad substrate specificity; can transport a wide range of aldoses including both pentoses and hexoses.
Gene Name:
SLC2A1
Uniprot ID:
P11166
Molecular Weight:
54083.325 Da
References
  1. Korcok J, Dixon SJ, Lo TC, Wilson JX: Differential effects of glucose on dehydroascorbic acid transport and intracellular ascorbate accumulation in astrocytes and skeletal myocytes. Brain Res. 2003 Dec 12;993(1-2):201-7. [PubMed:14642847 ]
Drug created on February 16, 2013 15:58 / Updated on June 30, 2017 00:50