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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
D-arabino-2-Deoxyhexose
External Identifiers 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
SaltsNot Available
Categories
UNII9G2MP84A8W
CAS number154-17-6
WeightAverage: 164.1565
Monoisotopic: 164.068473494
Chemical FormulaC6H12O5
InChI KeyInChIKey=PMMURAAUARKVCB-PHUJZJCSNA-N
InChI
InChI=1/C6H12O5/c7-2-4-6(10)3(8)1-5(9)11-4/h3-10H,1-2H2/t3-,4-,5?,6+/s2
IUPAC Name
(4R,5S,6R)-6-(hydroxymethyl)oxane-2,4,5-triol
SMILES
OC[[email protected]]1OC(O)C[C@@H](O)[C@@H]1O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as monosaccharides. These are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassMonosaccharides
Direct ParentMonosaccharides
Alternative Parents
Substituents
  • Oxane
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Hemiacetal
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationAs 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.
PharmacodynamicsPhysiologically 2-deoxyglucose is an inhibitor of glycolysis, certain viruses, and seizures.
Mechanism of actionSolid 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
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point147°C (296.6°F)From MSDS.
boiling pointDecomposesFrom MSDS.
Predicted Properties
PropertyValueSource
Water Solubility984.0 mg/mLALOGPS
logP-2.5ALOGPS
logP-2ChemAxon
logS0.78ALOGPS
pKa (Strongest Acidic)12.29ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area90.15 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.41 m3·mol-1ChemAxon
Polarizability15.29 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot 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)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

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 ]
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Drug created on February 16, 2013 15:58 / Updated on August 17, 2016 12:24