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Namespace Prefixes

PrefixIRI
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n10http://linked.opendata.cz/resource/drugbank/drug/DB08831/identifier/drugbank/
n6http://bio2rdf.org/drugbank:
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n8http://linked.opendata.cz/resource/drugbank/drug/DB08831/identifier/chebi/
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n4http://linked.opendata.cz/resource/drugbank/property/
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n11http://linked.opendata.cz/resource/drugbank/drug/DB08831/identifier/kegg-compound/

Statements

Subject Item
n2:DB08831
rdf:type
n3:Drug
n3: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.
n3:generalReferences
# 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":http://www.ncbi.nlm.nih.gov/pubmed/14642847 # Martindale: The Complete Drug Reference. # 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":http://www.ncbi.nlm.nih.gov/pubmed/23228990 # 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":http://www.ncbi.nlm.nih.gov/pubmed/17041593 # 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":http://www.ncbi.nlm.nih.gov/pubmed/6293188
n3:group
experimental investigational
n3: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.
owl:sameAs
n6:DB08831
dcterms:title
2-deoxyglucose
adms:identifier
n8:15866 n9:2-Deoxy-D-glucose n10:DB08831 n11:C00586
n3:mechanismOfAction
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.
n3:synonym
D-arabino-2-Deoxyhexose 2-Deoxy-D-arabino-hexose 2-Deoxy-D-glucose
n3:IUPAC-Name
n4:271B57CA-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B57D0-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B57CF-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B57CC-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B57CD-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B57CE-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B57C8-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B57C9-363D-11E5-9242-09173F13E4C5 n4:271B57C6-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B57C7-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Acceptor-Count
n4:271B57D6-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B57D7-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B57D1-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B57D2-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B57D4-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B57D3-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B57D5-363D-11E5-9242-09173F13E4C5
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
154-17-6
n3:category
n3:Bioavailability
n4:271B57DC-363D-11E5-9242-09173F13E4C5
n3:Boiling-Point
n4:271B57E1-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B57DE-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B57DF-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n4:271B57E0-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B57DB-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B57DA-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B57DD-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B57CB-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B57D8-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B57D9-363D-11E5-9242-09173F13E4C5