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
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
Molecular Formula | C6H12O5 |
Molecular Weight | 164.1565 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://drug.report/2-Deoxy-D-glucose/Curator's Comment: description was created based on several sources, including:
http://www.wikidoc.org/index.php/2-Deoxy-D-glucose
http://www.drugbank.ca/drugs/DB08831
Sources: http://drug.report/2-Deoxy-D-glucose/
Curator's Comment: description was created based on several sources, including:
http://www.wikidoc.org/index.php/2-Deoxy-D-glucose
http://www.drugbank.ca/drugs/DB08831
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/7108556 | http://www.ncbi.nlm.nih.gov/pubmed/6848656
Curator's Comment: Known to be CNS penetrant in rat. Human data not available.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2096907 Sources: http://www.ncbi.nlm.nih.gov/pubmed/19258070 |
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Target ID: cell surface glycoprotein HSV-1 receptor sites Sources: http://www.ncbi.nlm.nih.gov/pubmed/3015018 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Sources: http://www.neurogenomex.com/research.html |
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Evidence for the involvement of vicinal sulfhydryl groups in insulin-activated hexose transport by 3T3-L1 adipocytes. | 1985 Mar 10 |
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Inhibition of cyclic AMP-dependent induction of ornithine aminotransferase by simple carbohydrates in cultured hepatocytes. | 1987 Dec |
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A further comparison of insulin- and phorbol ester-stimulated glucose transport in adipocytes. | 1989 Aug |
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Neural mechanisms of dystonia: evidence from a 2-deoxyglucose uptake study in a primate model of dopamine agonist-induced dystonia. | 1990 |
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Uptake and binding of radiolabelled phenylarsine oxide in 3T3-L1 adipocytes. | 1990 Aug 1 |
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Effects of insulin and phospholipase C in control and denervated rat skeletal muscle. | 1991 Feb |
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Trafficking of glucose transporters in 3T3-L1 cells. Inhibition of trafficking by phenylarsine oxide implicates a slow dissociation of transporters from trafficking proteins. | 1992 Feb 1 |
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Nitrogen dioxide-induced expression of a 78 kDa protein in pulmonary artery endothelial cells. | 1996 |
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Effects of overexpression of glutamine:fructose-6-phosphate amidotransferase (GFAT) and glucosamine treatment on translocation of GLUT4 in rat adipose cells. | 1997 Nov 30 |
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Effects of antimetabolites to glucose and fatty acids on galanin-1 receptor mRNA levels in the hypothalamic paraventricular and supraoptic nuclei. | 1998 Dec 21 |
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Effect of inhibition of glucose and fat metabolism on galanin-R1 receptor mRNA levels in the rat hypothalamic paraventricular and supraoptic nuclei. | 1998 Nov 16 |
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Induction of superoxide dismutase and cytotoxicity by manganese in human breast cancer cells. | 1999 May 15 |
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Mitochondrial phospholipid hydroperoxide glutathione peroxidase suppresses apoptosis mediated by a mitochondrial death pathway. | 1999 Oct 8 |
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Calcineurin-mediated hypertrophy protects cardiomyocytes from apoptosis in vitro and in vivo: An apoptosis-independent model of dilated heart failure. | 2000 Feb 18 |
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Hypoxia-induced upregulation of eNOS gene expression is redox-sensitive: a comparison between hypoxia and inhibitors of cell metabolism. | 2001 Jul |
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Heterologous expression of the Na(+),K(+)-ATPase gamma subunit in Xenopus oocytes induces an endogenous, voltage-gated large diameter pore. | 2001 Sep 1 |
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Activation of the ERK pathway and atypical protein kinase C isoforms in exercise- and aminoimidazole-4-carboxamide-1-beta-D-riboside (AICAR)-stimulated glucose transport. | 2002 Jun 28 |
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Impaired gastric secretion and lack of trophic responses to hypergastrinemia in M3 muscarinic receptor knockout mice. | 2003 Dec |
|
Contribution of the PI 3-kinase/Akt survival pathway toward osmotic preconditioning. | 2005 Jan |
|
Corticosteroids inhibit cell death induced by doxorubicin in cardiomyocytes: induction of antiapoptosis, antioxidant, and detoxification genes. | 2005 Jun |
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2-Methoxyoestradiol-3,17-O,O-bis-sulphamate and 2-deoxy-D-glucose in combination: a potential treatment for breast and prostate cancer. | 2008 Dec 2 |
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Adipose tissue-specific PPARgamma deficiency increases resistance to oxidative stress. | 2008 Mar |
|
Stimulation of muscle cell glucose uptake by resveratrol through sirtuins and AMPK. | 2008 Sep 12 |
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The AMPK agonist AICAR inhibits the growth of EGFRvIII-expressing glioblastomas by inhibiting lipogenesis. | 2009 Aug 4 |
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Salacia oblonga extract increases glucose transporter 4-mediated glucose uptake in L6 rat myotubes: role of mangiferin. | 2009 Oct |
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Inhibition of glycolysis enhances cisplatin-induced apoptosis in ovarian cancer cells. | 2010 Apr |
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p53 Protects lung cancer cells against metabolic stress. | 2010 Dec |
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Glucosamine-induced endoplasmic reticulum stress affects GLUT4 expression via activating transcription factor 6 in rat and human skeletal muscle cells. | 2010 May |
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Involvement of H-Ras and reactive oxygen species in proinflammatory cytokine-induced matrix metalloproteinase-13 expression in human articular chondrocytes. | 2011 Mar 15 |
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Activation of peroxisome proliferator-activated receptor-alpha stimulates both differentiation and fatty acid oxidation in adipocytes. | 2011 May |
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Enhancement of carboplatin-mediated lung cancer cell killing by simultaneous disruption of glutathione and thioredoxin metabolism. | 2011 Oct 1 |
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Deletion of the Mint3/Apba3 gene in mice abrogates macrophage functions and increases resistance to lipopolysaccharide-induced septic shock. | 2011 Sep 16 |
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Cytotoxic effects of mithramycin DIG-MSK can depend on the rise of autophagy. | 2015 Oct |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23228990
The recommended dose of 2DG in combination with weekly docetaxel is 63 mg/kg/day.
Route of Administration:
Oral
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/19258070
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
Created
by
admin
on
Edited
Fri Dec 15 19:43:56 UTC 2023
by
admin
on
Fri Dec 15 19:43:56 UTC 2023
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Record UNII |
9G2MP84A8W
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Record Status |
Validated (UNII)
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Record Version |
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C344
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15866
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1733674
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SUB62474
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15193
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205-823-0
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108223
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61-58-5
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DB08831
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m4175
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100000134458
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9G2MP84A8W
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9G2MP84A8W
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84755
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2-DEOXY-D-GLUCOSE
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154-17-6
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DTXSID1037648
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5484
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C116618
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Related Record | Type | Details | ||
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PRODRUG -> METABOLITE ACTIVE |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |