2-DEOXYGLUCOSE

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

Structure Search

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
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
AMP-activated protein kinase, AMPK 17 Target ID: CHEMBL2096907 Sources: http://www.ncbi.nlm.nih.gov/pubmed/19258070	Activator 1430
neurotrophic tyrosine kinase receptor type 2 1 Target ID: 4915.0 Gene Symbol: NTRK2 Sources: http://www.ncbi.nlm.nih.gov/pubmed/17041593	Inhibitor 8297
cell surface glycoprotein HSV-1 receptor sites 1 Target ID: cell surface glycoprotein HSV-1 receptor sites Sources: http://www.ncbi.nlm.nih.gov/pubmed/3015018	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Non-small cell lung cancer 206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23228990 https://www.ncbi.nlm.nih.gov/pubmed/14729604 http://www.ncbi.nlm.nih.gov/pubmed/19258070	Primary	Phase I 428	Unknown Approved Use Unknown
Epilepsy 121 Sources: http://www.neurogenomex.com/research.html	Primary	Preclinical	Unknown Approved Use Unknown
Herpes simplex infection 28 Sources: http://www.ncbi.nlm.nih.gov/pubmed/6682121 http://www.ncbi.nlm.nih.gov/pubmed/6296282 http://www.ncbi.nlm.nih.gov/pubmed/3015018	Primary	Preclinical	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P0039E0	https://www.1pchem.com/search?query=1P0039E0
A2B Chem	AB51336	http://a2bchem.com/prod/AB51336
AK Scientific	F387	https://aksci.com/item_detail.php?cat=F387
AbovChem LLC	LN00189445	http://www.abovchem.com/pc/en/product_list.aspx?wd=LN00189445
Accela ChemBio Inc	SY031898	http://accelachem.com/cn/search.html?keyword=SY031898&attname=0
Achemo Scientific Limited	AC-17026	http://www.achemo.com/search/?Keyword=AC-17026
Alinda	ALBB-022735	http://alinda.ru/finechem_en_.html?i=ALBB-022735
Ambeed	A104420	http://www.ambeed.com/search/Search.html?keyword=A104420
Angene	AGN-PC-0O4E8I	http://www.angenechemical.com/productshow/AGN-PC-0O4E8I.html
AstaTech	41182	http://astatechinc.com/CPSResult.php?CRNO=41182
Capot Chemical	6032	https://www.capotchem.com/search.do?q=6032
Chem-Impex International	21916	http://www.chemimpex.com/category/search/21916/2?filter=&search=21916&type=q&keywordoption=ANY&cid=2&fltrdesc=
ChemDiv	BB57-4083	http://chemistryondemand.com:8080/eShop/search_results.jsp?idnumber=BB57-4083
Chemik	CHO0033	http://www.chemik.com/cgi/search-en.cgi?f=product_en+product_en1+company_en_1_&t=product_en7&w=product_en&terms=CHO0033
Chemspace	CSC000004159	https://chem-space.com/CSC000004159
Combi-Blocks	OR-3879	http://www.combi-blocks.com/cgi-bin/find.cgi?OR-3879
Debye Scientific	DB-024740	https://www.debyesci.com/index.php?id=product&ext[cno]=DB-024740
Enamine	BBV-39692573	http://www.enaminestore.com/catalog/BBV-39692573
Indofine	24080	https://indofinechemical.com/details.aspx?Sku=024080
KeyOrganics	AS-12502	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-12502
Lab Network	LN00189445	http://www.abovchem.com/pc/en/product_list.aspx?wd=LN00189445
Lab Seeker	SC-01330	http://www.labseeker.com/search.php?keywords=SC-01330&category=0
LabSeeker	SC-01330	http://www.labseeker.com/search.php?keywords=SC-01330&category=0
Matrix Scientific	90314	http://www.matrixscientific.com/090314.html
MolPort	MolPort-002-317-302	https://www.molport.com/shop/molecule-link/MolPort-002-317-302
Molnova	M12181	https://www.molnova.com/en/serch-list.html?keywords=M12181
Oakwood	24330	http://www.oakwoodchemical.com/ProductsList.aspx?txtSearch=024330
PI Chemicals	PI-15720	http://www.pipharm.com/catalog_products/PI-15720.html
Tetrahedron	TS02155	http://www.thsci.com/search.do?q=TS02155
TimTec	ST51037227	http://www.echemstore.com/catalogsearch/result/?q=ST51037227
Toronto Research Chemicals	D239000	https://www.trc-canada.com/product-detail/?CatNum=D239000
Wonderchem	WD02RMF	http://www.wonder-chem.com/search.html?text=WD02RMF
eMolecules	8294355	https://orderbb.emolecules.com/search/#?query=8294355
mcule	MCULE-2427523663	https://mcule.com/MCULE-2427523663/
mcule	MCULE-4718457404	https://mcule.com/MCULE-4718457404/

PubMed

Title	Date	PubMed
Evidence for the involvement of vicinal sulfhydryl groups in insulin-activated hexose transport by 3T3-L1 adipocytes.	1985 Mar 10	3882699
Inhibition of cyclic AMP-dependent induction of ornithine aminotransferase by simple carbohydrates in cultured hepatocytes.	1987 Dec	2827574
A preadipocyte clonal line from mouse brown adipose tissue. Short- and long-term responses to insulin and beta-adrenergics.	1987 Jan	2877896
A further comparison of insulin- and phorbol ester-stimulated glucose transport in adipocytes.	1989 Aug	2673889
Neural mechanisms of dystonia: evidence from a 2-deoxyglucose uptake study in a primate model of dopamine agonist-induced dystonia.	1990	2296259
Uptake and binding of radiolabelled phenylarsine oxide in 3T3-L1 adipocytes.	1990 Aug 1	2202293
Insulin regulation of hexose transport in mouse 3T3-L1 cells expressing the human HepG2 glucose transporter.	1990 Nov 25	2173694
Parallel increases in noradrenaline reuptake and release into plasma during activation of the sympathetic nervous system in rabbits.	1990 Sep	2280799
Effects of insulin and phospholipase C in control and denervated rat skeletal muscle.	1991 Feb	1847587
Evidence that erythroid-type glucose transporter intrinsic activity is modulated by cadmium treatment of mouse 3T3-L1 cells.	1991 Oct 15	1918056
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	1536656
Neonatal capsaicin-treatment in mice: effects on pancreatic peptidergic nerves and 2-deoxy-D-glucose-induced insulin and glucagon secretion.	1992 Jun 1	1378463
Kinetic analysis of the liver-type (GLUT2) and brain-type (GLUT3) glucose transporters in Xenopus oocytes: substrate specificities and effects of transport inhibitors.	1993 Mar 15	8457197
Nitrogen dioxide-induced expression of a 78 kDa protein in pulmonary artery endothelial cells.	1996	8818631
Effects of overexpression of glutamine:fructose-6-phosphate amidotransferase (GFAT) and glucosamine treatment on translocation of GLUT4 in rat adipose cells.	1997 Nov 30	9453242
Effects of antimetabolites to glucose and fatty acids on galanin-1 receptor mRNA levels in the hypothalamic paraventricular and supraoptic nuclei.	1998 Dec 21	9928191
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	9858361
Dual regulation of leptin secretion: intracellular energy and calcium dependence of regulated pathway.	2000 May	10780946
Sterol regulatory element-binding protein-1 is regulated by glucose at the transcriptional level.	2000 Oct 6	10913129
Hypoxia-induced upregulation of eNOS gene expression is redox-sensitive: a comparison between hypoxia and inhibitors of cell metabolism.	2001 Jul	11382920
Troglitazone induces GLUT4 translocation in L6 myotubes.	2001 May	11334413
Heterologous expression of the Na(+),K(+)-ATPase gamma subunit in Xenopus oocytes induces an endogenous, voltage-gated large diameter pore.	2001 Sep 1	11533133
Effect of glucoprivation on serotonin neurotoxicity induced by substituted amphetamines.	2002 Nov	12388670
Impaired gastric secretion and lack of trophic responses to hypergastrinemia in M3 muscarinic receptor knockout mice.	2003 Dec	14724830
Arsenite stimulated glucose transport in 3T3-L1 adipocytes involves both Glut4 translocation and p38 MAPK activity.	2003 Oct	14511371
Contribution of the PI 3-kinase/Akt survival pathway toward osmotic preconditioning.	2005 Jan	15786717
Corticosteroids inhibit cell death induced by doxorubicin in cardiomyocytes: induction of antiapoptosis, antioxidant, and detoxification genes.	2005 Jun	15755911
Redox regulation of the nutrient-sensitive raptor-mTOR pathway and complex.	2005 Nov 25	16183647
Contrasting actions of prolonged mitogen-activated protein kinase activation on cell survival.	2006 Jun 30	16701555
Effect of troglitazone on tumor necrosis factor alpha and transforming growth factor beta expression and action in human adipocyte precursor cells in primary culture.	2006 Mar	16483873
Effect of organophosphate pesticide diazinon on expression and activity of intestinal P-glycoprotein.	2006 Mar 1	16221533
NR4A orphan nuclear receptors modulate insulin action and the glucose transport system: potential role in insulin resistance.	2007 Oct 26	17785466
Fructose-1,6-bisphosphate has anticonvulsant activity in models of acute seizures in adult rats.	2007 Oct 31	17978042
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	18985042
The AMPK agonist AICAR inhibits the growth of EGFRvIII-expressing glioblastomas by inhibiting lipogenesis.	2009 Aug 4	19625624
Salacia oblonga extract increases glucose transporter 4-mediated glucose uptake in L6 rat myotubes: role of mangiferin.	2009 Oct	19477051
Inhibition of glycolysis enhances cisplatin-induced apoptosis in ovarian cancer cells.	2010 Apr	20138251
p53 Protects lung cancer cells against metabolic stress.	2010 Dec	21042727
Chronic ingestion of 2-deoxy-D-glucose induces cardiac vacuolization and increases mortality in rats.	2010 Mar 15	20026095
Glucosamine-induced endoplasmic reticulum stress affects GLUT4 expression via activating transcription factor 6 in rat and human skeletal muscle cells.	2010 May	20165829
2-Deoxy-D-glucose activates autophagy via endoplasmic reticulum stress rather than ATP depletion.	2011 Apr	20593179
eNOS activation mediated by AMPK after stimulation of endothelial cells with histamine or thrombin is dependent on LKB1.	2011 Feb	21145922
Involvement of H-Ras and reactive oxygen species in proinflammatory cytokine-induced matrix metalloproteinase-13 expression in human articular chondrocytes.	2011 Mar 15	21211511
Activation of peroxisome proliferator-activated receptor-alpha stimulates both differentiation and fatty acid oxidation in adipocytes.	2011 May	21324916
Enhancement of carboplatin-mediated lung cancer cell killing by simultaneous disruption of glutathione and thioredoxin metabolism.	2011 Oct 1	21844013
Deletion of the Mint3/Apba3 gene in mice abrogates macrophage functions and increases resistance to lipopolysaccharide-induced septic shock.	2011 Sep 16	21778228
Potential anti-aging agents suppress the level of constitutive mTOR- and DNA damage- signaling.	2012 Dec	23363784
2-Deoxy-D-glucose cooperates with arsenic trioxide to induce apoptosis in leukemia cells: involvement of IGF-1R-regulated Akt/mTOR, MEK/ERK and LKB-1/AMPK signaling pathways.	2012 Dec 15	23041229
Cytotoxic effects of mithramycin DIG-MSK can depend on the rise of autophagy.	2015 Oct	26079942
Lasting glycolytic stress governs susceptibility to urethane-induced lung carcinogenesis in vivo and in vitro.	2016 Jan 5	26524634

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.

Name

Type

Language

2-DEOXYGLUCOSE

Systematic Name

English

2-DEOXY-D-GLUCOSE [MI]

Common Name

English

2-DEOXY-D-MANNOSE

Common Name

English

2-DEOXY-D-GLUCOSE

Systematic Name

English

BA-2758

Code

English

2-DG

Common Name

English

D-ARABINO-2-DESOXYHEXOSE

Common Name

English

NSC-15193

Code

English

D-ARABINO-HEXOSE, 2-DEOXY-

Systematic Name

English

2-Deoxy-d-glucose [WHO-DD]

Common Name

English

BA 2758

Code

English

(3R,4S,5R)-3,4,5,6-TETRAHYDROXYHEXANAL

Systematic Name

English

(4R,5S,6R)-6-(HYDROXYMETHYL)TETRAHYDRO-2H-PYRAN-2,4,5-TRIOL

Systematic Name

English

2-DEOXY-D-ARABINO-HEXOSE

Systematic Name

English

2-DEOXY-D-GLUCOSE [MART.]

Common Name

English

2-DEOXY-D-GLUCOSE [HSDB]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C344