2-DEOXYGLUCOSE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C6H12O5
Molecular Weight	164.1567
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 1447
neurotrophic tyrosine kinase receptor type 2 1 Target ID: 4915.0 Gene Symbol: NTRK2 Sources: http://www.ncbi.nlm.nih.gov/pubmed/17041593	Inhibitor 8504
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 8504

Conditions

Condition	Modality	Highest Phase	Product
Non-small cell lung cancer 211 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 438	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

C_max

Value	Dose	Co-administered	Analyte	Population
449.2 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20687211	45 mg/kg single, oral dose: 45 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		2-DEOXYGLUCOSE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
1107.7 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20687211	45 mg/kg single, oral dose: 45 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		2-DEOXYGLUCOSE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
7.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20687211	45 mg/kg single, oral dose: 45 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		2-DEOXYGLUCOSE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P0039E0	https://www.1pchem.com/search?query=1P0039E0
A2B Chem	AB51336	http://a2bchem.com/prod/AB51336
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
AK Scientific	F387	https://aksci.com/item_detail.php?cat=F387
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
eMolecules	8294355	https://orderbb.emolecules.com/search/#?query=8294355
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
mcule	MCULE-2427523663	https://mcule.com/MCULE-2427523663/
mcule	MCULE-4718457404	https://mcule.com/MCULE-4718457404/
Molnova	M12181	https://www.molnova.com/en/serch-list.html?keywords=M12181
MolPort	MolPort-002-317-302	https://www.molport.com/shop/molecule-link/MolPort-002-317-302
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

PubMed

Title	Date	PubMed
Lasting glycolytic stress governs susceptibility to urethane-induced lung carcinogenesis in vivo and in vitro.	2016-01-05	26524634
Cytotoxic effects of mithramycin DIG-MSK can depend on the rise of autophagy.	2015-10	26079942
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.	2012-12-15	23041229
Potential anti-aging agents suppress the level of constitutive mTOR- and DNA damage- signaling.	2012-12	23363784
Enhancement of carboplatin-mediated lung cancer cell killing by simultaneous disruption of glutathione and thioredoxin metabolism.	2011-10-01	21844013
Deletion of the Mint3/Apba3 gene in mice abrogates macrophage functions and increases resistance to lipopolysaccharide-induced septic shock.	2011-09-16	21778228
Activation of peroxisome proliferator-activated receptor-alpha stimulates both differentiation and fatty acid oxidation in adipocytes.	2011-05	21324916
2-Deoxy-D-glucose activates autophagy via endoplasmic reticulum stress rather than ATP depletion.	2011-04	20593179
Involvement of H-Ras and reactive oxygen species in proinflammatory cytokine-induced matrix metalloproteinase-13 expression in human articular chondrocytes.	2011-03-15	21211511
eNOS activation mediated by AMPK after stimulation of endothelial cells with histamine or thrombin is dependent on LKB1.	2011-02	21145922
p53 Protects lung cancer cells against metabolic stress.	2010-12	21042727
The M3-muscarinic acetylcholine receptor stimulates glucose uptake in L6 skeletal muscle cells by a CaMKK-AMPK-dependent mechanism.	2010-07	20206685
Glucosamine-induced endoplasmic reticulum stress affects GLUT4 expression via activating transcription factor 6 in rat and human skeletal muscle cells.	2010-05	20165829
Inhibition of glycolysis enhances cisplatin-induced apoptosis in ovarian cancer cells.	2010-04	20138251
Chronic ingestion of 2-deoxy-D-glucose induces cardiac vacuolization and increases mortality in rats.	2010-03-15	20026095
Salacia oblonga extract increases glucose transporter 4-mediated glucose uptake in L6 rat myotubes: role of mangiferin.	2009-10	19477051
The AMPK agonist AICAR inhibits the growth of EGFRvIII-expressing glioblastomas by inhibiting lipogenesis.	2009-08-04	19625624
2-Methoxyoestradiol-3,17-O,O-bis-sulphamate and 2-deoxy-D-glucose in combination: a potential treatment for breast and prostate cancer.	2008-12-02	18985042
Stimulation of muscle cell glucose uptake by resveratrol through sirtuins and AMPK.	2008-09-12	18601907
Adipose tissue-specific PPARgamma deficiency increases resistance to oxidative stress.	2008-03	18083318
Fructose-1,6-bisphosphate has anticonvulsant activity in models of acute seizures in adult rats.	2007-10-31	17978042
NR4A orphan nuclear receptors modulate insulin action and the glucose transport system: potential role in insulin resistance.	2007-10-26	17785466
Altered subcellular distribution of the Alzheimer's amyloid precursor protein under stress conditions.	2007-01	17405930
Contrasting actions of prolonged mitogen-activated protein kinase activation on cell survival.	2006-06-30	16701555
Effect of organophosphate pesticide diazinon on expression and activity of intestinal P-glycoprotein.	2006-03-01	16221533
Effect of troglitazone on tumor necrosis factor alpha and transforming growth factor beta expression and action in human adipocyte precursor cells in primary culture.	2006-03	16483873
Redox regulation of the nutrient-sensitive raptor-mTOR pathway and complex.	2005-11-25	16183647
Corticosteroids inhibit cell death induced by doxorubicin in cardiomyocytes: induction of antiapoptosis, antioxidant, and detoxification genes.	2005-06	15755911
Contribution of the PI 3-kinase/Akt survival pathway toward osmotic preconditioning.	2005-01	15786717
Impaired gastric secretion and lack of trophic responses to hypergastrinemia in M3 muscarinic receptor knockout mice.	2003-12	14724830
Arsenite stimulated glucose transport in 3T3-L1 adipocytes involves both Glut4 translocation and p38 MAPK activity.	2003-10	14511371
Effect of glucoprivation on serotonin neurotoxicity induced by substituted amphetamines.	2002-11	12388670
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.	2002-06-28	11978788
Effects of antimetabolites to glucose and fatty acids on galanin-1 receptor mRNA levels in the hypothalamic paraventricular and supraoptic nuclei.	1998-12-21	9928191
Effect of inhibition of glucose and fat metabolism on galanin-R1 receptor mRNA levels in the rat hypothalamic paraventricular and supraoptic nuclei.	1998-11-16	9858361
Effects of overexpression of glutamine:fructose-6-phosphate amidotransferase (GFAT) and glucosamine treatment on translocation of GLUT4 in rat adipose cells.	1997-11-30	9453242
Nitrogen dioxide-induced expression of a 78 kDa protein in pulmonary artery endothelial cells.	1996	8818631
Kinetic analysis of the liver-type (GLUT2) and brain-type (GLUT3) glucose transporters in Xenopus oocytes: substrate specificities and effects of transport inhibitors.	1993-03-15	8457197
Neonatal capsaicin-treatment in mice: effects on pancreatic peptidergic nerves and 2-deoxy-D-glucose-induced insulin and glucagon secretion.	1992-06-01	1378463
Trafficking of glucose transporters in 3T3-L1 cells. Inhibition of trafficking by phenylarsine oxide implicates a slow dissociation of transporters from trafficking proteins.	1992-02-01	1536656
Evidence that erythroid-type glucose transporter intrinsic activity is modulated by cadmium treatment of mouse 3T3-L1 cells.	1991-10-15	1918056
Effects of insulin and phospholipase C in control and denervated rat skeletal muscle.	1991-02	1847587
Insulin regulation of hexose transport in mouse 3T3-L1 cells expressing the human HepG2 glucose transporter.	1990-11-25	2173694
Parallel increases in noradrenaline reuptake and release into plasma during activation of the sympathetic nervous system in rabbits.	1990-09	2280799
Uptake and binding of radiolabelled phenylarsine oxide in 3T3-L1 adipocytes.	1990-08-01	2202293
Neural mechanisms of dystonia: evidence from a 2-deoxyglucose uptake study in a primate model of dopamine agonist-induced dystonia.	1990	2296259
A further comparison of insulin- and phorbol ester-stimulated glucose transport in adipocytes.	1989-08	2673889
Inhibition of cyclic AMP-dependent induction of ornithine aminotransferase by simple carbohydrates in cultured hepatocytes.	1987-12	2827574
A preadipocyte clonal line from mouse brown adipose tissue. Short- and long-term responses to insulin and beta-adrenergics.	1987-01	2877896
Evidence for the involvement of vicinal sulfhydryl groups in insulin-activated hexose transport by 3T3-L1 adipocytes.	1985-03-10	3882699

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-DEOXY-D-GLUCOSE

Preferred Name

English

2-DEOXYGLUCOSE

Systematic Name

English

2-DEOXY-D-GLUCOSE [MI]

Common Name

English

2-DEOXY-D-MANNOSE

Common 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