Identification
- Generic Name
- 2-deoxyglucose
- DrugBank Accession Number
- DB08831
- Background
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.
- Type
- Small Molecule
- Groups
- Experimental, Investigational
- Structure
Structure for 2-deoxyglucose (DB08831)
- Weight
- Average: 164.1565
Monoisotopic: 164.068473494 - Chemical Formula
- C6H12O5
- Synonyms
- 2-Deoxy-D-arabino-hexose
- 2-deoxy-D-glucose
- 2-DG
- D-arabino-2-desoxyhexose
- External IDs
- BA 2758
- BA-2758
- NSC-15193
Pharmacology
- 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.
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Physiologically 2-deoxyglucose is an inhibitor of glycolysis, certain viruses, and seizures.
- Mechanism of action
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.
- Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Fatty Acyls
- Sub Class
- Fatty alcohols
- Direct Parent
- Fatty alcohols
- Alternative Parents
- Medium-chain aldehydes / Beta-hydroxy aldehydes / Alpha-hydrogen aldehydes / Secondary alcohols / Polyols / Primary alcohols / Organic oxides / Hydrocarbon derivatives
- Substituents
- Alcohol / Aldehyde / Aliphatic acyclic compound / Alpha-hydrogen aldehyde / Beta-hydroxy aldehyde / Carbonyl group / Fatty alcohol / Hydrocarbon derivative / Medium-chain aldehyde / Organic oxide
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 9G2MP84A8W
- CAS number
- 154-17-6
- InChI Key
- VRYALKFFQXWPIH-PBXRRBTRSA-N
- InChI
- 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
- IUPAC Name
- (3R,4S,5R)-3,4,5,6-tetrahydroxyhexanal
- SMILES
- [H]C([H])(C=O)[C@@]([H])(O)[C@]([H])(O)[C@]([H])(O)CO
References
- General References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- External Links
- Human Metabolome Database
- HMDB0062477
- KEGG Compound
- C00586
- PubChem Compound
- 108223
- PubChem Substance
- 175427111
- ChemSpider
- 97292
- 1733674
- ChEBI
- 15866
- ChEMBL
- CHEMBL2074932
- ZINC
- ZINC000002512351
- Wikipedia
- 2-Deoxy-D-glucose
- MSDS
- Download (46.6 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Recruiting Treatment Epilepsy; Seizure 1 1 Completed Treatment Breast Cancer / Gastric Cancer / Head And Neck Cancer / Lung Cancer / Pancreatic Cancer 1 1 Recruiting Prevention Acute nasopharyngitis 1 1 Withdrawn Treatment Brain Neoplasm / Metastatic Cancer 1 1, 2 Terminated Treatment Prostate Cancer 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 147°C (296.6°F) From MSDS. boiling point (°C) Decomposes From MSDS. - Predicted Properties
Property Value Source Water Solubility 379.0 mg/mL ALOGPS logP -2 ALOGPS logP -2.9 Chemaxon logS 0.36 ALOGPS pKa (Strongest Acidic) 12.84 Chemaxon pKa (Strongest Basic) -3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 97.99 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 36.01 m3·mol-1 Chemaxon Polarizability 15.47 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.6922 Blood Brain Barrier + 0.5304 Caco-2 permeable - 0.8684 P-glycoprotein substrate Non-substrate 0.6448 P-glycoprotein inhibitor I Non-inhibitor 0.9436 P-glycoprotein inhibitor II Non-inhibitor 0.9738 Renal organic cation transporter Non-inhibitor 0.8973 CYP450 2C9 substrate Non-substrate 0.8591 CYP450 2D6 substrate Non-substrate 0.8744 CYP450 3A4 substrate Non-substrate 0.6865 CYP450 1A2 substrate Non-inhibitor 0.9823 CYP450 2C9 inhibitor Non-inhibitor 0.976 CYP450 2D6 inhibitor Non-inhibitor 0.9613 CYP450 2C19 inhibitor Non-inhibitor 0.9644 CYP450 3A4 inhibitor Non-inhibitor 0.9776 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9888 Ames test Non AMES toxic 0.8531 Carcinogenicity Non-carcinogens 0.9609 Biodegradation Ready biodegradable 0.9092 Rat acute toxicity 1.0409 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9482 hERG inhibition (predictor II) Non-inhibitor 0.9383
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Transporters
- Kind
- Protein
- Organism
- Humans
- 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 b...
- Gene Name
- SLC2A1
- Uniprot ID
- P11166
- Uniprot Name
- Solute carrier family 2, facilitated glucose transporter member 1
- Molecular Weight
- 54083.325 Da
References
- 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. [Article]
Drug created at February 16, 2013 22:58 / Updated at June 12, 2020 16:52