2-Deoxyglucose
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2-Deoxyglucose
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CAS No:
154-17-6
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Formula:
C6H12O5
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Chemical Name:
2-Deoxyglucose
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Synonyms:
D-arabino-Hexose,2-deoxy-;2-Deoxy-D-arabino-hexose;D-Glucose,2-deoxy-;2-Deoxyglucose;Ba 2758;2-Deoxy-D-glucose;2-Desoxy-D-glucose;2-Deoxy-D-mannose;NSC 15193;2 DG;2092-72-0;3724-71-8;4825-30-3;7640-18-8
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CAS No:
Description
white to light yellow crystal powde
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.|2-Deoxy-D-glucose is a non-metabolizable glucose analog in which the hydroxyl group at position 2 of glucose is replaced by hydrogen, with potential glycolysis inhibiting and antineoplastic activities. Although the exact mechanism of action has yet to be fully elucidated, upon administration of 2-deoxy-D-glucose (2-DG), this agent competes with glucose for uptake by proliferating cells, such as tumor cells. 2-DG inhibits the first step of glycolysis and therefore prevents cellular energy production, which may result in decreased tumor cell proliferation.|2-Deoxy-D-arabino-hexose. An antimetabolite of glucose with antiviral activity.
2-Deoxyglucose Basic Attributes
164.16
164.16
1723331
205-823-0
9G2MP84A8W
DTXSID1037648
C116618
29400090
Characteristics
98
white crystalline
1.1738 (rough estimate)
146.5 °C
211.61°C (rough estimate)
244.1±25.2 °C
46.5 ° (C=1, H2O)
soluble in water.H2O: 50 mg/mL, clear, colorless to faintly yellow
0-6°C
45.5 º (c=2, H2O)
Safety Information
NONH for all modes of transport
3
20/21/22-36/37/38
24/25-37/39-36-26
MQ3325000
Xn,Xi
Toxicity
2-DEOXYGLUCOSE INJECTED INTRAPERITONEALLY IN RATS IN LARGE DOSES CAUSED CHANGES IN THE ELECTRORETINOGRAM CONSISTING OF A DECR IN BOTH ALPHA- AND BETA-WAVES. THE EFFECT WAS ANTAGONIZED BY D-GLUCOSE.|SIMULTANEOUS ADMIN OF GLUCOSE @ DOSE EXCEEDING ITS MAX TUBULAR TRANSPORT CAPACITY INHIBITED TUBULAR REABSORPTION OF 2-DEOXYGLUCOSE. THUS, THE PROCESS OF TUBULAR REABSORPTION IS PROBABLY THE SAME AS THAT FOR GLUCOSE.|IN ANESTROUS SHEEP, 2-DEOXYGLUCOSE INFUSION INHIBITED LH RELEASE INDUCED BY ESTRADIOL BUT NOT BY LH-RH.|2-DEOXY-D-GLUCOSE INHIBITED REPAIR OF POTENTIALLY LETHAL DAMAGE INDUCED BY X-RAYS IN MOUSE EHRLICH ASCITES TUMOR CELLS.|For more Interactions (Complete) data for 2-DEOXY-D-GLUCOSE (6 total), please visit the HSDB record page.
Drug Information
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.
Antimetabolites; Antiviral Agents|MEDICATION (VET): TOPICAL TREATMENT OF HERPES GENITALIS IN FEMALE GUINEA PIGS WITH 2-DEOXY-D-GLUCOSE IN EITHER AGAROSE GELS OR MICONAZOLE NITRATE OINTMENT FAILED TO PREVENT DEVELOPMENT OF GENITAL LESIONS OR TO REDUCE THE MEAN TITERS OF RECOVERABLE VIRUS IN VAGINAL SWABS FROM INFECTED ANIMALS.
Physiologically 2-deoxyglucose is an inhibitor of glycolysis, certain viruses, and seizures.
Drugs that are chemically similar to naturally occurring metabolites, but differ enough to interfere with normal metabolic pathways. (From AMA Drug Evaluations Annual, 1994, p2033) (See all compounds classified as Antimetabolites.)|Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)
WHEN THE RENAL EXCRETION OF 2-DEOXYGLUCOSE WAS STUDIED IN DOGS AND RATS BY CONVENTIONAL CLEARANCE AND STOP-FLOW TECHNIQUES, IT WAS REABSORBED BY THE RENAL TUBULES AT AN AVG OF 68-89% OF THE FILTERED LOADS AND THE REABSORPTION SITE WAS IN THE PROXIMAL TUBULES.
2-DEOXY-D-GLUCOSE WAS CONVERTED TO THE 6-PHOSPHATE IN MOUSE TESTIS AND LIVER AFTER IP INJECTION OF 50 MG/KG BODY WT DAILY FOR 7 DAYS.
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.
2 Deoxy D glucose
2-Deoxyglucose Use and Manufacturing
2-deoxy-D-Glucose is a non-metabolizable glucose analog that inhibits phosphorylation of glucose by hexokinase, the first step of glycolysis. This results in the depletion in cellular ATP, the inhibition of protein glycosylation, and the disruption of ER quality control by inducing the unfolded protein response. 2-deoxy-D-Glucose has been shown to cause cell cycle inhibition and cell death in in vitro models of hypoxia, induce autophagy, increase reactive oxygen species production, activate AMPK, and block tumor cell growth in animal models.[Cayman Chemical]
(1979) No Data|(1981) No Data
ESSENTIALLY 100% AS A RESEARCH CHEMICAL
D-arabino-Hexose, 2-deoxy-: ACTIVE|THE DEOXYSUGARS SUCH AS 2-DEOXYGLUCOSE ARE POTENT HERBICIDES. 2-DEOXYGLUCOSE SPRAYED AT 100 G/ACRE COMPLETELY CONTROLLED PLANTAGO ASIATICA IN AGROPYRON KAMOCHI AND ELEUSINE INDICA.
Computed Properties
Molecular Weight:164.16
XLogP3:-2.9
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:5
Exact Mass:164.06847348
Monoisotopic Mass:164.06847348
Topological Polar Surface Area:98
Heavy Atom Count:11
Complexity:116
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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