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2-Desoxy-D-glucose

2-Deoxyglucose

HCID 108223
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Grundinformationen

CAS
154-17-6
Standard-SMILES
O=CC[C@@H](O)[C@H](O)[C@H](O)CO
InChIKey
VRYALKFFQXWPIH-PBXRRBTRSA-N
Summenformel
C6H12O5
Durchschnittliche Molmasse
164,16 g/mol
Monoisotopische Masse
164,06847348

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
2-Deoxyglucose
IUPAC
(3R,4S,5R)-3,4,5,6-tetrahydroxyhexanal
Lokaler Name
2-Desoxy-D-glucose
Englischer Name
2-Deoxy-D-glucose
Summenformel
C6H12O5
Molmasse
164.16

Namen und Synonyme

2-deoxy-D-glucose154-17-6Deoxyglucose(3R,4S,5R)-3,4,5,6-tetrahydroxyhexanal2-Desoxy-D-glucose2-Deoxy-D-mannoseD-2-DeoxyglucoseD-arabino-2-desoxyhexose2 Deoxyglucose2 Deoxy D glucose2 Desoxy D glucoseD-Arabino-hexose, 2-deoxy-
Weitere Namen anzeigen
2-dg2-DEOXYGLUCOSE2-Dexoy-D-GlucoseD-Arabino-2-deoxyhexose2-deoxy-d-[UL-13C6]glucose(4R,5S,6R)-6-(Hydroxymethyl)tetrahydro-2H-pyran-2,4,5-triolba2758
9G2MP84A8WDTXSID1037648GlyTouCan:G23624QENSC 15193BA-2758NSC-15193RefChem:471277CHEBI:15866

Datenbank-Bezeichner

CAS
154-17-6、61-58-5
PubChem CID
108223
DTXSID
DTXSID1037648
ChEMBL
CHEMBL1880349、CHEMBL2074932
UNII
9G2MP84A8W
EC Number
205-823-0
Nikkaji
J59.831C

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-2,9
Polarare Oberfläche (TPSA)
98 Ų
H-Brücken-Donoren
4
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
5
Schwere Atome
11
Formalladung
0
Komplexität
116

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
Boiling PointDecomposes
Melting Point147°C (296.6°F)
Collision Cross Section136.7 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

Physikochemische Eigenschaften

Schmelzpunkt
146 · 146-147 °C(lit.)
Siedepunkt
211.61 °C · 211.61°C (rough estimate)
Dichte
1.1738 · 1.1738 (rough estimate)
Brechungsindex
46.5 ° · 46.5 ° (C=1, H2O)
storage temp.
2 · 2-8°C
Löslichkeit
2 O: · H2O: 50 mg/mL, clear, colorless to faintly yellow
Aggregatzustand
crystalline
pka
1 · pK1:12.52 (25°C)
Farbe
white
Biologische Quelle
synthetic
Wasserlöslichkeit
Soluble in water.
Merck
14 · 14,2904
BRN
1723331 · 1723331
Stabilität
1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month. Solutions in water are not stable and must be used within 1 working day.
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
InChIKey
PMMURAAUARKVCB-CEZCPVKQSA-N
SMILES
OC[C@@H](O)[C@@H](O)[C@H](O)CC=O
LogP
-1.46 · -1.460 (est)
CAS Datenbank
154 · 154-17-6(CAS DataBase Reference)
EPA chemische Informationen
2 · D-arabino-Hexose, 2-deoxy- (154-17-6)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 3 Einträge

This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports.

Not Classified

Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Regulatory Information · 2 Einträge

Chemical: D-arabino-Hexose, 2-deoxy-

D-arabino-Hexose, 2-deoxy-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - D-arabino-Hexose, 2-deoxy-: Environment tier I assessment
Hazard Classes and CategoriesNot Classified

Toxikologische Informationen

Interactions · 5 Einträge

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.

Non-Human Toxicity Excerpts · 5 Einträge

2-DEOXYGLUCOSE INJECTED INTRAPERITONEALLY IN RATS IN LARGE DOSES CAUSED CHANGES IN THE ELECTRORETINOGRAM CONSISTING OF A DECR IN BOTH ALPHA- AND BETA-WAVES.

...120 MG/DAY /GIVEN TO RAT/ FROM THE 9TH THROUGH THE 20TH GESTATIONAL DAY... RESORPTIONS WERE 69% AND THE SURVIVING FETUSES WERE ALL MALFORMED. ANOPHTHALMIA, CLEFT LIP AND PALATE AND LESIONS OF THE EXTREMITIES WERE OBSERVED. ...GAVE 1 G/KG ON DAYS 8, 9, 10 OR 11 & FOUND NO MALFORMATIONS IN SURVIVING RAT FETUSES.

2-DEOXY-D-GLUCOSE (DGLC) SELECTIVELY INHIBITED VIRUS DNA SYNTHESIS IN HUMAN EMBRYONIC LUNG CELLS INFECTED WITH HUMAN CYTOMEGALOVIRUS (HCMV). THE EFFECTIVE CONCN OF DGLC WAS APPROX 10-FOLD HIGHER IN CULTURE MEDIUM CONTAINING GLUCOSE INSTEAD OF SODIUM PYRUVATE. VIRUS DNA SYNTHESIS COULD BE SELECTIVELY INHIBITED BY ADDN OF DGLC EVEN AFTER INITIATION OF HCMV DNA REPLICATION. APPARENTLY, DGLC INTERFERES WITH THE FUNCTION OF AN EARLY CHROMATIN-ASSOCIATED GLYCOPROTEIN ESSENTIAL FOR VIRUS DNA SYNTHESIS.

2-DEOXY-D-GLUCOSE (0.3-1.2 MOL) INJECTED INTO THE 3RD VENTRICLE OF RATS DEPRESSED APPETITE FOR 72 HR. THE BLOOD SUGAR WAS INCR FOR 48 HR, WHILE FREE FATTY ACID INITIALLY INCR BUT DECR BY 24 HR.

For more Non-Human Toxicity Excerpts (Complete) data for 2-DEOXY-D-GLUCOSE (7 total), please visit the HSDB record page.

Sicherheitsdaten

F
3-10
wgk
3
tsca
TSCA listed
hs_code
29400090
RTECS-Nr.
MQ3325000
risk_code
20/21/22-36/37/38
hazard_code
Xn,Xi
safety_code
24/25-37/39-36-26
Speicherklasse
11 - Combustible Solids
Giftige Stoffe Daten
154-17-6(Hazardous Substances Data)

Chemie und Industrie

Pharmakologische Informationen

PharmacodynamicsPhysiologically 2-deoxyglucose is an inhibitor of glycolysis, certain viruses, and seizures.
Mechanism of Action · 1 Eintrag

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.

Metabolism/Metabolites2-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.
MeSH Pharmacological Classification · 2 Einträge

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)

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.

Absorption, Distribution and Excretion · 1 Eintrag

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.

Verwendung und Herstellung

Uses · 3 Einträge

2-DEOXYGLUCOSE IS A GLUCOSE ANTIMETABOLITE, INHIBITING GLYCOLYSIS; IT IS A WIDELY USED RESEARCH TOOL TO STUDY GLUCOSE-DEPENDENT OR -MEDIATED REACTIONS

RESEARCH CHEMICAL

MEDICATION (VET)

U.S. Exports · 2 Einträge

(1979) No Data

(1981) No Data

U.S. Imports · 2 Einträge

(1979) No Data

(1981) No Data

U.S. Production · 2 Einträge

(1979) No Data

(1981) No Data

Consumption PatternsESSENTIALLY 100% AS A RESEARCH CHEMICAL
General Manufacturing Information · 2 Einträge

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.

Anwendungen · 1 Eintrag

Verwenden2-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]

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

D-threo-Hexos-5-ulose, cyclic 1-(1,3-propanediyl acetal) (9CI)D-arabino-Hexose, 2-deoxy-, cyclic 1,3-propanediyl acetal (9CI)D-arabino-Heptose, 2,3-dideoxy-4,5:6,7-bis-O-(1-methylethylidene)-

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