Grundinformationen
- 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
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
Weitere Namen anzeigen
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
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
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports.
Not Classified;Reported as not meeting GHS hazard criteria by 2 of 2 companies. For more detailed information, please visit ECHA C&L website.
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.;Reported as not meeting GHS hazard criteria per 2 of 2 reports by companies.;There are 0 notifications provided by 0 of 2 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Gefahrenhinweise
Regulatory Information
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
Toxikologische Informationen
Interactions
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
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.
Regulatorische Informationen
Regulatory Information
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
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
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.
MeSH Pharmacological Classification
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
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
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
(1979) No Data
(1981) No Data
U.S. Imports
(1979) No Data
(1981) No Data
U.S. Production
(1979) No Data
(1981) No Data
General Manufacturing Information
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
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]
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