Name | 2-Deoxy-D-glucose |
CAS number | 154-17-6 |
EINECS number | 205-823-0 |
Synonym | 2-deoxy-d-arabino-hexos; 2-deoxy-d-glucos; 2-deoxy-d-mannose; 2-deoxy-glucos; 2-desoxy-d-glucose; 2-Deoxy-D-arabinohexose; 2-DG |
Description | 2-Deoxy-D-glucose (2-DG) is a glucose analog where the hydroxyl group at the second carbon atom is replaced by a hydrogen atom. This structural modification renders it a non-metabolizable form of glucose, preventing it from undergoing further glycolysis. Consequently, 2-DG acts as a competitive inhibitor of glucose-6-phosphate production at the phosphoglucoisomerase level, which is critical in the glycolytic pathway. It's primarily recognized for its role in inhibiting glycolysis and its potential applications in cancer therapy and viral infections, including COVID-19. |
Structure |  |
Molecular Formula | C6H12O5 |
Molecular Weight | 164.16 g/mol |
Appearance | Solid powder |
Quality Standard | Enterprise Standard |
Assay | ≥98% |
Shipping Condition | Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs. |
Storage Condition | Store in cool place. Keep container tightly closed in a dry and well ventilated place. |
Shelf Life | >2 years if stored properly |
Sample package | Aluminium foil bag |
Commercial package | Aluminium Tin, Fiber drum |
Origin | China |
HS Code | 2932999099 |
2-Deoxy-D-glucose More Info
2-Deoxy-D-glucose (2-DG) is a non-metabolizable glucose analog that has been extensively studied for its potential therapeutic applications, particularly in cancer treatment.
Mechanism of Action
2-DG mimics D-glucose but lacks the hydroxyl group at the second carbon. This structural alteration prevents it from undergoing glycolysis, leading to the formation of 2-deoxy-D-glucose-6-phosphate (2-DG6P) inside cells. The accumulation of 2-DG6P inhibits key enzymes such as hexokinase and phosphoglucose isomerase, disrupting glucose metabolism and energy production within cells. This mechanism is particularly effective against rapidly proliferating cancer cells, as they rely heavily on glycolysis for energy.
In addition to inhibiting glycolysis, 2-DG interferes with N-linked glycosylation processes due to its structural similarity to mannose. This interference can induce endoplasmic reticulum (ER) stress and activate the unfolded protein response (UPR), further contributing to its anti-cancer effects.
Applications
1. Cancer Treatment: 2-DG has been explored as a therapeutic agent in various cancers, often in combination with other treatments like chemotherapy and radiotherapy. Its ability to inhibit glycolysis makes it a candidate for enhancing the efficacy of existing cancer therapies.
2. COVID-19 Treatment: In May 2021, 2-DG was approved in India for emergency use as an adjunct therapy for moderate to severe COVID-19 patients. It is believed to help reduce the need for supplemental oxygen by inhibiting viral replication through similar mechanisms as those used against cancer cells.
Routes of Administration
2-DG is typically administered orally. In clinical settings, it has been given in divided doses based on body weight, often starting at a dose of 63 mg/kg/day for COVID-19 treatment . For cancer therapy, dosages may vary but are generally kept below 30 mg/kg/day for long-term use to minimize side effects
Safety and Side Effects
2-DG is generally well-tolerated, with mild side effects reported in some patients. Common side effects include:
Fatigue
Nausea
Light-headedness
Mildly elevated blood sugar levels (hyperglycemia)
Severe side effects are rare but may include reversible QTc prolongation at very high doses (over 200 mg/kg) and gastrointestinal issues in patients with pre-existing conditions. Long-term use should be monitored, especially in patients with chronic kidney disease or cardiovascular issues.
Pharmacokinetics
The pharmacokinetics of 2-DG involve absorption via glucose transporters in cells, which means that tissues with higher glucose uptake (such as tumors) will also absorb more 2-DG. It undergoes phosphorylation by hexokinase, trapping it within the cell as 2-DG6P. The drug's elimination primarily occurs through renal excretion, necessitating caution in patients with impaired kidney function.
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