2-deoxyglucose

Các tên gọi khác (3) :

2-Deoxy-D-arabino-hexose
2-Deoxy-D-glucose
D-arabino-2-Deoxyhexose

Thuốc điều trị ung thư

Thuốc Gốc

Small Molecule

CAS: 154-17-6

CTHH: C₆H₁₂O₅

PTK: 164.1565

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.

Nhận Dạng Quốc Tế & Đặc Tính Hóa Học

Công thức hóa học

C₆H₁₂O₅

Phân tử khối

164.1565

Monoisotopic mass

164.068473494

InChI

InChI=1/C6H12O5/c7-2-4-6(10)3(8)1-5(9)11-4/h3-10H,1-2H2/t3-,4-,5?,6+/s2

InChI Key

InChIKey=PMMURAAUARKVCB-PHUJZJCSNA-N

IUPAC Name

(4R,5S,6R)-6-(hydroxymethyl)oxane-2,4,5-triol

Traditional IUPAC Name

2-deoxy-D-glucose

SMILES

OC[C@H]1OC(O)C[C@@H](O)[C@@H]1O

Độ tan chảy

147°C (296.6°F)

Độ sôi

Decomposes

Độ hòa tan

9.84e+02 g/l

logP

-2

logS

0.78

pKa (strongest acidic)

12.29

pKa (Strongest Basic)

-3

PSA

90.15 Å²

Refractivity

34.41 m³·mol^-1

Polarizability

15.29 Å³

Rotatable Bond Count

H Bond Acceptor Count

H Bond Donor Count

Physiological Charge

Number of Rings

Bioavailability

Rule of Five

true

Dược Lực Học : Physiologically 2-deoxyglucose is an inhibitor of glycolysis, certain viruses, and seizures.

Cơ Chế Tác Dụng : 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. 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.

Chỉ Định : 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.

Tài Liệu Tham Khảo Thêm

drugbank

http://www.drugbank.ca/drugs/DB08831

KEGG Compound

http://www.genome.jp/dbget-bin/www_bget?cpd:C00586

Wikipedia

http://en.wikipedia.org/wiki/2-Deoxy-D-glucose

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