Tìm theo
Tirapazamine
Các tên gọi khác (3) :
  • 1,4-Dioxido-1,2,4-benzotriazin-3-ylamine
  • 3-Amino-1,2,4-benzotriazine 1,4-dioxide
  • SR-4233
Thuốc điều trị ung thư
Thuốc Gốc
Small Molecule
CAS: 27314-97-2
CTHH: C7H6N4O2
PTK: 178.1481
Tirapazamine (SR-4233) is an experimental anticancer drug that is activated to a toxic radical only at very low levels of oxygen (hypoxia). Such levels are common in human solid tumors, a phenomenon known as tumor hypoxia. Thus, tirapazamine is activated to its toxic form preferentially in the hypoxic areas of solid tumors. Cells in these regions are resistant to killing by radiotherapy and most anticancer drugs. Thus the combination of tirapazamine with conventional anticancer treatments is particularly effective. As of 2006, tirapazamine is undergoing phase III testing in patients with head and neck cancer and gynecological cancer, and similar trials are being undertaken for other solid tumor types. [Wikipedia]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C7H6N4O2
Phân tử khối
178.1481
Monoisotopic mass
178.049075456
InChI
InChI=1S/C7H6N4O2/c8-7-9-11(13)6-4-2-1-3-5(6)10(7)12/h1-4,8,12H
InChI Key
InChIKey=QVMPZNRFXAKISM-UHFFFAOYSA-N
IUPAC Name
4-hydroxy-3-imino-3,4-dihydro-1,2,4-benzotriazin-1-ium-1-olate
Traditional IUPAC Name
tirapazamine
SMILES
ON1C(=N)N=[N+]([O-])C2=CC=CC=C12
Độ hòa tan
2.95e-01 g/l
logP
-0.061
logS
-2.8
pKa (strongest acidic)
13.22
pKa (Strongest Basic)
-0.39
PSA
88.43 Å2
Refractivity
66.15 m3·mol-1
Polarizability
15.82 Å3
Rotatable Bond Count
0
H Bond Acceptor Count
5
H Bond Donor Count
2
Physiological Charge
0
Number of Rings
2
Bioavailability
1
Rule of Five
true
Dược Lực Học : Tirapazamine is a anticancer drug that is inactive in normal tissues that are well oxygenated, but becomes active at the low oxygen levels found in solid tumors. As a result, the drug kills these poorly oxygenated or hypoxic cells while limiting toxicity in normal tissue. Tirapazamine may prove highly effective when used in combination with standard anticancer therapy, as these hypoxic cells are characteristically resistant to radiation and common anticancer agents.
Cơ Chế Tác Dụng : Tirapazamine (SR-4233) is an experimental anticancer drug that is activated to a toxic radical only at very low levels of oxygen (hypoxia). Such levels are common in human solid tumors, a phenomenon known as tumor hypoxia. Thus, tirapazamine is activated to its toxic form preferentially in the hypoxic areas of solid tumors. Cells in these regions are resistant to killing by radiotherapy and most anticancer drugs. Thus the combination of tirapazamine with conventional anticancer treatments is particularly effective. As of 2006, tirapazamine is undergoing phase III testing in patients with head and neck cancer and gynecological cancer, and similar trials are being undertaken for other solid tumor types. [Wikipedia] Extensive preclinical testing has established that the mechanism for the selective toxicity towards hypoxic cells is the result of a one-electron reduction of the parent molecule to a free radical species that interacts with DNA to produce single- and double-strand breaks and lethal chromosome aberrations. It has also shown activity when combined with fractionated irradiation and when combined with some chemotherapy agents, particularly cisplatin and carboplatin.
Chỉ Định : For the treatment of head and neck cancer.
Dữ Kiện Thương Mại
Nhà Sản Xuất
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB04858
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=33776
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=10426937
ChemSpider
http://www.chemspider.com/Chemical-Structure.31132.html
Wikipedia
http://en.wikipedia.org/wiki/Tirapazamine
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