SML0552
Tirapazamine
≥98% (HPLC)
Synonym(s):
4-Hydroxy-1-oxido-1,2,4-benzotriazin-1-ium-3-imine, SR 259075, SR 4233, Tirazone, Win 59075
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About This Item
Empirical Formula (Hill Notation):
C7H6N4O2
CAS Number:
Molecular Weight:
178.15
MDL number:
UNSPSC Code:
12352116
PubChem Substance ID:
NACRES:
NA.77
Recommended Products
Quality Level
Assay
≥98% (HPLC)
form
powder
color
, orange to dark orange-red
solubility
DMSO: 10 mg/mL, clear
shipped in
wet ice
storage temp.
−20°C
SMILES string
Nc1n[n+]([O-])c2ccccc2[n+]1[O-]
InChI
1S/C7H6N4O2/c8-7-9-11(13)6-4-2-1-3-5(6)10(7)12/h1-4H,(H2,8,9)
InChI key
ORYDPOVDJJZGHQ-UHFFFAOYSA-N
Application
Tirapazamine has been used to evaluate its cytotoxic effect on U-251 MG (glioblastoma cell line) cell viability.
Biochem/physiol Actions
Under hypoxic conditions, tirapazamine is a potent cytotoxic agent that induces apoptosis by inducing breaks in single and double stranded DNA, as well as chromosomal breaks. The compound sensitizes cells to other ionizing radiation and other cytotoxic agents like cisplatin.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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S Chatterjee et al.
Clinical oncology (Royal College of Radiologists (Great Britain)), 31(8), 510-519 (2019-06-15)
There has been a surge in human papillomavirus (HPV)-positive oropharyngeal cancers (OPCs) in the West. Although the prognosis of HPV-positive OPC is good, de-escalation strategies have so far not been able to confirm comparable cancer control. We examine the strategies
Srini B Reddy et al.
Expert opinion on investigational drugs, 18(1), 77-87 (2008-12-05)
Tumor hypoxia remains one of the greatest challenges in the treatment of solid tumors, as cancer cells in these regions are resistant to killing by radiation therapy and most anticancer drugs. Tirapazamine (TPZ) is a newer class of cytotoxic drugs
K M Govaert et al.
The British journal of surgery, 99(4), 567-575 (2012-02-15)
Radiofrequency ablation (RFA) is a common procedure for the management of colorectal liver metastases. RFA-generated lesions are surrounded by a rim of hypoxia that is associated with aggressive outgrowth of intrahepatic micrometastases. Hypoxia-activated prodrugs such as tirapazamine are designed selectively
Yung-Ann Chen et al.
Lab on a chip, 11(21), 3626-3633 (2011-09-15)
This paper reports a microfluidic device capable of generating oxygen gradients for cell culture using spatially confined chemical reactions with minimal chemical consumption. The microfluidic cell culture device is constructed by single-layer polydimethylsiloxane (PDMS) microfluidic channels, in which the cells
Yunzhou Shi et al.
Neoplasia (New York, N.Y.), 19(11), 950-959 (2017-10-11)
The effect of anti-angiogenic agents on tumor oxygenation has been in question for a number of years, where both increases and decreases in tumor pO
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