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SML0552

Sigma-Aldrich

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:
27314-97-2
Molecular Weight:
178.15
MDL number:
MFCD00132954
UNSPSC Code:
12352116
PubChem Substance ID:
329825548
NACRES:
NA.77

Quality Level

100

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Goutam Chowdhury et al.
Chemical research in toxicology, 25(1), 197-206 (2011-11-17)
Heterocyclic N-oxides are an interesting class of antitumor agents that selectively kill the hypoxic cells found in solid tumors. The hypoxia-selective activity of the lead compound in this class, tirapazamine, stems from its ability to undergo intracellular one-electron reduction to
J M Brown et al.
Anti-cancer drug design, 13(6), 529-539 (1998-10-02)
Tirapazamine (TPZ, SR 4233, WIN 59075, 3-amino-1,2,4-benzotriazine 1,4-dioxide, Tirazone) is the lead compound in the benzotriazine di-N-oxide class of bioreductive anticancer agents. Extensive preclinical testing has established that the mechanism for the selective toxicity towards hypoxic cells is the result
Quynh-Thu Le et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 18(6), 1798-1807 (2012-03-03)
Hepatocyte growth factor (HGF) is a hypoxia-induced secreted protein that binds to cMet and regulates interleukin (IL)-8 expression. We evaluated the role of circulating HGF and IL-8 as prognostic and predictive factors for efficacy of tirapazamine (TPZ), a hypoxic cell
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
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