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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

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

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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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
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
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
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
A V Patterson et al.
Anti-cancer drug design, 13(6), 541-573 (1998-10-02)
The enzymology of triapazamine (TPZ, SR 4233, WIN 59075, 3-amino-1,2,4-benzotriazene 1,4-dioxide, Tirazone) has been extensively studied in rodents and to a lesser extent in human systems. While it is clear that the initial reductive step in TPZ activation is enzyme-mediated
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