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A9938

Sigma-Aldrich

3-Amino-1,2,4-benzotriazine 1,4-dioxide

Synonym(s):
Tirapazamine, SR-4233, TPZ
Empirical Formula (Hill Notation):
C7H6N4O2
CAS Number:
Molecular Weight:
178.15
MDL number:

storage temp.

2-8°C

SMILES string

Nc1n[n+]([O-])c2ccccc2[n+]1[O-]

Biochem/physiol Actions

Hypoxia-activated antineoplastic agent.

Certificate of Analysis

Certificate of Origin

M A Baker et al.
Cancer research, 48(21), 5947-5952 (1988-11-01)
The metabolism of SR 4233 (3-amino-1,2,4-bentotriazine-1,4-dioxide), recently reported as highly toxic to hypoxic cells in vitro, was studied by using suspensions of Chinese hamster ovary cells. The rates of formation of two known reduction products, the 1-oxide and the unoxygenated...
Mustafa Birincioglu et al.
Journal of the American Chemical Society, 125(38), 11607-11615 (2003-09-18)
Tirapazamine is a bioreductively activated DNA-damaging agent that selectively kills the hypoxic cells found in solid tumors. This compound shows clinical promise and is currently being examined in a variety of clinical trials, including several phase III studies. It is...
Yvette M Delahoussaye et al.
Biochemical pharmacology, 65(11), 1807-1815 (2003-06-05)
To improve the potency of the hypoxic cytotoxin tirapazamine (TPZ), we have constructed an analog, SN26955, with the TPZ moiety attached to an acridine chromophore to target the drug to DNA. The underlying reason for this is our previous finding...
Ming Yao et al.
Scientific reports, 11(1), 4020-4020 (2021-02-19)
Tumor tissue contains a continuous distribution of static and dynamically changing oxygen environments with levels ranging from physiologically normal oxygen down to anoxia. However, in vitro studies are often performed under oxygen levels that are far higher than those found...

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