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SML0552

Sigma-Aldrich

Tirapazamine

≥98% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C7H6N4O2
Numéro CAS:
27314-97-2
Poids moléculaire :
178.15
Numéro MDL:
MFCD00132954
Code UNSPSC :
12352116
ID de substance PubChem :
329825548
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Couleur

, orange to dark orange-red

Solubilité

DMSO: 10 mg/mL, clear

Conditions d'expédition

wet ice

Température de stockage

−20°C

Chaîne SMILES 

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)

Clé InChI

ORYDPOVDJJZGHQ-UHFFFAOYSA-N

Application

Tirapazamine has been used to evaluate its cytotoxic effect on U-251 MG (glioblastoma cell line) cell viability.

Actions biochimiques/physiologiques

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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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
J M Brown
British journal of cancer, 67(6), 1163-1170 (1993-06-01)
SR 4233 (3-amino-1,2,4-benzotriazine 1,4-dioxide, WIN 59075, tirapazamine) is the lead compound in a new class of bioreductive anticancer drugs, the benzotriazine di-N-oxides. It is currently undergoing Phase I clinical testing. The preferential tumour cell killing of SR 4233 is a
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