3-Aminobenzo[e][1,2,4]triazine1,4-dioxide , 98% , 27314-97-2

Synonym(s):
4-Hydroxy-1-oxido-1,2,4-benzotriazin-1-ium-3-imine;SR 259075;SR 4233;Tirazone;Win 59075

CAS NO.：27314-97-2

Empirical Formula: C7H6N4O2

Molecular Weight: 178.15

MDL number: MFCD00132954

EINECS: 636-678-5

PRODUCT Properties

• Melting point: 220°C dec.
• Boiling point: 493.6±28.0 °C(Predicted)
• Density: 1.68±0.1 g/cm3(Predicted)
• storage temp.: -20°C
• solubility: DMSO: soluble10mg/mL, clear
• form: powder
• pka: 1.51±0.30(Predicted)
• color: orange to dark orange-red
• InChI: InChI=1S/C7H6N4O2/c8-7-9-11(13)6-4-2-1-3-5(6)10(7)12/h1-4H,(H2,8,9)
• InChIKey: ORYDPOVDJJZGHQ-UHFFFAOYSA-N
• SMILES: [N+]1([O-])C2=CC=CC=C2[N+]([O-])=C(N)N=1

Description and Uses

Tirapazamine is a hypoxia-activated anticancer agent. It is converted to an oxidizing radical under hypoxic conditions and can induce single- and double-strand breaks in DNA, formation of trapped topoisomerase I- and II-DNA complexes, and other chromosomal aberrations, leading to cytotoxicity. Tirapazamine induces hypoxia-enhanced cytotoxicity in DT40 cells (IC₅₀s = 1.02 and 4.34 μM in hypoxic and normoxic conditions, respectively). It also induces cytotoxicity in HT-1080 and A549 cells in a concentration-dependent manner under hypoxic conditions. In vivo, tirapazamine sensitizes tumors to cisplatin in a mouse RIF-1 fibrosarcoma tumor model. Tirapazamine (0.08 mmol/kg) also sensitizes tumors to fractionated irradiation in a FaDu hypopharyngeal squamous cell carcinoma mouse xenograft model.

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

Safety

• Symbol(GHS): GHS07
• Signal word: Warning
• Hazard statements: H315-H319-H335
• Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338
• target organs: Respiratory system
• Hazard Codes: Xi
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: DM0671500
• HS Code: 2933.99.7500
• Storage Class: 11 - Combustible Solids
• Hazard Classifications: Eye Irrit. 2; Skin Irrit. 2; STOT SE 3