3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDE Property

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

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

DM0671500

HS Code 

2933.99.7500

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDE Chemical Properties,Usage,Production

Description

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.

Chemical Properties

Orange Needles

Uses

A bioreductive anticancer agent. Selectively toxic to cells under hypoxic conditions. An antineoplastic

Uses

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

Definition

ChEBI: A member of the class of benzotriazines that is 1,2,4-benzotriazine carrying an amino substituent at position 3 and two oxido substituents at positions 1 and 4.

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.