ChemicalBook > CAS DataBase List > 3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDE

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

Product Name
3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDE
CAS No.
27314-97-2
Chemical Name
3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDE
Synonyms
TPZ;TIRAPAZAMINE;CS-2810;SR-4233;Tirazone;SR 259075;Tirazamin;NSC130181;NSC 130181;NSC-130181
CBNumber
CB5442522
Molecular Formula
C7H6N4O2
Formula Weight
178.15
MOL File
27314-97-2.mol
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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
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
3
RTECS 
DM0671500
HS Code 
2933.99.7500
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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.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML0552
Product name
Tirapazamine
Purity
≥98% (HPLC)
Packaging
10mg
Price
$76.2
Updated
2024/03/01
Sigma-Aldrich
Product number
SML0552
Product name
Tirapazamine
Purity
≥98% (HPLC)
Packaging
50mg
Price
$156
Updated
2024/03/01
TCI Chemical
Product number
T3823
Product name
Tirapazamine
Packaging
50MG
Price
$182
Updated
2024/03/01
TCI Chemical
Product number
T3823
Product name
Tirapazamine
Packaging
250MG
Price
$665
Updated
2024/03/01
Cayman Chemical
Product number
25981
Product name
Tirapazamine
Purity
≥98%
Packaging
10mg
Price
$62
Updated
2024/03/01
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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.

3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDE Preparation Products And Raw materials

Raw materials

Preparation Products

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

Canada 1 China 120 Europe 2 Germany 1 India 4 Japan 1 Switzerland 1 United Kingdom 3 United States 17 Global 150
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27314-97-2, 3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDERelated Search:

Norfloxacin Gemcitabine POLYETHYLENEIMINE 3-Amino-7-chloro-1,2,4-benzotriazine 1,4-dioxide 1,2,4-benzotriazin-3-amine 3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDE 3-AMINO-1,2,4-BENZOTRIAZINE-1-N-OXIDE 3-AMINO-1,2,4-TRIAZINE

  • Tirapazamine (Synonyms: SR259075
  • CS-2810
  • Tirazazamine
  • 3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDE
  • SR-4233, Tirapazamine, TPZ
  • Tirapazamine(SR259075
  • 1,2,4-benzotriazin-3-amine,1,4-dioxide
  • 1,2,4-benzotriazine,3-amino-,1,4-dioxide
  • SR-4233
  • TIRAPAZAMINE
  • SR-4233, Tirapazamine
  • SR 259075
  • Tirazone
  • 4-Hydroxy-1-oxido-1,2,4-benzotriazin-1-ium-3-imine
  • TPZ
  • 3-Aminobenzo[e][1,2,4]triazine 1,4-Dioxide
  • irapazamine
  • Tirazamin
  • NSC 130181
  • NSC130181
  • NSC-130181
  • 27314-97-2
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Amines
  • Heterocycles
  • WMH
  • API