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

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;SR-4233;CS-2810;Tirazone;SR 259075;Tirazamin;NSC130181;NSC 130181;NSC-130181
CBNumber:
CB5442522
Molecular Formula:
C7H6N4O2
Molecular Weight:
178.15
MDL Number:
MFCD00132954
MOL File:
27314-97-2.mol
MSDS File:
SDS
Last updated:2024-11-19 23:02:33

3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDE 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
NCI Dictionary of Cancer Terms tirapazamine
FDA UNII 1UD32YR59G
NCI Drug Dictionary tirapazamine

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P264-P271-P280-P302+P352-P305+P351+P338
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36
WGK Germany  3
RTECS  DM0671500
HS Code  2933.99.7500
NFPA 704
0
2 0

3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDE price More Price(29)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich SML0552 Tirapazamine ≥98% (HPLC) 27314-97-2 10mg $76.2 2024-03-01 Buy
Sigma-Aldrich SML0552 Tirapazamine ≥98% (HPLC) 27314-97-2 50mg $156 2024-03-01 Buy
TCI Chemical T3823 Tirapazamine 27314-97-2 50MG $182 2024-03-01 Buy
TCI Chemical T3823 Tirapazamine 27314-97-2 250MG $665 2024-03-01 Buy
Cayman Chemical 25981 Tirapazamine ≥98% 27314-97-2 10mg $62 2024-03-01 Buy
Product number Packaging Price Buy
SML0552 10mg $76.2 Buy
SML0552 50mg $156 Buy
T3823 50MG $182 Buy
T3823 250MG $665 Buy
25981 10mg $62 Buy

3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDE Chemical Properties,Uses,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

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

Uses

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

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.

480-96-6
420-04-2
27314-97-2
Synthesis of 3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDE from Benzofuroxan and Cyanamide
Global( 153)Suppliers
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ATK CHEMICAL COMPANY LIMITED
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CONIER CHEM AND PHARMA LIMITED
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TargetMol Chemicals Inc.
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Zhejiang J&C Biological Technology Co.,Limited
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View Lastest Price from 3-AMINO-1,2,4-BENZOTRIAZINE-1,4-DIOXIDE manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Tirapazamine pictures 2024-11-19 Tirapazamine
27314-97-2
US $30.00-61.00 / mg 99.87% 10g TargetMol Chemicals Inc.
  • Tirapazamine pictures
  • Tirapazamine
    27314-97-2
  • US $30.00-61.00 / mg
  • 99.87%
  • TargetMol Chemicals Inc.

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

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