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SML0552

Sigma-Aldrich

Tirapazamine

≥98% (HPLC)

Synonym(e):

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

Empirische Formel (Hill-System):
C7H6N4O2
CAS-Nummer:
27314-97-2
Molekulargewicht:
178.15
MDL-Nummer:
MFCD00132954
UNSPSC-Code:
12352116
PubChem Substanz-ID:
329825548
NACRES:
NA.77

Qualitätsniveau

100

Assay

≥98% (HPLC)

Form

powder

Farbe

, orange to dark orange-red

Löslichkeit

DMSO: 10 mg/mL, clear

Versandbedingung

wet ice

Lagertemp.

−20°C

SMILES String

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)

InChIKey

ORYDPOVDJJZGHQ-UHFFFAOYSA-N

Anwendung

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

Biochem./physiol. Wirkung

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.
Under hypoxic conditions, tirapazamine is a potent cytotoxic agent..

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

Gefahreneinstufungen

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

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
0000187927
0000187927
0000123467
0000123468
0000121834

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Die Dokumentenbibliothek aufrufen

A V Patterson et al.
Anti-cancer drug design, 13(6), 541-573 (1998-10-02)
The enzymology of triapazamine (TPZ, SR 4233, WIN 59075, 3-amino-1,2,4-benzotriazene 1,4-dioxide, Tirazone) has been extensively studied in rodents and to a lesser extent in human systems. While it is clear that the initial reductive step in TPZ activation is enzyme-mediated
Prafull Ghatage et al.
Expert opinion on drug metabolism & toxicology, 8(12), 1589-1597 (2012-10-05)
Cervical cancer is the second-most common malignancy in women worldwide. Cisplatin was introduced as a radiosensitizer in 1999 to improve chances of survival. Tumor cell hypoxia, however, remains a major limiting factor in the treatment of solid tumors with chemotherapy
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
Klaas M Govaert et al.
Annals of surgery, 259(4), 750-759 (2013-11-21)
To assess the contribution of hypoxia and bone marrow-derived cells to aggressive outgrowth of micrometastases after liver surgery. Liver surgery generates a microenvironment that fosters aggressive tumor recurrence. These areas are characterized by chronic hypoxia and influx of bone marrow-derived
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
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