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Merck
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Principaux documents

SML0552

Sigma-Aldrich

Tirapazamine

≥98% (HPLC)

Synonyme(s) :

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

Formule empirique (notation de Hill):
C7H6N4O2
Numéro CAS:
Poids moléculaire :
178.15
Numéro MDL:
Code UNSPSC :
12352116
ID de substance PubChem :
Nomenclature NACRES :
NA.77
Le tarif et la disponibilité ne sont pas disponibles actuellement.

Niveau de qualité

Essai

≥98% (HPLC)

Forme

powder

Couleur

, orange to dark orange-red

Solubilité

DMSO: 10 mg/mL, clear

Conditions d'expédition

wet ice

Température de stockage

−20°C

Chaîne SMILES 

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)

Clé InChI

ORYDPOVDJJZGHQ-UHFFFAOYSA-N

Application

Tirapazamine has been used to evaluate its cytotoxic effect on U-251 MG (glioblastoma cell line) cell viability.[1]

Actions biochimiques/physiologiques

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..

Pictogrammes

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Mention d'avertissement

Warning

Mentions de danger

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


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Consulter la Bibliothèque de documents

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
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
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
W A Denny et al.
Expert opinion on investigational drugs, 9(12), 2889-2901 (2000-11-28)
Tirapazamine is the second clinical anticancer drug (after porfiromycin) that functions primarily as a hypoxia-selective cytotoxin. Hypoxic cells in tumours are relatively resistant to radiotherapy and to some forms of chemotherapy and are also biologically aggressive, thus representing an important

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