A hypoxia-activated anticancer agent
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Tirapazamine

Item No. 25981

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1,2,4-benzotriazin-3-amine 1,4-dioxide
CAS Number
27314-97-2
Synonyms
  • 3-Amino-1,2,4-benzotriazine 1,4-Dioxide
  • SR 259075
  • SR 4233
  • WIN 59075
Molecular Formula
C7H6N4O2
Formula Weight
178.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Soluble
λmax
223, 271 nm
SMILES
NC1=[N+]([O-])C2=CC=CC=C2[N+]([O-])=N1
InChi Code
InChI=1S/C7H6N4O2/c8-7-9-11(13)6-4-2-1-3-5(6)10(7)12/h1-4H,(H2,8,9)
InChi Key
ORYDPOVDJJZGHQ-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

    $69

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    50 mg

    $132

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    100 mg

    $198

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    250 mg

    $329

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    Product Description

    Tirapazamine is a hypoxia-activated anticancer agent.1 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.1,2,3 Tirapazamine induces hypoxia-enhanced cytotoxicity in DT40 cells (IC50s = 1.02 and 4.34 μM in hypoxic and normoxic conditions, respectively).3 It also induces cytotoxicity in HT-1080 and A549 cells in a concentration-dependent manner under hypoxic conditions.1 In vivo, tirapazamine sensitizes tumors to cisplatin (Item No. 13119) in a mouse RIF-1 fibrosarcoma tumor model.4 Tirapazamine (0.08 mmol/kg) also sensitizes tumors to fractionated irradiation in a FaDu hypopharyngeal squamous cell carcinoma mouse xenograft model.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Brown, J.M. SR 4233 (tirapazamine): A new anticancer drug exploiting hypoxia in solid tumours. Br. J. Cancer. 67(6), 1163-1170 (1993).

    2. Reddy, S.B., and Williamson, S.K. Tirapazamine: A novel agent targeting hypoxic tumor cells. Expert. Opin. Investig. Drugs 18(1), 77-87 (2009).

    3. Moriwaki, T., Okamoto, S., Sasanuma, H., et al. Cytotoxicity of tirapazamine (3-amino-1,2,4-benzotriazine-1,4-dioxide)-induced DNA damage in chicken DT40 cells. Chem. Res. Toxicol. 30(2), 699-704 (2017).

    4. Dorie, M.J., and Brown, J.M. Tumor-specific, schedule-dependent interaction between tirapazamine (SR 4233) and cisplatin. Cancer Res. 53(19), 4633-4636 (1993).

    5. El-Said, A., Menke, D., Dorie, M.J., et al. Comparison of the effectiveness of tirapazamine and carbogen with nicotinamide in enhancing the response of a human tumor xenograft to fractionated irradiation. Radiat. Oncol. Investig. 7(3), 163-169 (1999).