A nitroimidazole that targets hypoxic cells
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Misonidazole

Item No. 15606

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
α-(methoxymethyl)-2-nitro-1H-imidazole-1-ethanol
CAS Number
13551-87-6
Synonyms
  • NSC 261037
  • Ro 7-0582
  • SR 1354
Molecular Formula
C7H11N3O4
Formula Weight
201.2
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 15 mg/mlDMSO: 15 mg/mlEthanol: 5 mg/mlPBS (pH 7.2): 2 mg/ml
λmax
222, 317 nm
SMILES
OC(COC)CN1C=CN=C1[N+]([O-])=O
InChi Code
InChI=1S/C7H11N3O4/c1-14-5-6(11)4-9-3-2-8-7(9)10(12)13/h2-3,6,11H,4-5H2,1H3
InChi Key
OBBCSXFCDPPXOL-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $69

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    5 mg

    $118

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    10 mg

    $167

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    50 mg

    $393

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    Cayman Chemical
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    Product Description

    Misonidazole is a nitroimidazole with radiosensitizing and antineoplastic properties.1 Nitroimidazoles, including misonidazole, specifically accumulate as nitro anion radicals and their metabolites in hypoxic cells.1,2,3 The metabolites of misonidazole can themselves be cytotoxic or they can increase the chemosensitivity and radiosensitivity of the target cells.1 Misonidazole and derivatives, including fluoromisonidazole, are used in the imaging of hypoxic regions in tumors and in the cardiovascular system.3,4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Brown, J.M. The mechanisms of cytotoxicity and chemosensitization by misonidazole and other nitroimidazoles. Int. J. Radiat. Oncol. Biol. Phys. 8(3-4), 675-682 (1982).

    2. Josephy, P.D., Palcic, B., and Skarsgard, L.D. In vitro metabolism of misonidazole. Br. J. Cancer 43(4), 443-450 (1981).

    3. Handley, M.G., Medina, R.A., Nagel, E., et al. PET imaging of cardiac hypoxia: Opportunities and challenges. J. Mol. Cell. Cardiol. 51(5), 640-650 (2011).

    4. Bache, M., Kappler, M., Said, H.M., et al. Detection and specific targeting of hypoxic regions within solid tumors: current preclinical and clinical strategies. Curr. Med. Chem. 15(4), 322-338 (2008).

    5. Mendichovszky, I., and Jackson, A. Imaging hypoxia in gliomas. Br. J. Radiol. 84(Spec No 2), S145-S158 (2011).