An activated analog of cyclophosphamide
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4-hydroperoxy Cyclophosphamide

Item No. 19527

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[bis(2-chloroethyl)amino]tetrahydro-2-oxido-2H-1,3,2-oxazaphosphorin-4-yl, hydroperoxide
CAS Number
39800-16-3
Synonyms
  • 4-OOH-CY
Molecular Formula
C7H15Cl2N2O4P
Formula Weight
293.1
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: Slightly SolubleDMSO: Soluble
SMILES
O=P1(N(CCCl)CCCl)OCCC(OO)N1
InChi Code
InChI=1S/C7H15Cl2N2O4P/c8-2-4-11(5-3-9)16(13)10-7(15-12)1-6-14-16/h7,12H,1-6H2,(H,10,13)
InChi Key
VPAWVRUHMJVRHU-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    1 mg

    $102

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    5 mg

    $189

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    10 mg

    $368

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    25 mg

    $775

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    Cayman Chemical
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    Product Description

    4-hydroperoxy cyclophosphamide (4-OOH-CY) is an activated analog of cyclophosphamide (Item No. 13849).1 4-OOH-CY (1 and 3 µg/ml) crosslinks DNA and induces T cell apoptosis independent of death receptor activation but activates mitochondrial death pathways through the production of reactive oxygen species (ROS). In vivo, 4-OOH-CY (0.05, 0.1, and 0.15 mmol/kg) reduces tumor growth in an MX-1 breast cancer mouse xenograft model.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Strauss, G., Westhoff, M.-A., Fischer-Posovszky, P., et al. 4-hydroperoxy-cyclophosphamide mediates caspase-independent T-cell apoptosis involving oxidative stress-induced nuclear relocation of mitochondrial apoptogenic factors AIF and EndoG. Cell Death Differ. 15(2), 332-343 (2008).

    2. Kubota, T., Hanatani, Y., Tsuyuki, K., et al. Antitumor effect and metabolic activation of cyclophosphamide and 4-hydroperoxycyclophosphamide in the human breast carcinoma (MX-1)-nude mouse system. Gan. 74(3), 437-444 (1983).