Antitumor antibiotic used in the treatment of acute myeloid leukemias
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Labeled Version(s)
29101Daunorubicin-13C-d3
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Daunorubicin (hydrochloride)

Item No. 14159

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
8S-acetyl-10S-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione, monohydrochloride
CAS Number
23541-50-6
Synonyms
  • NDC 0082-4155
  • Ondena
  • RP 13057
Molecular Formula
C27H29NO10 • HCl
Formula Weight
564.0
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 10 mg/mlEthanol: 0.5 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
234, 251, 288, 480 nm
SMILES
COC1=C(C(C(C(O)=C([C@@H](O[C@@]2([H])C[C@H](N)[C@H](O)[C@H](C)O2)C[C@@](C(C)=O)(O)C3)C3=C4O)=C4C5=O)=O)C5=CC=C1.Cl
InChi Code
InChI=1S/C27H29NO10.ClH/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33;/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3;1H/t10-,14-,16-,17-,22+,27-;/m0./s1
InChi Key
GUGHGUXZJWAIAS-QQYBVWGSSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    Cayman Chemical
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    Product Description

    Daunorubicin is an antitumor antibiotic.1 At 0.2-1μM, daunorubicin induces apoptosis in mature monocytic U937 and myelocytic HL-60 acute myeloid leukemia (AML) cells. However, immature AML cells (CD 34+-KG1a, -KG1, or -HEL cells) appear resistant to apoptosis at similar concentrations.1 In mature AML cells, daunorubicin has been shown to trigger a reactive oxygen species-dependent sphingomyelin-ceramide pathway that activates the MEKK1-SEK1-JNK cascade leading to enhanced DNA binding activity of the transcription factor AP-1.1,2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Laurent, G., and Jaffrézou, J.P. Signaling pathways activated by daunorubicin. Blood 98(4), 913-924 (2001).

    2. Bose, R., Verheij, M., Haimovitz-Friedman, A., et al. Ceramide synthase mediates daunorubicin-induced apoptosis: An alternative mechanism for generating death signals. Cell 82(3), 405-414 (1995).