An anthracycline antitumor antibiotic
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Doxorubicin (hydrochloride)

Item No. 15007

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(8S,10S)-10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,12-naphthacenedione, monohydrochloride
CAS Number
25316-40-9
Synonyms
  • DOX
Molecular Formula
C27H29NO11 • HCl
Formula Weight
580.0
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: 10 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlEthanol: 1 mg/mlPBS (pH 7.2): >100 µg/ml
λmax
234, 252, 288, 479 nm
SMILES
OC1=C(C[C@](C(CO)=O)(O)C[C@@H]2O[C@@](O[C@@H](C)[C@H]3O)([H])C[C@@H]3N)C2=C(O)C(C4=O)=C1C(C5=CC=CC(OC)=C45)=O.Cl
InChi Code
InChI=1S/C27H29NO11.ClH/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34;/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3;1H/t10-,13-,15-,17-,22+,27-;/m0./s1
InChi Key
MWWSFMDVAYGXBV-RUELKSSGSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $43

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    10 mg

    $65

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    25 mg

    $129

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    50 mg

    $151

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    Cayman Chemical
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    Product Description

    Doxorubicin is an anthracycline antitumor antibiotic that inhibits DNA topoisomerase II by inducing double-stranded DNA breaks.1 By intercalating within DNA, doxorubicin inhibits nucleic acid synthesis and induces apoptosis by inducing the accumulation of the p53 tumor suppressor protein.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Patel, S., Sprung, A.U., Keller, B.A., et al. Identification of yeast DNA topoisomerase II mutants resistant to the antitumor drug doxorubicin: Implications for the mechanisms of doxorubicin action and cytotoxicity. Mol. Pharmacol. 52(4), 658-666 (1997).

    2. Lorenzo, E., Ruiz-Ruiz, C., Quesada, A.J., et al. Doxorubicin induces apoptosis and CD95 gene expression in human primary endothelial cells through a p53-dependent mechanism. The Journal of Biological Chemisty 277(17), 10883-10892 (2002).

    Product Citations

    Wong, F., Zheng, E.J., Valeri, J.A., et al. Discovery of a structural class of antibiotics with explainable deep learning. Nature 626(7997), 177-185 (2024).

    Du, W., Gu, M., Hu, M., et al. Lysosomal Zn2+ release triggers rapid, mitochondria-mediated, non-apoptotic cell death in metastatic melanoma. Cell Rep. 37(3), 109848 (2021).

    Yousefi, B., Azimi, A., Majidinia, M., et al. Balaglitazone reverses P-glycoprotein-mediated multidrug resistance via upregulation of PTEN in a PPARγ-dependent manner in leukemia cells. Tumour Biol. 39(10), (2017).

    Meyer, F.B., Goebel, S., Spangel, S.B., et al. Metformin alters therapeutic effects in the BALB/c tumor therapy model. BMC Cancer 21(1), 629 (2021).