A metabolite of doxorubicin
Related Products
Parent Compound(s)
15007Doxorubicin (hydrochloride)
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Doxorubicinone

Item No. 21693

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(8S,10S)-7,8,9,10-tetrahydro-6,8,10,11-tetrahydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,12-naphthacenedione
CAS Number
24385-10-2
Synonyms
  • Adriamycin aglycone
  • Adriamycinone
  • aglycone-DOX
  • Doxorubicin aglycone
  • Epirubicin aglycone
Molecular Formula
C21H18O9
Formula Weight
414.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 5 mg/mlDMSO: 5 mg/mlEthanol: 5 mg/ml
λmax
234, 252, 288, 496 nm
SMILES
OC1=C(C[C@](C(CO)=O)(O)C[C@@H]2O)C2=C(O)C(C3=O)=C1C(C4=CC=CC(OC)=C34)=O
InChi Code
InChI=1S/C21H18O9/c1-30-11-4-2-3-8-14(11)20(28)16-15(17(8)25)18(26)9-5-21(29,12(24)7-22)6-10(23)13(9)19(16)27/h2-4,10,22-23,26-27,29H,5-7H2,1H3/t10-,21-/m0/s1
InChi Key
IBZGBXXTIGCACK-CWKPULSASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    500 µg

    $75

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    1 mg

    $143

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    5 mg

    $662

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    10 mg

    $1,135

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    Cayman Chemical
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    Product Description

    Doxorubicinone is a metabolite of the anthracycline antitumor antibiotic doxorubicin (Item No. 15007).1,2 Doxorubicinone inhibits mitochondrial succinoxidase from bovine heart and reduces the mitochondrial inner membrane potential in rat heart and liver mitochondria in a concentration-dependent manner.3,4 Doxorubicinone (40 μM) increases pentose phosphate pathway flux by 45% and reduces activity of glutathione peroxidase (GPx) and superoxide dismutase (SOD) by 17 and 60%, respectively, in human erythrocytes.5 It also induces cytotoxicity in patient-derived ovarian cancer colonies in a concentration-dependent manner.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. Ozols, R.F., Willson, J.K.V., Weltz, M.D., et al. Inhibition of human ovarian cancer colony formation by adriamycin and its major metabolites. Cancer Res. 40(11), 4109-4112 (1980).

    3. Kishi, T., Watanabe, T., and Folkers, K. Bioenergetics in clinical medicine: Prevention by forms of coenzyme Q of the inhibition by adriamycin of coenzyme Q10-enzymes in mitochondria of the myocardium. Proc. Natl. Acad. Sci. USA 73(12), 4653-4656 (1976).

    4. Al-Nasser, I.A. Prevention of adriamycin aglycone-induced changes of inner mitochondrial membrane permeability by cyclosporin A. Med. Sci. Res. 25(4), 249-251 (1997).

    5. Misiti, F., Giardina, B., Mordente, A., et al. The secondary alcohol and aglycone metabolites of doxorubicin alter metabolism of human erythrocytes. Braz. J. Med. Biol. Res. 36(12), 1643-1651 (2003).