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

Item No. 22386

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]-8-(1,2-dihydroxyethyl)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione, monohydrochloride
Molecular Formula
C27H31NO11 • HCl
Formula Weight
582.0
Purity
≥90% (mixture of isomers)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleMethanol: Soluble
λmax
235, 253, 481, 496 nm
SMILES
OC1=C(C[C@](C(O)CO)(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/C27H31NO11.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-,16?,17-,22+,27-;/m0./s1
InChi Key
ORLHIGGRLIJIIM-VGDPNEAFSA-N
Shipping & Storage Information
Storage
4°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

    $103

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    1 mg

    $194

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    5 mg

    $902

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    Product Description

    Doxorubicinol is the major metabolite of doxorubicin (Item No. 15007), an anthracycline antitumor antibiotic that inhibits DNA topoisomerase II by inducing double-stranded DNA breaks.1,2 Doxorubicinol is formed by NADPH-dependent reduction of the side chain carbonyl group of doxorubicin in human, rabbit, and canine cardiac tissue.3,4 Doxorubicinol inhibits sodium-potassium-dependent ATPase activity (IC50 = 5.40 μg/ml) and ATP-dependent calcium uptake (IC50= 4.5 μg/ml) in canine cardiac muscle and increases resting stress in contracting rabbit cardiac muscle.2 Clinically observed cardiotoxicities following doxorubicin treatment have been attributed to the formation and cardiac action of doxorubicinol.2,3,4

    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. Boucek, R.J., Jr., Olson, R.D., Brenner, D.E., et al. The major metabolite of doxorubicin is a potent inhibitor of membrane-associated ion pumps. A correlative study of cardiac muscle with isolated membrane fractions. The Journal of Biological Chemisty 262(33), 15851-15856 (1987).

    3. Salvatorelli, E., Menna, P., Cascegna, S., et al. Paclitaxel and docetaxel stimulation of doxorubicinol formation in the human heart: Implications for cardiotoxicity of doxorubicin-taxane chemotherapies. J. Pharmacol. Exp. Ther. 318(1), 424-433 (2006).

    4. Mordente, A., Minotti, G., Martorana, G.E., et al. Anthracycline secondary alcohol metabolite formation in human or rabbit heart: Biochemical aspects and pharmacologic implications. Biochem. Pharmacol. 66(6), 989-998 (2003).