A cardiac glycoside with diverse biological activities
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Active Metabolite(s)
35356Digoxigenin Bisdigitoxoside
Metabolite(s)
22266Digoxin
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Digitoxin

Item No. 27825

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3β,5β)-3-[(O-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1→4)-O-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1→4)-2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy]-14-hydroxy-card-20(22)-enolide
CAS Number
71-63-6
Synonyms
  • Digitoxoside
  • Lanatoxin
  • NSC 7529
Molecular Formula
C41H64O13
Formula Weight
765.0
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: 20 mg/mlDMF: 25 mg/mlDMF:PBS (pH 7.2) (1:1): 0.5 mg/mlDMSO: 20 mg/mlEthanol: 5 mg/ml
λmax
217 nm
SMILES
C[C@@]12[C@@](CC[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@]3(O)CC[C@@H]4C(CO5)=CC5=O)([H])C[C@@H](O[C@]6([H])O[C@H](C)[C@@H](O[C@@]7([H])C[C@H](O)[C@H](O[C@]8([H])O[C@H](C)[C@@H](O)[C@@H](O)C8)[C@@H](C)O7)[C@@H](O)C6)CC1
InChi Code
InChI=1S/C41H64O13/c1-20-36(46)29(42)16-34(49-20)53-38-22(3)51-35(18-31(38)44)54-37-21(2)50-33(17-30(37)43)52-25-8-11-39(4)24(15-25)6-7-28-27(39)9-12-40(5)26(10-13-41(28,40)47)23-14-32(45)48-19-23/h14,20-22,24-31,33-38,42-44,46-47H,6-13,15-19H2,1-5H3/t20-,21-,22-,24-,25+,26-,27+,28-,29+,30+,31+,33+,34+,35+,36-,37-,38-,39+,40-,41+/m1/s1
InChi Key
WDJUZGPOPHTGOT-XUDUSOBPSA-N
Origin
Plant/Digitalis lanata
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    100 mg

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    Cayman Chemical
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    Product Description

    Digitoxin is a cardiac glycoside that has been found in Digitalis and has diverse biological activities.1,2,3,4,5 It inhibits human recombinant α1β1, α2β2, and α3β1 subunit-containing Na+/K+-ATPases with Ki values of 250, 63, and 136 nM, respectively.1 Digitoxin inhibits the human-ether-a-go-go (hERG) potassium channel, also known as Kv11.1, in HEK293 cells expressing hERG (IC50 = 11.1 nM).2 It enhances developed tension and contractile force in electrically stimulated isolated guinea pig left atrial muscle when used at concentrations of 0.2 and 0.4 µM, respectively.3 Dietary administration of digitoxin (~1 mg/kg per day) attenuates congestive heart failure and reduces myocardial hypertrophy in a rat model of myocardial infarction induced by coronary artery ligation.4 Digitoxin is also cytotoxic to a panel of 10 human cancer cell lines, including myeloma, lymphoma, and leukemia cancer cells, with IC50 values ranging from 12 to 76 nM.5 Formulations containing digitoxin have previously been used in the treatment of congestive heart failure and cardiac arrhythmias.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Katz, A., Lifshitz, Y., Bab-Dinitz, E., et al. Selectivity of digitalis glycosides for isoforms of human Na,K-ATPase. The Journal of Biological Chemisty 285(25), 19582-19592 (2010).

    2. Wang, L., Wible, B.A., Wan, X., et al. Cardiac glycosides as novel inhibitors of human ether-a-go-go-related gene channel trafficking. J. Pharmacol. Exp. Ther. 320(2), 525-534 (2007).

    3. Temma, K., Akera, T., and Brody, T.M. Inotropic effects of digitoxin in solated guines-pig heart under conditions which alter contraction. Eur. J. Pharm. 76(4), 361-370 (1981).

    4. Picollo, C.T., dos Santos, A.A., Antonio, E.L., et al. Digitoxin attenuates heart failure, reduces myocardial hypertrophy, and preserves the calcium-binding proteins in infarcted rats. J. Cardiovasc. Pharmacol. Ther. 25(3), 265-272 (2019).

    5. Johansson, S., Lindholm, P., Gullbo, J., et al. Cytotoxicity of digitoxin and related cardiac glycosides in human tumor cells. Anticancer Drugs 12(5), 475-483 (2001).