A cardiac glycoside with diverse biological activities
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Labeled Version(s)
40168Ouabain-d3
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Ouabain (hydrate)

Item No. 14319

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3β-[(6-deoxy-α-L-mannopyranosyl)oxy]-1β,5β,11α,14,19-pentahydroxy-card-20(22)-enolide, hydrate
CAS Number
340169-01-9
Synonyms
  • g-Strophanthin
Molecular Formula
C29H44O12 • XH2O
Formula Weight
584.7
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Methanol: Soluble
SMILES
O[C@H]1[C@@]2(CO)[C@@](CC[C@]3([H])[C@]2([H])[C@H](O)C[C@@]4(C)[C@]3(O)CC[C@@H]4C5=CC(OC5)=O)(O)C[C@@H](O[C@]6([H])O[C@@H](C)[C@H](O)[C@@H](O)[C@H]6O)C1.O
InChi Code
InChI=1S/C29H44O12.H2O/c1-13-22(34)23(35)24(36)25(40-13)41-15-8-19(32)28(12-30)21-17(3-5-27(28,37)9-15)29(38)6-4-16(14-7-20(33)39-11-14)26(29,2)10-18(21)31;/h7,13,15-19,21-25,30-32,34-38H,3-6,8-12H2,1-2H3;1H2/t13-,15-,16+,17+,18+,19+,21+,22-,23+,24+,25-,26+,27-,28+,29-;/m0./s1
InChi Key
MVMUAXUYSJSGSG-LGEKDJQSSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $43

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    5 mg

    $204

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    10 mg

    $366

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    25 mg

    $805

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    Product Description

    Ouabain is a cardiac glycoside that has been found in S. gratus and has diverse biological activities.1,2,3,4,5,6,7 It inhibits the Na+/K+-ATPase isoforms α1β1 and α2β1 and human-ether-a-go-go (hERG), also known as Kv11.1 (IC50s = 97, 90, and 15.2 nM, respectively).2,3 Ouabain reduces the proliferation of PC3 prostate cancer and U937 lymphoma cells (EC50s = 210 and 94 nM, respectively).4 It inhibits the cytopathic effect of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) in infected Vero cells (IC50 = <0.097 µM).5 Ouabain (~8 µg/animal) increases systolic blood pressure in normotensive rats.6 It has been used to induce ventricular arrythmias in vivo.7 Formulations containing ouabain have been used in the treatment of atrial fibrillation, atrial flutter, and heart failure.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Jacobs, W.A., and Bigelow, N.M. Ouabain or g-strophanthin. The Journal of Biological Chemisty 96(3), 647-658 (1932).

    2. Katz, A., Tal, D.M., Heller, D., et al. Digoxin derivatives with enhanced selectivity for the α2 isoform of Na,K-ATPase: Effects on intraocular pressure in rabbits. The Journal of Biological Chemisty 289(30), 21153-21162 (2014).

    3. 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).

    4. Bloise, E., Braca, A., De Tommasi, N., et al. Pro-apoptotic and cytostatic activity of naturally occurring cardenolides. Cancer Chemother. Pharmacol. 64(4), 793-802 (2009).

    5. Jeon, S., Ko, M., Lee, J., et al. Identification of antiviral drug candidates against SARS-CoV-2 from FDA-approved drugs. Antimicrob. Agents Chemother. 64(7), e00819-00820 (2020).

    6. Xavier, F.E., Rossoni, L.V., Alonso, M.J., et al. Ouabain-induced hypertension alters the participation of enothelial factors in α-adrenergic responses differently in rat resistance and conductance mesenteric arteries. Br. J. Pharmacol. 143(1), 215-225 (2004).

    7. Xue, Y.X., Aye, N.N., and Hashimoto, K. Antiarrhythmic effects of HOE642, a novel Na+-H+ exchange inhibitor, on ventricular arrhythmias in animal hearts. Eur. J. Pharmacol. 317(2-3), 309-316 (1996).