Ouabain octahydrate
Catalog #:
IN0065Shipping advice:
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Synomyms: Ouabain,1β,3β,5β,11α,14,19-Hexahydroxycard-20(22)-enolide 3-(6-deoxy-α-L-mannopyranoside), Acocantherine, G-Strophanthin
IUPAC Name:
4-[(1R,3S,5S,8R,9S,10R,11R,13R,14S,17R)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]furan-2(5H)-oneFunctional Activity:
Ouabain is obtained from Somali waabaayo, "arrow poison" which is a poisonous cardiac glycoside.
It inhibits Na+/K+ ATPase, regulates transcription of MDR (increase, Pgp) and MRP (increase MRP1 and decrease CFTR, cyctic fibrosis transport receptor or cAMP-activated Cl- channel) genes, also alters localization of MRP1.
Inhibition of the sodium pump and the secondary effect on the handling of calcium ions by sodium calcium exchanger (NCX) is widely believed to underlie the original beneficial effect as an inotropic agent following intravenous use of ouabain; digoxin is a structurally related and more lipophilic cardiac glycoside that largely replaced ouabain for therapy because of its superior bioavailability per os. Digoxin continues to be used therapeutically for many of the same indications in which ouabain was used (including atrial fibrillation and congestive heart failure).
Technical Data:
M.Wt: 728.77
Formula: C29H44O12.8H2O
Solubility: Soluble in water, 10 mg/mL (cold)
Purity: >95%
Storage: Dessicate at RT
CAS No.: 11018-89-6
Caution: Aqueous solutions can be autoclaved
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References for DNDS:
1. Xavier, F. E., Davel, A. P., Fukuda, L. E., and Rossoni, L. V. Chronic ouabain treatment exacerbates blood pressure elevation in spontaneously hypertensive rats: the role of vascular mechanisms. J Hypertens, 27: 1233-1242, 2009.
2. Tian, J., Li, X., Liang, M., Liu, L., Xie, J. X., Ye, Q., Kometiani, P., Tillekeratne, M., Jin, R., and Xie, Z. Changes in sodium pump expression dictate the effects of ouabain on cell growth. J Biol Chem, 284: 14921-14929, 2009.
3. Bersier, M. G. and Rodriguez de Lores Arnaiz, G. Intracerebroventricular administration of ouabain to rats changes the expression of NMDA receptor subunits in cerebral cortex and hippocampus. Neurochem Res, 34: 1650-1657, 2009.
4. Reddy, M. S., Zhang, H., Phoenix, S., and Deslongchamps, P. Total synthesis of ouabagenin and ouabain. Chem Asian J, 4: 725-741, 2009.
5. Campia, I., Gazzano, E., Pescarmona, G., Ghigo, D., Bosia, A., and Riganti, C. Digoxin and ouabain increase the synthesis of cholesterol in human liver cells. Cell Mol Life Sci, 66: 1580-1594, 2009.
6. Pousti, A., Bakhtiarian, A., Najafi, R., Deemyad, T., Brumand, K., and Hosseini, M. J. Effect of sertraline on ouabain-induced arrhythmia in isolated guinea-pig atria. Depress Anxiety, 26: E106-110, 2009.
