EMAIL THIS PAGE TO A FRIEND

O2627 Sigma

Ouabagenin

≥95%

Synonym: 1β,3β,5,11α,14,19-Hexahydroxy-5β-card-20(22)-enolide, G-Strophanthidin

  • CAS Number 508-52-1

  • Empirical Formula (Hill Notation) C23H34O8

  • Molecular Weight 438.51

  •  MDL number MFCD00057697

  •  PubChem Substance ID 24897964

Purchase

Properties

assay   ≥95%
storage temp.   2-8°C

Description

Biochem/physiol Actions

Ouabagenin exerts cardiotonic effects through inhibition of Na+/K+-ATPase like the glycosides, albeit at significantly lower potency.1

General description

The aglycone of the cardiac glycoside ouabain.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. O2627.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Price and Availability

Customers Also Viewed

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 1544PSN1 6.1 / PGI
WGK Germany 
3
RTECS 
FH5100000

Documents

Certificate of Analysis

Protocols & Articles

Peer-Reviewed Papers

References

Set your institution to view full text papers.

1. Amino acid residues of the Na,K-ATPase involved in ouabain sensitivity do not bind the sugar moiety of cardiac glycosides O'Brien, W.J., et al. J. Biol. Chem. 268, 7707-7712, (1993)

Loading...


Ouabain is not detectable in human plasma. Lewis LK, Yandle TG, Lewis JG, et al. Hypertension 24(5), 549-55, (1994)

Loading...


Theoretical calculation of circular dichroic exciton-split spectra in presence of three interacting 2-naphthoate chromophores. Dong JG, Akritopoulou-Zanze I, Guo J, et al. Enantiomer 2(5), 397-409, (1997)

Loading...


Strategic redox relay enables a scalable synthesis of ouabagenin, a bioactive cardenolide. Renata H, Zhou Q, and Baran PS Science 339(6115), 59-63, (2013)

Loading...


[The effects of digitalis compounds on K(+)-induced relaxation in aortic rings]. Dorantes AL, Aldana I, Pastelín G, et al. Arch. Inst. Cardiol. Mex. 64(6), 511-5, (1994)

Loading...


Role of sarcoplasmic reticulum in digitalis-induced electrical and mechanical oscillations in the heart. Chan TL, Chau TC, and Bose D Can. J. Cardiol. 3(4), 197-204, (1987)

Loading...


Formation of new high density glycogen-microtubule structures is induced by cardiac steroids. Fridman E, Lichtstein D, and Rosen H J. Biol. Chem. 287(9), 6518-29, (2012)

Loading...


Effects of three sodium-potassium adenosine triphosphatase inhibitors. Pamnani MB, Chen S, Bryant HJ, et al. Hypertension 18(3), 316-24, (1991)

Loading...


Progesterone derivatives that bind to the digitalis receptor: synthesis of 14 beta-hydroxyprogesterone. A novel steroid with positive inotropic activity. Templeton JF, Kumar VP, Cote D, et al. J. Med. Chem. 30(8), 1502-5, (1987)

Loading...


Total synthesis of ouabagenin and ouabain. Zhang H, Sridhar Reddy M, Phoenix S, et al. Angew. Chem. Int. Ed. Engl. 47(7), 1272-5, (2008)

Loading...


Ouabain uptake by endocytosis in isolated guinea pig atria. Núñez-Durán H, Riboni L, Ubaldo E, et al. Am. J. Physiol. 255(4 Pt 1), C479-85, (1988)

Loading...


Digitalis-like compounds in the toad Bufo viridis: interactions with plasma proteins. Lichtstein D, Gati I, and Ovadia H J. Cardiovasc. Pharmacol. 22 Suppl 2, S102-5, (1993)

Loading...


Ouabain increases sarcoplasmic reticulum calcium release in cardiac myocytes. Nishio M, Ruch SW, Kelly JE, et al. J. Pharmacol. Exp. Ther. 308(3), 1181-90, (2004)

Loading...


Effect of cardiac glycosides on action potential characteristics and contractility in cat ventricular myocytes: role of calcium overload. Ruch SR, Nishio M, and Wasserstrom JA J. Pharmacol. Exp. Ther. 307(1), 419-28, (2003)

Loading...


Chronic hypertension induced by ouabain but not digoxin in the rat: antihypertensive effect of digoxin and digitoxin. Manunta P, Hamilton J, Rogowski AC, et al. Hypertens. Res. 23 Suppl, S77-85, (2000)

Loading...


Role of homologous ASP334 and GLU319 in human non-gastric H,K- and Na,K-ATPases in cardiac glycoside binding. Radkov R, Kharoubi-Hess S, Schaer D, et al. Biochem. Biophys. Res. Commun. 356(1), 142-6, (2007)

Loading...


Total synthesis of ouabagenin and ouabain. Reddy MS, Zhang H, Phoenix S, et al. Chem. Asian J. 4(5), 725-41, (2009)

Loading...


Tylophora compounds as Na+/K(+)-ATPase inhibitors. Gnabre JN, Pinnas JL, Bates RB, et al. Gen. Pharmacol. 24(5), 1107-13, (1993)

Loading...


Technetium-99m radiolabeled ouabagenin-cysteine conjugate: biological evaluation in animal models. Chatterjee M, Ganguly S, Sarkar BR, et al. Nucl. Med. Biol. 23(2), 115-20, (1996)

Loading...


Scattered light intensity fluctuation in the canine ventricular myocardium: correlation with inotropic drug effect. Bose D, Kobayashi T, Bouchard RA, et al. Can. J. Physiol. Pharmacol. 66(9), 1232-8, (1988)

Loading...


Synergistic interaction between ouabain and 8-methoxy-3,9-dihydroxy coumestan, a non-steroidal synthetic inhibitor of Na+,K+-ATPase. Pôças ES, Touza NA, da Silva AJ, et al. Life Sci. 81(15), 1199-204, (2007)

Loading...


Diverse actions of ouabain and its aglycone ouabagenin in renal cells. Valente RC, Capella LS, Oliveira MM, et al. Cell Biol. Toxicol. 26(3), 201-13, (2010)

Loading...


Iodoacetylated ouabagenins: their syntheses, spectroscopic characterizations, and stability studies. Chatterjee M, Chakravarty AK, Ganguly S, et al. Steroids 60(6), 477-83, (1995)

Loading...


Preparation of 99mTc-labelled conjugates of ouabagenin and their biological evaluation in animal models. Debnath MC, Sarkar BR, Ganguly S, et al. Nucl. Med. Commun. 27(3), 271-9, (2006)

Loading...


Effect of ouabain on growth of skin explants in organotypic culture. Penniyaynen VA, Kipenko AV, Lopatina EV, et al. Bull. Exp. Biol. Med. 154(4), 419-20, (2013)

Loading...


Merck 14,6900

Related Products

Technical Service:

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Bulk Ordering & Pricing:

Need larger quantities for your development, manufacturing or research applications?