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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

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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.

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Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
Hazard Codes (Europe) 
T+
Risk Statements (Europe) 
Safety Statements (Europe) 
45
RIDADR 
UN 1544PSN1 6.1 / PGI
WGK Germany 
3
RTECS 
FH5100000

Documents

Certificate of Analysis

Protocols & Articles

Peer-Reviewed Papers

References

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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)

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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)

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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)

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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)

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[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)

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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)

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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)

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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)

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

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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)

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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)

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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)

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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)

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

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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)

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

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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)

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

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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)

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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)

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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)

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

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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)

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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)

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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)

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