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Chemical Compound Review

Echujetin     4-[(3S,5R,10S,13R,14S)-3,14- dihydroxy-10...

Synonyms: Evonogenin, Cerberigenin, Thevetigenin, SureCN13988799, CHEBI:100712, ...
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Disease relevance of Digitoxigenin


Psychiatry related information on Digitoxigenin


High impact information on Digitoxigenin


Biological context of Digitoxigenin


Anatomical context of Digitoxigenin


Associations of Digitoxigenin with other chemical compounds

  • The most active compounds showed Na(+),K(+)-ATPase inhibitory potencies (IC(50)) 17-25 times higher than the standards digitoxigenin and digoxin and 3-11 times higher inotropic potencies (EC(50)) in isolated guinea pig left atria [17].
  • Other cardiotonic steroids including ouabain, digitoxigenin and cinobufagin did not enhance VDR activation [18].
  • Additionally, structure-activity relationships among four cardiotonic steroids were determined by comparing the contractile force effects of bolus i.v. injections of digitoxigenin (the genin), digitoxigenin-galactose (genin-neutral sugar combination), digitoxigenin-aminogalactose (ASI-222, genin-aminosugar combination) and digoxin [14].
  • A weak reactivity component was similar to the one of the corresponding glycosides (IC50 of about 10(-6) M) and a high reactivity component exhibited IC50 values varying from 0.1 to 0.5 X 10(-6) M for digitoxigenin and ouabagenin respectively [19].
  • Intravenous administration of digitoxigenin (DTXGN) evokes seizure episodes in mice which may be dependent on brain biogenic amines such as serotonin (5-HT) [2].

Gene context of Digitoxigenin

  • It was proven that digitoxigenin (dt-0) is by far the best substrate for the cytosolic sulfotransferases (ST) [20].

Analytical, diagnostic and therapeutic context of Digitoxigenin

  • EEG was recorded from several brain regions during the i.v. infusion of digitoxigenin to conscious, freely-moving rats [21].
  • At a dosage of 20 mg/kg in the intact rat, it elicited ECG changes similar to those seen with a 10-mg/kg dose of digitoxigenin [22].


  1. Kinetics of digitoxin and the bis- and monodigitoxosides of digitoxigenin in renal insufficiency. Graves, P.E., Fenster, P.E., MacFarland, R.T., Marcus, F.I., Perrier, D. Clin. Pharmacol. Ther. (1984) [Pubmed]
  2. Altered distribution and toxicity of digitoxigenin in fasted mice. Warwick, R.O., Smith, M.P., Graffy, M.A., Lage, G.L. Life Sci. (1985) [Pubmed]
  3. The effects of digitoxin and its metabolites on the transmembrane potential and contractile characteristics of guinea-pig ventricle strips. Stephen, P.M., Marks, B.H., Hollander, P.B. Archives internationales de pharmacodynamie et de thérapie. (1976) [Pubmed]
  4. The relationship between magnitude of electroshock stimulation and the effects of digitoxigenin, pentylenetetrazol and brain monoamine reduction on electroshock convulsive thresholds. Buterbaugh, G.G., London, E.D. Neuropharmacology (1977) [Pubmed]
  5. Digitalis metabolism and human liver alcohol dehydrogenase. Frey, W.A., Vallee, B.L. Proc. Natl. Acad. Sci. U.S.A. (1980) [Pubmed]
  6. Induction of digitoxigenin monodigitoxoside UDP-glucuronosyltransferase activity by glucocorticoids and other inducers of cytochrome P-450p in primary monolayer cultures of adult rat hepatocytes and in human liver. Schuetz, E.G., Hazelton, G.A., Hall, J., Watkins, P.B., Klaassen, C.D., Guzelian, P.S. J. Biol. Chem. (1986) [Pubmed]
  7. In situ assembly states of (Na+,K+)-pump ATPase in human erythrocytes. Radiation target size analyses. Hah, J., Goldinger, J.M., Jung, C.Y. J. Biol. Chem. (1985) [Pubmed]
  8. Kinetics of digitoxin and the bis- and monodigitoxosides of digitoxigenin in normal subjects. Graves, P.E., Fenster, P.E., MacFarland, R.T., Marcus, F.I., Perrier, D. Clin. Pharmacol. Ther. (1984) [Pubmed]
  9. Digitoxigenin 3-O-beta-D-furanosides. Prisbe, E.J., Verheyden, J.P., Montgomery, W.W., Strosberg, A.M. J. Med. Chem. (1986) [Pubmed]
  10. Immunodetection and enzymatic characterization of the alpha 3-isoform of Na,K-ATPase in dog heart. Berrebi-Bertrand, I., Maixent, J.M. FEBS Lett. (1994) [Pubmed]
  11. A Stereoselective Synthesis of Digitoxin and Digitoxigen Mono- and Bisdigitoxoside from Digitoxigenin via a Palladium-Catalyzed Glycosylation. Zhou, M., O'doherty, G.A. Org. Lett. (2006) [Pubmed]
  12. Changes in cardiac glycoside activity produced by aminosugar addition. Cook, L.S., Caldwell, R.W., Nash, C.B. J. Pharmacol. Exp. Ther. (1980) [Pubmed]
  13. On the substrate specificity of the digitoxigenin monodigitoxoside conjugating UDP-glucuronyltransferase in rat liver. Schmoldt, A., Promies, J. Biochem. Pharmacol. (1982) [Pubmed]
  14. Adrenergic and cholinergic mechanisms in digitalis inotropy. Cook, L.S., Caldwell, R.W., Nash, C.B., Doherty, J.E., Straub, K.D. J. Pharmacol. Exp. Ther. (1982) [Pubmed]
  15. Metabolism and cardiac actions of a polar aminocardenolide and digoxin in the conscious dog. Songu-Mize, E., Nash, C.B., Elam, J.T., Caldwell, R.W. J. Pharmacol. Exp. Ther. (1983) [Pubmed]
  16. Bufalin as a potent inducer of differentiation of human myeloid leukemia cells. Zhang, L.S., Nakaya, K., Yoshida, T., Kuroiwa, Y. Biochem. Biophys. Res. Commun. (1991) [Pubmed]
  17. 17beta-O-Aminoalkyloximes of 5beta-androstane-3beta,14beta-diol with digitalis-like activity: synthesis, cardiotonic activity, structure-activity relationships, and molecular modeling of the Na(+),K(+)-ATPase receptor. Cerri, A., Almirante, N., Barassi, P., Benicchio, A., Fedrizzi, G., Ferrari, P., Micheletti, R., Quadri, L., Ragg, E., Rossi, R., Santagostino, M., Schiavone, A., Serra, F., Zappavigna, M.P., Melloni, P. J. Med. Chem. (2000) [Pubmed]
  18. Enhancement of ligand-dependent vitamin D receptor transactivation by the cardiotonic steroid bufalin. Nakano, H., Matsunawa, M., Yasui, A., Adachi, R., Kawana, K., Shimomura, I., Makishima, M. Biochem. Pharmacol. (2005) [Pubmed]
  19. High sensitivity of the Na+, K+-pump of human red blood cells to genins of cardiac glycosides. Senn, N., Lelièvre, L.G., Braquet, P., Garay, R. Br. J. Pharmacol. (1988) [Pubmed]
  20. Purification of a rat liver cytosolic sulfotransferase responsible for the conjugation of digitoxigenin. Johannes, A., von Meyerinck, L., Schmoldt, A. Biochem. Pharmacol. (1990) [Pubmed]
  21. Hippocampal seizure discharge produced by systemic digitoxigenin is antagonized by reserpine or p-chlorophenylalanine. Vocci, F.J., Buterbaugh, G.G. Neuropharmacology (1982) [Pubmed]
  22. Thiocardenolides I: synthesis and biological actions of 3beta-thiocyanato-14beta-hydroxy-5beta-card-20(22)-enolide. Abramson, H.N., Huang, C.L., Wu, T.F., Tobin, T. Journal of pharmaceutical sciences. (1976) [Pubmed]
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