A cardiac glycoside with cardiotonic and antiarrhythmic activities
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Isomer(s)
22266Digoxin
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Gitoxin

Item No. 38888

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3β,5β,16β)-3-[(O-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1→4)-O-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1→4)-2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy]-14,16-dihydroxy-card-20(22)-enolide
CAS Number
4562-36-1
Synonyms
  • NSC 95099
Molecular Formula
C41H64O14
Formula Weight
780.9
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: Slightly SolubleMethanol: Slightly Soluble
SMILES
O[C@@]12[C@@]3([H])[C@@](CC[C@@]1([C@@H](C(CO4)=CC4=O)[C@H](C2)O)C)([H])[C@@]5([C@](C[C@H](CC5)O[C@H]6C[C@@H]([C@@H]([C@H](O6)C)O[C@@H]7O[C@@H]([C@H]([C@H](C7)O)O[C@@H]8O[C@@H]([C@H]([C@H](C8)O)O)C)C)O)([H])CC3)C
InChi Code
InChI=1S/C41H64O14/c1-19-36(47)27(42)14-33(50-19)54-38-21(3)52-34(16-29(38)44)55-37-20(2)51-32(15-28(37)43)53-24-8-10-39(4)23(13-24)6-7-26-25(39)9-11-40(5)35(22-12-31(46)49-18-22)30(45)17-41(26,40)48/h12,19-21,23-30,32-38,42-45,47-48H,6-11,13-18H2,1-5H3/t19-,20-,21-,23-,24+,25+,26-,27+,28+,29+,30+,32+,33+,34+,35+,36-,37-,38-,39+,40-,41+/m1/s1
InChi Key
LKRDZKPBAOKJBT-CNPIRKNPSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Gitoxin is a cardiac glycoside originally found in Digitalis that has cardiotonic and antiarrhythmic activities.1,2,3 It inhibits Na+/K+-ATPase in an isoform-specific biphasic manner with IC50 values of 0.298 and 410 µM for the high- and low affinity human erythrocyte isoenzymes, respectively, and 1.18 and 28.5 µM for the high- and low affinity porcine cerebral cortex isoenzymes, respectively.2 Gitoxin increases contractility and rhythmicity in isolated guinea pig heart in a concentration-dependent manner.3 It is also a degradation product of the cardiac glycoside digoxin (Item No. 22266).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Windaus, A., and Schwarte, G. A chloroform-insoluble glucoside from digitalis leaves, gitoxin. Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen 58B, 1515-1519 (1925).

    2. Krstić, D., Krinulović, K., Spasojević-Tisma, V., et al. Effects of digoxin and gitoxin on the enzymatic activity and kinetic parameters of Na+/K+-ATPase. J. Enzyme Inhib. Med. Chem. 19(5), 409-415 (2004).

    3. Haustein, K.O., and Hauptmann, J. Studies on cardioactive steroids. II. Structure-activity relationships in the isolated guinea-pig heart. Pharmacology 11(3), 129-138 (1974).

    4. Desta, B., Kwong, E., and McErlane, K.M. Separation of digoxin, digitoxin and their potential metabolites, impurities or degradation products by high-performance liquid chromatography. J. Chromatogr. 240(1), 137-143 (1982).