| Stereochemistry | ABSOLUTE |
| Molecular Formula | C23H34O4 |
| Molecular Weight | 374.5137 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 8 / 8 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12CC[C@]3([H])[C@]([H])(CC[C@]4(C)[C@H](CC[C@]34O)C5=CC(=O)OC5)[C@@]1(C)CC[C@H](O)C2
InChI
InChIKey=XZTUSOXSLKTKJQ-CESUGQOBSA-N
InChI=1S/C23H34O4/c1-21-8-5-16(24)12-15(21)3-4-19-18(21)6-9-22(2)17(7-10-23(19,22)26)14-11-20(25)27-13-14/h11,15-19,24,26H,3-10,12-13H2,1-2H3/t15-,16+,17-,18+,19-,21+,22-,23+/m1/s1
Digitoxigenin is a cardenolide and aglycone constituent of digitoxin, an extract from the foxglove plant, D. purpurea. It elicits cardiac contraction and cardiotonic effects by inhibiting the Na+/K+ ATPase via binding at the digitalis receptor site with nanomolar potency. Digitoxigenin is highly cytotoxic, inhibiting Na+/K+ ATPase-dependent protein synthesis, and has been examined for use as an antitumor compound.
Originator
Approval Year
Sample Use Guides
LD50 (cat) = 0.6mg/kg
LD50 (guinea-pig) = 2,65 mg/kg
Route of Administration:
Intravenous
The effects of ouabain, digitoxigenin, and INCICH-D7 were determined in the standard reaction medium at different concentrations (0.1 nM–1 mM). The enzyme (7 mkg/ml) was preincubated for 10 min at 37 C in the reaction medium with ouabain, digitoxigenin or INCICH-D7. The reaction was started by adding ATP (2.5 mM), lasted for 10 min, and stopped by adding an equal volume of 10% iced-cold trichloroacetic acid. The tubes were then centrifuged at 3000 rpm for 5 min. The hydrolyzed ATP was measured by determining inorganic phosphate (Pi) released according to the method of Taussky and Shorr
SUBSTANCE RECORD
