Details
| 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
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/29101813 | https://www.ncbi.nlm.nih.gov/pubmed/28303962 | https://www.ncbi.nlm.nih.gov/pubmed/16081050 | https://www.ncbi.nlm.nih.gov/pubmed/13873586
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/29101813 | https://www.ncbi.nlm.nih.gov/pubmed/28303962 | https://www.ncbi.nlm.nih.gov/pubmed/16081050 | https://www.ncbi.nlm.nih.gov/pubmed/13873586
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| Cytotoxicity of digitoxin and related cardiac glycosides in human tumor cells. | 2001 Jun |
|
| Defective activity and isoform of the Na,K-ATPase in the dilated cardiomyopathic hamster. | 2001 Mar |
|
| Structure-based design and synthesis of novel potent Na+,K+ -ATPase inhibitors derived from a 5alpha,14alpha-androstane scaffold as positive inotropic compounds. | 2003 Aug 14 |
|
| [Study of the relation between the electromolecular characteristics of digitalis compounds and their pharmacological action]. | 2003 Jan-Mar |
|
| Structural mechanism of specific ligand recognition by a lipocalin tailored for the complexation of digoxigenin. | 2003 Jul 4 |
|
| Constituents of the Vietnamese medicinal plant Streptocaulon juventas and their antiproliferative activity against the human HT-1080 fibrosarcoma cell line. | 2003 Nov |
|
| Determination of strophanthidin in ingesta and plant material by LC-MS/MS. | 2004 Apr 21 |
|
| Enhancement of ligand-dependent vitamin D receptor transactivation by the cardiotonic steroid bufalin. | 2005 Nov 15 |
|
| A new antihypertensive agent that antagonizes the prohypertensive effect of endogenous ouabain and adducin. | 2006 Jan |
|
| De novo approach to 2-deoxy-beta-glycosides: asymmetric syntheses of digoxose and digitoxin. | 2007 Mar 30 |
|
| [Chemical constituents of Periploca forrestii]. | 2009 Dec |
|
| Cardiac glycosides induce cell death in human cells by inhibiting general protein synthesis. | 2009 Dec 16 |
|
| Interaction between cardiotonic steroids and Na,K-ATPase. Effects of pH and ouabain-induced changes in enzyme conformation. | 2009 Oct 27 |
|
| Inhibitory activity of a phytochemically characterized fraction from Streptocaulon juventas on lung cancer in nude mice. | 2010 Apr |
|
| Electrophysiological characterization of ATPases in native synaptic vesicles and synaptic plasma membranes. | 2010 Mar 15 |
|
| A cardiac glucoside with in vitro anti-HIV activity isolated from Elaeodendron croceum. | 2010 Nov |
|
| Acute cardiac toxicity of nerium oleander/indicum poisoning (kaner) poisoning. | 2010 Oct |
|
| 12β,14-Dihy-droxy-3-oxo-5β,20(22)-cardenolide monohydrate. | 2010 Oct 2 |
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
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
DTXSID80162276
Created by
admin on Sat Dec 16 08:31:26 GMT 2023 , Edited by admin on Sat Dec 16 08:31:26 GMT 2023
|
PRIMARY | |||
|
205-603-4
Created by
admin on Sat Dec 16 08:31:26 GMT 2023 , Edited by admin on Sat Dec 16 08:31:26 GMT 2023
|
PRIMARY | |||
|
Digitoxigenin
Created by
admin on Sat Dec 16 08:31:26 GMT 2023 , Edited by admin on Sat Dec 16 08:31:26 GMT 2023
|
PRIMARY | |||
|
S63WOD4VOL
Created by
admin on Sat Dec 16 08:31:26 GMT 2023 , Edited by admin on Sat Dec 16 08:31:26 GMT 2023
|
PRIMARY | |||
|
4369270
Created by
admin on Sat Dec 16 08:31:26 GMT 2023 , Edited by admin on Sat Dec 16 08:31:26 GMT 2023
|
PRIMARY | |||
|
DB04177
Created by
admin on Sat Dec 16 08:31:26 GMT 2023 , Edited by admin on Sat Dec 16 08:31:26 GMT 2023
|
PRIMARY | |||
|
407806
Created by
admin on Sat Dec 16 08:31:26 GMT 2023 , Edited by admin on Sat Dec 16 08:31:26 GMT 2023
|
PRIMARY | |||
|
m4451
Created by
admin on Sat Dec 16 08:31:26 GMT 2023 , Edited by admin on Sat Dec 16 08:31:26 GMT 2023
|
PRIMARY | Merck Index | ||
|
143-62-4
Created by
admin on Sat Dec 16 08:31:26 GMT 2023 , Edited by admin on Sat Dec 16 08:31:26 GMT 2023
|
PRIMARY | |||
|
42219
Created by
admin on Sat Dec 16 08:31:26 GMT 2023 , Edited by admin on Sat Dec 16 08:31:26 GMT 2023
|
PRIMARY |
SUBSTANCE RECORD
