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
| Molecular Formula | C23H34O4 |
| Molecular Weight | 374.5137 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 8 / 8 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 |
|---|---|---|
| Measurement of serum digitoxin in patients by radioimmunoassay using specific antiserum. | 2001 Dec |
|
| Cytotoxicity of digitoxin and related cardiac glycosides in human tumor cells. | 2001 Jun |
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| Defective activity and isoform of the Na,K-ATPase in the dilated cardiomyopathic hamster. | 2001 Mar |
|
| 17 alpha-O-(aminoalkyl)oxime derivatives of 3 beta,14 beta-dihydroxy-5 beta-androstane and 3 beta-hydroxy-14-oxoseco-D-5 beta-androstane as inhibitors of Na(+),K(+)-ATPase at the digitalis receptor. | 2001 Nov 8 |
|
| 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 |
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| [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 |
|
| The endogenous ouabain: molecular basis of its role in hypertension and cardiovascular complications. | 2005 Sep 1 |
|
| Effect of the digitoxigenin derivative, INCICH-D7, on Na+, K+-ATPase. | 2005 Sep 15 |
|
| A new antihypertensive agent that antagonizes the prohypertensive effect of endogenous ouabain and adducin. | 2006 Jan |
|
| Cardenolide genin pattern in Isoplexis plants and shoot cultures. | 2006 Oct |
|
| A stereoselective synthesis of digitoxin and digitoxigen mono- and bisdigitoxoside from digitoxigenin via a palladium-catalyzed glycosylation. | 2006 Sep 14 |
|
| Cardenolides content in wild Sardinian Digitalis purpurea L. populations. | 2007 Jul 20 |
|
| De novo approach to 2-deoxy-beta-glycosides: asymmetric syntheses of digoxose and digitoxin. | 2007 Mar 30 |
|
| Anti-tumor-Promoting activity of tibolone and its metabolites. | 2008 |
|
| A simple chemical method for synthesizing malonyl hemiesters of 21-hydroxypregnanes, potential intermediates in cardenolide biosynthesis. | 2008 Apr |
|
| [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 |
|
| Periplogenin-3-O- -D-glucopyranosyl -(1-->6)- -D-glucopyaranosyl- -(1-->4) -D-cymaropyranoside, isolated from Aegle marmelos protects doxorubicin induced cardiovascular problems and hepatotoxicity in rats. | 2009 Summer |
|
| Inhibitory activity of a phytochemically characterized fraction from Streptocaulon juventas on lung cancer in nude mice. | 2010 Apr |
|
| Cell-based and cytokine-directed chemical screen to identify potential anti-multiple myeloma agents. | 2010 Jul |
|
| Selectivity of digitalis glycosides for isoforms of human Na,K-ATPase. | 2010 Jun 18 |
|
| 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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 08:31:26 GMT 2023
by
admin
on
Sat Dec 16 08:31:26 GMT 2023
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| Record UNII |
S63WOD4VOL
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| Record Status |
Validated (UNII)
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| Record Version |
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DTXSID80162276
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205-603-4
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Digitoxigenin
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S63WOD4VOL
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4369270
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DB04177
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407806
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m4451
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143-62-4
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42219
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