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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
Structure of DIGITOXIGENIN

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

HIDE SMILES / InChI

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

Description
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

Sources: Berichte der Deutschen Chemischen Gesellschaft (1918), 51, 1613-39.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Defective activity and isoform of the Na,K-ATPase in the dilated cardiomyopathic hamster.
2001 Mar
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
A simple chemical method for synthesizing malonyl hemiesters of 21-hydroxypregnanes, potential intermediates in cardenolide biosynthesis.
2008 Apr
Interaction between cardiotonic steroids and Na,K-ATPase. Effects of pH and ouabain-induced changes in enzyme conformation.
2009 Oct 27
Cell-based and cytokine-directed chemical screen to identify potential anti-multiple myeloma agents.
2010 Jul
Electrophysiological characterization of ATPases in native synaptic vesicles and synaptic plasma membranes.
2010 Mar 15
12β,14-Dihy-droxy-3-oxo-5β,20(22)-cardenolide monohydrate.
2010 Oct 2
Patents

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 Sat Dec 16 08:31:26 GMT 2023
Edited
by admin
on Sat Dec 16 08:31:26 GMT 2023
Record UNII
S63WOD4VOL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIGITOXIGENIN
MI  
Common Name English
CERBERIGENIN
Common Name English
CARD-20(22)-ENOLIDE, 3,14-DIHYDROXY-, (3.BETA.,5.BETA.)-
Common Name English
(+)-DIGITOXIGENIN
Common Name English
NSC-407806
Code English
.DELTA.20:22-3,14,21-TRIHYDROXYNORCHOLENIC ACID LACTONE
Common Name English
DIGITOXIGENIN [MI]
Common Name English
Code System Code Type Description
EPA CompTox
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
ECHA (EC/EINECS)
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
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WIKIPEDIA
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
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FDA UNII
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
PUBCHEM
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
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DRUG BANK
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
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NSC
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
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MERCK INDEX
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
CAS
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
CHEBI
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