DIGITOXIGENIN

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28139268
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

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium/potassium-transporting ATPase 39 Target ID: CHEMBL2095186 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20016840	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20016840	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Measurement of serum digitoxin in patients by radioimmunoassay using specific antiserum.	2001 Dec	11718703
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	12904068
A new antihypertensive agent that antagonizes the prohypertensive effect of endogenous ouabain and adducin.	2006 Jan	16529550
Anti-tumor-Promoting activity of tibolone and its metabolites.	2008	18412022
A simple chemical method for synthesizing malonyl hemiesters of 21-hydroxypregnanes, potential intermediates in cardenolide biosynthesis.	2008 Apr	18249427
[Chemical constituents of Periploca forrestii].	2009 Dec	20353006
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	19426248
Cell-based and cytokine-directed chemical screen to identify potential anti-multiple myeloma agents.	2010 Jul	20116850

Patents

Sample Use Guides

In Vivo Use Guide

LD50 (cat) = 0.6mg/kg LD50 (guinea-pig) = 2,65 mg/kg

Route of Administration: Intravenous

In Vitro Use Guide

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

DIGITOXIGENIN

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