Page last updated: 2024-11-06

gitoxin

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Gitoxin is a cardiac glycoside extracted from the foxglove plant (Digitalis lanata). It is a potent inhibitor of the sodium-potassium ATPase pump in the heart, which leads to an increase in intracellular calcium and a strengthening of heart muscle contractions. This effect makes gitoxin useful in treating heart failure, but it also carries a significant risk of toxicity. Due to its narrow therapeutic index and the availability of safer alternatives, gitoxin is rarely used in modern medicine. Research on gitoxin continues to focus on understanding its mechanism of action, exploring potential therapeutic applications, and developing safer and more effective cardiac glycosides.'

gitoxin: an isomer of digoxin; the OH group which is in the C16 position while it is in the C12 position for Digoxin [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

gitoxin : A cardenolide glycoside that is gitoxigenin in which the 3beta-hydroxy group has been glycosylated with tridigitoxose. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID91540
CHEMBL ID109317
CHEBI ID28503
SCHEMBL ID309847
MeSH IDM0046268

Synonyms (40)

Synonym
card-20(22)-enolide, 3-((o-2,6-dideoxy-beta-d-ribo-hexopyranosyl-(1-4)-o-2,6-dideoxy-beta-d-ribo-hexopyranosyl-(1-4)-2,6-dideoxy-beta-d-ribo-hexopyranosyl)oxy)-14,16-dihydroxy-, (3beta,5beta,16beta)-
einecs 224-934-5
nsc 95099
gitoxigenin-tridigitoxosid [german]
brn 0077015
3beta-[2,6-dideoxy-beta-d-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-d-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-d-ribo-hexopyranosyloxy]-14,16beta-dihydroxy-5beta-card-20(22)-enolide
CHEBI:28503 ,
anhydrogitalin
nsc-95099
gitoksin
bigitalin
gitoxim
pseudodigitoxin
gitoxigenin 3-o-tridigitoxoside
C08866
4562-36-1
gitoxin
CHEMBL109317
LMST01120017
3beta-[2,6-dideoxy-beta-d-ribo-hexopyranosyl-(1-4)-2,6-dideoxy-beta-d-ribo-hexopyranosyl-(1-4)-2,6-dideoxy-beta-d-ribo-hexopyranosyloxy]-14,16beta-dihydroxy-5beta-card-20(22)-enolide
3-[(3s,5r,8r,9s,10s,13r,14s,16s,17r)-3-[(2r,4s,5s,6r)-5-[(2s,4s,5s,6r)-5-[(2s,4s,5s,6r)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-14,16-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tet
gitoxigenin-tridigitoxosid
vor2td6so4 ,
unii-vor2td6so4
SCHEMBL309847
gitoxin [mi]
3.beta.-((2,6-dideoxy-.beta.-d-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-.beta.-d-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-.beta.-d-ribo-hexopyranosyl)oxy)-14,16.beta.-dihydroxy-5.beta.-card-20(22)-enolide
(3.beta.,5.beta.,16.beta.)-3-((o-2,6-dideoxy-.beta.-d-ribo-hexopyranosyl-(1->4)-o-2,6-dideoxy-.beta.-d-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-.beta.-d-ribo-hexopyranosyl)oxy)-14,16-dihydroxycard-20(22)-enolide
gitoxin [who-dd]
W-202805
gitoxin, >=99% (hplc)
gitoxin, united states pharmacopeia (usp) reference standard
gitoxin, european pharmacopoeia (ep) reference standard
LKRDZKPBAOKJBT-CNPIRKNPSA-N
Q27103741
DTXSID101017007
CS-0135363
HY-136933
AT38443
AKOS040761783

Research Excerpts

Effects

ExcerptReferenceRelevance
"Gitoxin has been compared in these experimental conditions with digoxin, one of the most often used cardiotonic's."( Hepatic clearance of gitoxin: pharmacokinetic study on rabbit isolated liver. Influence of protein binding and comparison with digoxin.
Lesne, M; Pellegrin, P, 1983
)
1.31

Pharmacokinetics

ExcerptReferenceRelevance
" Pharmacokinetic parameters were estimated for the liposoluble (dichloromethane soluble) material in the water phase obtained by centrifugation of the emulsion, for the liposoluble material and unchanged gitoxin in the total emulsion."( A further study of the pharmacokinetics of gitoxin in rabbit isolated liver: clearance of 3H-gitoxin.
Lesne, M; Pellegrin, PL,
)
0.58
" Other pharmacokinetic parameters (alpha, beta, V1, V2."( Hepatic clearance of gitoxin: pharmacokinetic study on rabbit isolated liver. Influence of protein binding and comparison with digoxin.
Lesne, M; Pellegrin, P, 1983
)
0.58
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
cardenolide glycosideAny member of the class of cardenolides with glycosyl residues attached to position 3.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID977602Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID127350Binding affinity against human monoclonal antibody (mAb)-1B32002Journal of medicinal chemistry, Jul-18, Volume: 45, Issue:15
Three-dimensional quantitative structure-activity relationship analysis of ligand binding to human sequence antidigoxin monoclonal antibodies using comparative molecular field analysis.
AID127352Binding affinity against human monoclonal antibody (mAb)-7F22002Journal of medicinal chemistry, Jul-18, Volume: 45, Issue:15
Three-dimensional quantitative structure-activity relationship analysis of ligand binding to human sequence antidigoxin monoclonal antibodies using comparative molecular field analysis.
AID127479Binding affinity against murine monoclonal antibody (mAb)-40-502002Journal of medicinal chemistry, Jul-18, Volume: 45, Issue:15
Three-dimensional quantitative structure-activity relationship analysis of ligand binding to human sequence antidigoxin monoclonal antibodies using comparative molecular field analysis.
AID399010Cytotoxicity against human TK10 cells after 48 hrs by SRB assay2005Journal of natural products, Nov, Volume: 68, Issue:11
Digitoxin inhibits the growth of cancer cell lines at concentrations commonly found in cardiac patients.
AID399012Cytotoxicity against human UACC62 cells after 48 hrs by SRB assay2005Journal of natural products, Nov, Volume: 68, Issue:11
Digitoxin inhibits the growth of cancer cell lines at concentrations commonly found in cardiac patients.
AID399011Cytotoxicity against human MCF7 cells after 48 hrs by SRB assay2005Journal of natural products, Nov, Volume: 68, Issue:11
Digitoxin inhibits the growth of cancer cell lines at concentrations commonly found in cardiac patients.
AID127349Binding affinity against human monoclonal antibody (mAb)-11E62002Journal of medicinal chemistry, Jul-18, Volume: 45, Issue:15
Three-dimensional quantitative structure-activity relationship analysis of ligand binding to human sequence antidigoxin monoclonal antibodies using comparative molecular field analysis.
AID977599Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID335137DNA damaging activity against DNA repair-deficient Saccharomyces cerevisiae W303-1A RS188N mutant assessed as drug concentration required to produce 12 mm zone of inhibition up to 800 ug/well by agar diffusion assay1993Journal of natural products, Sep, Volume: 56, Issue:9
A screen for inhibitors of DNA recombination: identification of two new spirostanol glycosides from Chamaedorea linearis.
AID357577Binding affinity to mouse Monoclonal antibody DIG 64.2B.5 by ELISA relative to digoxin
AID127351Binding affinity against human monoclonal antibody (mAb)-5C22002Journal of medicinal chemistry, Jul-18, Volume: 45, Issue:15
Three-dimensional quantitative structure-activity relationship analysis of ligand binding to human sequence antidigoxin monoclonal antibodies using comparative molecular field analysis.
AID1159550Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening2015Nature cell biology, Nov, Volume: 17, Issue:11
6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (45)

TimeframeStudies, This Drug (%)All Drugs %
pre-199028 (62.22)18.7374
1990's8 (17.78)18.2507
2000's6 (13.33)29.6817
2010's3 (6.67)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 46.19

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index46.19 (24.57)
Research Supply Index4.03 (2.92)
Research Growth Index4.16 (4.65)
Search Engine Demand Index72.10 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (46.19)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (1.85%)5.53%
Reviews2 (3.70%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other51 (94.44%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]