Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C41H64O14 |
Molecular Weight | 780.9385 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 21 / 21 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(C[C@H](O)[C@H](O[C@@]2([H])C[C@H](O)[C@H](O[C@@]3([H])C[C@H](O)[C@H](O)[C@@H](C)O3)[C@@H](C)O2)[C@@H](C)O1)O[C@H]4CC[C@@]5(C)[C@]([H])(CC[C@]6([H])[C@]5([H])CC[C@]7(C)[C@H]([C@@H](O)C[C@]67O)C8=CC(=O)OC8)C4
InChI
InChIKey=LKRDZKPBAOKJBT-CNPIRKNPSA-N
InChI=1S/C41H64O14/c1-19-36(47)27(42)14-33(50-19)54-38-21(3)52-34(16-29(38)44)55-37-20(2)51-32(15-28(37)43)53-24-8-10-39(4)23(13-24)6-7-26-25(39)9-11-40(5)35(22-12-31(46)49-18-22)30(45)17-41(26,40)48/h12,19-21,23-30,32-38,42-45,47-48H,6-11,13-18H2,1-5H3/t19-,20-,21-,23-,24+,25+,26-,27+,28+,29+,30+,32+,33+,34+,35+,36-,37-,38-,39+,40-,41+/m1/s1
Molecular Formula | C41H64O14 |
Molecular Weight | 780.9385 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 21 / 21 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Gitoxin is a cardiac glycoside from the Woolly Foxglove (Digitalis lanata), may be studied for its potential cardiac applications similar to those of digoxin. Gitoxin acts as in inhibitor of the sodium and potassium ion channels, interfering with ATPase activity and used in cancer treatment as a growth inhibitor. Gitoxin is a starting material for the synthesis of gitoxin derivatives with activity as cardiac glycosides. Although the cardiotonic activity of gitoxin is known for almost half a century, this digitalis glycoside has never been used in therapy, due to its apparent lack of resorption after administration by oral route.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P05023|||Q9UJ20 Gene ID: 476.0 Gene Symbol: ATP1A1 Target Organism: Homo sapiens (Human) |
123.0 nM [Kd] | ||
Target ID: P50993 Gene ID: 477.0 Gene Symbol: ATP1A2 Target Organism: Homo sapiens (Human) |
85.0 nM [Kd] | ||
Target ID: P13637 Gene ID: 478.0 Gene Symbol: ATP1A3 Target Organism: Homo sapiens (Human) |
108.0 nM [Kd] | ||
Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14531018 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Phage display-selected sequences of the heavy-chain CDR3 loop of the anti-digoxin antibody 26-10 define a high affinity binding site for position 16-substituted analogs of digoxin. | 2001 Mar 16 |
|
Modifying specificity of antidigoxin antibodies using insertional mutagenesis. | 2002 Dec |
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Anti-tumour activity of Digitalis purpurea L. subsp. heywoodii. | 2003 Aug |
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Effects of digoxin and gitoxin on the enzymatic activity and kinetic parameters of Na+/K+-ATPase. | 2004 Oct |
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Simple coacervates of zein to encapsulate Gitoxin. | 2006 Aug 1 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7406600
Curator's Comment: Humans: Gitoxin given as a solution is quasi-completely absorbed after oral administration in a fasting man. A dose of 1.5 mg modifies the left ventricular ejection time index (LVETI) as digoxin or digitoxin does. https://www.ncbi.nlm.nih.gov/pubmed/700907
Kinetics and metabolism of 3H-gitoxin were determined in the guinea-pig after the i.v. administration of 80 ug gitoxin/kg.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15648655
The activity of Na+/K+-ATPase was measured as a
function of the separate exposure to digoxin and
gitoxin within the concentration range from 1 x 10(-10) to 1 x 10(-3) M in the incubation mixture. The simultaneous exposure to
high concentrations of inhibitors, digoxin(mmol)/
gitoxin(mmol) concentrations of 0.1/1.0 and 10/0.1
inhibited erythrocyte Na+/K+-ATPase activity
antagonistically.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:44:35 GMT 2023
by
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on
Fri Dec 15 15:44:35 GMT 2023
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Record UNII |
VOR2TD6SO4
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Record Status |
Validated (UNII)
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28503
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4562-36-1
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Gitoxin
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91540
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DTXSID10101700
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100000078185
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C005003
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SUB13969MIG
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m5739
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VOR2TD6SO4
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PARENT -> IMPURITY |
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