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
C[C@H]1O[C@H](C[C@H](O)[C@@H]1O)O[C@H]2[C@@H](O)C[C@H](O[C@H]3[C@@H](O)C[C@H](O[C@H]4CC[C@@]5(C)[C@H](CC[C@@H]6[C@@H]5CC[C@]7(C)[C@H]([C@@H](O)C[C@]67O)C8=CC(=O)OC8)C4)O[C@@H]3C)O[C@@H]2C
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 |
|---|---|---|
| Simple coacervates of zein to encapsulate Gitoxin. | 2006-08-01 |
|
| Effects of digoxin and gitoxin on the enzymatic activity and kinetic parameters of Na+/K+-ATPase. | 2004-10 |
|
| Anti-tumour activity of Digitalis purpurea L. subsp. heywoodii. | 2003-08 |
|
| Modifying specificity of antidigoxin antibodies using insertional mutagenesis. | 2002-12 |
|
| Complementary combining site contact residue mutations of the anti-digoxin Fab 26-10 permit high affinity wild-type binding. | 2002-05-10 |
|
| A single H:CDR3 residue in the anti-digoxin antibody 26-10 modulates specificity for C16-substituted digoxin analogs. | 2001-04 |
|
| 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. | 2001-03-16 |
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
Mon Mar 31 18:07:18 GMT 2025
by
admin
on
Mon Mar 31 18:07:18 GMT 2025
|
| Record UNII |
VOR2TD6SO4
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Preferred Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
28503
Created by
admin on Mon Mar 31 18:07:18 GMT 2025 , Edited by admin on Mon Mar 31 18:07:18 GMT 2025
|
PRIMARY | |||
|
4562-36-1
Created by
admin on Mon Mar 31 18:07:18 GMT 2025 , Edited by admin on Mon Mar 31 18:07:18 GMT 2025
|
PRIMARY | |||
|
95099
Created by
admin on Mon Mar 31 18:07:18 GMT 2025 , Edited by admin on Mon Mar 31 18:07:18 GMT 2025
|
PRIMARY | |||
|
3262
Created by
admin on Mon Mar 31 18:07:18 GMT 2025 , Edited by admin on Mon Mar 31 18:07:18 GMT 2025
|
PRIMARY | |||
|
Gitoxin
Created by
admin on Mon Mar 31 18:07:18 GMT 2025 , Edited by admin on Mon Mar 31 18:07:18 GMT 2025
|
PRIMARY | |||
|
91540
Created by
admin on Mon Mar 31 18:07:18 GMT 2025 , Edited by admin on Mon Mar 31 18:07:18 GMT 2025
|
PRIMARY | |||
|
100000078185
Created by
admin on Mon Mar 31 18:07:18 GMT 2025 , Edited by admin on Mon Mar 31 18:07:18 GMT 2025
|
PRIMARY | |||
|
DTXSID101017007
Created by
admin on Mon Mar 31 18:07:18 GMT 2025 , Edited by admin on Mon Mar 31 18:07:18 GMT 2025
|
PRIMARY | |||
|
C005003
Created by
admin on Mon Mar 31 18:07:18 GMT 2025 , Edited by admin on Mon Mar 31 18:07:18 GMT 2025
|
PRIMARY | |||
|
SUB13969MIG
Created by
admin on Mon Mar 31 18:07:18 GMT 2025 , Edited by admin on Mon Mar 31 18:07:18 GMT 2025
|
PRIMARY | |||
|
m5739
Created by
admin on Mon Mar 31 18:07:18 GMT 2025 , Edited by admin on Mon Mar 31 18:07:18 GMT 2025
|
PRIMARY | Merck Index | ||
|
224-934-5
Created by
admin on Mon Mar 31 18:07:18 GMT 2025 , Edited by admin on Mon Mar 31 18:07:18 GMT 2025
|
PRIMARY | |||
|
VOR2TD6SO4
Created by
admin on Mon Mar 31 18:07:18 GMT 2025 , Edited by admin on Mon Mar 31 18:07:18 GMT 2025
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|