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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
Structure of GITOXIN

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

HIDE SMILES / InChI

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.

Originator

Curator's Comment: Gitoxin was first prepared in an impure state by Kraft

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
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]
Conditions
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [Inhibition 10 uM]
yes [Inhibition 10 uM]
PubMed

PubMed

TitleDatePubMed
A single H:CDR3 residue in the anti-digoxin antibody 26-10 modulates specificity for C16-substituted digoxin analogs.
2001 Apr
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
Complementary combining site contact residue mutations of the anti-digoxin Fab 26-10 permit high affinity wild-type binding.
2002 May 10
Anti-tumour activity of Digitalis purpurea L. subsp. heywoodii.
2003 Aug
Effects of digoxin and gitoxin on the enzymatic activity and kinetic parameters of Na+/K+-ATPase.
2004 Oct
Simple coacervates of zein to encapsulate Gitoxin.
2006 Aug 1
Patents

Sample Use Guides

In Vivo Use Guide
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
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 Fri Dec 15 15:44:35 GMT 2023
Edited
by admin
on Fri Dec 15 15:44:35 GMT 2023
Record UNII
VOR2TD6SO4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GITOXIN
MI   USP-RS   WHO-DD  
Common Name English
NSC-95099
Code English
(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
Common Name English
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
Systematic Name English
ANHYDROGITALIN
Common Name English
BIGITALIN
Common Name English
GITOXIN [MI]
Common Name English
PSEUDODIGITOXIN
Common Name English
Gitoxin [WHO-DD]
Common Name English
Code System Code Type Description
CHEBI
28503
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
PRIMARY
CAS
4562-36-1
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
PRIMARY
NSC
95099
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
PRIMARY
DRUG CENTRAL
3262
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
PRIMARY
WIKIPEDIA
Gitoxin
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
PRIMARY
PUBCHEM
91540
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
PRIMARY
EPA CompTox
DTXSID10101700
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
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SMS_ID
100000078185
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
PRIMARY
MESH
C005003
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
PRIMARY
EVMPD
SUB13969MIG
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
PRIMARY
MERCK INDEX
m5739
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
224-934-5
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
PRIMARY
FDA UNII
VOR2TD6SO4
Created by admin on Fri Dec 15 15:44:35 GMT 2023 , Edited by admin on Fri Dec 15 15:44:35 GMT 2023
PRIMARY
Related Record Type Details
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