EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

gitoxin
gitoxoside

Supplier Sponsors

CAS Number: 4562-36-1Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:224-934-5
FDA UNII: VOR2TD6SO4
Nikkaji Web:J20.339D
Beilstein Number:0077015
MDL:MFCD00021173
XlogP3:1.50 (est)
Molecular Weight:780.94988000
Formula:C41 H64 O14
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 285.00 °C. @ 760.00 mm Hg
Boiling Point: 932.00 °C. @ 760.00 mm Hg (est)
Flash Point: 533.00 °F. TCC ( 278.60 °C. ) (est)
logP (o/w): 1.670
Soluble in:
 water, 0.3776 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Digoxin Impurity B > 95%
Odor: characteristic
Use: Digoxin Impurity.
Carbosynth
For experimental / research use only.
Gitoxin
ExtraSynthese
For experimental / research use only.
Gitoxin (HPLC) ≥99%
Santa Cruz Biotechnology
For experimental / research use only.
Gitoxin ≥98%
Sigma-Aldrich: Sigma
For experimental / research use only.
Gitoxin ≥99% (HPLC)
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-cat LD50 > 25 mg/kg
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 159, Pg. 1, 1966.

intravenous-cat LDLo 590 ug/kg
Toxicon. Vol. 8, Pg. 85, 1970.

unreported-cat LDLo 222 ug/kg
Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 37, Pg. 364, 1948.

oral-guinea pig LD50 > 130 mg/kg
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 159, Pg. 1, 1966.

intravenous-guinea pig LDLo 4400 ug/kg
CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 155, Pg. 251, 1965.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for gitoxin usage levels up to:
 not for fragrance use.
 
Recommendation for gitoxin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :91540
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
Chemidplus:0004562361
RTECS:LZ0525000 for cas# 4562-36-1
 
References:
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):91540
Pubchem (sid):135047872
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C08866
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
 anhydrogitalin
 bigitalin
pseudodigitoxin
 gitoksin
 gitoxigenin-tridigitoxosid
 gitoxim
 gitoxoside
 

Articles:

PubMed:Hellebrin and its aglycone form hellebrigenin display similar in vitro growth inhibitory effects in cancer cells and binding profiles to the alpha subunits of the Na+/K+-ATPase.
PubMed:A structural view on the functional importance of the sugar moiety and steroid hydroxyls of cardiotonic steroids in binding to Na,K-ATPase.
PubMed:HPLC method validation for Digitalis and its analogue by pulsed amperometric detection.
PubMed:Simple coacervates of zein to encapsulate Gitoxin.
PubMed:Effects of digoxin and gitoxin on the enzymatic activity and kinetic parameters of Na+/K+-ATPase.
PubMed:Anti-tumour activity of Digitalis purpurea L. subsp. heywoodii.
PubMed:Modifying specificity of antidigoxin antibodies using insertional mutagenesis.
PubMed:Complementary combining site contact residue mutations of the anti-digoxin Fab 26-10 permit high affinity wild-type binding.
PubMed:A single H:CDR3 residue in the anti-digoxin antibody 26-10 modulates specificity for C16-substituted digoxin analogs.
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.
PubMed:A non-fatal case of intoxication with foxglove, documented by means of liquid chromatography-electrospray-mass spectrometry.
PubMed:Cardiovascular activity of a methanolic extract of Digitalis purpurea spp. heywoodii.
PubMed:Multiresidue screen for cardiotoxins by two-dimensional thin-layer chromatography.
PubMed:Monoclonal antibodies that distinguish between two related digitalis glycosides, ouabain and digoxin.
PubMed:Induction of digoxin-like material production, and the digoxin binding in the unicellular organism Tetrahymena by digitoxin.
PubMed:Studies on cardiac ingredients of plants. XIII: Chemical modification of gitoxin to cardiotonic compounds without vascular effect.
PubMed:Ultra-specific immunoassays for small molecules: roles of wash steps and multiple binding formats.
PubMed:Structure and specificity of the anti-digoxin antibody 40-50.
PubMed:Extraordinary efficacy of 16 alpha-gitoxin, an ultra-short acting semi-synthetic digitalis glycoside.
PubMed:Recovery of digoxin and related glycosides from an injection dosage form by liquid-liquid and solid-phase extraction.
PubMed:High-performance thin-layer chromatographic determination of digoxin and related compounds, digoxigenin bisdigitoxoside and gitoxin, in digoxin drug substance and tablets.
PubMed:Altered hapten recognition by two anti-digoxin hybridoma variants due to variable region point mutations.
PubMed:High-performance liquid chromatographic determination of secondary cardiac glycosides in Digitalis purpurea leaves.
PubMed:High sensitivity of the Na+, K+-pump of human red blood cells to genins of cardiac glycosides.
PubMed:Pharmacokinetics of pengitoxin and its therapeutic efficacy in congestive heart failure.
PubMed:Human cell mutants affected in the interaction of the 12 beta-OH group of cardiac glycosides with the digitalis receptor.
PubMed:Elimination of 16-acetyl-gitoxin in patients suffering from impaired liver function.
PubMed:Dose-dependent shortening of systolic time intervals after intake of pengitoxin.
PubMed:Uptake and liberation of [3H]16-acetyl-gitoxin in the isolated guinea pig atrium.
PubMed:On the pharmacokinetics of 16-acetyl-gitoxin and its bioavailability from pengitoxin-containing tablet formulations.
PubMed:Cellular basis for the species differences in sensitivity to cardiac glycosides (digitalis).
PubMed:Laser desorption/Fourier transform mass spectra of glycoalkaloids and steroid glycosides.
PubMed:Biochemical and cross-resistance studies with HeLa cell mutants resistant to cardiac glycoside SC4453. Regulation of the resistant form of Na+/K+-ATPase in the mutant cells.
PubMed:A new alternative in the field of cardiac glycosides: gitoxin.
PubMed:Gitoxin--a challenger for digoxin?
PubMed:Cross-resistance and biochemical studies with two classes of HeLa cell mutants resistant to cardiac glycosides. The unusual behavior of cardenolide SC4453.
PubMed:A further study of the pharmacokinetics of gitoxin in rabbit isolated liver: clearance of 3H-gitoxin.
PubMed:Synthesis and biological activity of some cardiotonic compounds related to gitoxigenin.
PubMed:[Plasma levels of gitoxin (by RIA and rubidium-86 uptake) and systolic time after treatment with a single dose of gitoformate].
PubMed:Hepatic clearance of gitoxin. Metabolism and biliary excretion by rabbit isolated liver.
PubMed:Therapeutic range of cardiac glycosides.
PubMed:Hepatic clearance of gitoxin: pharmacokinetic study on rabbit isolated liver. Influence of protein binding and comparison with digoxin.
PubMed:On the pharmacokinetics of pengitoxin and its cardioactive derivative 16-acetyl-gitoxin.
PubMed:Metabolism of gitoxin by the rabbit isolated liver.
PubMed:Bio-Transformation of (G-3H)-digitoxin and (G-3H)-digoxin by Digitalis purpurea.
PubMed:Studies on the pharmacokinetics and the metabolism of gitoxin in the guinea-pig: II. the enteral absorption and the enterohepatic recirculation.
PubMed:Separation of digoxin, digitoxin and their potential metabolites, impurities or degradation products by high-performance liquid chromatography.
PubMed:Isolation and mass spectrometric identification of gitoxin metabolites excreted in bile.
PubMed:Contrasting effect on cardiac output of digoxin and gitoxin in humans during congestive heart failure.
PubMed:Cardiac glycosides and their metabolites levels in plasma and heart of guinea-pigs after I. V. administration.
PubMed:On the plasma protein binding of 16-acetyl-gitoxin.
PubMed:Reverse phase thin layer chromatographic procedure for identification of digoxin and related fluorescing substances.
PubMed:Direct radioimmunoassay for the determination of 16-acetyl-gitoxin in serum.
PubMed:Studies on the pharmacokinetics and the metabolism of gitoxin in the guinea-pig: I. Disposition kinetics following an i.v. bolus of 3H-gitoxin.
PubMed:Studies on cardioactive steroids. V. Structure-activity relationships of derivatives of 16 alpha-gitoxin.
PubMed:Binding of digitoxin, digoxin and gitoxin to human serum albumin.
PubMed:Uptake and pharmacological effect of gitoxin and gitaloxin in rat and guinea-pig perfused hearts. Comparison with digitoxin and digoxin.
PubMed:The binding of gitoxin to human plasma proteins.
PubMed:Perfusion of rabbit's liver with gitoxin: application of a model of compartmental analysis to preliminary results.
PubMed:Comparative study of the pharmacological effects and the binding of gitoxin, gitaloxin, digitoxin and digoxin to isolated guinea-pig hearts.
PubMed:Bioavailability study of gitoxin in a solid dosage form.
PubMed:[Comparative study of myocardial and plasma radioactivity following bolus injections of various amounts of tritiated gitoxin, digitoxin and digoxin to guinea-pigs (author's transl)].
PubMed:[Kinetic of elimination of gitoxin by isolated and perfused rabbit liver: application of two models for compartmental analysis (author's transl)].
PubMed:[Preliminary aspects of the distribution and elimination of tritiated gitoxin in guinea-pig (author's transl)].
PubMed:Investigation into the species-specific deacylation of penta-acetyl-gitoxin.
PubMed:Pharmacological reevaluation of gitoxin in man.
PubMed:Reduction of the equilibrium binding of cardiac glycosides and related compounds to Na+,K+-ATPase as a possible mechanism for the potassium-induced reversal of their toxicity.
PubMed:Measurement of plasma glycoside level following pengitoxin administration.
PubMed:[Clinical experience with the cardiac glycoside Gitoformat (author's transl)].
PubMed:Pharmacokinetic investigations with 3H-penta-acetyl-gitoxin in volunteers and patients with respect to the occurrence of drug latentiation.
PubMed:Cardiac effects of 16-acetyl-gitoxin, the active glycoside after penta-acetyl-gitoxin administration.
PubMed:Kinetic properties of 3H-16alpha-gitoxin in the isolated guinea-pig atrium.
PubMed:Pharmacokinetic investigations in man of two acetyl derivatives of 16alpha-gitoxin.
PubMed:Penta-acetyl-gitoxin: the prototype of a prodrug in the cardiac glycoside series.
PubMed:Binding of 16alpha-gitoxin and its 16-acetate to human serum albumin.
PubMed:Absorption and metabolism in man of 16-epi-gitoxin, a new semi-synthetic cardioactive glycoside.
PubMed:Some pharmacological studies on the cardiotonic effects of furanosteroidal glycosides.
PubMed:Extraordinary cardiac effects of 16-epi-gitoxin in comparison to ouabain in cats and dogs.
PubMed:[Fluorescent method of determining the activity of gitoxin].
PubMed:Different toxic effects of ouabain and 16-epi-gitoxin on Purkinje fibres and ventricular muscle fibres.
PubMed:Isolation and quantitation of picomole quantities of digoxin, digitoxin and their metabolites by high-pressure liquid chromatography.
PubMed:Studies on cardioactive steroids. III. Characterization of different cardiac glycosides by their effects on contractility and rhythmicity at different extracellular potassium concentrations.
PubMed:[Cardiac effect of a new penta-acetylated gitoxin (pengitoxin)].
PubMed:[Resorption of derivatives of gitoxin and helveticosol in rat jejunum].
PubMed:Quantitative determination of digitoxin, gitaloxin, gitoxin, verodoxin and strospesid in the leaves of Digitalis purpurea by means of fluorescence.
PubMed:Comparison of therapeutic and toxic actions of ouabain, gitoxin and 16-epi-gitoxin on isolated atria at different extracellular potassium concentrations.
PubMed:Rapid identification and estimation of gitoxin in digitoxin and digoxin tablets by TLC.
PubMed:[Application of diffuse reflection and fluorescence for direct determination of digitaloids on chromatographic plates. 1. Determination of digitoxin, gitoxin and digoxin by fluorescence].
PubMed:[Spectrophotometric method for the quantitative determination of digitoxin, gitoxin, celanide and digoxin].
PubMed:Different relationships between therapeutic and toxic actions of 16-epi-gitoxin, gitoxin and ouabain on isolated cardiac preparations.
PubMed:Colorimetric assay of digitoxin and gitoxin in mixtures after thin-layer chromatographic separation.
PubMed:A fluorometric determination of myocardial digoxin at autopsy, with identification of digitalis leaf, digitoxin, and gitoxin.
PubMed:Studies on digitalis glycosides. Gitoxin acetates. 2. Deacetylation of pentaacetylgitoxin with liver and heart homogenates.
PubMed:Studies on digitalis glycosides. XXVI. Gitoxin acetates. (1). Deacetylation of pentaacetylgitoxin.
PubMed:[Identification of a mono-formyl-xi-gitoxin obtained after formylation of gitoxin].
PubMed:[Determination of digitoxin and gitoxin in digitalis leaves according to the foregoing thin-layer chromatographic isolation].
PubMed:Clinical trial of a new cardiotonic agent: AC 2770, a pentaformylated derivative of gitoxin.
PubMed:[CARDIAC THERAPY WITH PENTA-ACETYL-GITOXIN, A NEW HALF-SYNTHETIC PURPUREAGLYCOSIDE].
PubMed:[CLINICAL TRIAL OF A NEW CARDIOTONIC AGENT (16-FORMYL-GITOXIN) IN PATIENTS WITH CARDIAC INSUFFICIENCY].
PubMed:[CLINICAL STUDY OF A NEW DIGITALIS DRUG: 16-FORMYL-GITOXIN].
PubMed:[The determination of gitoxin].
PubMed:[Analysis of the cardiotonic activity of gitoxin and gitoxigenin in the guinea pig].
PubMed:[Preparation of pure digitoxin & gitoxin].
PubMed:Studies on digitalis glycosides: acetylgitoxin-alpha from gitoxin.
PubMed:Studies on digitalis glycosides. VII. Gitoroside, digitalonin, and gitoxin pentaacetate.
PubMed:[Effect of gitoxin on the cardiovascular system].
PubMed:[Method of chemical assay of digitoxin-gitoxin mixtures and digitalis drugs].
PubMed:[Clinical studies on gitoxin. I. The problem of the effects of enteral gitoxin administration on the human heart].
PubMed:[Investigations on pharmacodynamics of gitoxin].
PubMed:[Clinical use of digitalis; combined digitoxin and gitoxin (crystafolin CIBA) in the therapy of cardiovascular disorders].
PubMed:[The fluorometric determination of gitoxin].
PubMed:[Enteral resorption of lanatosid A, B and C and gitoxin in cat and dog].
PubMed:Paper-chromatographic separation and fluorimetric determination of gitoxigenin, gitoxin, and purpureaglycoside B.
PubMed:[Enteral resorption of digitoxin and gitoxin].
PubMed:[Biologic evaluation of the effects of gitoxin with the aid of a surface active solvent].
PubMed:A polarographic method for the determination of digitoxin and gitoxin and its application to pharmacological studies.
 
Notes:
an isomer of digoxin; the oh group which is in the c16 position while it is in the c12 position for digoxin.
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