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D5878

Sigma-Aldrich

Digitoxin

≥92% (HPLC), powder

Synonym(s):
5β,20(22)-Cardenolide-3β,14-diol-3-(O-2,6-dideoxy-β-D-ribo-hexopyranosyl-[1→4]-O-2,6-dideoxy-β-D-ribo-hexopyranosyl-[1→4]-2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy, Digitoxoside, Lanatoxin
Empirical Formula (Hill Notation):
C41H64O13
CAS Number:
Molecular Weight:
764.94
Beilstein:
76678
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥92% (HPLC)

form

powder

mp

240 °C (dec.) (lit.)

solubility

chloroform: soluble

SMILES string

[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])(CC[C@]67O)C8=CC(=O)OC8)C4

InChI

1S/C41H64O13/c1-20-36(46)29(42)16-34(49-20)53-38-22(3)51-35(18-31(38)44)54-37-21(2)50-33(17-30(37)43)52-25-8-11-39(4)24(15-25)6-7-28-27(39)9-12-40(5)26(10-13-41(28,40)47)23-14-32(45)48-19-23/h14,20-22,24-31,33-38,42-44,46-47H,6-13,15-19H2,1-5H3/t20-,21-,22-,24-,25+,26-,27+,28-,29+,30+,31+,33+,34+,35+,36-,37-,38-,39+,40-,41+/m1/s1

InChI key

WDJUZGPOPHTGOT-XUDUSOBPSA-N

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General description

Digitoxin is a cardiac glycoside (CG). It is a cardiotonic drug, which exhibits cardiac and anti-cancer properties. Digitoxin inhibits nuclear factor kappa B (NF-κB) signaling. It is used to treat congestive heart failure and cardiac arrhythmia. Digitoxin prevents microtubule formation.

Application

Digitoxin has been used as a labeled drugs for binding sites on human serum albumin (HSA). It has also been used to test its anti-transmissible gastroenteritis virus (TGEV) activity.

Packaging

1, 5, 10 g in glass bottle
250, 500 mg in glass bottle

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 2 Oral - Acute Tox. 3 Inhalation - STOT RE 2

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Biointeractions of herbicide atrazine with human serum albumin: UV-Vis, fluorescence and circular dichroism approaches
Zhu M, et al.
International Journal of Environmental Research and Public Health, 15(1), 116-116 (2018)
Identification of anti-viral activity of the cardenolides, Na+/K+-ATPase inhibitors, against porcine transmissible gastroenteritis virus
Yang CW, et al.
Toxicology and Applied Pharmacology, 337, 129-137 (2017)
Digitoxin and its analogs as novel cancer therapeutics
Elbaz HA, et al.
Experimental Hematology & Oncology, 1(1), 4-4 (2012)
A stereoselective synthesis of digitoxin and digitoxigen mono-and bisdigitoxoside from digitoxigenin via a palladium-catalyzed glycosylation
Zhou M and George AO
Experimental Hematology & Oncology, 8(19), 4339-4342 (2006)
Comparative interactions of dihydroquinazolin derivatives with human serum albumin observed via multiple spectroscopy
Wang Y, et al.
Applied Sciences, 7(2), 200-200 (2017)

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