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D5878

Sigma-Aldrich

Digitoxin

≥92% (HPLC), powder

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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:
71-63-6
Molecular Weight:
764.94
Beilstein:
76678
EC Number:
200-760-5
MDL number:
MFCD00003686
UNSPSC Code:
12161501
PubChem Substance ID:
24893976
NACRES:
NA.77

Quality Level

200

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

Gene Information

human ... ATP1A1(476) , ATP1A2(477) , ATP1A3(478) , ATP1A4(480) , ATP1B1(481) , ATP1B2(482) , ATP1B3(483) , FXYD2(486)

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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.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H300,H331,H373

Hazard Classifications

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

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Digitoxin for airway inflammation in cystic fibrosis: preliminary assessment of safety, pharmacokinetics, and dose finding
Zeitlin PL, et al.
Annals of the American Thoracic Society, 14(2), 220-229 (2017)
Compound library screening identified cardiac glycoside digitoxin as an effective growth inhibitor of gefitinib-resistant non-small cell lung cancer via downregulation of ?-tubulin and inhibition of microtubule formation
Zhang YZ, et al.
Molecules (Basel), 21(3), 374-374 (2016)
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)
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