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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:
Molecular Weight:
764.94
Beilstein/REAXYS Number:
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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1 of 4

This Item
BP855PHL825161199002
Digitoxin ≥92% (HPLC), powder

D5878

Digitoxin

Digitoxin British Pharmacopoeia (BP) Reference Standard

BP855

Digitoxin

Digitoxin phyproof® Reference Substance

PHL82516

Digitoxin

Digitoxin United States Pharmacopeia (USP) Reference Standard

1199002

Digitoxin

form

powder

form

-

form

-

form

-

Quality Level

200

Quality Level

-

Quality Level

-

Quality Level

-

solubility

chloroform: soluble

solubility

-

solubility

-

solubility

-

mp

240 °C (dec.) (lit.)

mp

240 °C (dec.) (lit.)

mp

240 °C (dec.) (lit.)

mp

240 °C (dec.) (lit.)

Gene Information

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

Gene Information

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

Gene Information

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

Gene Information

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

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

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk_germany

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges


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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 and its analogs as novel cancer therapeutics
Elbaz HA, et al.
Experimental Hematology & Oncology, 1(1), 4-4 (2012)
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)

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