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Merck
CN

D1800000

Digitoxin

European Pharmacopoeia (EP) Reference Standard

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

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About This Item

Empirical Formula (Hill Notation):
C41H64O13
CAS Number:
71-63-6
Molecular Weight:
764.94
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329798710
MDL number:
MFCD00003686
Beilstein/REAXYS Number:
76678

Key Documents

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Product Name

Digitoxin, European Pharmacopoeia (EP) Reference Standard

InChI key

WDJUZGPOPHTGOT-XUDUSOBPSA-N

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

grade

pharmaceutical primary standard

API family

digitoxin

manufacturer/tradename

EDQM

mp

240 °C (dec.) (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

Gene Information

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

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Application

Digitoxin EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.

General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the Issuing Pharmacopoeia. For further information and support please go to the website of the issuing Pharmacopoeia.

Other Notes

Sales restrictions may apply.

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

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

WGK 3

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Horng-Heng Juang et al.
The Journal of urology, 184(5), 2158-2164 (2010-09-21)
While cardiac glycosides are the mainstay of congestive heart failure treatment, early studies showed that pharmacological doses of cardiac glycosides inhibited prostate cancer cell line proliferation. We evaluated the mechanisms of cardiac glycosides, including digoxin, digitoxin and ouabain (Sigma®), on
Erik S Anderson et al.
RNA (New York, N.Y.), 18(5), 1041-1049 (2012-03-30)
Modulation of alternative pre-mRNA splicing is a potential approach to therapeutic targeting for a variety of human diseases. We investigated the mechanism by which digitoxin, a member of the cardiotonic steroid class of drugs, regulates alternative splicing. Transcriptome-wide analysis identified
Helene Hallböök et al.
PloS one, 6(1), e15718-e15718 (2011-01-20)
Despite years of interest in the anti-cancerous effects of cardiac glycosides (CGs), and numerous studies in vitro and in animals, it has not yet been possible to utilize this potential clinically. Reports have demonstrated promising in vitro effects on different
Thomas M Beale et al.
Organic letters, 15(6), 1358-1361 (2013-03-08)
The cardiac glycoside natural product digitoxin was selectively glycosylated at one of its five hydroxyl groups using a borinic acid derived catalyst. This method provided access to the glycosylation pattern characteristic of a subclass of natural products from Digitalis purpurea.
Hosam A Elbaz et al.
Toxicology and applied pharmacology, 258(1), 51-60 (2011-11-01)
Mechanisms of digitoxin-inhibited cell growth and induced apoptosis in human non-small cell lung cancer (NCI-H460) cells remain unclear. Understanding how digitoxin or derivate analogs induce their cytotoxic effect below therapeutically relevant concentrations will help in designing and developing novel, safer
View All Related Papers

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