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Digoxin

$93

  • Brand : BIOFRON

  • Catalogue Number : BF-D2007

  • Specification : 98%

  • CAS number : 20830-75-5

  • Formula : C41H64O14

  • Molecular Weight : 780.94

  • PUBCHEM ID : 2724385

  • Volume : 20mg

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Catalogue Number

BF-D2007

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

780.94

Appearance

powder

Botanical Source

herbs of Digitalis lanata

Structure Type

Others

Category

Standards;Natural Pytochemical;API

SMILES

CC1C(C(CC(O1)OC2C(OC(CC2O)OC3C(OC(CC3O)OC4CCC5(C(C4)CCC6C5CC(C7(C6(CCC7C8=CC(=O)OC8)O)C)O)C)C)C)O)O

Synonyms

Dixina/Digacin/Digonix/Cordioxil/Homolle's digitalin/Mapluxin/Lanocardin/card-20(22)-enolide, 3-[[O-2,6-dideoxy-b-D-ribo-hexopyranosyl-(1®4)-O-2,6-dideoxy-b-D-ribo-hexopyranosyl-(1®4)-2,6-dideoxy-b-D-ribo-hexopyranosyl]oxy]-12,14-dihydroxy-, (3b,5b,12b)-/5-18-04-00381/Lanacrist/4-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-3-{[(2R,4S,5S,6R)-5-{[(2S,4S,5S,6R)-5-{[(2S,4S,5S,6R)-4,5-Dihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-4-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-4-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-12,14-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2(5H)-furanon/Purgoxin/Longdigox/Digoxina-Sandoz/ROUGOXIN/Stillaco/NeoDioxanin/SK-Digoxin/Natigoxin/Davoxin/Digoxin Nativelle/Fargoxin/4-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-3-{[(2R,4S,5S,6R)-5-{[(2S,4S,5S,6R)-5-{[(2S,4S,5S,6R)-4,5-Dihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-4-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-4-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-12,14-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]furan-2(5H)-on/Digos/Dimecip/Neo-Lanicor/digoxin/12b-Hydroxydigitoxin/Digon/(3b,5b,12b)-3-{[2,6-dideoxy-b-D-ribo-hexopyranosyl-(1®4)-2,6-dideoxy-b-D-ribo-hexopyranosyl-(1®4)-2,6-dideoxy-b-D-ribo-hexopyranosyl]oxy}-12,14-dihydroxycard-20(22)-enolide/card-20(22)-enolide, 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]-12,14-dihydroxy-, (3β,5β,12β)/Lanacordin/Dynamos/Saroxin/Coragoxine/Dokim/Lenoxin/4-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-3-{[(2R,4S,5S,6R)-5-{[(2S,4S,5S,6R)-5-{[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-4-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-4-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-12,14-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]furan-2(5H)-oneLOE 908 hydrochloride/Grexin/Digoxin-Zori/4-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-3-{[(2R,4S,5S,6R)-5-{[(2S,4S,5S,6R)-5-{[(2S,4S,5S,6R)-4,5-Dihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-4-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-4-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-12,14-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2(5H)-furanone/Cardiogoxin/Digossina/Cardigox/Hemigoxine Nativelle/(3β,5β,12β)-3-{[2,6-Dideoxy-β-D-ribo-hexopyranosyl-(1->;4)-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-β-D-ribo-hexopyranosyl]oxy}-12,14-dihydroxycard-20(22)-enolid/4-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-3-{[(2R,4S,5S,6R)-5-{[(2S,4S,5S,6R)-5-{[(2S,4S,5S,6R)-4,5-Dihydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-4-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-4-hydroxy/(3β,5β,12β)-3-{[2,6-Didesoxy-β-D-ribo-hexopyranosyl-(1->4)-2,6-didesoxy-β-D-ribo-hexopyranosyl-(1->4)-2,6-didesoxy-β-D-ribo-hexopyranosyl]oxy}-12,14-dihydroxycard-20(22)-enolide/Lanatilin/Digomal/Digosin/Lanoxin PG/Lanikor/Lanorale/Lanoxicaps/Toloxin/Lanoxin/(3b,5b,12b)-3-[(O-2,6-Dideoxy-b-D-ribo-hexopyranosyl-(1®4)-O-2,6-dideoxy-b-D-ribo-hexopyranosyl-(1®4)-2,6-dideoxy-b-D-ribo-hexopyranosyl)oxy]-12,14-dihydroxycard-20(22)-enolide/Cardioxin/card-20(22)-enolide, 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]-12,14-dihydroxy-, (3β,5β,12β)-/Lanicor/Card-20(22)-enolide, 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]-12,14-dihydroxy-, (3β,5β,12β) -/Novodigal-Amp./Dilanacin/Vanoxin/[2H]-Digoxin/Lenoxicaps/Lifusin/(3β,5β,12β)-3-{[2,6-Dideoxy-β-D-ribo-hexopyranosyl-(1->;4)-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-β-D-ribo-hexopyranosyl]oxy}-12,14-dihydroxycard-20(22)-enolide/Eudigox/[14C]-Digoxin

IUPAC Name

3-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-3-[(2R,4S,5S,6R)-5-[(2S,4S,5S,6R)-5-[(2S,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-12,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

Density

1.4±0.1 g/cm3

Solubility

Methanol; Pyridine; DMSO

Flash Point

278.5±27.8 °C

Boiling Point

931.6±65.0 °C at 760 mmHg

Melting Point

248-250ºC

InChl

InChI=1S/C41H64O14/c1-19-36(47)28(42)15-34(50-19)54-38-21(3)52-35(17-30(38)44)55-37-20(2)51-33(16-29(37)43)53-24-8-10-39(4)23(13-24)6-7-26-27(39)14-31(45)40(5)25(9-11-41(26,40)48)22-12-32(46)49-18-22/h12,19-21,23-31,33-38,42-45,47-48H,6-11,13-18H2,1-5H3/t19-,20-,21-,23-,24+,25-,26-,27+,28+,29+,30+,31-,33+,34+,35+,36-,37-,38-,39+,40+,41+/m1/s1

InChl Key

LTMHDMANZUZIPE-PUGKRICDSA-N

WGK Germany

RID/ADR

HS Code Reference

2938900000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:20830-75-5) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31636264

Abstract

Compounds with specific cytotoxic activity in senescent cells, or senolytics, support the causal involvement of senescence in aging and offer therapeutic interventions. Here we report the identification of Cardiac Glycosides (CGs) as a family of compounds with senolytic activity. CGs, by targeting the Na+/K+ATPase pump, cause a disbalanced electrochemical gradient within the cell causing depolarization and acidification. Senescent cells present a slightly depolarized plasma membrane and higher concentrations of H+, making them more susceptible to the action of CGs. These vulnerabilities can be exploited for therapeutic purposes as evidenced by the in vivo eradication of tumors xenografted in mice after treatment with the combination of a senogenic and a senolytic drug. The senolytic effect of CGs is also effective in the elimination of senescence-induced lung fibrosis. This experimental approach allows the identification of compounds with senolytic activity that could potentially be used to develop effective treatments against age-related diseases.

Title

Identification and characterization of Cardiac Glycosides as senolytic compounds.

Author

Triana-Martinez F1,2, Picallos-Rabina P1, Da Silva-alvarez S1, Pietrocola F3, Llanos S4, Rodilla V5, Soprano E6, Pedrosa P1, Ferreiros A1, Barradas M7, Hernandez-Gonzalez F3,8, Lalinde M5, Prats N3, Bernado C5, Gonzalez P9, Gomez M9, Ikonomopoulou MP10, Fernandez-Marcos PJ7, Garcia-Caballero T11, Del Pino P6, Arribas J5,12, Vidal A13, Gonzalez-Barcia M14, Serrano M3,12, Loza MI2, Dominguez E15, Collado M16.

Publish date

2019 Oct 21

PMID

31527358

Abstract

Digitoxin and digoxin are plant-derived cardiac glycosides. They are Na+,K+-ATPase (sodium pump) inhibitors, and have been used clinically for treatment and prevention of heart failure and various tachycardia. On the other hand, some epidemiological studies showed that digoxin users have a lower cancer risk compared to the non-users, and that cancer patients who had been treated with digoxin face on improvement of their survival. In various in vitro studies, cardiac glycosides at sub-μM concentrations, which have no significant effect on enzymatic and ion-transporting activities of Na+,K+-ATPase, show anti-cancer effects. Na+,K+-ATPase is ubiquitously expressed, so it remains unclear why low concentrations of cardiac glycosides have cancer-specific effects. Recently, we found that the receptor-type Na+,K+-ATPase, which has no pumping activity, is associated with leucine-rich repeat-containing 8 family, member A(LRRC8A), one of the components of volume-regulated anion channel (VRAC), in the membrane microdomains of plasma membrane of cancer cells, and that this crosstalk contributes to the inhibition of the cancer cell growth by sub-μM cardiac glycosides. In this mechanism, cardiac glycosides bind to the receptor-type Na+,K+-ATPase, and then stimulate the production of reactive oxygen species (ROS) via NADPH oxidase. The ROS activate VRAC within the membrane microdomains, thus eliciting anti-proliferative effects. VRAC is ubiquitously expressed, and it is normally activated by cell swelling. However, VRAC is activated by cardiac glycoside without cell swelling. On the other hand, the cardiac glycosides-induced effects were not observed in non-cancer cells. Our findings can partly explain why cardiac glycosides elicit selective effects in cancer cells.

Title

[Cancer cell-specific functional relation between Na+,K+-ATPase and volume-regulated anion channel].

Author

Fujii T1, Shimizu T1, Takeshima H2, Sakai H1.

Publish date

2019

PMID

31509043

Abstract

Cardiotonic steroids (CTS) are steroidal drugs, processed from the seeds and dried leaves of the genus Digitalis as well as from the skin and parotid gland of amphibians. The most commonly known CTS are ouabain, digoxin, digoxigenin and bufalin. CTS can be used for safer medication of congestive heart failure and other related conditions due to promising pharmacological and medicinal properties. Ouabain isolated from plants is widely utilized in in vitro studies to specifically block the sodium potassium (Na+/K+-ATPase) pump. For checking, whether ouabain derivatives are robust inhibitors of Na+/K+-ATPase pump, molecular docking simulation was performed between ouabain and its derivatives using YASARA software. The docking energy falls within the range of 8.470 kcal/mol to 7.234 kcal/mol, in which digoxigenin was found to be the potential ligand with the best docking energy of 8.470 kcal/mol. Furthermore, pharmacophore modeling was applied to decipher the electronic features of CTS. Molecular dynamics simulation was also employed to determine the conformational properties of Na+/K+-ATPase-ouabain and Na+/K+-ATPase-digoxigenin complexes with the plausible structural integrity through conformational ensembles for 100 ns which promoted digoxigenin as the most promising CTS for treating conditions of congestive heart failure patients.

KEYWORDS

Cardiotonic steroids (CTS); docking simulation; molecular dynamics simulation; pharmacophores; sodium potassium (Na+/K+-ATPase) pump

Title

Cardiotonic steroids as potential Na+/K+-ATPase inhibitors - a computational study.

Publish date

2019 Jun


Description :

Digoxin is a potent inhibitor of Na+/K+-ATPase, clinically used to treat arrhythmia and heart failure.