Deslanoside

Synonyms :
(3beta,5beta,12beta)-3-{[beta-D-glucopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl]oxy}-12,14-dihydroxycard-20(22)-enolide, 3-[(O-beta-D-Glucopyranosyl-(1->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy]-12,14-dihydroxy-3beta,5beta,12beta-card-20(22)-enolide, Deacetyllanatoside C, Desacetyllanatoside C, Deslanosido, Deslanosidum, Glucodigoxin

Status : approved

Category

Enzyme Inhibitors

Therapeutic Classification

CARDIAC GLYCOSIDES

CARDIOVASCULAR SYSTEM
CARDIAC THERAPY
CARDIAC GLYCOSIDES
Anti-Arrhythmia Agents

Description

Deacetyllanatoside C. A cardiotonic glycoside from the leaves of Digitalis lanata. [PubChem]

Used

For the treatment and management of Congestive cardiac insufficiency, arrhythmias and heart failure.

Mechanism Of Action

Deslanoside inhibits the Na-K-ATPase membrane pump, resulting in an increase in intracellular sodium and calcium concentrations. Increased intracellular concentrations of calcium may promote activation of contractile proteins (e.g., actin, myosin). Deslanoside also acts on the electrical activity of the heart, increasing the slope of phase 4 depolarization, shortening the action potential duration, and decreasing the maximal diastolic potential.

Pharmacodynamics

Deslanoside is a cardiac glycoside used to treat congestive heart failure and supraventricular arrhythmias due to reentry mechanisms, and to control ventricular rate in the treatment of chronic atrial fibrillation.

Toxic Effect

Symptoms of overdose include ventricular tachycardia, ventricular fibrillation, progressive bradyarrhythmias, or heart block.

Absorption

Little absorption from the gastrointestinal tract (40%).

Half Life

36 hours

Protein Binding

20%

Chemical Classification

This compound belongs to the class of organic compounds known as cardenolide glycosides and derivatives. These are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety.

Cardenolide glycosides and derivatives

Organic compounds

Lipids and lipid-like molecules

Steroids and steroid derivatives

Steroid lactones

Chemical Name

(3beta,5beta,12beta)-3-{[beta-D-glucopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl]oxy}-12,14-dihydroxycard-20(22)-enolide

Calculated Property

kind Value Source
logP -0.49 ALOGPS
logS -3.3 ALOGPS
Water Solubility 4.68e-01 g/l ALOGPS
logP 0.6 ChemAxon
IUPAC Name 4-[(1S,2S,5S,7R,10R,11S,14R,15S,16R)-11,16-dihydroxy-5-{[(2R,4S,5S,6R)-4-hydroxy-5-{[(2S,4S,5S,6R)-4-hydroxy-5-{[(2S,4S,5S,6R)-4-hydroxy-6-methyl-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-6-methyloxan-2-yl]oxy}-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-2,5-dihydrofuran-2-one ChemAxon
Traditional IUPAC Name deslanoside ChemAxon
Molecular Weight 943.0791 ChemAxon
Monoisotopic Weight 942.482430186 ChemAxon
SMILES C[C@H]1O[C@H](C[C@H](O)[C@@H]1O[C@H]1C[C@H](O)[C@H](O[C@H]2C[C@H](O)[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](C)O2)[C@@H](C)O1)O[C@H]1CC[C@@]2(C)[C@H](CC[C@@H]3[C@@H]2C[C@@H](O)[C@]2(C)[C@H](CC[C@]32O)C2=CC(=O)OC2)C1 ChemAxon
Molecular Formula C47H74O19 ChemAxon
InChI InChI=1S/C47H74O19/c1-20-41(64-36-16-30(50)42(21(2)60-36)65-37-17-31(51)43(22(3)61-37)66-44-40(56)39(55)38(54)32(18-48)63-44)29(49)15-35(59-20)62-25-8-10-45(4)24(13-25)6-7-27-28(45)14-33(52)46(5)26(9-11-47(27,46)57)23-12-34(53)58-19-23/h12,20-22,24-33,35-44,48-52,54-57H,6-11,13-19H2,1-5H3/t20-,21-,22-,24-,25+,26-,27-,28+,29+,30+,31+,32-,33-,35+,36+,37+,38-,39+,40-,41-,42-,43-,44+,45+,46+,47+/m1/s1 ChemAxon
InChIKey InChIKey=OBATZBGFDSVCJD-LALPQLPRSA-N ChemAxon
Polar Surface Area (PSA) 282.21 ChemAxon
Refractivity 225.65 ChemAxon
Polarizability 100.65 ChemAxon
Rotatable Bond Count 10 ChemAxon
H Bond Acceptor Count 18 ChemAxon
H Bond Donor Count 9 ChemAxon
pKa (strongest acidic) 7.15 ChemAxon
pKa (strongest basic) -3.2 ChemAxon
Physiological Charge 0 ChemAxon
Number of Rings 9 ChemAxon
Bioavailability 0 ChemAxon
Rule of Five 0 ChemAxon
Ghose Filter 0 ChemAxon
MDDR-Like Rule 1 ChemAxon

Affected organism

Humans and other mammals

Target within organism

  • Sodium/potassium-transporting ATPase subunit alpha-1 : in Human