Identification

Name
Deslanoside
Accession Number
DB01078  (APRD00909)
Type
Small Molecule
Groups
Approved
Description

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

Structure
Thumb
Synonyms
  • (3β,5β,12β)-3-{[β-D-glucopyranosyl-(1→4)-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
  • 3-[(O-β-D-glucopyranosyl-(1→4)-O-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1→4)-O-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1→4)-O-2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy]-12,14-dihydroxy-3β,5β,12β-card-20(22)-enolide
  • Deacetyllanatoside C
  • Desacetyllanatoside C
  • Deslanoside
  • Deslanosido
  • Deslanosidum
  • Glucodigoxin
International/Other Brands
Cedilanid-d
Categories
UNII
YGY317RK75
CAS number
17598-65-1
Weight
Average: 943.0791
Monoisotopic: 942.482430186
Chemical Formula
C47H74O19
InChI Key
OBATZBGFDSVCJD-LALPQLPRSA-N
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
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
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

Pharmacology

Indication

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

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.

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.

TargetActionsOrganism
ASodium/potassium-transporting ATPase subunit alpha-1
inhibitor
Human
Absorption

Little absorption from the gastrointestinal tract (40%).

Volume of distribution
Not Available
Protein binding

20%

Metabolism
Not Available
Route of elimination
Not Available
Half life

36 hours

Clearance
Not Available
Toxicity

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

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
1alpha-Hydroxyvitamin D5The risk or severity of ventricular arrhythmias and Cardiac Arrhythmia can be increased when 1alpha-Hydroxyvitamin D5 is combined with Deslanoside.
3,5-diiodothyropropionic acidThe serum concentration of Deslanoside can be increased when it is combined with 3,5-diiodothyropropionic acid.
6-Deoxyerythronolide BThe serum concentration of Deslanoside can be increased when it is combined with 6-Deoxyerythronolide B.
AbaloparatideThe serum concentration of Deslanoside can be increased when it is combined with Abaloparatide.
AcebutololAcebutolol may increase the bradycardic activities of Deslanoside.
Acetylsalicylic acidThe serum concentration of Deslanoside can be decreased when it is combined with Acetylsalicylic acid.
AgmatineThe serum concentration of Deslanoside can be increased when it is combined with Agmatine.
AlcuroniumThe risk or severity of Cardiac Arrhythmia can be increased when Alcuronium is combined with Deslanoside.
AldoxorubicinDeslanoside may decrease the cardiotoxic activities of Aldoxorubicin.
AlfacalcidolThe risk or severity of ventricular arrhythmias and Cardiac Arrhythmia can be increased when Alfacalcidol is combined with Deslanoside.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0015211
KEGG Drug
D01240
PubChem Compound
28620
PubChem Substance
46507176
ChemSpider
26618
ChEBI
31468
ChEMBL
CHEMBL1614
Therapeutic Targets Database
DAP000464
PharmGKB
PA164747478
Wikipedia
Deslanoside
ATC Codes
C01AA07 — Deslanoside

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP0.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.468 mg/mLALOGPS
logP-0.49ALOGPS
logP0.6ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)7.15ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area282.21 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity225.65 m3·mol-1ChemAxon
Polarizability100.65 Å3ChemAxon
Number of Rings9ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8985
Blood Brain Barrier-0.5781
Caco-2 permeable-0.924
P-glycoprotein substrateSubstrate0.8738
P-glycoprotein inhibitor IInhibitor0.5533
P-glycoprotein inhibitor IIInhibitor0.6189
Renal organic cation transporterNon-inhibitor0.8371
CYP450 2C9 substrateNon-substrate0.8483
CYP450 2D6 substrateNon-substrate0.8905
CYP450 3A4 substrateSubstrate0.7052
CYP450 1A2 substrateNon-inhibitor0.9197
CYP450 2C9 inhibitorNon-inhibitor0.9182
CYP450 2D6 inhibitorNon-inhibitor0.938
CYP450 2C19 inhibitorNon-inhibitor0.9284
CYP450 3A4 inhibitorNon-inhibitor0.9194
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9237
Ames testNon AMES toxic0.9309
CarcinogenicityNon-carcinogens0.9583
BiodegradationNot ready biodegradable0.9845
Rat acute toxicity4.9815 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9515
hERG inhibition (predictor II)Inhibitor0.8395
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Steroid lactones
Direct Parent
Cardenolide glycosides and derivatives
Alternative Parents
Steroidal glycosides / Oligosaccharides / 12-hydroxysteroids / 14-hydroxysteroids / O-glycosyl compounds / Butenolides / Oxanes / Tertiary alcohols / Enoate esters / Secondary alcohols
show 10 more
Substituents
Cardanolide-glycoside / Steroidal glycoside / Oligosaccharide / 12-hydroxysteroid / 14-hydroxysteroid / Hydroxysteroid / Glycosyl compound / O-glycosyl compound / 2-furanone / Oxane
show 22 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
tetrasaccharide derivative, 14beta-hydroxy steroid, cardenolide glycoside, 12beta-hydroxy steroid (CHEBI:31468)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Steroid hormone binding
Specific Function
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates th...
Gene Name
ATP1A1
Uniprot ID
P05023
Uniprot Name
Sodium/potassium-transporting ATPase subunit alpha-1
Molecular Weight
112895.01 Da
References
  1. Zhao YN, Pan Y, Tao JL, Xing DM, Du LJ: Study on cardioactive effects of brazilein. Pharmacology. 2006;76(2):76-83. Epub 2005 Nov 24. [PubMed:16319518]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Drug created on June 13, 2005 07:24 / Updated on December 14, 2018 05:32