Basic information
- CAS
17598-65-1- Standard SMILES
C[C@H]1O[C@@H](O[C@H]2CC[C@@]3(C)[C@H](CC[C@@H]4[C@@H]3C[C@@H](O)[C@]3(C)[C@@H](C5=CC(=O)OC5)CC[C@]43O)C2)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- InChIKey
OBATZBGFDSVCJD-LALPQLPRSA-N- Molecular formula
- C47H74O19
- Average molar mass
- 943.1 g/mol
- Monoisotopic mass
- 942.48243013
Overview
Deslanoside is a cardenolide glycoside that is lanatoside C with the acetoxy group replaced by a hydroxy group. It has a role as a metabolite, an anti-arrhythmia drug, a cardiotonic drug and an EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor. It is a 12beta-hydroxy steroid, a 14beta-hydroxy steroid, a cardenolide glycoside and a tetrasaccharide derivative.
Names & identifiers
- Preferred name
- Deslanoside
- IUPAC
- 3-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-12,14-dihydroxy-3-[(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]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-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
- English name
- Deslanoside
- Molecular formula
- C47H74O19
- Molecular weight
- 943.08
Names & synonyms
deslanoside17598-65-1Deacetyllanatoside CDesacetyllanatoside CCedilanid-DDeslanosidoDeslanosidumglucodigoxinDeacetylanatoside CDTXSID1022897Desacetyl-Lanatoside CYGY317RK75
Show more names
DesaceDesacicedilaniddsediranidoeslanosidedeslanatosideDeslanoside CDeslanoside RS
Deslanatoside CDTXCID302897CHEBI:31468Cedilanid DCard-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)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-12,14-dihydroxy-, (3beta,5beta,12beta)-Desacetyldigilanide C(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)-enolideCard-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)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-12,14-dihydroxy-, (3beta,5beta,12beta)-
Properties
Computed structural properties
- XLogP
- -0.3
- Topological polar surface area
- 282 Ų
- Hydrogen bond donors
- 9
- Hydrogen bond acceptors
- 19
- Rotatable bonds
- 10
- Heavy atoms
- 66
- Formal charge
- 0
- Complexity
- 1,760
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP0.2
Solubility4.68e-01 g/L
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 220 · 220-235°C
- alpha
- 20 · D20 +12° (c = 1.084 in 75% alc)
- Boiling point
- 732.1 °C · 732.1°C (rough estimate)
- Density
- 1.1255 · 1.1255 (rough estimate)
- refractive index
- 1.65 · 1.6500 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- 1 mg/ml; · DMSO: 1 mg/ml; DMSO:PBS (pH 7.2) (1:6): 0.14 mg/ml
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H300 (50%): Fatal if swallowed [Danger Acute toxicity, oral]
P260, P261, P264, P270, P271, P284, P301+P316, P304+P340, P316, P319, P320, P321, P330, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Other Safety Information
IMAP assessments - Card-20(22)-enolide, 3-[(O-.beta.-D-glucopyranosyl-(1.fwdarw.4)-O-2,6-dideoxy-.beta.-D-ribo-hexopyranosyl-(1.fwdarw.4)-O-2,6-dideoxy-.beta.-D-ribo-hexopyranosyl-(1.fwdarw.4)-2,6-dideoxy-.beta.-D-ribo-hexopyranosyl)oxy]-12,14-dihydroxy-, (3.beta.,5.beta.,12.beta.)-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 2 (50%)
Safety data
- wgk
- WGK 3
- ridadr
- 2811
- hs_code
- 2938900000
- Toxicity
- cat,LD50,intravenous,230ug/kg (0.23mg/kg),"Die Herzwirksamen Glykoside," Baumgarten, G., and W. Forster, Leipzig, Ger. Dem. Rep., VEB Georg Thieme, 1963Vol. -, Pg. 190, 1963.
- risk_code
- 23/25-33
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS08
- safety_code
- 1-22-45
- Storage Class
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Chemistry & industry
Pharmacology
ATC Code
C - Cardiovascular system
QC - Cardiovascular system
Protein Binding20%
PharmacodynamicsDeslanoside 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.
Biological Half-Life36 hours
MeSH Pharmacological Classification
Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade.
Agents that have a strengthening effect on the heart or that can increase cardiac output. They may be CARDIAC GLYCOSIDES; SYMPATHOMIMETICS; or other drugs. They are used after MYOCARDIAL INFARCT; CARDIAC SURGICAL PROCEDURES; in SHOCK; or in congestive heart failure (HEART FAILURE).
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Absorption, Distribution and ExcretionLittle absorption from the gastrointestinal tract (40%).
Related reactions
1 records
Compound notes
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