Deslanoside

Names

[ Name ]:
Deslanoside

[Synonym ]:
Card-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)-2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy)-12,14-dihydroxy-, (3β,5β,12β)-
Deacetyllanatoside C
Desacetyllanatoside C
Deslanatoside C
Deslanoside
Deacetyllanatoside C,Desacetyllanatoside C
Cedilanide
(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
deacetyl-lanatoside
4-18-00-02455 (Beilstein Handbook Reference)
Desacetyldigilanide C
Descetyldigilanide C
DESLANOSIDUM
4-[(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)tetrahydro-2H-pyran-2-yl]oxy}tetrahydro-2H-pyran-2-yl]oxy}-6-methyltetrahydro-2H-pyran-2-yl]oxy}-6-methyltetrahydro-2H-pyran-2-yl]oxy}-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2(5H)-furanone
Desaci
Desace
MFCD00135818
deacetyl-lanatoside C
Card-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)-2,6-dideoxy-β-D-ribo-hexopyranosyl]oxy]-12,14-d ihydroxy-, (3β,5β,12β)-
Deslanatoside
Purpurea Glycoside C
Desacetyllanatosid C
card-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)-2,6-dideoxy-β-D-ribo-hexopyranosyl]oxy]-12,14-dihydroxy-, (3β,5β,12β)-
glucodigoxin
Deslanosidum C
(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-dihydro xycard-20(22)-enolide
4-[(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-méthyl-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxyméthyl)tétrahydro-2H-pyran-2-yl]oxy}tétrahydro-2H-pyran-2-yl]oxy}-6-méthyltétrahydro-2H-pyran-2-yl]oxy}-6-méthyltétrahydro-2H-pyran-2-yl]oxy}-10,13-diméthylhexadécahydro-1H-cyclopenta[a]phénanthrén-17-yl]-2(5H)-furanone
cedilanidd
sediranido
EINECS 241-568-1
de-O-acetyl-lanatoside C
4-[(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)tetrahydro-2H-pyran-2-yl]oxy}tetrahydro-2H-pyran-2-yl]oxy}-6-methyltetrahydro-2H-pyran-2-yl]oxy}-6-methyltetrahydro-2H-pyran-2-yl]oxy}-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2(5H)-furanon

Biological Activity

[Description]:

Deslanoside (Desacetyllanatoside C) is a rapidly acting 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. Deslanoside inhibits the Na-K-ATPase membrane pump, resulting in an increase in intracellular sodium and calcium concentrations [1][2][3].

[Related Catalog]:

Research Areas >> Cardiovascular Disease

[In Vitro]

Deslanoside (Desacetyllanatoside C) is a metabolite of Lanatoside C[4]. Deslanoside increases forearm blood flow and cardiac index and decreased heart rate concomitant with a marked decrease in skeletal muscle sympathetic nerve activity measured as an indicator of centrally mediated sympathetic nervous system activity[1].

[References]

[1]. Hauptman PJ, et al. Digitalis. Circulation. 1999 Mar 9;99(9):1265-70.

[2]. Wang L, et al. Ontology-based systematical representation and drug class effect analysis of package insert-reported adverse events associated with cardiovascular drugs used in China. Sci Rep. 2017 Oct 23;7(1):13819.

[3]. Deslanoside.

[4]. Klys M, et al. Determination of deslanoside in antemortem and postmortem specimens. Unusual case report. Forensic Sci Int. 1990 Apr;45(3):231-8.

[5]. Klys M, et al. Determination of deslanoside in antemortem and postmortem specimens. Unusual case report. Forensic Sci Int. 1990 Apr;45(3):231-8.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Melting Point ]:
220-235ºC

[ Molecular Formula ]:
C₄₇H₇₄O₁₉

[ Molecular Weight ]:
943.079

[ Exact Mass ]:
942.482422

[ PSA ]:
282.21000

[ LogP ]:
-1.40

[ Index of Refraction ]:
1.620

[ Storage condition ]:
2-8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: OE2100500

CHEMICAL NAME :: Lanatoside C, deacetyl-

CAS REGISTRY NUMBER :: 17598-65-1

BEILSTEIN REFERENCE NO. :: 0078187

LAST UPDATED :: 199612

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C47-H74-O19

MOLECULAR WEIGHT :: 943.21

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 10360 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,489,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 8100 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,489,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 230 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85ELDJ "Die Herzwirksamen Glykoside," Baumgarten, G., and W. Forster, Leipzig, Ger. Dem. Rep., VEB Georg Thieme, 1963 Volume(issue)/page/year: -,190,1963 *** REVIEWS *** TOXICOLOGY REVIEW 85ELDJ "Die Herzwirksamen Glykoside," Baumgarten, G., and W. Forster, Leipzig, Ger. Dem. Rep., VEB Georg Thieme, 1963 Volume(issue)/page/year: -,190,1963 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X7349 No. of Facilities: 7 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 103 (estimated) No. of Female Employees: 52 (estimated)

Safety Information

[ Risk Phrases ]:
R23/25

[ Safety Phrases ]:
1-22-45

[ RIDADR ]:
UN 2811

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Effects of acute administration of ethanol on experimental arrhythmia.

Chin. J. Physiol. 55(5) , 307-13, (2012)

Many studies have shown that the relationship between alcohol consumption and most cardiovascular diseases is U-shaped, with nondrinkers and heavier drinkers having higher risks than moderate drinkers...

Altered vagal and sympathetic control of heart rate in left ventricular dysfunction and heart failure.

Am. J. Physiol. 268(2 Pt 2) , R310-16, (1995)

We investigated alterations in autonomic control of heart rate in conscious dogs with left ventricular (LV) dysfunction in the presence and absence of heart failure (HF) due to rapid pacing. In dogs w...

Two-stage cultivation of Digitalis lanata cells: semicontinuous production of deacetyllanatoside C in 20-litre airlift bioreactors.

J. Biotechnol. 16(1-2) , 123-35, (1990)

A two-stage cultivation method was employed to develop a semicontinuous biotransformation process for the production of deacetyllanatoside C, a cardenolide of the important digoxin series. Digitoxin w...