Lanatoside C

Lanatoside C
Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Oral, intravenous
ATC code	C01AA06 (WHO)
Identifiers
IUPAC name (3β,5β,12β)- 3-{[β-D- glucopyranosyl- (1→4)- 3-O-acetyl- 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
Synonyms	[6-[6-[6-[[12,14-dihydroxy- 10,13-dimethyl- 17-(5-oxo-2H-furan-3-yl)- 1,2,3,4,5,6,7,8,9,11,12,15,16,17- tetradecahydrocyclopenta[a]phenanthren- 3-yl]oxy]- 4-hydroxy- 2-methyloxan- 3-yl]oxy- 4-hydroxy- 2-methyloxan-3-yl]oxy- 2-methyl- 3-[3,4,5-trihydroxy- 6-(hydroxymethyl)oxan-2-yl]oxyoxan- 4-yl] acetate
CAS Number	17575-22-3^Y
PubChem CID	656630
ChemSpider	570984^Y
UNII	5RR3JFZ771
KEGG	D01972^Y
ChEMBL	CHEMBL506569^Y
ECHA InfoCard	100.037.754
Chemical and physical data
Formula	C₄₉H₇₆O₂₀
Molar mass	985.116 g/mol
3D model (JSmol)	Interactive image
SMILES C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2CC[C@]3([C@@H](C2)CC[C@@H]4[C@@H]3C[C@H]([C@]5([C@@]4(CC[C@@H]5C6=CC(=O)OC6)O)C)O)C)O)O[C@H]7C[C@@H]([C@@H]([C@H](O7)C)O[C@H]8C[C@@H]([C@@H]([C@H](O8)C)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)OC(=O)C)O
InChI InChI=1S/C49H76O20/c1-21-43(67-38-17-32(53)44(22(2)62-38)68-39-18-33(64-24(4)51)45(23(3)63-39)69-46-42(58)41(57)40(56)34(19-50)66-46)31(52)16-37(61-21)65-27-9-11-47(5)26(14-27)7-8-29-30(47)15-35(54)48(6)28(10-12-49(29,48)59)25-13-36(55)60-20-25/h13,21-23,26-35,37-46,50,52-54,56-59H,7-12,14-20H2,1-6H3/t21-,22-,23-,26-,27+,28-,29-,30+,31+,32+,33+,34-,35-,37+,38+,39+,40-,41+,42-,43-,44-,45-,46+,47+,48+,49+/m1/s1^Y Key:JAYAGJDXJIDEKI-PTGWOZRBSA-N^Y
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Lanatoside C (or isolanid) is a cardiac glycoside, a type of drug that can be used in the treatment of congestive heart failure and cardiac arrhythmia (irregular heartbeat). Lanatoside C can be used orally^[1] or by the intravenous route.^[2] It is marketed in a number of countries and is also available in generic form.^[3] Its main indications are rapid response atrial fibrilation and paroxysmal supraventricular tachycardia, two common types of arrhythmia.

It is found in Digitalis lanata.^[4]

Chemistry

The substance is composed of four monosaccharides (glucose, 3-acetyldigitoxose and two digitoxoses) and an aglycon named digoxigenin.^[5]

References

↑ Lypka, A.; Lazowski, J. (1979). "(title in Polish)" [Comparative study of blood serum concentrations of digoxin and lanatoside C after single oral administration]. Wiadomości Lekarskie (in Polish). Warsaw, Poland. 32 (18): 1277–1281. PMID 506267.
↑ Tàmmaro, A. E.; Baldoli, C. (1967). "On some immediate effects of the intravenous administration of desacetyl-lanatoside C in aged subjects" [On some immediate effects of the intravenous administration of desacetyl-lanatoside C in aged subjects]. La Clinica Terapeutica (in Italian). 40 (2): 157–161. PMID 5600177.
↑ "Lanatoside C". International Drug Names. Drugs.com.
↑ Determination of Lanatoside C and Digoxin in Digitalis lanata by Hplc and Its Application to Analysis of the Fermented Leaf Powder. Yukari Ikeda, Youichi Fujii and Mitsuru Yamazaki, J. Nat. Prod., 1992, volume 55, issue 6, pages 748–752, doi:10.1021/np50084a007
↑ Desai, U. R. (2005). "Cardiac Glycosides". VCU School of Pharmacy.

Cardiac glycosides (C01A)

Bufadienolides

Bufo	Arenobufagin Bufotalin Cinobufagin Marinobufagin
Scilla	Proscillaridin Scilliroside

Cardenolides

Digitalis	Acetyldigitoxin Acetyldigoxin Digitoxin^# Digoxin^# Lanatoside C Deslanoside Metildigoxin Gitoformate
Kalanchoe	Daigremontianin
Strophanthus	Ouabain (g-Strophanthin) k-Strophanthin Cymarin
Thevetia	Peruvoside

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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