Lanatoside C

Lanatoside C

Systematic (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
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral, intravenous
Identifiers
CAS Number	17575-22-3
ATC code	C01AA06
PubChem	CID 656630
ChemSpider	570984
UNII	5RR3JFZ771
KEGG	D01972
ChEMBL	CHEMBL506569
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
Chemical data
Formula	C49H76O20
Molar mass	985.116 g/mol
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 Key:JAYAGJDXJIDEKI-PTGWOZRBSA-N
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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

1. 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.
2. 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.
3. "Lanatoside C". International Drug Names. Drugs.com.
4. 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
5. Desai, U. R. (2005). "Cardiac Glycosides". VCU School of Pharmacy.