Lanatoside C

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.

Lanatoside C

Clinical data
Other names	[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
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
CAS Number	17575-22-3
PubChem CID	656630
ChemSpider	570984
UNII	5RR3JFZ771
KEGG	D01972
ChEMBL	ChEMBL506569
CompTox Dashboard (EPA)	DTXSID7023198
ECHA InfoCard	100.037.754
Chemical and physical data
Formula	C49H76O20
Molar mass	985.127 g·mol^−1
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 Key:JAYAGJDXJIDEKI-PTGWOZRBSA-N
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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 (September 1979). "[Comparative study of blood serum concentrations of digoxin and lanatoside C after single oral administration]" [Comparative study of blood serum concentrations of digoxin and lanatoside C after single oral administration]. Wiadomosci Lekarskie (in Polish). 32 (18): 1277–81. PMID 506267.
2. Tàmmaro AE, Baldoli C (January 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): 157–61. PMID 5600177.
3. "Lanatoside C". International Drug Names. Drugs.com.
4. Ikeda Y, Fujii Y, Yamazaki M (June 1992). "Determination of Lanatoside C and Digoxin in Digitalis lanata by HPLC and its Application to Analysis of the Fermented Leaf Powder". Journal of Natural Products. 55 (6): 748–52. doi:10.1021/np50084a007.
5. Desai UR (2005). "Cardiac Glycosides". VCU School of Pharmacy.