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CAS 17575-20-1

:

LANATOSIDE A

Description:
Lanatoside A is a cardiac glycoside derived from the leaves of the plant Digitalis lanata, commonly known as woolly foxglove. It is characterized by its ability to increase the force of myocardial contraction, making it useful in the treatment of certain heart conditions, particularly heart failure and atrial fibrillation. The compound features a steroid nucleus with a lactone ring and multiple sugar moieties, which contribute to its pharmacological activity. Lanatoside A exhibits a relatively high potency and has a narrow therapeutic window, necessitating careful monitoring of serum levels during treatment to avoid toxicity. Its mechanism of action involves the inhibition of the Na+/K+ ATPase pump, leading to increased intracellular sodium and calcium concentrations, which enhances cardiac contractility. Additionally, Lanatoside A is known for its potential side effects, including gastrointestinal disturbances and arrhythmias, particularly in cases of overdose. As with other cardiac glycosides, it is important to consider patient-specific factors when prescribing this medication.
Formula:C49H76O19
InChI:InChI=1/C49H76O19/c1-22-43(66-38-18-33(53)44(23(2)61-38)67-39-19-34(63-25(4)51)45(24(3)62-39)68-46-42(57)41(56)40(55)35(20-50)65-46)32(52)17-37(60-22)64-28-9-12-47(5)27(16-28)7-8-31-30(47)10-13-48(6)29(11-14-49(31,48)58)26-15-36(54)59-21-26/h15,22-24,27-35,37-46,50,52-53,55-58H,7-14,16-21H2,1-6H3/t22-,23-,24?,27-,28+,29-,30+,31-,32+,33+,34+,35-,37+,38+,39+,40-,41+,42-,43-,44-,45-,46+,47+,48-,49+/m1/s1
InChI key:InChIKey=YFGQJKBUXPKSAW-YSTAXILLSA-N
SMILES:O[C@@]12[C@]3([C@@]([C@]4(C)[C@](CC3)(C[C@@H](O[C@H]5C[C@H](O)[C@H](O[C@H]6C[C@H](O)[C@H](O[C@H]7C[C@H](OC(C)=O)[C@H](O[C@@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@H]8O)[C@@H](C)O7)[C@@H](C)O6)[C@@H](C)O5)CC4)[H])(CC[C@]1(C)[C@H](CC2)C=9COC(=O)C9)[H])[H]
Synonyms:
  • (3beta,5beta)-3-{[beta-D-glucopyranosyl-(1->4)-(5xi)-3-O-acetyl-2,6-dideoxy-beta-D-erythro-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl]oxy}-14-hydroxycard-20(22)-enolide
  • (3β,5β)-3-[(O-β-<span class="text-smallcaps">D</smallcap>-Glucopyranosyl-(1→4)-O-3-O-acetyl-2,6-dideoxy-β-<smallcap>D</smallcap>-ribo-hexopyranosyl-(1→4)-O-2,6-dideoxy-β-<smallcap>D</smallcap>-ribo-hexopyranosyl-(1→4)-2,6-dideoxy-β-<smallcap>D</span>-ribo-hexopyranosyl)oxy]-14-hydroxycard-20(22)-enolide
  • 20(22),5Beta-Cardenolid-3Beta,14Beta-Diol 3Beta-(O-Beta-D-Glucopyranosyl-(1->4)-O-Beta-D-[3-O-Acetyldigitoxopyranosyl]-1(1->4)O-Beta-D-Digitoxopyranosyl-(1->4)-O-Beta-D-Digitoxopyranoside)
  • 3-{[hexopyranosyl-(1->4)-3-O-acetyl-2,6-dideoxyhexopyranosyl-(1->4)-2,6-dideoxyhexopyranosyl-(1->4)-2,6-dideoxyhexopyranosyl]oxy}-14-hydroxycard-20(22)-enolide
  • 5β-Card-20(22)-enolide, 3β-[[O-[O-(O-glucosyldigitoxosyl)digitoxosyl]digitoxosyl]oxy]-14-hydroxy-, acetate
  • Adigal
  • Card-20(22)-enolide, 3-[(O-β-<span class="text-smallcaps">D</smallcap>-glucopyranosyl-(1→4)-O-3-O-acetyl-2,6-dideoxy-β-<smallcap>D</smallcap>-ribo-hexopyranosyl-(1→4)-O-2,6-dideoxy-β-<smallcap>D</smallcap>-ribo-hexopyranosyl-(1→4)-2,6-dideoxy-β-<smallcap>D</span>-ribo-hexopyranosyl)oxy]-14-hydroxy-, (3β,5β)-
  • Digilanida
  • Digilanide A
  • Digitoxigenin+2Digitoxose+Acetyl-Digilanidobose
  • See more synonyms
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Found 1 products.
  • Lanatoside A
    Biosynth
    + Info

    Lanatoside A

    CAS:
    <p>Lanatoside A is a cardiac glycoside found in the plant "Lantana camara" and other plants of the family Verbenaceae. Lanatoside A is structurally characterized by an oxygenated hydroxyl group at C-3, which is present in the natural compound secoisolariciresinol. It has been shown to have inhibitory effects on enzymes involved in congestive heart failure such as myosin light chain kinase and serine/threonine protein kinase. Lanatoside A also has been shown to have immunomodulatory properties and may be beneficial for autoimmune diseases such as rheumatoid arthritis. The enzyme activities are inhibited by lanatosides at low pH values (pH 5-6) but not at high pH values (pH 7-8).</p>
    Purity:Min. 95%

    Ref: 3D-FL137799

    5mg
    348.00€
    10mg
    370.00€
    25mg
    658.00€