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Lanicor

HCID 3062
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
1380169-08-3
Standard SMILES
CC1OC(OC2C(O)CC(OC3C(O)CC(OC4CCC5(C)C(CCC6C5CC(O)C5(C)C(C7=CC(=O)OC7)CCC65O)C4)OC3C)OC2C)CC(O)C1O
InChIKey
LTMHDMANZUZIPE-UHFFFAOYSA-N
Molecular formula
C41H64O14
Average molar mass
780.9 g/mol
Monoisotopic mass
780.42960671

Overview

lanoxin has been reported in Streptomyces purpurascens and Streptomyces violaceus with data available.

Names & identifiers

Preferred name
Lanicor
IUPAC
3-[3-[5-[5-(4,5-dihydroxy-6-methyloxan-2-yl)oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-12,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

Names & synonyms

Lanicor3-[3-[5-[5-(4,5-dihydroxy-6-methyloxan-2-yl)oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-12,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one3-(3-(5-(5-(4,5-dihydroxy-6-methyloxan-2-yl)oxy-4-hydroxy-6-methyloxan-2-yl)oxy-4-hydroxy-6-methyloxan-2-yl)oxy-12,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta(a)phenanthren-17-yl)-2H-furan-5-oneRefChem:798432CogoxinDigoxin NativelleCoragoxineLenoxicapsNeodioxaninCardigoxDigomalLanikor
Show more names
LanoralePurgoxinGrexinDigonDokim3-{[2,6-dideoxyhexopyranosyl-(1->4)-2,6-dideoxyhexopyranosyl-(1->4)-2,6-dideoxyhexopyranosyl]oxy}-12,14-dihydroxycard-20(22)-enolideNSC 95100Lanoxine-PG

Database identifiers

CAS

Properties

Computed structural properties

XLogP
1.3
Topological polar surface area
203 Ų
Hydrogen bond donors
6
Hydrogen bond acceptors
14
Rotatable bonds
7
Heavy atoms
55
Formal charge
0
Complexity
1,450

Experimental & physicochemical properties

Human DrugsBreast Feeding; Lactation; Milk, Human; Antiarrhythmics; Cardiac Glycosides

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Toxicology

TreatmentTreatment of dioxin overdose includes supportive measure and administration of the antidote, antidigoxin (DIGIBIND). Toxicity can also be treated with higher than normal doses of potassium. (L1247)
Health EffectsDigoxin mainly affects the heart. (L1247)
Exposure RoutesInjestion or dermal contact. (L1817) Absorption of digoxin from the elixir pediatric formulation has been demonstrated to be 70% to 85% complete (90% to 100% from the capsules, and 60% to 80% for tablets).
Toxicity Summary · 1 item

Digoxin binds to a site on the extracellular aspect of the alpha-subunit of the Na+/K+ ATPase pump in the membranes of heart cells (myocytes) and decreases its function. This causes an increase in the level of sodium ions in the myocytes. This effect causes an increase in the length the cardiac action potential, which when combined with the effects of digoxin on the parasympathetic nervous system, lead to a decrease in heart rate. Increased amounts of calcium are then stored in the sarcoplasmic reticulum and released by each action potential, which is unchanged by digoxin. This leads to increased contractility of the heart. Digoxin also increases vagal activity via its action on the central nervous system, thus decreasing the conduction of electrical impulses through the AV node. (L1247)

Signs and Symptoms · 1 item

Adverse affects of digoxin include loss of appetite, nausea, vomiting, diarrhea, blurred vision, visual disturbances (yellow-green halos), confusion, drowsiness, dizziness, nightmares, agitation, and/or depression, as well as a higher acute sense of sensual activities. (L1247)

Carcinogen Classification2B, possibly carcinogenic to humans. (L135)
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

Hepatic (but not dependent upon the cytochrome P-450 system). The end metabolites, which include 3 b-digoxigenin, 3-keto-digoxigenin, and their glucuronide and sulfate conjugates, are polar in nature and are postulated to be formed via hydrolysis, oxidation, and conjugation. Route of Elimination: Following intravenous administration to healthy volunteers, 50% to 70% of a digoxin dose is excreted unchanged in the urine. Half Life: 3.5 to 5 days

MeSH Pharmacological Classification · 3 items

Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade.

Agents that have a strengthening effect on the heart or that can increase cardiac output. They may be CARDIAC GLYCOSIDES; SYMPATHOMIMETICS; or other drugs. They are used after MYOCARDIAL INFARCT; CARDIAC SURGICAL PROCEDURES; in SHOCK; or in congestive heart failure (HEART FAILURE).

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.

Uses & manufacturing

Uses · 1 item

For the treatment and management of congestive cardiac insufficiency, arrhythmias and heart failure. Digoxin is a plant toxin found in the foxglove plant (Digitalis lanata). It is used as a drug to treat various heart conditions, namely atrial fibrillation, atrial flutter and sometimes heart failure. (L1247)

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
1380169-08-3、20830-75-5
PubChem CID
3062
DTXSID
DTXSID10860258
Toxicity DataLD<sub>50</sub> = 7.8 mg/kg (orally in mice).