Digitoxin

Digitoxin
Compound Structure:
Synonyms: digitoxin ;71-63-6 Digitoxoside ;Crystodigin; Digitoxinum
Compound ID: NMPC-965
PubChem ID:

441207

Molecular Formula: C41H64O13
Canonical SMILES: CC1C(C(CC(O1)OC2C(OC(CC2O)OC3C(OC(CC3O)OC4CCC5(C(C4)CCC6C5CCC7(C6(CCC7C8=CC(=O)OC8)O)C)C)C)C)O)O
InChIKey: WDJUZGPOPHTGOT-XUDUSOBPSA-N
About the compound:

Digitoxin is a cardenolide glycoside where the 3beta-hydroxy group of digitoxigenin is attached to a trisaccharide chain consisting of 2,6-dideoxy-beta-D-ribo-hexopyranosyl units. This compound functions as an inhibitor of the enzyme Na(+)/K(+)-transporting ATPase and is closely related to digitoxigenin. Chemically, it is the conjugate acid of a digitoxin(1-). As a cardiac glycoside, digitoxin is occasionally used as an alternative to digoxin. It is distinguished by its longer half-life compared to digoxin, and although its toxic effects are similar, they tend to be more prolonged. This distinction is noted in medical resources such as Martindale's The Extra Pharmacopoeia. Digitoxin is utilized in the treatment of heart failure and specific types of heart arrhythmias. It is a phytosteroid and bears structural and functional similarities to digoxin, but with more lasting effects. Unlike digoxin, which is primarily excreted through the kidneys, digitoxin is eliminated via the liver. This makes it a suitable option for patients with impaired or inconsistent kidney function. While digoxin's efficacy in treating heart failure has been supported by several controlled trials, the evidence base for digitoxin is not as robust. However, it is presumed to be similarly effective. The primary applications of digitoxin include the treatment of heart failure, particularly in individuals with compromised kidney function, and the management of certain heart arrhythmias like atrial fibrillation.

GHS Hazard Statements

H301: Toxic if swallowed [Danger Acute toxicity, oral]

H331: Toxic if inhaled [Danger Acute toxicity, inhalation]

H373 **: May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]

First Aid

Digitoxin is highly dangerous and can lead to death or serious harm even with brief exposure. Symptoms may not manifest immediately and could appear up to 12 hours later. Be extremely cautious and closely monitor vital signs.

Symptoms of digitoxin ingestion include nausea, vomiting, headache, weakness, confusion, slow pulse, and heart irregularities. In severe cases, it can progress to convulsions, coma, respiratory failure, and heart failure.

In case of exposure:

Inhalation: Move victims to fresh air, check vital signs, perform CPR if necessary, and seek medical assistance for antidote administration.

Dermal/Eye: Remove victims from exposure, flush eyes with water, wash skin thoroughly, and seek medical advice for antidote administration.

Ingestion: Check vital signs, seek medical advice for antidote administration, and induce vomiting only if ingestion was recent and victim is alert. Administer activated charcoal and rush to a healthcare facility.

Immediate medical attention is crucial in cases of digitoxin exposure.

U.S. Environmental Protection Agency. 1998. Extremely Hazardous Substances (EHS) Chemical Profiles and Emergency First Aid Guides. Washington, D.C.: U.S. Government Printing Office.

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

764.9 g/mol

XLogP3

2.3

Hydrogen Bond Donor Count

5

Hydrogen Bond Acceptor Count

13

Rotatable Bond Count

7

Exact Mass

764.43469209 g/mol

Monoisotopic Mass

764.43469209 g/mol

Topological Polar Surface Area

183Ų

Heavy Atom Count

54

Formal Charge

0

Complexity

1410

Isotope Atom Count

0

Defined Atom Stereocenter Count

20

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Digitoxin appears as odorless white or pale buff microcrystalline powder. Used as a cardiotonic drug. (EPA, 1998)

Melting Point

255.5°C

Solubility 

Very soluble in ethanol; soluble in ethyl ether, chloroform, methanol, pyridine

Source: PubChem

Source Species: Vernonia blumeoides
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