CAS 5297-10-9

Dihydrodigoxin

Description:

Dihydrodigoxin is a cardiac glycoside, a class of compounds known for their ability to influence heart function. It is derived from the plant Digitalis lanata and is structurally related to digoxin, which is commonly used in the treatment of heart conditions such as atrial fibrillation and heart failure. Dihydrodigoxin exhibits a similar mechanism of action, primarily by inhibiting the Na+/K+ ATPase pump, leading to increased intracellular calcium concentrations and enhanced cardiac contractility. This compound is characterized by its steroid nucleus, which is essential for its biological activity, and it typically has a high affinity for cardiac tissues. Dihydrodigoxin is less commonly used than digoxin but may be of interest in pharmacological research due to its unique properties and potential therapeutic applications. As with other cardiac glycosides, careful monitoring of dosage is crucial, as the therapeutic window is narrow, and toxicity can occur, leading to serious side effects.

Formula: C₄₁H₆₆O₁₄

InChI: InChI=1S/C41H66O14/c1-19-36(47)28(42)15-34(50-19)54-38-21(3)52-35(17-30(38)44)55-37-20(2)51-33(16-29(37)43)53-24-8-10-39(4)23(13-24)6-7-26-27(39)14-31(45)40(5)25(9-11-41(26,40)48)22-12-32(46)49-18-22/h19-31,33-38,42-45,47-48H,6-18H2,1-5H3/t19-,20-,21-,22+,23-,24+,25-,26-,27+,28+,29+,30+,31-,33+,34+,35+,36-,37-,38-,39+,40+,41+/m1/s1

InChI key: InChIKey=QYVJGQUFXQMOOE-STPZNEFBSA-N

SMILES: O[C@@]12[C@@](C)([C@](CC1)([C@]3(CC(=O)OC3)[H])[H])[C@H](O)C[C@]4([C@]2(CC[C@]5([C@]4(C)CC[C@H](O[C@H]6C[C@H](O)[C@H](O[C@H]7C[C@H](O)[C@H](O[C@H]8C[C@H](O)[C@H](O)[C@@H](C)O8)[C@@H](C)O7)[C@@H](C)O6)C5)[H])[H])[H]

Synonyms:

• (3β,5β,12β)-3-[(O-2,6-Dideoxy-β-<span class="text-smallcaps">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]-12,14-dihydroxycardanolide
• 20,22-Dihydrodigoxin
• 3-{[2,6-Dideoxyhexopyranosyl-(1->4)-2,6-Dideoxyhexopyranosyl-(1->4)-2,6-Dideoxyhexopyranosyl]Oxy}-12,14-Dihydroxycardanolide
• 5β-Cardanolide, 3β-[(O-2,6-dideoxy-β-<span class="text-smallcaps">D</smallcap>-ribo-hexopyranosyl-(1→4)-O-2,6-β-<smallcap>D</smallcap>-ribo-hexopyranosyl-(1→4)-2,6-dideoxy-β-<smallcap>D</span>-ribo-hexopyranosyl)oxy]-12β,14-dihydroxy-
• Brn 1339019
• Cardanolide, 3-((O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-4)-O-2,6-dideoxy-beta-D-ribo-hexopyranosyl-(1-4)-2,6-dideoxy-beta-D-ribo-hexopyranosyl)oxy)-12,14-dihydroxy-, (3-beta,5-beta,12-beta)-
• Cardanolide, 3-((O-2,6-dideoxy-beta-d-ribo-hexopyranosyl-(1.4)-O-2,6-dideoxy-beta-d-ribo-hexopyranosyl-(1.4)-2,6-dideoxy-beta-d-ribo-hexopyranosyl)oxy)-12,14-dihydroxy-, (3beta,5beta,12beta)-
• Cardanolide, 3-[(O-2,6-dideoxy-β-<span class="text-smallcaps">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]-12,14-dihydroxy-, (3β,5β,12β)-
• Digoxin, 20,22-dihydro-
• Digoxin, dihydro-
• Digoxin, dihydro- (6CI)
• Dihydrodigoxin
• 5β-Cardanolide, 3β-[(O-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1→4)-O-2,6-β-D-ribo-hexopyranosyl-(1→4)-2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy]-12β,14-dihydroxy-
• (3β,5β,12β)-3-[(O-2,6-Dideoxy-β-D-ribo-hexopyranosyl-(1→4)-O-2,6-dideoxy-β-D-ribo-hexopyranosyl-(1→4)-2,6-dideoxy-β-D-ribo-hexopyranosyl)oxy]-12,14-dihydroxycardanolide

Dihydrodigoxin

CAS: 5297-10-9

Formula: C₄₁H₆₆O₁₄

Molecular weight: 782.97

Ref: 4Z-D-7519

Dihydrodigoxin (Mixture of Diastereomers)

Controlled Product

CAS: 5297-10-9

Applications Dihydrodigoxin is a cardioinactive metabolite of Digoxin (D446575) that gets excreted in the urine after Digoxin administration in humans.
Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package
References Clark, D.R., et al.: Drug Metab. Dispos., 2, 148 (1974); Reuning, R.H., et al.: Drug Metab. Dispos., 13, 51 (1985); Butler, V.P., et al.: Pharmacology, 221, 123 (1982)

Formula: C₄₁H₆₆O₁₄

Color and Shape: Neat

Molecular weight: 782.95

Ref: TR-D452680

Dihydrodigoxin

CAS: 5297-10-9

Dihydrodigoxin is a cardiac glycoside that has been used in the treatment of congestive heart failure. It is usually administered orally and can be detected by fluorescence detector because it contains a fluorescent derivative. Dihydrodigoxin has been shown to decrease renal excretion of digoxin, which may lead to drug interactions. This drug also decreases the activity of several enzymes, including dehydroascorbic acid reductase (DHAR). DHAR catalyzes the conversion of dehydroascorbic acid to ascorbic acid, which is necessary for collagen synthesis. Dihydrodigoxin also causes preeclampsia in pregnant women and decreases blood flow to the uterus.

Formula: C₄₁H₆₆O₁₄

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 783 g/mol

Ref: 3D-FAA29710