ACETYLDIGITOXIN
Acetyldigitoxin is a cardiac glycoside that increases myocardial contractility by inhibiting Na⁺/K⁺‑ATPase. It is used in heart failure and certain arrhythmias. Benefits include strong inotropic action and long duration. Risks include toxicity, arrhythmias, nausea, and visual disturbances, requiring careful monitoring.
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Product Description
Mechanism of action
Acetyldigitoxin is an acetylated cardiac glycoside structurally related to digitoxin. It inhibits the sodium–potassium ATPase pump in cardiac myocytes, leading to an increase in intracellular sodium and a secondary increase in intracellular calcium via the sodium–calcium exchanger. The resulting positive inotropic effect enhances myocardial contractility.
Benefits and advantages
Cardiac glycosides such as acetyldigitoxin have been used for the management of certain forms of heart failure and supraventricular arrhythmias. Chemical modifications like acetylation can alter pharmacokinetic properties, including absorption and tissue distribution, which may be valuable in formulation development or research.
Side effects and risks
The therapeutic index of cardiac glycosides is narrow. Toxicity manifests with nausea, vomiting, visual disturbances, bradyarrhythmias and potentially lethal ventricular arrhythmias. Electrolyte disturbances, renal insufficiency and drug interactions greatly increase risk. Handling of acetyldigitoxin as an API demands stringent controls to prevent accidental exposure.
Datasheet
| Molecular Formula | C43H66O14 |
|---|---|
| Molecular Weight | 807.0 g/mol |
| CAS Number | 1111-39-3 |
| Storage Condition | Store in a cool, dry place. Keep container tightly closed. Protect from moisture and light. |
| Solubility | Solubility depends on solvent and conditions (e.g., pH). Please contact us for solvent-specific guidance. |
| Purity | Purity information is available upon request (COA). |
| Synonym | acetyldigitoxin; 1111-39-3; alpha-Acetyldigitoxin; Desglucolanatoside A; Acylanid |
| IUPAC/Chemical Name | [(2R,3R,4S,6S)-3-hydroxy-6-[(2R,3S,4S,6S)-4-hydroxy-6-[(2R,3S,4S,6R)-4-hydroxy-6-[[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-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]-2-methyloxan-3-yl]oxy-2-methyloxan-3-yl]oxy-2-methyloxan-4-yl] acetate |
| InChl Key | HPMZBILYSWLILX-UMDUKNJSSA-N |
| InChl Code | InChI=1S/C43H66O14/c1-21-38(48)33(54-24(4)44)19-37(51-21)57-40-23(3)53-36(18-32(40)46)56-39-22(2)52-35(17-31(39)45)55-27-9-12-41(5)26(16-27)7-8-30-29(41)10-13-42(6)28(11-14-43(30,42)49)25-15-34(47)50-20-25/h15,21-23,26-33,35-40,45-46,48-49H,7-14,16-20H2,1-6H3/t21-,22-,23-,26-,27+,28-,29+,30-,31+,32+,33+,35+,36+,37+,38-,39-,40-,41+,42-,43+/m1/s1 |
| References |
3D Conformer.
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