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    Acetyldigitoxins

    FINISHED DOSAGE FORMULATIONS

    PharmaCompass
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    2D Structure
    Also known as: Alpha-acetyldigitoxin, 1111-39-3, Acylanid, Desglucolanatoside a, Acetyldiginatin, Acylanide
    Molecular Formula
    C43H66O14
    Molecular Weight
    807.0  g/mol
    InChI Key
    HPMZBILYSWLILX-UMDUKNJSSA-N
    FDA UNII
    0ZV4Q4L2FU
    Cardioactive derivatives of lanatoside A or of DIGITOXIN. They are used for fast digitalization in congestive heart failure.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC 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
    2.1.2 InChI
    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
    2.1.3 InChI Key
    HPMZBILYSWLILX-UMDUKNJSSA-N
    2.1.4 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)OC(=O)C)O
    2.1.5 Isomeric SMILES
    C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@@H]2[C@H](O[C@H](C[C@@H]2O)O[C@@H]3[C@H](O[C@H](C[C@@H]3O)O[C@H]4CC[C@]5([C@@H](C4)CC[C@@H]6[C@@H]5CC[C@]7([C@@]6(CC[C@@H]7C8=CC(=O)OC8)O)C)C)C)C)OC(=O)C)O
    2.2 Other Identifiers
    2.2.1 UNII
    0ZV4Q4L2FU
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Acedoxin

    2. Acetyldigitoxins

    3. Adicin

    4. Alpha Acetyldigitoxin

    5. Alpha-acetyldigitoxin

    6. Desglucolanatosides A

    7. Digitoxin Monoacetate

    8. Monoacetate, Digitoxin

    2.3.2 Depositor-Supplied Synonyms

    1. Alpha-acetyldigitoxin

    2. 1111-39-3

    3. Acylanid

    4. Desglucolanatoside A

    5. Acetyldiginatin

    6. Acylanide

    7. Acetildigitoxina

    8. Alpha-monoacetyldigitoxin

    9. Acetyldigitoxinum

    10. Acetyl-digitoxin-alpha

    11. Acetylgitoxin

    12. Digitoxin 3'''-acetate

    13. Acetyldigitoxin [inn]

    14. 3'''-o-acetyldigitoxin

    15. Alpha-acetylgitaloxin

    16. Acetyldigitoxin (inn)

    17. 0zv4q4l2fu

    18. Acetyldigitoxins .alpha.-form

    19. Chebi:53773

    20. (3beta,5beta)-3-((o-3-o-acetyl-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)-14-hydroxycard-20(22)-enolide

    21. Acedigal

    22. Adicin

    23. [(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

    24. Digitoxin, 3'''-acetate

    25. Acylanid (tn)

    26. Acetyldigitoxinum [inn-latin]

    27. Alpha-acetyldigitoxins

    28. Acetildigitoxina [inn-spanish]

    29. Digitoxin, Alpha-acetyl-

    30. Acetyldigitoxin [inn:nf]

    31. Unii-0zv4q4l2fu

    32. Acetyldigitoxins

    33. Einecs 214-178-4

    34. Brn 0077291

    35. 3'''-acetyldigitoxin

    36. Digitoxin, Acetate, Alpha-

    37. Schembl309649

    38. Gtpl6794

    39. Acetyldigitoxin [mart.]

    40. Acetyldigitoxin [who-dd]

    41. Chembl3545057

    42. Acetyldigitoxin [orange Book]

    43. Zinc96006012

    44. Db00511

    45. (3beta,5beta)-3-((o-3-o-acetyl-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)-14-hydroxycard-20(22)-enolide

    46. (3beta,5beta)-3-{[3-o-acetyl-2,6-dideoxy-beta-d-ribo-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

    47. 3beta-[3-o-acetyl-2,6-dideoxy-beta-d-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-d-ribo-hexopyranosyl-(1->4)-2,6-dideoxy-beta-d-ribo-hexopyranosyloxy]-14-hydroxy-5beta-card-20(22)-enolide

    48. Hy-16022

    49. Acetyldigitoxins .alpha.-form [mi]

    50. Cs-0006116

    51. C22191

    52. D06881

    53. (2r,3r,4s,6s)-3-hydroxy-6-{[(2r,3s,4s,6s)-4-hydroxy-6-{[(2r,3s,4s,6r)-4-hydroxy-6-{[(1s,2s,5s,7r,10r,11s,14r,15r)-11-hydroxy-2,15-dimethyl-14-(5-oxo-2,5-dihydrofuran-3-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}-2-methyloxan-3-yl]oxy}-2-methyloxan-3-yl]oxy}-2-methyloxan-4-yl Acetate

    54. (3.beta.,5.beta.)-3-((o-3-o-acetyl-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)-14-hydroxycard-20(22)-enolide

    55. Card-20(22)-enolide, 3-((o-3-o-acetyl-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)-14-hydroxy-, (3beta,5beta)-

    2.4 Create Date
    2005-11-20
    3 Chemical and Physical Properties
    Molecular Weight 807.0 g/mol
    Molecular Formula C43H66O14
    XLogP32.8
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count14
    Rotatable Bond Count9
    Exact Mass806.44525677 g/mol
    Monoisotopic Mass806.44525677 g/mol
    Topological Polar Surface Area189 Ų
    Heavy Atom Count57
    Formal Charge0
    Complexity1520
    Isotope Atom Count0
    Defined Atom Stereocenter Count20
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Used for fast digitalization in congestive heart failure.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    The main pharmacological effects of acetyldigitoxin are on the heart. Extracardiac effects are responsible for many of the adverse effects. Its main cardiac effects are 1) a decrease of conduction of electrical impulses through the AV node, making it a commonly used drug in controlling the heart rate during atrial fibrillation or atrial flutter, and 2) an increase of force of contraction via inhibition of the Na+/K+ ATPase pump.

    5.2 MeSH Pharmacological Classification

    Enzyme Inhibitors

    Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

    Cardiotonic Agents

    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). (See all compounds classified as Cardiotonic Agents.)

    Anti-Arrhythmia Agents

    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. (See all compounds classified as Anti-Arrhythmia Agents.)

    5.3 ATC Code

    C - Cardiovascular system

    C01 - Cardiac therapy

    C01A - Cardiac glycosides

    C01AA - Digitalis glycosides

    C01AA01 - Acetyldigitoxin

    5.4 Absorption, Distribution and Excretion

    Absorption

    Bioavailability is 60 to 80% following oral administration.

    5.5 Mechanism of Action

    Acetyldigitoxin binds to a site on the extracellular aspect of the α-subunit of the Na+/K+ ATPase pump in the membranes of heart cells (myocytes). This causes an increase in the level of sodium ions in the myocytes, which then leads to a rise in the level of calcium ions. The proposed mechanism is the following: inhibition of the Na+/K+ pump leads to increased Na+ levels, which in turn slows down the extrusion of Ca2+ via the Na+/Ca2+ exchange pump. Increased amounts of Ca2+ are then stored in the sarcoplasmic reticulum and released by each action potential, which is unchanged by acetyldigitoxin. This is a different mechanism from that of catecholamines. Acetyldigitoxin also increases vagal activity via its central action on the central nervous system, thus decreasing the conduction of electrical impulses through the AV node. This is important for its clinical use in different arrhythmias.