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Chemistry

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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

Acetyldigitoxins
Cardioactive derivatives of lanatoside A or of DIGITOXIN. They are used for fast digitalization in congestive heart failure.
1 2D Structure

Acetyldigitoxins

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.


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