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Deslanoside

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Chemistry

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Also known as: 17598-65-1, Desacetyllanatoside c, Deacetyllanatoside c, Cedilanid-d, Deslanosidum, Deslanosido

Molecular Formula

C₄₇H₇₄O₁₉

Molecular Weight

943.1 g/mol

InChI Key

OBATZBGFDSVCJD-LALPQLPRSA-N

FDA UNII

YGY317RK75

Deacetyllanatoside C. A cardiotonic glycoside from the leaves of Digitalis lanata.

1 2D Structure

Deslanoside

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-[(3S,5R,8R,9S,10S,12R,13S,14S,17R)-12,14-dihydroxy-3-[(2R,4S,5S,6R)-4-hydroxy-5-[(2S,4S,5S,6R)-4-hydroxy-5-[(2S,4S,5S,6R)-4-hydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-6-methyloxan-2-yl]oxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

2.1.2 InChI

InChI=1S/C47H74O19/c1-20-41(64-36-16-30(50)42(21(2)60-36)65-37-17-31(51)43(22(3)61-37)66-44-40(56)39(55)38(54)32(18-48)63-44)29(49)15-35(59-20)62-25-8-10-45(4)24(13-25)6-7-27-28(45)14-33(52)46(5)26(9-11-47(27,46)57)23-12-34(53)58-19-23/h12,20-22,24-33,35-44,48-52,54-57H,6-11,13-19H2,1-5H3/t20-,21-,22-,24-,25+,26-,27-,28+,29+,30+,31+,32-,33-,35+,36+,37+,38-,39+,40-,41-,42-,43-,44+,45+,46+,47+/m1/s1

2.1.3 InChI Key

OBATZBGFDSVCJD-LALPQLPRSA-N

2.1.4 Canonical SMILES

CC1C(C(CC(O1)OC2CCC3(C(C2)CCC4C3CC(C5(C4(CCC5C6=CC(=O)OC6)O)C)O)C)O)OC7CC(C(C(O7)C)OC8CC(C(C(O8)C)OC9C(C(C(C(O9)CO)O)O)O)O)O

2.1.5 Isomeric SMILES

C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2CC[C@]3([C@@H](C2)CC[C@@H]4[C@@H]3C[C@H]([C@]5([C@@]4(CC[C@@H]5C6=CC(=O)OC6)O)C)O)C)O)O[C@H]7C[C@@H]([C@@H]([C@H](O7)C)O[C@H]8C[C@@H]([C@@H]([C@H](O8)C)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O)O

2.2 Other Identifiers

2.2.1 UNII

YGY317RK75

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cedilanid D

2. Cedilanid-d

3. Cedilanidd

4. Desacetyl Lanatoside

5. Desacetyldigilanide C

6. Desacetyllanatoside C

7. Deslanatoside C

8. Lanatoside, Desacetyl

2.3.2 Depositor-Supplied Synonyms

1. 17598-65-1

2. Desacetyllanatoside C

3. Deacetyllanatoside C

4. Cedilanid-d

5. Deslanosidum

6. Deslanosido

7. Glucodigoxin

8. Deslanosid

9. Deacetylanatoside C

10. Desacetyl-lanatoside C

11. Desace

12. Lanatoside C, Deacetyl-

13. Ygy317rk75

14. Sediranido

15. Lekozid

16. Chebi:31468

17. Deslanosidum C

18. Dsstox_cid_2897

19. Dsstox_rid_76778

20. Dsstox_gsid_22897

21. (3beta,5beta,12beta)-3-{[beta-d-glucopyranosyl-(1->4)-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}-12,14-dihydroxycard-20(22)-enolide

22. Deslanosidum [inn-latin]

23. Deslanosido [inn-spanish]

24. Deacetyl-lanatoside C

25. Cedilanid-d (tn)

26. Cas-17598-65-1

27. Einecs 241-568-1

28. Brn 0078187

29. Unii-ygy317rk75

30. Cedilanide

31. Deslanoside [usp:inn:ban:jan]

32. Ncgc00159441-02

33. Deslanoside [mi]

34. Deslanoside [inn]

35. Deslanoside [jan]

36. Deslanoside [vandf]

37. Chembl1614

38. Deslanoside [mart.]

39. Deslanoside [usp-rs]

40. Deslanoside [who-dd]

41. 3beta-(o-beta-d-glucopyranosyl-(1-4)-o-beta-d-digitoxosyl-(1-4)-o-beta-d-digitoxosyl-(1-4)-beta-d-digitoxosyloxy-12beta,14-dihydroxy-5beta,14beta-card-20(22)-enolid

42. 4-18-00-02455 (beilstein Handbook Reference)

43. Card-20(22)-enolide, 3-((o-beta-d-glucopyranosyl-(1-4)-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)-

44. Schembl125311

45. Gtpl6806

46. Deslanoside (jp17/usp/inn)

47. Dtxsid1022897

48. Deslanoside [orange Book]

49. Deslanoside [ep Monograph]

50. Deslanoside [usp Impurity]

51. Hy-a0154

52. Tox21_111671

53. Mfcd00135818

54. Tox21_111671_1

55. Zinc253668332

56. Db01078

57. Ncgc00159441-03

58. 3-[(o-beta-d-glucopyranosyl-(1->4)-o-2,6-dideoxy-beta-d-ribo-hexopyranosyl-(1->4)-o-2,6-dideoxy-beta-d-ribo-hexopyranosyl-(1->4)-o-2,6-dideoxy-beta-d-ribo-hexopyranosyl)oxy]-12,14-dihydroxy-3beta,5beta,12beta-card-20(22)-enolide

59. 3beta-{[beta-d-glucopyranosyl-(1->4)-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}-12beta,14-dihydroxy-5beta-card-20(22)-enolide

60. Card-20(22)-enolide, 3-((o-beta-d-glucopyranosyl-(1->4)-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)-

61. Cs-0017480

62. D01240

63. E88575

64. 598d651

65. Q5264583

66. (3beta,5beta,12beta)-3-{[beta-d-glucopyranosyl-(1-->4)-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}-12,14-dihydroxycard-20(22)-enolide

67. 3-[(o-beta-d-glucopyranosyl-(1-->4)-o-2,6-dideoxy-beta-d-ribo-hexopyranosyl-(1-->4)-o-2,6-dideoxy-beta-d-ribo-hexopyranosyl-(1-->4)-o-2,6-dideoxy-beta-d-ribo-hexopyranosyl)oxy]-12,14-dihydroxy-3beta,5beta,12beta-card-20(22)-enolide

68. Card-20(22)-enolide, 3-((o-.beta.-d-glucopyranosyl-(1->4)-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.)-

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₄₇H₇₄O₁₉
Molecular Weight	943.1 g/mol
XLogP3	-0.3
Hydrogen Bond Donor Count	9
Hydrogen Bond Acceptor Count	19
Rotatable Bond Count	10
Exact Mass	942.48243013 g/mol
Monoisotopic Mass	942.48243013 g/mol
Topological Polar Surface Area	282 Å²
Heavy Atom Count	66
Formal Charge	0
Complexity	1760
Isotope Atom Count	0
Defined Atom Stereocenter Count	26
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For the treatment and management of Congestive cardiac insufficiency, arrhythmias and heart failure.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Deslanoside is a cardiac glycoside used to treat congestive heart failure and supraventricular arrhythmias due to reentry mechanisms, and to control ventricular rate in the treatment of chronic atrial fibrillation.

5.2 MeSH Pharmacological Classification

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.)

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.)

5.3 ATC Code

C - Cardiovascular system

C01 - Cardiac therapy

C01A - Cardiac glycosides

C01AA - Digitalis glycosides

C01AA07 - Deslanoside

5.4 Absorption, Distribution and Excretion

Absorption

Little absorption from the gastrointestinal tract (40%).

5.5 Biological Half-Life

36 hours

5.6 Mechanism of Action

Deslanoside inhibits the Na-K-ATPase membrane pump, resulting in an increase in intracellular sodium and calcium concentrations. Increased intracellular concentrations of calcium may promote activation of contractile proteins (e.g., actin, myosin). Deslanoside also acts on the electrical activity of the heart, increasing the slope of phase 4 depolarization, shortening the action potential duration, and decreasing the maximal diastolic potential.

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