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Quinidine Gluconate

Quinidine Gluconate

Synopsis, Chemistry

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Also known as: Duraquin, 7054-25-3, Gluquinate, Dura-tab, Quinidine mono-d-gluconate, 6587-33-3

Molecular Formula

C₂₆H₃₆N₂O₉

Molecular Weight

520.6 g/mol

InChI Key

XHKUDCCTVQUHJQ-LCYSNFERSA-N

FDA UNII

R6875N380F

Quinidine Gluconate is the gluconate salt form of quinidine, an alkaloid with antimalarial and antiarrhythmic (Class la) properties. Quinidine gluconate exerts its anti-malarial activity by acting primarily as an intra-erythrocytic schizonticide through association with the hemepolymer (hemozoin) in the acidic food vacuole of the parasite thereby preventing further polymerization by heme polymerase enzyme. This results in accumulation of toxic heme and death of the parasite. Quinidine gluconate exerts its antiarrhythmic effects by depressing the flow of sodium ions into cells during phase 0 of the cardiac action potential, thereby slowing the impulse conduction through the atrioventricular (AV) node, reducing the maximal rate of phase 0 depolarization and prolonging the refractory period. Quinidine gluconate also reduces the slope of phase 4 depolarization in Purkinje-fibres resulting in slowed conduction and reduced automaticity in the heart.

1 2D Structure

Quinidine Gluconate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid

2.1.2 InChI

InChI=1S/C20H24N2O2.C6H12O7/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18;7-1-2(8)3(9)4(10)5(11)6(12)13/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;2-5,7-11H,1H2,(H,12,13)/t13-,14-,19+,20-;2-,3-,4+,5-/m01/s1

2.1.3 InChI Key

XHKUDCCTVQUHJQ-LCYSNFERSA-N

2.1.4 Canonical SMILES

COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C=C)O.C(C(C(C(C(C(=O)O)O)O)O)O)O

2.1.5 Isomeric SMILES

COC1=CC2=C(C=CN=C2C=C1)[C@@H]([C@H]3C[C@@H]4CCN3C[C@@H]4C=C)O.C([C@H]([C@H]([C@@H]([C@H](C(=O)O)O)O)O)O)O

2.2 Other Identifiers

2.2.1 UNII

R6875N380F

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Quinact

2. Quinaglute

3. Quinidine Gluconate, (8alpha,9r)-isomer

4. Quinidine Gluconate, (9s)-isomer

2.3.2 Depositor-Supplied Synonyms

1. Duraquin

2. 7054-25-3

3. Gluquinate

4. Dura-tab

5. Quinidine Mono-d-gluconate

6. 6587-33-3

7. Nsc-757297

8. Gluconic Acid Quinidine Salt

9. Quinidine Monogluconate, D-

10. Chebi:27502

11. R6875n380f

12. Quinidine Gluconate Salt

13. Cinchonan-9-ol, 6'-methoxy-, (9s)-, Mono-d-gluconate (salt)

14. D-gluconic Acid, Compd. With (9s)-6'-methoxycinchonan-9-ol (1:1)

15. Quinidine Gluconate [usp]

16. (s)-[(2r,4s,5r)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanoic Acid

17. Quinidine D-gluconate

18. Sr-05000001710

19. Quinidine, D-gluconate (salt)

20. Unii-r6875n380f

21. Quinidine Mono-d-gluconate (salt)

22. Einecs 229-517-1

23. Einecs 230-333-9

24. Spectrum_000910

25. Spectrum2_000408

26. Spectrum3_000893

27. Spectrum4_000987

28. Spectrum5_001080

29. Schembl41479

30. Kbiogr_001393

31. Kbioss_001390

32. Divk1c_000228

33. Spectrum1500523

34. Spbio_000336

35. Chembl1200437

36. Quinidine Gluconate [mi]

37. Schembl15541190

38. Hms500l10

39. Hy-b1751f

40. Kbio1_000228

41. Kbio2_001390

42. Kbio2_003958

43. Kbio2_006526

44. Kbio3_001806

45. Ninds_000228

46. Dtxsid801027497

47. Hms1920n18

48. Hms2092e19

49. Pharmakon1600-01500523

50. Quinidine Gluconate [vandf]

51. D-gluconic Acid, Compound With (9s)-6'-methoxycinchonan-9-ol

52. Quinidine Gluconate [mart.]

53. Ccg-38674

54. Nsc757297

55. Quinidine Gluconate [usp-rs]

56. Quinidine Gluconate [who-dd]

57. Ex-6000

58. Nsc 757297

59. Idi1_000228

60. Quinidine Gluconate [orange Book]

61. Quinidine Gluconate [usp Monograph]

62. Cs-0030857

63. Quinidine Gluconate Salt, Analytical Standard

64. 054q253

65. Gluconic Acid, Compd. With Quinidine (1:1), D-

66. Sr-05000001710-1

67. Sr-05000001710-2

68. W-110193

69. Q27094388

70. (9s)-6'-methoxycinchonan-9-ol--d-gluconic Acid (1:1)

71. Cinchonan-9-ol, 6'-methoxy-, (9s)-, Mono-d-gluconate

72. D-gluconic Acid, Compd. With (9s)-6'-methoxycinchonan-9-ol (1:?)

73. Quinidine Gluconate, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₃₆N₂O₉
Molecular Weight	520.6 g/mol
Hydrogen Bond Donor Count	7
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	9
Exact Mass	520.24208073 g/mol
Monoisotopic Mass	520.24208073 g/mol
Topological Polar Surface Area	184 Å²
Heavy Atom Count	37
Formal Charge	0
Complexity	627
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Antimalarials

Agents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585) (See all compounds classified as Antimalarials.)

4.2 FDA Pharmacological Classification

4.2.1 Pharmacological Classes

Cytochrome P450 2D6 Inhibitor [EPC]; Cytochrome P450 2D6 Inhibitors [MoA]; Antiarrhythmic [EPC]