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    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
    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 Weight 520.6 g/mol
    Molecular Formula C26H36N2O9
    Hydrogen Bond Donor Count7
    Hydrogen Bond Acceptor Count11
    Rotatable Bond Count9
    Exact Mass520.24208073 g/mol
    Monoisotopic Mass520.24208073 g/mol
    Topological Polar Surface Area184 Ų
    Heavy Atom Count37
    Formal Charge0
    Complexity627
    Isotope Atom Count0
    Defined Atom Stereocenter Count8
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    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]

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