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    Chemistry

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    Also known as: Primaquine diphosphate, 63-45-6, Primaquine bisphosphate, Primaquine (diphosphate), Malquine, 1,4-pentanediamine, n4-(6-methoxy-8-quinolinyl)-, phosphate (1:2)
    Molecular Formula
    C15H27N3O9P2
    Molecular Weight
    455.34  g/mol
    InChI Key
    GJOHLWZHWQUKAU-UHFFFAOYSA-N
    FDA UNII
    H0982HF78B
    Primaquine Diphosphate
    An aminoquinoline that is given by mouth to produce a radical cure and prevent relapse of vivax and ovale malarias following treatment with a blood schizontocide. It has also been used to prevent transmission of falciparum malaria by those returning to areas where there is a potential for re-introduction of malaria. Adverse effects include anemias and GI disturbances. (From Martindale, The Extra Pharmacopeia, 30th ed, p404)
    1 2D Structure

    Primaquine Diphosphate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-N-(6-methoxyquinolin-8-yl)pentane-1,4-diamine;phosphoric acid
    2.1.2 InChI
    InChI=1S/C15H21N3O.2H3O4P/c1-11(5-3-7-16)18-14-10-13(19-2)9-12-6-4-8-17-15(12)14;2*1-5(2,3)4/h4,6,8-11,18H,3,5,7,16H2,1-2H3;2*(H3,1,2,3,4)
    2.1.3 InChI Key
    GJOHLWZHWQUKAU-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC(CCCN)NC1=C2C(=CC(=C1)OC)C=CC=N2.OP(=O)(O)O.OP(=O)(O)O
    2.2 Other Identifiers
    2.2.1 UNII
    H0982HF78B
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Diphosphate, Primaquine

    2. Phosphate, Primaquine

    3. Primacin

    4. Primaquine

    5. Primaquine Diphosphate

    2.3.2 Depositor-Supplied Synonyms

    1. Primaquine Diphosphate

    2. 63-45-6

    3. Primaquine Bisphosphate

    4. Primaquine (diphosphate)

    5. Malquine

    6. 1,4-pentanediamine, N4-(6-methoxy-8-quinolinyl)-, Phosphate (1:2)

    7. Primaquine Phosphate;primaquine Bisphosphate

    8. N4-(6-methoxyquinolin-8-yl)pentane-1,4-diamine Bis(phosphate)

    9. H0982hf78b

    10. Nsc-149765

    11. N-(5-aminopentan-2-yl)-6-methoxyquinolin-8-amine; Bis(phosphoric Acid)

    12. Primaquine Bis(phosphate)

    13. Wr 2975

    14. Dsstox_cid_25248

    15. Dsstox_rid_80773

    16. Dsstox_gsid_45248

    17. Ccris 1946

    18. Sr-05000001864

    19. Ncgc00178754-06

    20. Einecs 200-560-8

    21. Nsc 149765

    22. Primaquine Phosphate [usp]

    23. Unii-h0982hf78b

    24. Primaquine (tn)

    25. Prestwick_406

    26. Primaquini Diphosphas

    27. Camden

    28. Sn13272 Diphosphate

    29. 8-((4-amino-1-methylbutyl)amino)-6-methoxyquinoline Diphosphate

    30. Cas-63-45-6

    31. Ncgc00016284-01

    32. 8-((4-amino-1-methylbutyl)amino)-6-methoxyquinoline Phosphate (1:2)

    33. Primachine Phosphate

    34. Schembl41096

    35. Chembl43128

    36. Primaquine Bisphosphate, 98%

    37. Spectrum1500500

    38. Dtxsid6045248

    39. Hms502i08

    40. Primaquine Phosphate (jan/usp)

    41. 8-(4-amino-1-methylbutylamino)-6-methoxyquinoline Diphosphate

    42. 8-(4-amino-1-methylbutylamino)-6-methoxyquinolinediphosphate

    43. Hms1569o14

    44. Hms1920j18

    45. Hms2092a19

    46. Hms2096o14

    47. Hms3652b19

    48. Hms3713o14

    49. Primaquine Phosphate [jan]

    50. Primaquine Diphosphate [mi]

    51. Ibscreen-bb Bb_sc-03079

    52. Primaquine Phosphate [vandf]

    53. Tox21_110350

    54. Ccg-40283

    55. Mfcd00013166

    56. Primaquine Phosphate [mart.]

    57. S4237

    58. Primaquine Phosphate [usp-rs]

    59. Primaquine Phosphate [who-dd]

    60. (+-)-8-((4-amino-1-methylbutyl)amino)-6-methoxyquinoline Phosphate (1:2)

    61. 1,4-pentanediamine, N(sup 4)-(6-methoxy-8-quinolinyl)-, Phosphate (1:2)

    62. Akos026749962

    63. Quinoline, 8-((4-amino-1-methylbutyl)amino)-6-methoxy-, Phosphate (1:2)

    64. Tox21_110350_1

    65. Cs-3875

    66. Primaquine Diphosphate [who-ip]

    67. 1,4-pentanediamine, N(sup 4)-(6-methoxy-8-quinolinyl)-, (+-)-, Phosphate (1:2)

    68. Ncgc00094767-01

    69. Ncgc00094767-02

    70. As-13148

    71. Hy-12651

    72. Primaquine Phosphate [orange Book]

    73. Db-054488

    74. Primaquine Phosphate [usp Monograph]

    75. Primaquine Diphosphate [ep Monograph]

    76. Primaquini Diphosphas [who-ip Latin]

    77. Sw196647-3

    78. D02126

    79. E75742

    80. 013p166

    81. Sr-05000001864-1

    82. Sr-05000001864-3

    83. Sr-05000001864-7

    84. Q27279400

    85. N4-(6-methoxyquinolin-8-yl)pentane-1,4-diaminebis(phosphate)

    86. 8-(4-amino-1-methylbutylamino)-6-methoxyquinoline Diphosphate Salt

    87. 1,4-pentanediamine, N^4-(6-methoxy-8-quinolinyl)-, Phosphate (1:2)

    88. 8-?(4-?amino-?1-?methylbutylamino)?-?6-?methoxyquinoline Diphosphate Salt

    89. Primaquine Diphosphate, European Pharmacopoeia (ep) Reference Standard

    90. Primaquine Phosphate, United States Pharmacopeia (usp) Reference Standard

    91. Quinoline, 8-((4-amino-1-methylbutyl)amino)-6-methoxy-, Diphosphate

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 455.34 g/mol
    Molecular Formula C15H27N3O9P2
    Hydrogen Bond Donor Count8
    Hydrogen Bond Acceptor Count12
    Rotatable Bond Count6
    Exact Mass455.12225344 g/mol
    Monoisotopic Mass455.12225344 g/mol
    Topological Polar Surface Area216 Ų
    Heavy Atom Count29
    Formal Charge0
    Complexity312
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count3
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NamePrimaquine phosphate
    Drug LabelPrimaquine phosphate is 8-[(4-Amino-1-methylbutyl)amino]-6-methoxyquinoline phosphate, a synthetic compound with potent antimalarial activity. Each tablet contains 26.3 mg of Primaquine phosphate (equivalent to 15 mg of primaquine base). The dosage i...
    Active IngredientPrimaquine phosphate
    Dosage FormTablet
    RouteOral
    Strengtheq 15mg base
    Market StatusPrescription
    CompanyBayshore Pharms; Alvogen

    2 of 2  
    Drug NamePrimaquine phosphate
    Drug LabelPrimaquine phosphate is 8-[(4-Amino-1-methylbutyl)amino]-6-methoxyquinoline phosphate, a synthetic compound with potent antimalarial activity. Each tablet contains 26.3 mg of Primaquine phosphate (equivalent to 15 mg of primaquine base). The dosage i...
    Active IngredientPrimaquine phosphate
    Dosage FormTablet
    RouteOral
    Strengtheq 15mg base
    Market StatusPrescription
    CompanyBayshore Pharms; Alvogen

    5 Pharmacology and Biochemistry
    5.1 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.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Antimalarial [EPC]

    API Reference Price

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    13-Jan-2021
    23-May-2024
    KGS
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    Average Price (USD/KGS)

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