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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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06-Feb-2021
11-Jul-2024
KGS
overview
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Average Price (USD/KGS)

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

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