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Chemistry

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Also known as: Chloroquine diphosphate, 50-63-5, Resochin, Arechin, Aralen phosphate, Chingamin phosphate
Molecular Formula
C18H32ClN3O8P2
Molecular Weight
515.9  g/mol
InChI Key
QKICWELGRMTQCR-UHFFFAOYSA-N
FDA UNII
6E17K3343P

Chloroquine Phosphate
Chloroquine Phosphate is the phosphate salt of chloroquine, a quinoline compound with antimalarial and anti-inflammatory properties. Chloroquine is the most widely used drug against malaria, except for those cases caused by chloroquine resistant Plasmodium falciparum. Although the mechanism of action is not fully understood, chloroquine is shown to inhibit the parasitic enzyme heme polymerase that converts the toxic heme into non-toxic hemazoin, thereby resulting in the accumulation of toxic heme within the parasite. Chloroquine may also interfere with the biosynthesis of nucleic acids.
1 2D Structure

Chloroquine Phosphate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-N-(7-chloroquinolin-4-yl)-1-N,1-N-diethylpentane-1,4-diamine;phosphoric acid
2.1.2 InChI
InChI=1S/C18H26ClN3.2H3O4P/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18;2*1-5(2,3)4/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21);2*(H3,1,2,3,4)
2.1.3 InChI Key
QKICWELGRMTQCR-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCN(CC)CCCC(C)NC1=C2C=CC(=CC2=NC=C1)Cl.OP(=O)(O)O.OP(=O)(O)O
2.2 Other Identifiers
2.2.1 UNII
6E17K3343P
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Arechin

2. Chingamin Phosphate

3. Chloroquine Bis(dihydrogenphosphate) Dihydrate

4. Chloroquine Diphosphate

5. Chloroquine Diphosphate, (+)-isomer

6. Chloroquine Diphosphate, (+-)-isomer

7. Chloroquine Diphosphate, (-)-isomer

8. Delagil

9. Khingamin Phosphate

10. N(4)-(7-chloro-4-quinolinyl)-n(1),n(1)-diethyl-1,4-pentanediamine, Phosphate (1:2)

11. Resochin

12. Unspecified Phosphate Of Chloroquine Diphosphate

2.3.2 Depositor-Supplied Synonyms

1. Chloroquine Diphosphate

2. 50-63-5

3. Resochin

4. Arechin

5. Aralen Phosphate

6. Chingamin Phosphate

7. Chloroquine Bis(phosphate)

8. Chloroquine Diphosphate Salt

9. Avloclor

10. Delagil

11. Chloroquine (phosphate)

12. Khingamin

13. Miniquine

14. Tanakan

15. Tanakene

16. Aralen Diphosphate

17. Gontochin Phosphate

18. N4-(7-chloroquinolin-4-yl)-n1,n1-diethylpentane-1,4-diamine Bis(phosphate)

19. Chloroquin Diphosphate

20. Nsc 14050

21. Ipsen 225

22. Chloroquinediphosphate

23. Mfcd00069852

24. 3377 Rp

25. 50-63-5 (diphosphate)

26. Sn 7,618

27. Nsc-14050

28. 6e17k3343p

29. Sn-7618

30. Wr-1522

31. Chingaminum

32. Alermine

33. H-stadur

34. Dsstox_cid_24681

35. Dsstox_rid_80393

36. Dsstox_gsid_44681

37. 1,4-pentanediamine, N(sup 4)-(7-chloro-4-quinolinyl)-n(sup 1),n(sup 1)-diethyl-, Phosphate (1:2)

38. Chlorochin Diphosphate

39. Tanakan (antimalarial)

40. 4-n-(7-chloroquinolin-4-yl)-1-n,1-n-diethylpentane-1,4-diamine;phosphoric Acid

41. Dl-chloroquine Diphosphate

42. Ccris 1554

43. Sr-01000075548

44. Einecs 200-055-2

45. Wr 1522

46. Chloroquine Dihydrogen Phosphate (1:2)

47. Unikinon

48. Ai3-14952

49. Unii-6e17k3343p

50. Chloroquine Phosphate [usp:ban]

51. Chloroquindiphosphat

52. Chloroquini Phosphas

53. Prestwick_867

54. Aralen (tn)

55. Cas-50-63-5

56. Ncgc00015256-01

57. 7-chlor-4-(4-(diaethylamino)-1-methylbutylamino)-chinolindiphosphat [german]

58. 7-chloro-4-((4-(diethylamino)-1-methylbutyl)amino)quinoline Phosphate (1:2)

59. N4-(7-chloro-4-quinolinyl)-n1,n1-dimethyl-1,4-pentanediamine Diphosphate Salt

60. Chloroquine Diphosphate,(s)

61. 1,4-pentanediamine, N4-(7-chloro-4-quinolinyl)-n1,n1-diethyl-, Phosphate (1:2)

62. N(4)-(7-chloro-4-quinolinyl)-n(1),n(1)-diethyl-1,4-pentanediamine, Phosphate (1:2)

63. 1,4-diamine Bis(phosphate)

64. Chloroquine Phosphate (usp)

65. Schembl40827

66. Chembl58510

67. Spectrum1500179

68. Chloroquine Diphosphate, Sulfate

69. Dtxsid7044681

70. Hms501e06

71. Hms1569n17

72. Hms1920o05

73. Hms2091c16

74. Hms2096n17

75. Hms3260l14

76. Hms3713n17

77. Bcp31956

78. Chloroquine Diphosphate [mi]

79. Tox21_110115

80. Tox21_202838

81. Tox21_500296

82. 7-chlor-4-(4-(diaethylamino)-1-methylbutylamino)-chinolindiphosphat

83. Ccg-39643

84. Chloroquine Phosphate [vandf]

85. S4157

86. Chloroquine Phosphate [mart.]

87. Akos004910410

88. Chloroquine Phosphate [usp-rs]

89. Chloroquine Phosphate [who-dd]

90. Chloroquine Phosphate [who-ip]

91. N4-(7-chloro-4-quinolyl)-n1,n1-diethyl-pentane-1,4-diamine; Phosphoric Acid

92. Quinoline, 7-chloro-4-(4-diethylamino-1-methyl-butylamino)-, Diphosphate

93. Tox21_110115_1

94. Cs-3811

95. Dt-0015

96. Lp00296

97. 1,4-pentanediamine, N4-(7-chloro-4-quinolinyl)-n',n'-diethyl-, (+-)-, Phosphate (1:2)

98. Quinoline, 7-chloro-4-((4-(diethylamino)-1-methylbutyl)amino)-, Phosphate (1:2)

99. Ncgc00015256-12

100. Ncgc00093746-01

101. Ncgc00093746-02

102. Ncgc00093746-03

103. Ncgc00260384-01

104. Ncgc00260981-01

105. Ac-12463

106. Chloroquine Phosphate [green Book]

107. Hy-17589

108. Sy021941

109. Chloroquine Phosphate [orange Book]

110. Chloroquine Phosphate [ep Monograph]

111. Chloroquini Phosphas [who-ip Latin]

112. Db-051808

113. Chloroquine Diphosphate Salt, Solid, >=98%

114. Chloroquine Phosphate [usp Monograph]

115. Eu-0100296

116. Ft-0602804

117. C 6628

118. D02125

119. D70732

120. 069c852

121. A828213

122. N4-(7-chloroquinolin-4-yl)-n1,n1-diethylpentane-

123. Sr-01000075548-1

124. Sr-01000075548-3

125. Sr-01000075548-5

126. Q27264629

127. F2173-1139

128. 7-chloro-4-[[4-(diethylamino)-1-methylbutyl]amino]quinoline Phosphate

129. 7-chloro-4-[4-(diethylamino)-1-methylbutylamino]quinoline Bis(phosphate)

130. 7-chloro-4-[4-(diethylamino)-1-methylbutylamino]quinoline Diphosphate

131. Chloroquine Phosphate, United States Pharmacopeia (usp) Reference Standard

132. N4-(7-chloro-4-quinolyl)-n1,n1-diethyl-1,4-pentanediamine Diphosphate

133. 7-chloro-4-((4-(diethylamino)-1-methylbutyl)amino)quinoline Phosphate (1:2).

134. Chloroquine Phosphate, Pharmaceutical Secondary Standard; Certified Reference Material

135. Chloroquine Phosphate;aralen Phosphate;7-chloro-4-((4 Inverted Exclamation Mark -diethylamino-1-methylbutyl)amino)quinolinediphosphate

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 515.9 g/mol
Molecular Formula C18H32ClN3O8P2
Hydrogen Bond Donor Count7
Hydrogen Bond Acceptor Count11
Rotatable Bond Count8
Exact Mass515.1353167 g/mol
Monoisotopic Mass515.1353167 g/mol
Topological Polar Surface Area184 Ų
Heavy Atom Count32
Formal Charge0
Complexity359
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 NameChloroquine phosphate
Drug LabelChloroquine phosphate, USP is a 4-aminoquinoline compound for oral administration. It is a white crystalline powder; odorless; has a bitter taste, and is discolored slowly on exposure to light. It is freely soluble in water, practically insoluble in...
Active IngredientChloroquine phosphate
Dosage FormTablet
RouteOral
Strengtheq 300mg base; eq 150mg base
Market StatusPrescription
CompanyIpca Labs; Natco Pharma; Hikma Pharms; Impax Labs

2 of 2  
Drug NameChloroquine phosphate
Drug LabelChloroquine phosphate, USP is a 4-aminoquinoline compound for oral administration. It is a white crystalline powder; odorless; has a bitter taste, and is discolored slowly on exposure to light. It is freely soluble in water, practically insoluble in...
Active IngredientChloroquine phosphate
Dosage FormTablet
RouteOral
Strengtheq 300mg base; eq 150mg base
Market StatusPrescription
CompanyIpca Labs; Natco Pharma; Hikma Pharms; Impax Labs

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anti-Inflammatory Agents, Non-Steroidal

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)


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.)


Filaricides

Pharmacological agents destructive to nematodes in the superfamily Filarioidea. (See all compounds classified as Filaricides.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Antimalarial [EPC]

API Reference Price

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07-Jan-2021
31-Aug-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

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