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    Chloroquine Phosphate

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    2D Structure
    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 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

    2D Structure

    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]