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Hydroxychloroquine Sulfate

Synopsis, Chemistry

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Also known as: 747-36-4, Hydroxychloroquine sulphate, Ercoquin, Plaquenil, 2-((4-((7-chloroquinolin-4-yl)amino)pentyl)(ethyl)amino)ethanol sulfate, Quensyl

Molecular Formula

C₁₈H₂₈ClN₃O₅S

Molecular Weight

434.0 g/mol

InChI Key

JCBIVZZPXRZKTI-UHFFFAOYSA-N

FDA UNII

8Q2869CNVH

A chemotherapeutic agent that acts against erythrocytic forms of malarial parasites. Hydroxychloroquine appears to concentrate in food vacuoles of affected protozoa. It inhibits plasmodial heme polymerase. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p970)

1 2D Structure

Hydroxychloroquine Sulfate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[4-[(7-chloroquinolin-4-yl)amino]pentyl-ethylamino]ethanol;sulfuric acid

2.1.2 InChI

InChI=1S/C18H26ClN3O.H2O4S/c1-3-22(11-12-23)10-4-5-14(2)21-17-8-9-20-18-13-15(19)6-7-16(17)18;1-5(2,3)4/h6-9,13-14,23H,3-5,10-12H2,1-2H3,(H,20,21);(H2,1,2,3,4)

2.1.3 InChI Key

JCBIVZZPXRZKTI-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCN(CCCC(C)NC1=C2C=CC(=CC2=NC=C1)Cl)CCO.OS(=O)(=O)O

2.2 Other Identifiers

2.2.1 UNII

8Q2869CNVH

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Hydroxychlorochin

2. Hydroxychloroquine

3. Hydroxychloroquine Sulfate (1:1) Salt

4. Oxychlorochin

5. Oxychloroquine

6. Plaquenil

2.3.2 Depositor-Supplied Synonyms

1. 747-36-4

2. Hydroxychloroquine Sulphate

3. Ercoquin

4. Plaquenil

5. 2-((4-((7-chloroquinolin-4-yl)amino)pentyl)(ethyl)amino)ethanol Sulfate

6. Quensyl

7. Oxiklorin

8. Tcmdc-123987

9. Hcq Sulfate

10. Plaquenil Sulfate

11. Nsc 4375

12. Hydroxychloroquine (sulfate)

13. Oxichlorochine Sulfate

14. Nsc-4375

15. 8q2869cnvh

16. 2-[4-[(7-chloroquinolin-4-yl)amino]pentyl-ethylamino]ethanol;sulfuric Acid

17. 2-({4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino)ethan-1-ol; Sulfuric Acid

18. Plaquinol

19. Toremonil

20. 2-((4-((7-chloroquinolin-4-yl)amino)pentyl)(ethyl)amino)ethan-1-ol Sulfate

21. Dsstox_cid_27788

22. Dsstox_rid_82563

23. N4-(7-chloro-4-quinolyl)-n1-ethyl-n1-(2-hydroxyethyl)-1,4-pentanediamine Sulfate

24. Dsstox_gsid_47811

25. 2-((4-(7-chloroquinolin-4-ylamino)pentyl)(ethyl)amino)ethanol Sulfate

26. 2-((4-((7-chloroquinolin-4-yl)amino)-pentyl)(ethyl)amino)ethanol Sulfate

27. Cas-747-36-4

28. Hydroxychloroquine Sulfate [usp]

29. Ethanol, 2-((4-((7-chloro-4-quinolinyl)amino)pentyl)ethylamino)-, Sulfate (1:1)

30. Sr-05000001881

31. Ncgc00159483-02

32. Einecs 212-019-3

33. Unii-8q2869cnvh

34. Quinoric

35. Ai3-52706

36. Plaquenil (tn)

37. Ethanol, Monosulfate

38. Mfcd00078203

39. Ethanol, 2-[[4-[(7-chloro-4-quinolinyl)amino]pentyl]ethylamino]-, Sulfate (1:1)

40. Hydroxychlorquine Sulfate

41. 2-((4-((7-chloro-4-quinolinyl)amino)pentyl)ethylamino)ethanol Sulfate (1:1) (salt)

42. 2-((4-((7-chloro-4-quinolyl)amino)pentyl)ethylamino)ethanol Sulfate (1:1) (salt)

43. Chembl1690

44. Ethanol, 2-((4-((7-chloro-4-quinolyl)amino)pentyl)ethylamino)-, Sulfate (1:1) (salt)

45. Schembl41114

46. Spectrum1503978

47. 747-36-4 (sulfate)

48. Dtxsid1047811

49. Hydroxychloroquine Sulfate ,(s)

50. Hydroxychloroquine Sulfate- Bio-x

51. Ethanol, Sulfate (1:1) (salt)

52. Hms1922o12

53. Hms2093o05

54. Hms3713j22

55. Pharmakon1600-01503978

56. Bcp12823

57. Hy-b1370

58. Tox21_111707

59. Bdbm50247975

60. Ccg-39154

61. Nsc758663

62. S4430

63. Hydroxychloroquine Sulfate (jan/usp)

64. Akos015897337

65. Tox21_111707_1

66. Cs-8017

67. Hydroxychloroquine Sulfate [mi]

68. Ks-5311

69. Nsc-758663

70. Sb19140

71. (+-)-2-((4-((7-chloro-4-quinolyl)amino)pentyl)ethylamino)ethanol Sulfate (1:1) (salt)

72. 7-chloro-4-[4-[n-ethyl-n-(2-hydroxyethyl)amino]-1-methylbutylamino]quinoline Sulfate

73. Hydroxychloroquine Sulfate [jan]

74. Ncgc00095090-01

75. Ncgc00095090-02

76. Ncgc00159483-04

77. Bh164525

78. Ethanol, 2-((4-((7-chloro-4-quinolinyl)amino)pentyl)ethyl)amino-, (+-)-, Sulfate (1:1) Salt

79. Hydroxychloroquine Sulfate [mart.]

80. Hydroxychloroquine Sulfate [vandf]

81. Hydroxychloroquine Sulfate [usp-rs]

82. Hydroxychloroquine Sulfate [who-dd]

83. Db-055904

84. Ft-0603511

85. Ft-0669460

86. H1306

87. Hydroxycloroquine Sulfate, Analytical Standard

88. D02114

89. H10433

90. Hydroxychloroquine Sulfate [orange Book]

91. Hydroxychloroquine Sulfate [ep Monograph]

92. 747h364

93. A838213

94. Hydroxychloroquine Sulfate [usp Monograph]

95. Hydroxychloroquine Sulfate, >=98% (hplc), Powder

96. Sr-05000001881-1

97. Sr-05000001881-2

98. W-104413

99. Q27270879

100. Z1551900864

101. Hydroxychloroquine Sulphate 1.0 Mg/ml In Methanol (as Free Base)

102. 2-[[4-[(7-chloro-4-quinolinyl)amino]pentyl]ethylamino]ethanol Sulfate

103. Hydroxychloroquine Sulfate, Pharmaceutical Secondary Standard; Certified Reference Material

104. Hydroxychloroquine Sulfate, United States Pharmacopeia (usp) Reference Standard

105. (+/-)-2-((4-((7-chloro-4-quinolyl)amino)pentyl)ethylamino)ethanol Sulfate (1:1) (salt)

106. (+/-)-2-((4-((7-chloro-4-quinolyl)amino)pentyl)ethylamino)ethanol Sulphate (1:1) (salt)

107. 14480-75-2

108. Ethanol, 2-((4-((7-chloro-4-quinolinyl)amino)pentyl)ethyl)amino-, (+/-)-, Sulfate (1:1) Salt

109. Ethanol, 2-((4-((7-chloro-4-quinolinyl)amino)pentyl)ethyl)amino-, (+/-)-, Sulphate (1:1) Salt

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₂₈ClN₃O₅S
Molecular Weight	434.0 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	9
Exact Mass	433.1438199 g/mol
Monoisotopic Mass	433.1438199 g/mol
Topological Polar Surface Area	131 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	413
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Hydroxychloroquine sulfate
Drug Label	Hydroxychloroquine sulfate, USP is a colorless crystalline solid, soluble in water to at least 20 percent; chemically the drug is 2-[[4-[(7-Chloro-4-quinolyl) amino]pentyl] ethylamino] ethanol sulfate (1:1). Hydroxychloroquine sulfate, USP has the fo...
Active Ingredient	Hydroxychloroquine sulfate
Dosage Form	Tablet
Route	Oral
Strength	200mg
Market Status	Prescription
Company	Sandoz; Hikma Pharms; Teva Pharms; Ipca Labs; Zydus Pharms Usa; Mylan

2 of 2
Drug Name	Hydroxychloroquine sulfate
Drug Label	Hydroxychloroquine sulfate, USP is a colorless crystalline solid, soluble in water to at least 20 percent; chemically the drug is 2-[[4-[(7-Chloro-4-quinolyl) amino]pentyl] ethylamino] ethanol sulfate (1:1). Hydroxychloroquine sulfate, USP has the fo...
Active Ingredient	Hydroxychloroquine sulfate
Dosage Form	Tablet
Route	Oral
Strength	200mg
Market Status	Prescription
Company	Sandoz; Hikma Pharms; Teva Pharms; Ipca Labs; Zydus Pharms Usa; Mylan

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.)

Enzyme Inhibitors

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

Antirheumatic Agents

Drugs that are used to treat RHEUMATOID ARTHRITIS. (See all compounds classified as Antirheumatic Agents.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Antirheumatic Agent [EPC]; Antimalarial [EPC]