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Chloroxine

Synopsis, Chemistry

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Also known as: 773-76-2, 5,7-dichloroquinolin-8-ol, 5,7-dichloro-8-hydroxyquinoline, 5,7-dichloro-8-quinolinol, Capitrol, Chlorquinol

Molecular Formula

C₉H₅Cl₂NO

Molecular Weight

214.04 g/mol

InChI Key

WDFKMLRRRCGAKS-UHFFFAOYSA-N

FDA UNII

2I8BD50I8B

Chloroxine is a synthetic quinoline derivative with antibacterial activity. Although the mechanism of action is not fully understood, topical administration of chloroxine diminishes mitotic activity in the epidermis, thereby reducing excessive scaling associated with dandruff or seborrheic dermatitis of the scalp, including psoriasis and eczema.

1 2D Structure

Chloroxine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5,7-dichloroquinolin-8-ol

2.1.2 InChI

InChI=1S/C9H5Cl2NO/c10-6-4-7(11)9(13)8-5(6)2-1-3-12-8/h1-4,13H

2.1.3 InChI Key

WDFKMLRRRCGAKS-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC2=C(C(=C(C=C2Cl)Cl)O)N=C1

2.2 Other Identifiers

2.2.1 UNII

2I8BD50I8B

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Chloroxine Hydrofluoride

2. Chlorquinol

3. Dichlorohydroxyquinoline

4. Dichloroquine

5. Quixalin

2.3.2 Depositor-Supplied Synonyms

1. 773-76-2

2. 5,7-dichloroquinolin-8-ol

3. 5,7-dichloro-8-hydroxyquinoline

4. 5,7-dichloro-8-quinolinol

5. Capitrol

6. Chlorquinol

7. Dichloroxin

8. Quixalin

9. Chloroxyquinoline

10. Dichloroquinolinol

11. Dikhloroskin

12. Clofuzid

13. Endiaron

14. Quinolor

15. Dichlorohydroxyquinoline

16. Chlofucid

17. Quesyl

18. 5,7-dichlorooxine

19. 5,7-dichloroxine

20. 8-quinolinol, 5,7-dichloro-

21. 5,7-dichloro-8-oxyquinoline

22. Chlorohydroxyquinoline

23. Chloroxine [usan]

24. 5,7-dichlor-8-hydroxychinolin

25. Nsc 3904

26. Nsc-3904

27. Mfcd00006786

28. 2i8bd50i8b

29. 5,7-dichloro-8-hydroquinoline

30. Chebi:59477

31. Nsc3904

32. Chloroxine (usan)

33. As-229

34. Ncgc00095264-01

35. Dsstox_cid_2801

36. Dsstox_rid_76734

37. Dsstox_gsid_22801

38. Cas-773-76-2

39. Ccris 5751

40. Capitrol Cream Shampoo

41. Sr-01000747474

42. Einecs 212-258-3

43. Brn 0153606

44. Unii-2i8bd50i8b

45. 5,7-dichlor-8-hydroxychinolin [german]

46. Sq 16401

47. Capitrol (tn)

48. Spectrum_001434

49. Chloroxine [mi]

50. 5,7-dichloro-8-oxine

51. Spectrum2_000687

52. Spectrum3_001156

53. Spectrum4_000744

54. Spectrum5_001444

55. Chloroxine [vandf]

56. 8-quinolinol,7-dichloro-

57. Chloroxine [mart.]

58. Cid_2722

59. Schembl3350

60. Chloroxine [who-dd]

61. Oprea1_486275

62. Regid_for_cid_2722

63. Bspbio_002711

64. Kbiogr_001068

65. Kbioss_001914

66. 5-21-03-00286 (beilstein Handbook Reference)

67. Mls000681736

68. Bidd:gt0763

69. Divk1c_000578

70. Spectrum1503202

71. Spbio_000813

72. Zinc1131

73. Chembl1200596

74. Chloroxine [orange Book]

75. Dtxsid5022801

76. Bdbm32147

77. Hms501m20

78. Kbio1_000578

79. Kbio2_001914

80. Kbio2_004482

81. Kbio2_007050

82. Kbio3_002211

83. Ninds_000578

84. Hms1923k05

85. Hms2092n04

86. Hms2609a16

87. Hms3259e17

88. Hms3655g16

89. Hms3712o06

90. Pharmakon1600-01503202

91. Capitrol Cream Shampoo (salt/mix)

92. Amy23282

93. Component Of Capitrol Cream Shampoo

94. Hy-b0295

95. 5,7-dichloro-8-quinolinol, 99%

96. Tox21_111494

97. Ac9195

98. Ccg-40039

99. Nsc758398

100. S1839

101. Stk075368

102. 5,7-dichloroquinolin-8-ol;chloroxine

103. Akos000271338

104. Tox21_111494_1

105. Ac-4820

106. Db01243

107. Nc00505

108. Nsc-758398

109. Idi1_000578

110. Upcmld0enat5752182:001

111. Ncgc00095264-02

112. Ncgc00095264-03

113. Ncgc00095264-04

114. Ncgc00095264-05

115. Smr000312779

116. Sy016017

117. Tg2-36-1

118. Sbi-0051782.p002

119. A9795

120. D0412

121. Ft-0623709

122. Sw198618-2

123. D03472

124. Ab00052323-08

125. Ab00052323_09

126. Ab00052323_10

127. Sr-01000747474-2

128. Sr-01000747474-3

129. W-104320

130. Brd-k17075857-001-06-9

131. Q12029435

132. F0918-0943

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₉H₅Cl₂NO
Molecular Weight	214.04 g/mol
XLogP3	3.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Exact Mass	212.9748192 g/mol
Monoisotopic Mass	212.9748192 g/mol
Topological Polar Surface Area	33.1 Å²
Heavy Atom Count	13
Formal Charge	0
Complexity	191
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Used in the treatment of dandruff and mild to moderately severe seborrheic dermatitis of the scalp.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Chloroxine has an antibacterial action, inhibiting the growth of gram-positive as well as some gram-negative organisms. Also, chloroxine has shown some antifungal activity against certain dermatophytes and yeasts.

5.2 MeSH Pharmacological Classification

Antifungal Agents

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

5.3 Mechanism of Action

Although the mechanism of action is not understood, chloroxine may slow down mitotic activity in the epidermis, thereby reducing excessive scaling associated with dandruff or seborrheic dermatitis of the scalp. Chloroxine induces SOS-DNA repair in E. coli, so chloroxine may be genotoxic to bacteria.