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Chlorquinaldol

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Chemistry

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Also known as: 72-80-0, 5,7-dichloro-8-hydroxyquinaldine, 5,7-dichloro-2-methylquinolin-8-ol, 5,7-dichloro-8-hydroxy-2-methylquinoline, Chloroquinaldol, 5,7-dichloro-2-methyl-8-quinolinol

Molecular Formula

C₁₀H₇Cl₂NO

Molecular Weight

228.07 g/mol

InChI Key

GPTXWRGISTZRIO-UHFFFAOYSA-N

FDA UNII

D6VHC87LLS

Local anti-infective agent used for skin, gastrointestinal, and vaginal infections with fungi, protozoa, and certain bacteria. In animals, it causes central nervous system damage and is not administered parenterally. It is also used as antiseptic, fungistat, or deodorant.

Chlorquinaldol is a Standardized Chemical Allergen. The physiologic effect of chlorquinaldol is by means of Increased Histamine Release, and Cell-mediated Immunity.

1 2D Structure

Chlorquinaldol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5,7-dichloro-2-methylquinolin-8-ol

2.1.2 InChI

InChI=1S/C10H7Cl2NO/c1-5-2-3-6-7(11)4-8(12)10(14)9(6)13-5/h2-4,14H,1H3

2.1.3 InChI Key

GPTXWRGISTZRIO-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=NC2=C(C=C1)C(=CC(=C2O)Cl)Cl

2.2 Other Identifiers

2.2.1 UNII

D6VHC87LLS

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 5,7 Dichloro 2 Methyl 8 Quinolinol

2. 5,7-dichloro-2-methyl-8-quinolinol

3. Afungil

4. Chlorchinaldine

5. Chlorchinaldol

6. Chloroquinaldol

7. Sterosan

2.3.2 Depositor-Supplied Synonyms

1. 72-80-0

2. 5,7-dichloro-8-hydroxyquinaldine

3. 5,7-dichloro-2-methylquinolin-8-ol

4. 5,7-dichloro-8-hydroxy-2-methylquinoline

5. Chloroquinaldol

6. 5,7-dichloro-2-methyl-8-quinolinol

7. Clorquinaldol

8. Sterosan

9. 5,7-dichloro-8-quinaldinol

10. Siasteran

11. Siosteran

12. Steroxin

13. Siogene

14. Chlorquinaldolum

15. Gyno-sterosan

16. 5,7-dichloro-2-methyl-8-hydroxyquinoline

17. 8-quinolinol, 5,7-dichloro-2-methyl-

18. Chloquinan

19. Hydroxydichloroquinaldine

20. Siogen

21. 5,7-dichloro-2-methyl-quinolin-8-ol

22. D6vhc87lls

23. Nsc-755830

24. Mls002695929

25. Chlorchinaldol

26. Chebi:74500

27. Chlorchinaldolum

28. Chlorquinaldol (inn)

29. Ncgc00095795-04

30. Clorchinaldolo

31. Smr001549973

32. 2-methyl-5,7-dichloro-8-hydroxyquinoline

33. Chlorquinaldol [inn]

34. Dsstox_cid_28924

35. Dsstox_rid_83190

36. Dsstox_gsid_48998

37. Chlorchinaldin

38. Chlorguinaldon

39. Clorchinaldolo [dcit]

40. Chlorquinaldol, Chlorquinaldol (5,7-dichloro-2-methyl-8-quinolinol)

41. Cas-72-80-0

42. Clorquinaldol [inn-spanish]

43. Chlorquinaldolum [inn-latin]

44. Chlorquinaldol [inn:ban:dcf]

45. Einecs 200-789-3

46. Unii-d6vhc87lls

47. Brn 0156683

48. Gynotherax

49. Vagisteran

50. Florabina

51. Saprosan

52. Siogenal

53. Siogeno

54. Siogenon

55. Siosept

56. Sterozan

57. Quesil

58. Mfcd00023984

59. Hydroxydichloroquinaldinol

60. Spectrum2_000524

61. Spectrum3_001092

62. Spectrum4_001263

63. Chlorquinaldol [mi]

64. Cid_6301

65. Oprea1_721210

66. Bspbio_002764

67. Kbiogr_001846

68. Spectrum212151

69. 5-21-03-00346 (beilstein Handbook Reference)

70. Schembl301405

71. Spbio_000507

72. Chlorquinaldol [mart.]

73. Chembl224325

74. Chlorquinaldol [who-dd]

75. Dtxsid3048998

76. Bdbm76302

77. Kbio3_001984

78. 5-bromo 2-isobutoxy Benzonitirle

79. Hms3089a18

80. Hms3264i07

81. Hms3652h09

82. Pharmakon1600-00212151

83. Zinc119403

84. Bcp11865

85. Hy-b1360

86. Tox21_113490

87. Ccg-39580

88. Nsc755830

89. S4192

90. Stl502989

91. Akos000119838

92. Tox21_113490_1

93. Cs-4899

94. Db13306

95. Nsc 755830

96. Ps-7753

97. S10253

98. Ncgc00095795-01

99. Ncgc00095795-02

100. Ncgc00095795-03

101. Ncgc00095795-06

102. Ac-29743

103. Quinolin-8-ol, 5,7-dichloro-2-methyl-

104. Sbi-0207012.p001

105. Db-055679

106. 5,7-bis(chloranyl)-2-methyl-quinolin-8-ol

107. Ft-0623717

108. Sw220230-1

109. A16448

110. D07208

111. 5,7-dichloro-8-hydroxy-2-methylquinoline, 98%

112. Ab00443827_06

113. Ab00443827_07

114. A837624

115. Sr-01000872737

116. Q1645622

117. Sr-01000872737-1

118. W-104478

119. Z118257784

120. 5,7-dichloro-8-hydroxyquinaldine 5,7-dichloro-2-methyl-8-hydroxyquinoline

2.4 Create Date

2005-03-27

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₇Cl₂NO
Molecular Weight	228.07 g/mol
XLogP3	3.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Exact Mass	226.9904692 g/mol
Monoisotopic Mass	226.9904692 g/mol
Topological Polar Surface Area	33.1 Å²
Heavy Atom Count	14
Formal Charge	0
Complexity	214
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

Chlorquinaldol was used historically as a topical antiseptic agent for skin infections. It maintains use in European countries as a combination vaginal tablet with promestriene for use in the treatment of vaginal infections.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Chlorquinaldol is bacteriocidal in both gram positive and gram negative bacteria. It is more effective in targeting gram positive bacteria, particularly staphylococci.

5.2 MeSH Pharmacological Classification

Anti-Infective Agents

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

CHLORQUINALDOL

5.3.2 FDA UNII

D6VHC87LLS

5.3.3 Pharmacological Classes

Chemical Structure [CS] - Allergens

5.4 ATC Code

D - Dermatologicals

D08 - Antiseptics and disinfectants

D08A - Antiseptics and disinfectants

D08AH - Quinoline derivatives

D08AH02 - Chlorquinaldol

G - Genito urinary system and sex hormones

G01 - Gynecological antiinfectives and antiseptics

G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids

G01AC - Quinoline derivatives

G01AC03 - Chlorquinaldol

P - Antiparasitic products, insecticides and repellents

P01 - Antiprotozoals

P01A - Agents against amoebiasis and other protozoal diseases

P01AA - Hydroxyquinoline derivatives

P01AA04 - Chlorquinaldol

R - Respiratory system

R02 - Throat preparations

R02A - Throat preparations

R02AA - Antiseptics

R02AA11 - Chlorquinaldol

5.5 Absorption, Distribution and Excretion

Absorption

There is a high degree of variability in the extent of absorption of topically applied chorquinaldol preparations. It is reported to be between 4.2 and 23.5% of the applied dose. This is quite low compared to orally administered preparations which displayed 67.6% absorption in the same study.

Route of Elimination

Chlorquinadol is primarily excreted in the urine as the sulfate form. About 2% is excreted as the parent drug.

5.6 Metabolism/Metabolites

98% of drug is converted to the sulfate form and renally excreted.

5.7 Mechanism of Action

The mechanism by which Chlorquinaldol exerts it's bacteriocidal effect is unknown. 8-hydroxyquinolines are known to be bidentate chelators of several metal ions which act as critical enzyme cofactors. However, the addition of exogenous metal ions does not appear to alter the minimum inhibitory concentration for mycobacterium tuberculosis suggesting that the primary mechanism does not rely on chelation.

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