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Oxyquinoline

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Chemistry

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Also known as: Quinolin-8-ol, 8-quinolinol, 148-24-3, Oxyquinoline, Oxine, Quinophenol

Molecular Formula

C₉H₇NO

Molecular Weight

145.16 g/mol

InChI Key

MCJGNVYPOGVAJF-UHFFFAOYSA-N

FDA UNII

5UTX5635HP

An antiseptic with mild fungistatic, bacteriostatic, anthelmintic, and amebicidal action. It is also used as a reagent and metal chelator, as a carrier for radio-indium for diagnostic purposes, and its halogenated derivatives are used in addition as topical anti-infective agents and oral antiamebics.

1 2D Structure

Oxyquinoline

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

quinolin-8-ol

2.1.2 InChI

InChI=1S/C9H7NO/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11H

2.1.3 InChI Key

MCJGNVYPOGVAJF-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC2=C(C(=C1)O)N=CC=C2

2.2 Other Identifiers

2.2.1 UNII

5UTX5635HP

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 8 Hydroxyquinoline

2. 8 Hydroxyquinoline Sulfate

3. 8 Oxyquinoline

4. 8 Quinolinol

5. 8-hydroxyquinoline Sulfate

6. 8-oxyquinoline

7. 8-quinolinol

8. Bioquin

9. Chinosol

10. Khinozol

11. Leioderm

12. Oxine

13. Oxyquinol

14. Oxyquinoline

15. Oxyquinoline Potassium Sulfate (2:1)

16. Oxyquinoline Sulfate

17. Quinosol

18. Sulfate, 8-hydroxyquinoline

19. Sulfate, Oxyquinoline

20. Superol

2.3.2 Depositor-Supplied Synonyms

1. Quinolin-8-ol

2. 8-quinolinol

3. 148-24-3

4. Oxyquinoline

5. Oxine

6. Quinophenol

7. Oxychinolin

8. 8-quinol

9. 8-oxyquinoline

10. Phenopyridine

11. 8-hydroxychinolin

12. Bioquin

13. Oxybenzopyridine

14. Hydroxybenzopyridine

15. Oxin

16. 1-azanaphthalene-8-ol

17. Tumex

18. 8-chinolinol

19. 8-oq

20. 8-hydroxy-chinolin

21. Fennosan H 30

22. 8-oxychinolin

23. Fennosan

24. Oxyquinol

25. O-oxychinolin

26. Usaf Ek-794

27. Hydroxyquinoline

28. Oxyquinoline [usan]

29. 8-hydroxy-quinoline

30. Nci-c55298

31. Nsc 2039

32. Mfcd00006807

33. Oxoquinoline

34. Albisal

35. Nsc 615011

36. Nsc-2039

37. Nsc285166

38. 8-quinolinol, Homopolymer

39. Nsc-285166

40. Nsc-402623

41. Nsc-615011

42. Mls002702126

43. 5utx5635hp

44. Chembl310555

45. Chebi:48981

46. Nsc 82408

47. Quinoline-8-ol

48. Oxyquinoline (8-hydroxyquinoline)

49. Nsc 82404

50. Nsc-48037

51. Nsc-54230

52. Nsc-82404

53. Nsc-82405

54. Nsc-82409

55. Nsc-82410

56. Nsc-82412

57. Nsc615011

58. J2.960b

59. Oxyquinoline (usan)

60. Ncgc00090708-03

61. Ncgc00090708-05

62. Dsstox_cid_730

63. Dsstox_rid_75758

64. Wln: T66 Bnj Jq

65. Dsstox_gsid_20730

66. Oxine;8-hydroxyquinoline;quinophenol;8-quinolinone

67. Fennosan Hf-15

68. Caswell No. 719

69. 8-chinolinol [czech]

70. O-oxychinolin [german]

71. Quinoline, 8-hydroxy-

72. 84063-18-3

73. Cas-148-24-3

74. Manganese, Bis(8-quinolinolato)-

75. Smr000112313

76. 8-hydroxy-chinolin [german]

77. Ccris 340

78. 8-hydroxy Quinoline

79. Hsdb 4073

80. Einecs 205-711-1

81. Epa Pesticide Chemical Code 059803

82. Brn 0114512

83. Unii-5utx5635hp

84. Oxychinoline

85. Ai3-00483

86. 8-oxyquinolin

87. 8-quinolinone

88. 8-quinolol

89. 8-hydroxiquinoline

90. 8-hydroxychinoline

91. 8-hydroxylquinoline

92. Hqy

93. 8-quinolinol, P.a.

94. Spectrum_001053

95. 3vh9

96. 8-hydroxyquinoline Oxine

97. Spectrum2_000697

98. Spectrum3_000534

99. Spectrum4_000465

100. Spectrum5_001280

101. Oxyquinoline [ii]

102. 8-hydroxyquinoline, 99%

103. Ec 205-711-1

104. Ncimech_000694

105. Oxyquinoline [hsdb]

106. Oxyquinoline [inci]

107. Cid_1923

108. Ncistruc1_000152

109. Ncistruc2_000240

110. Oxyquinol Reference Spectrum

111. Nciopen2_000962

112. Nciopen2_001020

113. Nciopen2_001220

114. Nciopen2_004264

115. Oxyquinoline [vandf]

116. Schembl37189

117. Bspbio_002147

118. Kbiogr_000910

119. Kbioss_001533

120. 5-21-03-00252 (beilstein Handbook Reference)

121. Mls001055492

122. Bidd:er0371

123. Divk1c_000757

124. Spbio_000853

125. 8-hydroxyquinoline, Crystalline

126. Zinc8492

127. Hydroxyquinoline [vandf]

128. 8-hydroxyquinoline [mi]

129. Dtxsid5020730

130. Bdbm32203

131. Hms502f19

132. Kbio1_000757

133. Kbio2_001533

134. Kbio2_004101

135. Kbio2_006669

136. Kbio3_001647

137. Hydroxyquinoline [who-dd]

138. Nsc2039

139. 8-hydroxyquinoline [iarc]

140. Ninds_000757

141. 8-quinolinol (7ci,8ci,9ci)

142. Act08881

143. Hy-b1005

144. Str00721

145. Tox21_113083

146. Tox21_202986

147. Tox21_400006

148. 8-oxychinolin, 8-quinolinol, Oxine

149. Ccg-35870

150. Nsc 48037

151. Nsc 54230

152. Nsc 82405

153. Nsc 82409

154. Nsc 82410

155. Nsc 82412

156. Nsc402623

157. S4547

158. Stk943764

159. 8-hydroxyquinoline Acs Reagent Grade

160. Akos001061311

161. Ac-5109

162. Cs-4502

163. Db11145

164. Nsc 285166

165. Nsc 402623

166. Ps-4553

167. Sb40773

168. 8-hydroxyquinoline, Acs Reagent, 99%

169. Idi1_000757

170. Ncgc00090708-01

171. Ncgc00090708-02

172. Ncgc00090708-04

173. Ncgc00090708-06

174. Ncgc00090708-07

175. Ncgc00090708-08

176. Ncgc00090708-11

177. Ncgc00260531-01

178. Nci60_001712

179. Nci60_002335

180. 8-hydroxyquinoline Acs Grade 100g

181. Sbi-0051472.p003

182. Db-012222

183. Am20050821

184. Ft-0621550

185. H0305

186. 8-quinolinol, Jis Special Grade, >=99.0%

187. 8-quinolinol, Vetec(tm) Reagent Grade, 99%

188. En300-17403

189. C19434

190. D05321

191. P17615

192. Us9394254, 6

193. 8-quinolinol, Pestanal(r), Analytical Standard

194. Ab00052065_08

195. 8-quinolinol, >=99% (perchloric Acid Titration)

196. A808745

197. Ap-065/40180076

198. Q270162

199. Cu-01000012874-2

200. W-108106

201. Brd-k66808046-065-01-1

202. Z56926518

203. F0001-0526

204. 8-quinolinol, Puriss. P.a., Acs Reagent, For The Detection And Determination Of Al, Mg And Others, >=99.0% (nt)

205. 8-quinolinol, Puriss. P.a., Acs Reagent, Reag. Ph. Eur., >=99% (perchloric Acid Titration)

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₉H₇NO
Molecular Weight	145.16 g/mol
XLogP3	2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Exact Mass	145.052763847 g/mol
Monoisotopic Mass	145.052763847 g/mol
Topological Polar Surface Area	33.1 Å²
Heavy Atom Count	11
Formal Charge	0
Complexity	138
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 Therapeutic Uses

A BACTERIOSTATIC & FUNGISTATIC COMPOUND; USED PRINCIPALLY IN TREATMENT OF MINOR BURNS & OF HEMORRHOIDS.

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 1111

OXYQUINOLINE SULFATE ... IS ... USED ... IN TREATMENT OF ATHLETE'S FOOT, VAGINITIS, & AS A GARGLE, EYEWASH, NASAL DOUCHE, & IN HEMORRHOIDAL PREPARATIONS ... /OXYQUINOLINE SULFATE/

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 1111

/OVER THE COUNTER/ HYDROXYQUINOLINE IS 1 OF 4 ANTIFUNGAL AGENTS RECOMMENDED FOR ACTIVE TREATMENT OF FUNGUS ASSOCIATED WITH DIAPER RASH & PRICKLY HEAT IN BABIES. /HYDROXYQUINOLINE/

SADIK F; J AM PHARM ASSOC NS10 (JAN): 19-24 (1970)

8-HYDROXYQUNIOLINE SULFATE INHIBITED FORMATION OF ARTIFICIAL CALCULUS IN VITRO & RAT CALCULUS IN VIVO. IN RATS, IT PREVENTED CALCULUS FORMATION WHEN APPLIED BY SWABBING OR BY INTRAORAL INSTILLATION. IN DOGS, FORMATION OF DENTAL PLAQUE WAS INHIBITED 33 TO 98% IN COMPARISON TO PLACEBO. ALSO, 25 TO 58% OF ESTABLISHED PLAQUE ACCUMULATIONS WERE REMOVED, WHEREAS PLACEBO REMOVED 2 TO 22%.

PMID:815301 DEPALMA PD ET AL; J DENT RES 55 (2): 292-8 (1976)

For more Therapeutic Uses (Complete) data for 8-HYDROXYQUINOLINE (7 total), please visit the HSDB record page.

4.2 Drug Indication

Oxyquinoline is used as a biocidal component of several over the counter products. These products are marketed for the purposes of inhibiting abnormal biological growth in the vagina and restoring natural pH.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Oxyquinoline acts as a biocide to eliminate bacteria and fungi.

5.2 ATC Code

A - Alimentary tract and metabolism

A01 - Stomatological preparations

A01A - Stomatological preparations

A01AB - Antiinfectives and antiseptics for local oral treatment

A01AB07 - Oxyquinoline

D - Dermatologicals

D08 - Antiseptics and disinfectants

D08A - Antiseptics and disinfectants

D08AH - Quinoline derivatives

D08AH03 - Oxyquinoline

G - Genito urinary system and sex hormones

G01 - Gynecological antiinfectives and antiseptics

G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids

G01AC - Quinoline derivatives

G01AC30 - Oxyquinoline

R - Respiratory system

R02 - Throat preparations

R02A - Throat preparations

R02AA - Antiseptics

R02AA14 - Oxyquinoline

5.3 Absorption, Distribution and Excretion

Route of Elimination

Oxyquinoline is excreted in both the primarily in the urine with some in the bile.

IN RATS /MALE, DONRYU STRAIN, IV INJECTION/ 8-HYDROXYQUINOLINE WAS METABOLIZED TO GLUCURONIDE & SULFATE CONJUGATES. MORE 8-HYDROXYQUINOLINE GLUCURONIDE WAS EXCRETED IN URINE THAN 8-HYDROXYQUINOLINE SULFATE CONJUGATE. ONLY THE GLUCURONIDE CONJUGATE WAS EXCRETED IN BILE.

PMID:409509 KIWADA H ET AL; CHEM PHARM BULL 25 (7): 1566-73 (1977)

8-HYDROXYQUINOLINE WAS METABOLIZED TO GLUCURONIDE & SULFATE CONJUGATES AFTER IV ADMIN IN RATS /MALE, DONRYU STRAIN/. THE GLUCURONIDES WERE EXCRETED IN BILE & URINE, BUT THE SULFATES WERE EXCRETED EXCLUSIVELY IN THE URINE. UNMETABOLIZED FORMS WERE ONLY SLIGHTLY EXCRETED.

PMID:96945 SAWADA Y ET AL; CHEM PHARM BULL 26 (5): 1357-63 (1978)

5.4 Metabolism/Metabolites

In the urine, 60% of the dose is excreted as glucuronide conjugates and 23% of the dose as sulfate conjugates. In the bile, 9% of the total dose is found as glucuronide conjugates.

IN RATS /MALE, DONRYU STRAIN, IV INJECTION/ 8-HYDROXYQUINOLINE WAS METABOLIZED TO GLUCURONIDE & SULFATE CONJUGATES.

PMID:409509 KIWADA H ET AL; CHEM PHARM BULL 25 (7): 1566-73 (1977)

8-HYDROXYQUINOLINE WAS METABOLIZED TO GLUCURONIDE & SULFATE CONJUGATES AFTER IV ADMIN IN RATS /MALE, DONRYU STRAIN/. UNMETABOLIZED FORMS WERE ONLY SLIGHTLY EXCRETED.

PMID:96945 SAWADA Y ET AL; CHEM PHARM BULL 26 (5): 1357-63 (1978)

5.5 Mechanism of Action

The mechanism by which oxyquinoline exerts its biocidal effect is unknown.

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