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CAS 148-24-3
PharmaCompass
CAS 148-24-3
Also known as: 8-hydroxyquinoline, Quinolin-8-ol, 8-quinolinol, 148-24-3, Oxine, Quinophenol
Molecular Formula
C9H7NO
Molecular Weight
145.161  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

CAS 148-24-3

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 Depositor-Supplied Synonyms

1. 8-hydroxyquinoline

2. Quinolin-8-ol

3. 8-quinolinol

4. 148-24-3

5. Oxine

6. Quinophenol

7. 8-quinol

8. 8-oxyquinoline

9. Phenopyridine

10. Oxychinolin

11. Bioquin

12. Oxybenzopyridine

13. Hydroxybenzopyridine

14. Oxin

15. 1-azanaphthalene-8-ol

16. Tumex

17. 8-chinolinol

18. 8-hydroxychinolin

19. 8-oq

20. 8-hydroxy-chinolin

21. Fennosan H 30

22. Fennosan

23. O-oxychinolin

24. 8-oxychinolin

25. Usaf Ek-794

26. Fennosan Hf-15

27. Nci-c55298

28. Nsc 2039

29. Caswell No. 719

30. Oxoquinoline

31. 8-chinolinol [czech]

32. O-oxychinolin [german]

33. Quinoline, 8-hydroxy-

34. Nsc 615011

35. Unii-5utx5635hp

36. 8-hydroxy-chinolin [german]

37. Ccris 340

38. 8-hydroxy Quinoline

39. 8-hydroxy-quinoline

40. Oxyquinoline [usan]

41. Hsdb 4073

42. Einecs 205-711-1

43. Nsc 82408

44. Nsc285166

45. Epa Pesticide Chemical Code 059803

46. Brn 0114512

47. Ai3-00483

48. Mls002702126

49. Chembl310555

50. Chebi:48981

51. Mcjgnvypogvajf-uhfffaoysa-n

52. Mfcd00006807

53. Nsc 82404

54. Nsc615011

55. Oxyquinoline (usan)

56. Ncgc00090708-03

57. Ncgc00090708-05

58. Dsstox_cid_730

59. Dsstox_rid_75758

60. Wln: T66 Bnj Jq

61. Dsstox_gsid_20730

62. Oxyquinoline (8-hydroxyquinoline)

63. Oxyquinol

64. 8 Hydroxyquinoline

65. 24804-14-6

66. Cas-148-24-3

67. Smr000112313

68. Oxychinolil

69. Oxyquinolinl

70. Phenopyridinl

71. Hydroxychinolin

72. Oxychinoline

73. Oxyquinoline;

74. 8-quinolinyloxy

75. Hoxybenzopyridinl

76. 8-oxyquinolin

77. 8-quinolinone

78. 8-quinolol

79. 8-hydroxiquinoline

80. 8-hydroxychinoline

81. Hqy

82. 8-:hydroxyquinoline

83. Azanaphthalene-8-ol

84. 8-quinolinol, P.a.

85. Pubchem17430

86. Spectrum_001053

87. 3vh9

88. Spectrum2_000697

89. Spectrum3_000534

90. Spectrum4_000465

91. Spectrum5_001280

92. 8-hydroxyquinoline, 99%

93. 8-quinolinol, Acs

94. D0fo2b

95. Ncimech_000694

96. Ac1l1cj0

97. Cid_1923

98. Ncistruc1_000152

99. Ncistruc2_000240

100. Acmc-1c26c

101. Nciopen2_000962

102. Nciopen2_001020

103. Nciopen2_001220

104. Nciopen2_004264

105. Schembl37189

106. Bspbio_002147

107. Kbiogr_000910

108. Kbioss_001533

109. 5-21-03-00252 (beilstein Handbook Reference)

110. Mls001055492

111. Aronis24185

112. Bidd:er0371

113. Divk1c_000757

114. Spbio_000853

115. 5utx5635hp

116. 8-hydroxyquinoline, Crystalline

117. Ac1q78i6

118. Zinc8492

119. 8-hydroxyquinoline, Acs 50g

120. Dtxsid5020730

121. Bdbm32203

122. Ctk0h4800

123. Hms502f19

124. Kbio1_000757

125. Kbio2_001533

126. Kbio2_004101

127. Kbio2_006669

128. Kbio3_001647

129. Nsc2039

130. Molport-000-139-947

131. Ninds_000757

132. 8-quinolinol (7ci,8ci,9ci)

133. Bb_sc-7381

134. Act08881

135. Hy-b1005

136. Ks-000005kh

137. Ks-000046xj

138. Nsc-2039

139. Str00721

140. Fennosan H 30, Hydroxybenzopyridinl

141. Tox21_113083

142. Tox21_202986

143. Tox21_400006

144. Anw-21125

145. Bbl011608

146. Ccg-35870

147. Ls-863

148. Nsc 48037

149. Nsc 54230

150. Nsc 82405

151. Nsc 82409

152. Nsc 82410

153. Nsc 82412

154. Nsc402623

155. Rw2005

156. S4547

157. Sbb009097

158. Stk943764

159. Akos001061311

160. Ac-5109

161. Cs-4502

162. Db11145

163. Ebd2203585

164. Mcule-7753869266

165. Nsc 285166

166. Nsc 402623

167. Nsc-285166

168. Nsc-402623

169. Nsc-615011

170. Ps-4553

171. Rp20988

172. Rtc-061968

173. Tra0064997

174. Tra0075211

175. Tra0087229

176. 8-hydroxyquinoline, Acs Reagent, 99%

177. Idi1_000757

178. Ncgc00090708-01

179. Ncgc00090708-02

180. Ncgc00090708-04

181. Ncgc00090708-06

182. Ncgc00090708-07

183. Ncgc00090708-08

184. Ncgc00260531-01

185. Aj-08313

186. Ak-33354

187. An-11332

188. Br-33354

189. Cj-00120

190. He017394

191. He312822

192. Kb-74253

193. Nci60_001712

194. Nci60_002335

195. Sc-18904

196. Zb000666

197. Sbi-0051472.p003

198. Db-012222

199. Tc-063627

200. Am20050821

201. Ft-0621550

202. St24033311

203. St45053772

204. 134-31-6 (hydrogen Sulfate (2:1) Salt)

205. 8-quinolinol, Jis Special Grade, >=99.0%

206. 8-quinolinol, Vetec(tm) Reagent Grade, 99%

207. En300-17403

208. C19434

209. D05321

210. M-5832

211. 26097-ep2270006a1

212. 26097-ep2270895a2

213. 26097-ep2272813a2

214. 26097-ep2275395a2

215. 26097-ep2275409a1

216. 26097-ep2275469a1

217. 26097-ep2278637a1

218. 26097-ep2287940a1

219. 26097-ep2289965a1

220. 26097-ep2295421a1

221. 26097-ep2296654a1

222. 26097-ep2298828a1

223. 26097-ep2299785a1

224. 26097-ep2301934a1

225. 26097-ep2305667a2

226. 26097-ep2306788a1

227. 26097-ep2306789a1

228. 26097-ep2308926a1

229. 26097-ep2309564a1

230. 26097-ep2311826a2

231. 26097-ep2314558a1

232. 26097-ep2371810a1

233. 26097-ep2371812a1

234. 26097-ep2372804a1

235. 26097-ep2378585a1

236. 26100-ep2275469a1

237. 26100-ep2287940a1

238. 26100-ep2295421a1

239. 26100-ep2298767a1

240. 26100-ep2298828a1

241. 26100-ep2301983a1

242. 26100-ep2308926a1

243. 26100-ep2309564a1

244. 26100-ep2314558a1

245. 26100-ep2314587a1

246. 26100-ep2371810a1

247. 26100-ep2371812a1

248. 26100-ep2372804a1

249. 26100-ep2378585a1

250. 8-quinolinol, Pestanal(r), Analytical Standard

251. Ab00052065_08

252. 135659-ep2275422a1

253. 135659-ep2292608a1

254. 8-quinolinol, >=99% (perchloric Acid Titration)

255. Ap-065/40180076

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

257. Cu-01000012874-2

258. I08-0122

259. W-108106

260. Brd-k66808046-065-01-1

261. Z56926518

262. 8-hydroxyquinoline, 8-oxychinolin, 8-quinolinol, Oxine

263. F0001-0526

264. Inchi=1/c9h7no/c11-8-5-1-3-7-4-2-6-10-9(7)8/h1-6,11

265. 123574-67-4

266. 8-hydroxyquinoline (see Also 8-hydroxyquinoline Sulfate 134-31-6; Transgenic Model Evaluation (8-hyd)

267. 8-quinolinol, Puriss. P.a., Acs Reagent, For The Detection And Determination Of Al, Mg And Others, >=99.0% (nt)

268. 8-quinolinol, Puriss. P.a., Acs Reagent, Reag. Ph. Eur., >=99% (perchloric Acid Titration)

269. Transgenic Model Evaluation (8-hydroxyquinoline) (see Also 8-hydroxyquinoline Sulfate 134-31-6)

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 145.161 g/mol
Molecular Formula C9H7NO
XLogP32
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass145.053 g/mol
Monoisotopic Mass145.053 g/mol
Topological Polar Surface Area33.1 A^2
Heavy Atom Count11
Formal Charge0
Complexity138
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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%.

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


TREATMENT OF MINOR BURNS & HEMORRHOIDS; USED AS BACTERIOSTATIC ADDITIVE IN HAIRDRESSING PREPN FOR DANDRUFF; ANTISEPTIC SPRAY; PREPN OF NUMBER OF DERIVATIVES USED IN MEDICINE; CHEM INTERMEDIATE FOR PREPN OF AMEBACIDE, DIIODOHYDROXYQUIN

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: http://monographs.iarc.fr/ENG/Classification/index.php, p. V13 103 (1977)


FOR TREATMENT OF DYSENTERY, MEN HAVE RECEIVED ORAL DOSES OF 3 G IN SOLN 4 TIMES DAILY, WITHOUT APPARENT ILL-EFFECT. /FORMER USE/

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-383


The effect of oxyquinoline ointment for diaper dermatitis was tested in a randomized double-blind trial. Compared to a combined control treatment group using Desitin or A&D ointment, use of oxyquinoline significantly improved rash resolution.

Minnich SM et al; Dermatol Nurs 3 (1): 25-8 (1991)


5 Pharmacology and Biochemistry
5.1 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


5.2 Absorption, Distribution and Excretion

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.

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.

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


5.3 Metabolism/Metabolites

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

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.

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


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