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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
    Oxyquinoline
    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 Weight 145.16 g/mol
    Molecular Formula C9H7NO
    XLogP32
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count0
    Exact Mass145.052763847 g/mol
    Monoisotopic Mass145.052763847 g/mol
    Topological Polar Surface Area33.1 Ų
    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%.

    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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CN","customerAddress":"NATCO HOUSE, ROAD NO.2,"}]
    04-Jan-2021
    23-Sep-2024
    KGS
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