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    Nitroxoline

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    PharmaCompass
    $ API Ref.Price (USD/KG) : 151Xls

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    2D Structure
    Also known as: 5-nitroquinolin-8-ol, 8-hydroxy-5-nitroquinoline, 4008-48-4, 5-nitro-8-hydroxyquinoline, 5-nitro-8-quinolinol, Nitroxolin
    Molecular Formula
    C9H6N2O3
    Molecular Weight
    190.16  g/mol
    InChI Key
    RJIWZDNTCBHXAL-UHFFFAOYSA-N
    FDA UNII
    A8M33244M6
    Nitroxoline is a urinary antibacterial agent active against susceptible gram-positive and gram-negative organisms commonly found in urinary tract infections. It is a hydroxyquinoline derivative unrelated to other classes of drugs. Nitroxoline is active against bacterial gyrases.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5-nitroquinolin-8-ol
    2.1.2 InChI
    InChI=1S/C9H6N2O3/c12-8-4-3-7(11(13)14)6-2-1-5-10-9(6)8/h1-5,12H
    2.1.3 InChI Key
    RJIWZDNTCBHXAL-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1=CC2=C(C=CC(=C2N=C1)O)[N+](=O)[O-]
    2.2 Other Identifiers
    2.2.1 UNII
    A8M33244M6
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 5-nitro-8-hydroxyquinoline

    2. 5-nitroquinolin-8-ol

    3. 5-nitrox

    4. 5-nok

    5. Cysto-saar Plus

    6. Nibiol

    7. Nitroxoline Monofluoride

    8. Nitroxoline, Potassium Salt

    2.3.2 Depositor-Supplied Synonyms

    1. 5-nitroquinolin-8-ol

    2. 8-hydroxy-5-nitroquinoline

    3. 4008-48-4

    4. 5-nitro-8-hydroxyquinoline

    5. 5-nitro-8-quinolinol

    6. Nitroxolin

    7. 5-nitrox

    8. Noxibiol

    9. Nibiol

    10. Noxin

    11. 8-quinolinol, 5-nitro-

    12. 5-nitroxine

    13. 5-nitroks

    14. 5-nok

    15. 5-nitro-8-oxyquinoline

    16. 5nok

    17. Nitroxolinum

    18. 5-nitro-8-oxychinoline

    19. Nitroxolina

    20. Nitroxolinum [inn-latin]

    21. Nitroxolina [inn-spanish]

    22. A-82

    23. Bas 58

    24. Nsc 74947

    25. Mls000069750

    26. Nsc-74947

    27. Smr000059036

    28. Galinok

    29. Chebi:67121

    30. Isinok

    31. Nicene Forte

    32. Nitroxoline (inn)

    33. A8m33244m6

    34. Ncgc00160664-01

    35. Nitroxoline [inn]

    36. Uro-coli

    37. Dsstox_cid_26284

    38. Dsstox_rid_81510

    39. Dsstox_gsid_46284

    40. Cas-4008-48-4

    41. Nitroxoline [inn:ban:dcf]

    42. Einecs 223-662-4

    43. Brn 0166146

    44. Nitroxlina

    45. Unii-a8m33244m6

    46. Nitroxoline (tn)

    47. Hnq

    48. Nitrohydroxyquinoline

    49. Mfcd00006791

    50. 3ai8

    51. 5-nitroquinoline-8-ol

    52. Opera_id_204

    53. 5-nitro-quinolin-8-ol

    54. Nitroxoline [mi]

    55. 5-nitro-8hydroxyquinoline

    56. Quinolin-8-ol, 5-nitro-

    57. Nitroxoline [mart.]

    58. Oprea1_594857

    59. 8-hydroxy-5-nitro-chinoline

    60. Nitroxoline [who-dd]

    61. 5-21-03-00297 (beilstein Handbook Reference)

    62. Cid_19910

    63. Mls001148594

    64. Schembl151248

    65. Regid_for_cid_19910

    66. 5-nitroquinolin-8-ol, 96%

    67. Wln: T66 Bnj Gnw Jq

    68. Chembl1454910

    69. Dtxsid4046284

    70. Bdbm64987

    71. Hms2230i14

    72. Hms3264c05

    73. Hms3374d08

    74. Kuc105356n

    75. Pharmakon1600-01506173

    76. 8-hydroxy-5-nitroquinoline, 96%

    77. Amy23308

    78. Hy-b1159

    79. Nsc74947

    80. Tox21_111969

    81. Ksc-8-140

    82. Nsc760393

    83. S4591

    84. Stk099582

    85. Zinc15831592

    86. Akos001053242

    87. Tox21_111969_1

    88. Ac-7828

    89. Ccg-213981

    90. Cs-4761

    91. Db01422

    92. Nsc-760393

    93. Ps-5547

    94. Ncgc00160664-03

    95. Db-049530

    96. A6696

    97. Ft-0621541

    98. H0805

    99. 08n484

    100. D07245

    101. 5-nitro-8-quinolinol

    102. 5-nitro-8-hydroxyquinoline

    103. Ab00572598_14

    104. Ag-205/04556035

    105. Q304570

    106. Sr-01000721863

    107. Sr-01000721863-4

    108. W-106391

    109. Z56922155

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 190.16 g/mol
    Molecular Formula C9H6N2O3
    XLogP32.1
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count0
    Exact Mass190.03784206 g/mol
    Monoisotopic Mass190.03784206 g/mol
    Topological Polar Surface Area78.9 Ų
    Heavy Atom Count14
    Formal Charge0
    Complexity229
    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 Drug Indication

    Nitroxoline is an antibiotic agent.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Anti-Infective Agents, Urinary

    Substances capable of killing agents causing urinary tract infections or of preventing them from spreading. (See all compounds classified as Anti-Infective Agents, Urinary.)

    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.)

    5.2 ATC Code

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01X - Other antibacterials

    J01XX - Other antibacterials

    J01XX07 - Nitroxoline

    5.3 Mechanism of Action

    This drug may also have antitumor activity by inhibition of type 2 methionine aminopeptidase (MetAP2) protein which is involved in angiogenesis. Its antibacterial activity may stem from the metal ion complexation vital for bacterial growth.