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    Fleroxacin

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    2D Structure
    Also known as: 79660-72-3, Megalone, Megalocin, Fleroxicin, Quinodis, Fleroxacino
    Molecular Formula
    C17H18F3N3O3
    Molecular Weight
    369.34  g/mol
    InChI Key
    XBJBPGROQZJDOJ-UHFFFAOYSA-N
    FDA UNII
    N804LDH51K
    A broad-spectrum antimicrobial fluoroquinolone. The drug strongly inhibits the DNA-supercoiling activity of DNA GYRASE.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    6,8-difluoro-1-(2-fluoroethyl)-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
    2.1.2 InChI
    InChI=1S/C17H18F3N3O3/c1-21-4-6-22(7-5-21)15-12(19)8-10-14(13(15)20)23(3-2-18)9-11(16(10)24)17(25)26/h8-9H,2-7H2,1H3,(H,25,26)
    2.1.3 InChI Key
    XBJBPGROQZJDOJ-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CN1CCN(CC1)C2=C(C=C3C(=C2F)N(C=C(C3=O)C(=O)O)CCF)F
    2.2 Other Identifiers
    2.2.1 UNII
    N804LDH51K
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Am 833

    2. Am-833

    3. Am833

    4. Quinodis

    5. Ro 23 6240

    6. Ro 23-6240

    7. Ro 236240

    2.3.2 Depositor-Supplied Synonyms

    1. 79660-72-3

    2. Megalone

    3. Megalocin

    4. Fleroxicin

    5. Quinodis

    6. Fleroxacino

    7. Fleroxacinum

    8. 6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid

    9. Fleroxacine

    10. Am-833

    11. Ro 23-6240

    12. Ro 23-6240/000

    13. Flrx

    14. Fleroxacin (quinodis)

    15. Ro-236240

    16. 6,8-difluoro-1-(2-fluoroethyl)-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic Acid

    17. Chebi:31810

    18. 6,8-difluoro-1-(2-fluoroethyl)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

    19. Ro-236240000

    20. N804ldh51k

    21. 3-quinolinecarboxylic Acid, 6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-

    22. Ro-23-6240/000

    23. Ncgc00167558-01

    24. Fleroxacine [french]

    25. Fleroxacinum [latin]

    26. Fleroxacino [spanish]

    27. Ro 23-6240;am-833

    28. Am 833

    29. 6,8-difluoro-1-(2-fluoroethyl)-7-(4-methylpiperazin-1-yl)-4-oxo-quinoline-3-carboxylic Acid

    30. Dsstox_cid_26714

    31. Dsstox_rid_81846

    32. Dsstox_gsid_46714

    33. Megalosin

    34. Megalocin (tn)

    35. Megalone (tn)

    36. Smr000466302

    37. Cas-79660-72-3

    38. Ccris 3972

    39. Sr-01000759379

    40. Brn 4300996

    41. Unii-n804ldh51k

    42. Fleroxacin (jan/usan/inn)

    43. Fleroxacin,(s)

    44. Fleroxacin [usan:inn:ban:jan]

    45. Mfcd00864880

    46. Fleroxacin [mi]

    47. Fleroxacin [inn]

    48. Fleroxacin [jan]

    49. Fleroxacin [usan]

    50. F0646

    51. Fleroxacin [mart.]

    52. Chembl6273

    53. Fleroxacin [who-dd]

    54. Schembl48145

    55. Mls000759401

    56. Mls006010715

    57. Dtxsid1046714

    58. Hms2090i08

    59. Hms3715b11

    60. Bcp28939

    61. Hy-b0414

    62. Rkl10075

    63. Zinc3786299

    64. Tox21_112553

    65. Bdbm50247892

    66. S2469

    67. Zinc03786299

    68. Akos015907011

    69. Fleroxacin 100 Microg/ml In Methanol

    70. Tox21_112553_1

    71. Ccg-221125

    72. Db04576

    73. Ks-5124

    74. Ncgc00167558-02

    75. 3-quinolinecarboxylic Acid, 1,4-dihydro-6,8-difluoro-1-(2-fluoroethyl)-7-(4-methyl-1-piperazinyl)-4-oxo-

    76. Am-833;am833;am 833

    77. Fleroxacin 100 Microg/ml In Acetonitrile

    78. Ft-0630874

    79. D01716

    80. Fleroxacin, Vetranal(tm), Analytical Standard

    81. Ab00640001-02

    82. Ab00640001-03

    83. Ab00640001_04

    84. 660f723

    85. A839732

    86. Q3746573

    87. Sr-01000759379-2

    88. Sr-01000759379-3

    89. 6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid-

    90. 6,8-difluoro-1-(2-fluoroethyl)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylicacid

    91. 6,8-difluoro-1-(2-fluoroethyl)-7-(4-methylpiperazin-1-yl)-4-oxo-quinoline-3-carboxylic Acid;fleroxacin

    92. 79660-53-0

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 369.34 g/mol
    Molecular Formula C17H18F3N3O3
    XLogP3-0.1
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count4
    Exact Mass369.13002593 g/mol
    Monoisotopic Mass369.13002593 g/mol
    Topological Polar Surface Area64.1 Ų
    Heavy Atom Count26
    Formal Charge0
    Complexity595
    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

    Fleroxacin is a broad-spectrum antimicrobial fluoroquinolone.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Fleroxacin is a broad-spectrum antimicrobial fluoroquinolone. It strongly inhibits the DNA-supercoiling activity of DNA gyrase.

    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.)

    Topoisomerase II Inhibitors

    Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II. (See all compounds classified as Topoisomerase II Inhibitors.)

    5.3 ATC Code

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01M - Quinolone antibacterials

    J01MA - Fluoroquinolones

    J01MA08 - Fleroxacin

    5.4 Absorption, Distribution and Excretion

    Absorption

    Rapidly and well absorbed from the gastrointestinal tract after oral administration.

    5.5 Mechanism of Action

    The inhibition of DNA gyrase and DNA topoisomerase 2 leads ultimately to cell death as these enzymes are required for bacterial DNA replication, transcription, repair, strand supercoiling repair, and recombination.