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    Finafloxacin

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    DIGITAL CONTENT

    MARKET PLACE

    PATENTS & EXCLUSIVITIES

    PharmaCompass
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    2D Structure
    Also known as: 209342-40-5, Xtoro, Finafloxacin [inn], D26osn9q4r, Al-60371, Chebi:85176
    Molecular Formula
    C20H19FN4O4
    Molecular Weight
    398.4  g/mol
    InChI Key
    FYMHQCNFKNMJAV-HOTGVXAUSA-N
    FDA UNII
    D26OSN9Q4R
    Finafloxacin is a fluoroquinolone antibiotic indicated in the treatment of acute otitis externa (swimmer's ear) caused by the bacteria Pseudomonas aeruginosa and Staphylococcus aureus. Finafloxacin is marketed by Novartis under the brand Xtoro, and was approved by the FDA in December 2014.
    Finafloxacin is a Quinolone Antimicrobial.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    7-[(4aS,7aS)-3,4,4a,5,7,7a-hexahydro-2H-pyrrolo[3,4-b][1,4]oxazin-6-yl]-8-cyano-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid
    2.1.2 InChI
    InChI=1S/C20H19FN4O4/c21-14-5-11-17(25(10-1-2-10)7-13(19(11)26)20(27)28)12(6-22)18(14)24-8-15-16(9-24)29-4-3-23-15/h5,7,10,15-16,23H,1-4,8-9H2,(H,27,28)/t15-,16-/m0/s1
    2.1.3 InChI Key
    FYMHQCNFKNMJAV-HOTGVXAUSA-N
    2.1.4 Canonical SMILES
    C1CC1N2C=C(C(=O)C3=CC(=C(C(=C32)C#N)N4CC5C(C4)OCCN5)F)C(=O)O
    2.1.5 Isomeric SMILES
    C1CC1N2C=C(C(=O)C3=CC(=C(C(=C32)C#N)N4C[C@H]5[C@H](C4)OCCN5)F)C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    D26OSN9Q4R
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 3-quinolinecarboxylic Acid, 8-cyano-1-cyclopropyl-6-fluoro-7-((4as,7as)-hexahydropyrrolo(3,4-b)-1,4-oxazin-6(2h)-yl)-1,4-dihydro-4-oxo-

    2. Xtoro

    2.3.2 Depositor-Supplied Synonyms

    1. 209342-40-5

    2. Xtoro

    3. Finafloxacin [inn]

    4. D26osn9q4r

    5. Al-60371

    6. Chebi:85176

    7. Finafloxacin (inn)

    8. 8-cyano-1-cyclopropyl-6-fluoro-7-((4as,7as)-hexahydropyrrolo[3,4-b][1,4]oxazin-6(2h)-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

    9. Bay35-3377

    10. (-)-8-cyano-1-cyclopropyl-6-fluoro-7-((4as,7as)-hexahydropyrrolo(3,4-b)-1,4-oxazin-6(2h)-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

    11. 7-[(4as,7as)-3,4,4a,5,7,7a-hexahydro-2h-pyrrolo[3,4-b][1,4]oxazin-6-yl]-8-cyano-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic Acid

    12. Gastrochinolon

    13. Gastroquinolone

    14. 8-cyano-1-cyclopropyl-6-fluoro-7-[(4as,7as)-hexahydropyrrolo[3,4-b][1,4]oxazin-6(2h)-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

    15. Xtoro (tn)

    16. Finafloxacin [mi]

    17. Unii-d26osn9q4r

    18. Finafloxacin [who-dd]

    19. Schembl1002869

    20. Chembl1908370

    21. Gtpl10809

    22. Dtxsid10175096

    23. Finafloxacin [orange Book]

    24. Bcp23882

    25. Zinc3985346

    26. Al60371

    27. Cs-5557

    28. Db09047

    29. Ncgc00510315-02

    30. (-)-8-cyano-1-cyclopropyl-6-fluoro-7-((4as,7as)-hexahydropyrrolo(3,4-b)-1,4-oxazin-6(2h)-yl)-4-oxo-1

    31. Ac-29291

    32. Hy-13451

    33. D10575

    34. Q21011229

    35. 3-quinolinecarboxylic Acid,8-cyano-1-cyclopropyl-6-fluoro-7-[(4as,7as)-hexahydropyrrolo[3,4-b]-1,4-oxazin-6(2h)-yl]-1,4-dihydro-4-oxo-

    36. 7-[(4as,7as)-3,4,4a,5,7,7a-hexahydro-2h-pyrrolo[3,4-b][1,4]oxazin-6-yl]-8-cyano-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic Acid,hydrochloride

    37. 8-cyano-1-cyclopropyl-6-fluoro-7-((1s,6s)-2-oxa-5,8-diazabicyclo[4.3.0]non-8-yl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid

    38. 8-cyano-1-cyclopropyl-6-fluoro-7-[(4as,7as)-hexahydropyrrolo[3,4-b][1,4]oxazin-6(2h)-yl]-4-oxo-1,4-dihydro-3-quinolinecarboxylic Acid

    2.4 Create Date
    2006-10-26
    3 Chemical and Physical Properties
    Molecular Weight 398.4 g/mol
    Molecular Formula C20H19FN4O4
    XLogP3-0.7
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count3
    Exact Mass398.13903326 g/mol
    Monoisotopic Mass398.13903326 g/mol
    Topological Polar Surface Area106 Ų
    Heavy Atom Count29
    Formal Charge0
    Complexity806
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    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

    Finafloxacin is indicated for the treatment of acute otitis externa (AOE) with or without an otowick, caused by susceptible strains of Pseudomonas aeruginosa and Staphylococcus aureus in patients age 1 year and older.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Anti-Bacterial Agents

    Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

    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.)

    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.)

    5.2 FDA Pharmacological Classification
    5.2.1 Active Moiety
    FINAFLOXACIN
    5.2.2 FDA UNII
    D26OSN9Q4R
    5.2.3 Pharmacological Classes
    Chemical Structure [CS] - Quinolones
    5.3 Mechanism of Action

    Finafloxacin is a fluoroquinolone antibiotic, which selectively inhibit bacterial type II topoisomerase enzymes, DNA gyrase and topoisomerase IV, which are required for bacterial DNA replication, transcription, repair and recombination.