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    Gatifloxacin

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

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    2D Structure
    Also known as: 112811-59-3, Tequin, Gatiflo, Zymar, Am-1155, Zymaxid
    Molecular Formula
    C19H22FN3O4
    Molecular Weight
    375.4  g/mol
    InChI Key
    XUBOMFCQGDBHNK-UHFFFAOYSA-N
    FDA UNII
    81485Y3A9A
    A fluoroquinolone antibacterial agent and DNA TOPOISOMERASE II inhibitor that is used as an ophthalmic solution for the treatment of BACTERIAL CONJUNCTIVITIS.
    Gatifloxacin anhydrous is a Quinolone Antimicrobial.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
    2.1.2 InChI
    InChI=1S/C19H22FN3O4/c1-10-8-22(6-5-21-10)16-14(20)7-12-15(18(16)27-2)23(11-3-4-11)9-13(17(12)24)19(25)26/h7,9-11,21H,3-6,8H2,1-2H3,(H,25,26)
    2.1.3 InChI Key
    XUBOMFCQGDBHNK-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1CN(CCN1)C2=C(C=C3C(=C2OC)N(C=C(C3=O)C(=O)O)C4CC4)F
    2.2 Other Identifiers
    2.2.1 UNII
    81485Y3A9A
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 1-cyclopropyl-1,4-dihydro-6-fluoro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid

    2. Am 1155

    3. Am-1155

    4. Bms 206584

    5. Bms-206584

    6. Bms206584

    7. Cg 5501

    8. Gatifloxacine

    9. Tequin

    10. Zymar

    2.3.2 Depositor-Supplied Synonyms

    1. 112811-59-3

    2. Tequin

    3. Gatiflo

    4. Zymar

    5. Am-1155

    6. Zymaxid

    7. Gatifloxacin Anhydrous

    8. Am 1155

    9. Zymer

    10. Cg 5501

    11. 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid

    12. 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

    13. Bms-206584

    14. Gtfx

    15. Bms 206584-01

    16. Pd 135432

    17. 1-cyclopropyl-1,4-dihydro-6-fluoro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid

    18. Gatifloxacin Hydrate

    19. Gatifloxacin (inn)

    20. Chembl31

    21. 3-quinolinecarboxylic Acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-

    22. Nsc-758701

    23. 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic Acid

    24. Pd-135432

    25. Chebi:5280

    26. Gatilox

    27. Gatiquin

    28. Gatispan

    29. 160738-57-8

    30. Gaity

    31. Cg5501

    32. Mfcd00895399

    33. 81485y3a9a

    34. Gatifloxin

    35. Ncgc00068236-02

    36. Gatifloxacin 100 Microg/ml In Acetonitrile

    37. Gatifloxacin [inn]

    38. 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-quinoline-3-carboxylic Acid

    39. Dsstox_cid_25704

    40. Dsstox_rid_81076

    41. Dsstox_gsid_45704

    42. Gatifloxacin [usan:inn]

    43. Bms-206584-01

    44. Bonoq

    45. Gatifloxacin (sesquihydrate)

    46. Tymer

    47. 1-cyclopropyl-6-fluoro- 8-methoxy-7-(3-methylpiperazin-1-yl)- 4-oxo-quinoline-3-carboxylic Acid

    48. 3-quinolinecarboxylic Acid,1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-

    49. Smr000043336

    50. Gatifloxacin (tn)

    51. Cas-112811-59-3

    52. Zymer (tn)

    53. 1-cyclopropyl-6-fluoro-8-methoxy-7-

    54. Sr-01000610458

    55. (3-methylpiperazin-1-yl)-4-oxo-1,4-

    56. Bms-20658401

    57. Gatifloxacino

    58. Gatifloxacinum

    59. Gatifloxcin

    60. Tequin In Dextrose 5% In Plastic Container

    61. Am-1155 (*sesquihydrate*)

    62. Gatifloxacin & Gamma Interferon

    63. Unii-81485y3a9a

    64. Gatifloxacin,(s)

    65. (+-)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid

    66. Cg-5501

    67. Kinome_3137

    68. Spectrum_001909

    69. Cpd000043336

    70. Pd135432

    71. Spectrum2_000487

    72. Spectrum3_000999

    73. Spectrum4_001127

    74. Spectrum5_001468

    75. Gatifloxacin [mi]

    76. Schembl22591

    77. Bspbio_002697

    78. Kbiogr_001613

    79. Kbioss_002448

    80. 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid

    81. Mls000040259

    82. Mls000759493

    83. Mls006011836

    84. Gatifloxacin [who-dd]

    85. Spectrum1504272

    86. Spbio_000353

    87. Gatifloxacin Sesquihydrate,(s)

    88. Dtxsid5045704

    89. Gtpl10816

    90. Kbio2_002442

    91. Kbio2_005010

    92. Kbio2_007578

    93. Kbio3_001917

    94. Hms1922j15

    95. Hms2090k10

    96. Hms2093g06

    97. Hms2233d20

    98. Hms3259p06

    99. Hms3372j10

    100. Hms3372j12

    101. Hms3715n03

    102. Pharmakon1600-01504272

    103. Albb-028535

    104. Amy17781

    105. Bcp13408

    106. Rkl10068

    107. Tox21_110984

    108. Bbl010485

    109. Bdbm50117914

    110. Ccg-39529

    111. Nsc758701

    112. S1340

    113. Stk801620

    114. C19h22fn3o4.1.5h2o

    115. Akos004119932

    116. Akos016340697

    117. Tox21_110984_1

    118. Ac-1944

    119. Cs-1841

    120. Db01044

    121. Ks-1066

    122. Nc00702

    123. Nsc 758701

    124. Gatifloxacin 100 Microg/ml In Methanol

    125. Ncgc00068236-03

    126. Ncgc00068236-04

    127. Ncgc00068236-05

    128. Ncgc00068236-06

    129. Ncgc00068236-07

    130. Ncgc00068236-08

    131. Ncgc00095126-01

    132. Ncgc00095126-02

    133. Ncgc00178525-01

    134. Hy-10581

    135. Sbi-0206764.p001

    136. Db-019145

    137. Ft-0626635

    138. Ft-0631189

    139. Ft-0668952

    140. G0325

    141. C07661

    142. D08011

    143. G-2380

    144. Ab00171654-13

    145. Ab00171654-14

    146. Ab00171654_16

    147. Ab00171654_17

    148. 811g593

    149. A802657

    150. Gatifloxacin, Antibiotic For Culture Media Use Only

    151. Q2365016

    152. Sr-01000610458-2

    153. Sr-01000610458-3

    154. Brd-a74980173-001-02-8

    155. Brd-a74980173-001-06-9

    156. (+/-)-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic Acid

    157. 1-cyclopropyl-6-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-3-quinolinecarboxylic Acid

    158. 1-cyclopropyl-6-6-fluoro-1,4-dihydro-8-methoxy-7-(3methylpiperazin-1-yl)-4-oxo-3-quinolinecarboxylic Acid

    159. 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-3-quinolinecarboxylic Acid

    160. 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic Acid

    161. 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylicacid

    162. 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazin-1yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic A

    163. 1-cyclopropyl-6-fluoro-8-methoxy-7-(3-methylpiperazino)-4-oxo-1,4-dihydro-3-quinolinecarboxylic Acid

    164. 1-cyclopropyl-7-(3-methyl-1-piperazinyl)-6-fluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 375.4 g/mol
    Molecular Formula C19H22FN3O4
    XLogP3-0.7
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count4
    Exact Mass375.15943435 g/mol
    Monoisotopic Mass375.15943435 g/mol
    Topological Polar Surface Area82.1 Ų
    Heavy Atom Count27
    Formal Charge0
    Complexity653
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 6  
    Drug NameGatifloxacin
    PubMed HealthGatifloxacin (Into the eye)
    Drug ClassesAntibiotic
    Drug LabelZYMAXID sterile ophthalmic solution is an 8-methoxyfluoroquinolone anti-infective for the treatment of bacterial conjunctivitis. Its chemical name is ()-1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarb...
    Active IngredientGatifloxacin
    Dosage FormSolution/drops; Solution
    RouteOphthalmic; ophthalmic
    Strength0.5%; 0.3%
    Market StatusTentative Approval; Prescription
    CompanyHi-tech Pharma; Lupin; Hi-tech Pharmacal

    2 of 6  
    Drug NameZymar
    PubMed HealthGatifloxacin (Into the eye)
    Drug ClassesAntibiotic
    Drug LabelZYMAXID sterile ophthalmic solution is an 8-methoxyfluoroquinolone anti-infective for the treatment of bacterial conjunctivitis. Its chemical name is ()-1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarb...
    Active IngredientGatifloxacin
    Dosage FormSolution/drops
    RouteOphthalmic
    Strength0.3%
    Market StatusPrescription
    CompanyAllergan

    3 of 6  
    Drug NameZymaxid
    Active IngredientGatifloxacin
    Dosage FormSolution/drops
    RouteOphthalmic
    Strength0.5%
    Market StatusPrescription
    CompanyAllergan

    4 of 6  
    Drug NameGatifloxacin
    PubMed HealthGatifloxacin (Into the eye)
    Drug ClassesAntibiotic
    Drug LabelZYMAXID sterile ophthalmic solution is an 8-methoxyfluoroquinolone anti-infective for the treatment of bacterial conjunctivitis. Its chemical name is ()-1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarb...
    Active IngredientGatifloxacin
    Dosage FormSolution/drops; Solution
    RouteOphthalmic; ophthalmic
    Strength0.5%; 0.3%
    Market StatusTentative Approval; Prescription
    CompanyHi-tech Pharma; Lupin; Hi-tech Pharmacal

    5 of 6  
    Drug NameZymar
    PubMed HealthGatifloxacin (Into the eye)
    Drug ClassesAntibiotic
    Drug LabelZYMAXID sterile ophthalmic solution is an 8-methoxyfluoroquinolone anti-infective for the treatment of bacterial conjunctivitis. Its chemical name is ()-1-Cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarb...
    Active IngredientGatifloxacin
    Dosage FormSolution/drops
    RouteOphthalmic
    Strength0.3%
    Market StatusPrescription
    CompanyAllergan

    6 of 6  
    Drug NameZymaxid
    Active IngredientGatifloxacin
    Dosage FormSolution/drops
    RouteOphthalmic
    Strength0.5%
    Market StatusPrescription
    CompanyAllergan

    4.2 Drug Indication

    For the treatment of bronchitis, sinusitis, community-acquired pneumonia, and skin infections (abscesses, wounds) caused by S. pneumoniae, H. influenzae, S. aureus, M. pneumoniae, C. pneumoniae, L. pneumophila, S. pyogenes

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Gatifloxacin is a synthetic broad-spectrum 8-methoxyfluoroquinolone antibacterial agent for oral or intravenous administration. is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase, which allows the untwisting required to replicate one DNA double helix into two. Notably the drug has 100 times higher affinity for bacterial DNA gyrase than for mammalian. Gatifloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria. It should be used only to treat or prevent infections that are proven or strongly suspected to be caused by bacteria.

    5.2 MeSH Pharmacological Classification

    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.)

    Anti-Bacterial Agents

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

    Ophthalmic Solutions

    Sterile solutions that are intended for instillation into the eye. It does not include solutions for cleaning eyeglasses or CONTACT LENS SOLUTIONS. (See all compounds classified as Ophthalmic Solutions.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    GATIFLOXACIN ANHYDROUS
    5.3.2 FDA UNII
    81485Y3A9A
    5.3.3 Pharmacological Classes
    Quinolones [CS]; Quinolone Antimicrobial [EPC]
    5.4 ATC Code

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01M - Quinolone antibacterials

    J01MA - Fluoroquinolones

    J01MA16 - Gatifloxacin

    S - Sensory organs

    S01 - Ophthalmologicals

    S01A - Antiinfectives

    S01AE - Fluoroquinolones

    S01AE06 - Gatifloxacin

    5.5 Absorption, Distribution and Excretion

    Absorption

    Well absorbed from the gastrointestinal tract after oral administration with absolute bioavailability of gatifloxacin is 96%

    5.6 Metabolism/Metabolites

    Gatifloxacin undergoes limited biotransformation in humans with less than 1% of the dose excreted in the urine as ethylenediamine and methylethylenediamine metabolites

    5.7 Biological Half-Life

    7-14 hours

    5.8 Mechanism of Action

    The bactericidal action of Gatifloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV, which are required for bacterial DNA replication, transcription, repair, and recombination.