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    Enoxacin

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

    FINISHED DOSAGE FORMULATIONS

    PharmaCompass
    $ API Ref.Price (USD/KG) : 3,586Xls

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    2D Structure
    Also known as: 74011-58-8, Penetrex, Enoxacine, Comprecin, 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid, At-2266
    Molecular Formula
    C15H17FN4O3
    Molecular Weight
    320.32  g/mol
    InChI Key
    IDYZIJYBMGIQMJ-UHFFFAOYSA-N
    FDA UNII
    325OGW249P
    A broad-spectrum 6-fluoronaphthyridinone antibacterial agent that is structurally related to NALIDIXIC ACID.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1-ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,8-naphthyridine-3-carboxylic acid
    2.1.2 InChI
    InChI=1S/C15H17FN4O3/c1-2-19-8-10(15(22)23)12(21)9-7-11(16)14(18-13(9)19)20-5-3-17-4-6-20/h7-8,17H,2-6H2,1H3,(H,22,23)
    2.1.3 InChI Key
    IDYZIJYBMGIQMJ-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCN1C=C(C(=O)C2=CC(=C(N=C21)N3CCNCC3)F)C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    325OGW249P
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. At 2266

    2. At-2266

    3. At2266

    4. Ci 919

    5. Ci-919

    6. Ci919

    7. Enoxacin Sesquihydrate

    8. Enoxin

    9. Enoxor

    10. Pd 107779

    11. Pd-107779

    12. Pd107779

    13. Penetrex

    14. Sesquihydrate, Enoxacin

    2.3.2 Depositor-Supplied Synonyms

    1. 74011-58-8

    2. Penetrex

    3. Enoxacine

    4. Comprecin

    5. 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic Acid

    6. At-2266

    7. Bactidan

    8. Enoxacino

    9. Enoxacinum

    10. Flumark

    11. Enoxor

    12. Ci-919

    13. Almitil

    14. Pd 107779

    15. Ci 919

    16. Enoxacin (penetrex)

    17. Pd-107779

    18. 1-ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,8-naphthyridine-3-carboxylic Acid

    19. 1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic Acid

    20. Nsc 629661

    21. Enoxacin (hydrate)

    22. Chebi:157175

    23. Chembl826

    24. Nsc-629661

    25. Nsc-758416

    26. 1-ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,4-dihydro-[1,8]naphthyridine-3-carboxylic Acid

    27. Enoram

    28. Enoxin

    29. 325ogw249p

    30. Nsc629661

    31. 1,8-naphthyridine-3-carboxylic Acid, 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-

    32. At 2266;ci 919

    33. Enoxacine [french]

    34. Enoxacinum [latin]

    35. Enofloxacin

    36. Ncgc00016927-01

    37. Enoxacino [spanish]

    38. Enoksetin

    39. Cas-74011-58-8

    40. Dsstox_cid_2984

    41. 1,8-naphthyridine-3-carboxylic Acid, 1,4-dihydro-1-ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)-

    42. 1-ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,4-dihydro-1,8-naphthyridine-3-carboxylic Acid

    43. Dsstox_rid_76818

    44. Dsstox_gsid_22984

    45. Enoxacin Sesquihydrate;at-2266 Hydrate;ci-919 Hydrate

    46. Bactidron

    47. Enoxen

    48. Penetrex (tn)

    49. Smr000058233

    50. Ccris 5242

    51. Enoxacin (usan/inn)

    52. Sr-01000000202

    53. Nsc 627409

    54. At 2266

    55. Brn 3628995

    56. Pd107779

    57. Abenox

    58. Unii-325ogw249p

    59. Enoxacin [usan:inn:ban:jan]

    60. Enx

    61. Prestwick_708

    62. Mfcd00133308

    63. Spectrum_001539

    64. Enoxacin [usan]

    65. Enoxacin [inn]

    66. Enoxacin [mi]

    67. Enoxacin [vandf]

    68. Prestwick0_000353

    69. Prestwick1_000353

    70. Prestwick2_000353

    71. Prestwick3_000353

    72. Spectrum2_001731

    73. Spectrum3_001570

    74. Spectrum4_000166

    75. Spectrum5_001044

    76. E0762

    77. Enoxacin [mart.]

    78. Enoxacin [who-dd]

    79. Epitope Id:119069

    80. Oprea1_147866

    81. Schembl33963

    82. Bspbio_000445

    83. Bspbio_003080

    84. Enoxacin, Analytical Standard

    85. Kbiogr_000651

    86. Kbioss_002019

    87. Mls000069645

    88. Mls006011976

    89. Bidd:gt0191

    90. Divk1c_000420

    91. Spectrum1503215

    92. Spbio_001802

    93. Spbio_002366

    94. Enoxacin [orange Book]

    95. Bpbio1_000491

    96. Gtpl8882

    97. Dtxsid5022984

    98. Bcbcmap01_000009

    99. Hms501e22

    100. Kbio1_000420

    101. Kbio2_002019

    102. Kbio2_004587

    103. Kbio2_007155

    104. Kbio3_002580

    105. Ninds_000420

    106. Hms1569g07

    107. Hms1922i17

    108. Hms2090e10

    109. Hms2092n20

    110. Hms2233k20

    111. Hms3372a12

    112. Hms3655m08

    113. Hms3715h13

    114. Pharmakon1600-01503215

    115. Bcp22623

    116. Hy-b0268

    117. Tox21_110688

    118. Bdbm50296358

    119. Ccg-39452

    120. Enoxacin 100 Microg/ml In Methanol

    121. Nsc758416

    122. S1756

    123. Zinc19594549

    124. Akos015838626

    125. Tox21_110688_1

    126. Db00467

    127. Ks-5190

    128. 1-ethyl-6-fluoro-4-oxo-7-piperazinylhydropyridino[2,3-b]pyridine-3-carboxylic Acid

    129. Enoxacin 100 Microg/ml In Acetonitrile

    130. Idi1_000420

    131. Smp1_000113

    132. Ncgc00016927-02

    133. Ncgc00016927-03

    134. Ncgc00016927-04

    135. Ncgc00016927-05

    136. Ncgc00016927-06

    137. Ncgc00016927-07

    138. Ncgc00016927-08

    139. Ncgc00016927-10

    140. Ncgc00016927-11

    141. Ncgc00023864-03

    142. Ncgc00023864-04

    143. Ncgc00178309-01

    144. Ncgc00178309-02

    145. Nci60_009618

    146. Sbi-0051788.p002

    147. Db-055829

    148. Ft-0630825

    149. Sw196857-3

    150. C06979

    151. D00310

    152. 1, 6-fluoro-1,4-dihydro- 4-oxo-7-piperazinyl

    153. Ab00052328-09

    154. Ab00052328_10

    155. Ab00052328_11

    156. 011e588

    157. A837996

    158. Q1639616

    159. Sr-01000000202-2

    160. Sr-01000000202-3

    161. Brd-k78113049-001-05-5

    162. Brd-k78113049-001-07-1

    163. Brd-k78113049-001-12-1

    164. Z1551429746

    165. 1-ethyl-6-fluoranyl-4-oxidanylidene-7-piperazin-1-yl-1,8-naphthyridine-3-carboxylic Acid

    166. 1-ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydro[1,8]naphthyridine-3-carboxylic Acid

    167. 1-ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic Acid

    168. 1,8-naphthyridine-3-carboxylic Acid, 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 320.32 g/mol
    Molecular Formula C15H17FN4O3
    XLogP3-0.2
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count3
    Exact Mass320.12846858 g/mol
    Monoisotopic Mass320.12846858 g/mol
    Topological Polar Surface Area85.8 Ų
    Heavy Atom Count23
    Formal Charge0
    Complexity521
    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

    For the treatment of adults (≥18 years of age) with the following infections caused by susceptible strains of the designated microorganisms: (1) uncomplicated urethral or cervical gonorrhea due to Neisseria gonorrhoeae, (2) uncomplicated urinary tract infections (cystitis) due to Escherichia coli, Staphylococcus epidermidis, or Staphylococcus saprophyticus, and (3) complicated urinary tract infections due to Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Pseudomonas aeruginosa, Staphylococcus epidermidis, or Enterobacter cloacae.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Enoxacin is a quinolone/fluoroquinolone antibiotic. Enoxacin 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. Enoxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria. Enoxacin may be active against pathogens resistant to drugs that act by different mechanisms.

    5.2 MeSH Pharmacological Classification

    Anti-Bacterial Agents

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

    Cytochrome P-450 CYP1A2 Inhibitors

    Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP1A2. (See all compounds classified as Cytochrome P-450 CYP1A2 Inhibitors.)

    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

    J01MA04 - Enoxacin

    5.4 Absorption, Distribution and Excretion

    Absorption

    Rapidly absorbed following oral administration, with an absolute oral bioavailability of approximately 90%.

    5.5 Metabolism/Metabolites

    Hepatic. Some isozymes of the cytochrome P-450 hepatic microsomal enzyme system are inhibited by enoxacin. After a single dose, greater than 40% was recovered in urine by 48 hours as unchanged drug.

    5.6 Biological Half-Life

    Plasma half-life is 3 to 6 hours.

    5.7 Mechanism of Action

    Enoxacin exerts its bactericidal action via the inhibition of the essential bacterial enzyme DNA gyrase (DNA Topoisomerase II).