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Chemistry

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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

Enoxacin

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 Formula	C₁₅H₁₇FN₄O₃
Molecular Weight	320.32 g/mol
XLogP3	-0.2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	3
Exact Mass	320.12846858 g/mol
Monoisotopic Mass	320.12846858 g/mol
Topological Polar Surface Area	85.8 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	521
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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).

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