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Technical details about Enoxacin, learn more about the structure, uses, toxicity, action, side effects and more

Also known as: Penetrex, Comprecin, Enoxacine, Enoxacino, Enoxacinum, 74011-58-8
Molecular Formula
C15H17FN4O3
Molecular Weight
320.318883  g/mol
InChI Key
IDYZIJYBMGIQMJ-UHFFFAOYSA-N
FDA UNII
325OGW249P

A broad-spectrum 6-fluoronaphthyridinone antibacterial agent (FLUOROQUINOLONES) structurally related to NALIDIXIC ACID.
1 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. Faulding Brand Of Enoxacin

11. Pd 107779

12. Pd-107779

13. Pd107779

14. Penetrex

15. Pierre Fabre Brand Of Enoxacin Sesquihydrate

16. Rhône Poulenc Rorer Brand Of Enoxacin Sesquihydrate

17. Rhône-poulenc Rorer Brand Of Enoxacin Sesquihydrate

18. Sesquihydrate, Enoxacin

2.3.2 Depositor-Supplied Synonyms

1. Penetrex

2. Comprecin

3. Enoxacine

4. Enoxacino

5. Enoxacinum

6. 74011-58-8

7. Bactidan

8. Flumark

9. Enoxor

10. Almitil

11. Enoxin

12. At-2266

13. Ci 919

14. Ci-919

15. Enoram

16. 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic Acid

17. Enoxacine [french]

18. Enoxacinum [latin]

19. Enoxacino [spanish]

20. Enoksetin

21. Enroxil

22. Enoxen

23. Chebi:157175

24. Pd 107779

25. Pd-107779

26. Penetrex (tn)

27. Prestwick_708

28. Unii-325ogw249p

29. At 2266

30. Ccris 5242

31. Spectrum_001539

32. Enoxacin (usan/inn)

33. Ac1l1fgq

34. Prestwick0_000353

35. Prestwick1_000353

36. Prestwick2_000353

37. Prestwick3_000353

38. Spectrum2_001731

39. Spectrum3_001570

40. Spectrum4_000166

41. Spectrum5_001044

42. Nsc629661

43. Chembl826

44. Nsc 627409

45. Nsc 629661

46. Enoxacin Sesquihydrate

47. Brn 3628995

48. Oprea1_147866

49. Ncgc00016927-01

50. Bspbio_000445

51. Bspbio_003080

52. Kbiogr_000651

53. Kbio_002019

54. Bidd:gt0191

55. Divk1c_000420

56. E3764_fluka

57. E3764_sigma

58. Spbio_001802

59. Spbio_002366

60. Spectrum1503215

61. Cas-74011-58-8

62. Mls000069645

63. Bpbio1_000491

64. Bcbcmap01_000009

65. C15h17fn4o3

66. Hms501e22

67. Kbio1_000420

68. Kbio2_002019

69. Kbio2_004587

70. Kbio2_007155

71. Kbio3_002580

72. Enoxacin [usan:ban:inn:jan]

73. Ninds_000420

74. Hms1569g07

75. Hms1922i17

76. Hms2090e10

77. Hms2092n20

78. 1,8-naphthyridine-3-carboxylic Acid, 1,4-dihydro-1-ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)-

79. 1,8-naphthyridine-3-carboxylic Acid, 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-

80. Cl23362

81. Db00467

82. Idi1_000420

83. Smp1_000113

84. Ncgc00016927-02

85. Ncgc00023864-03

86. Ncgc00023864-04

87. Ncgc00178309-01

88. Ncgc00178309-02

89. Ls-95946

90. Nci60_009618

91. Smr000058233

92. Tl8005116

93. E0762

94. Dtox_cid_2984

95. C06979

96. D00310

97. 1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic Acid

98. 1-ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,4-dihydro-[1,8]naphthyridine-3-carboxylic Acid

99. Dtox_rid_76818

100. Dtox_gsid_22984

101. Brd-k78113049-001-05-5

102. I06-0290

103. 1-ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,8-naphthyridine-3-carboxylic Acid

104. 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7- [1-piperazinyl]-1,8-naphthyridine-3-carboxylic Acid

105. 1-ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,4-dihydro-1,8-naphthyridine-3-carboxylic Acid

106. Sesquihydrate, Enoxacin

107. 84294-96-2

108. Faulding Brand Of Enoxacin

109. Bactidron

110. Enoxacina

111. Gyramid

112. Vinone

113. 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-[1-piperazinyl]-1,8-naphthyridine-3-carboxylic Acid

114. Cid3229

115. Ci919

116. At2266

117. Pd107779

118. Surecn33963

119. Pierre Fabre Brand Of Enoxacin Sesquihydrate

120. Agn-pc-00aiod

121. Epitope Id:119069

122. D015365

123. Rhone Poulenc Rorer Brand Of Enoxacin Sesquihydrate

124. Rhone-poulenc Rorer Brand Of Enoxacin Sesquihydrate

125. Ctk8e3243

126. Enoxacin [usan:inn:ban:jan]

127. 8-naphthyridine-3-carboxylic Acid

128. 325ogw249p

129. Hms2233k20

130. Hms3372a12

131. Pharmakon1600-01503215

132. Hy-b0268

133. Tox21_110688

134. Ccg-39452

135. Dap001000

136. Nsc758416

137. Akos015838626

138. Tox21_110688_1

139. Ag-g-93622

140. Cs-2257

141. Ks-5190

142. Mcule-2632820619

143. Nsc-629661

144. Nsc-758416

145. Ncgc00016927-03

146. Ncgc00016927-04

147. Ncgc00016927-05

148. Ncgc00016927-06

149. Ncgc00016927-07

150. Ncgc00016927-08

151. Ncgc00016927-10

152. Ncgc00016927-11

153. K259

154. Kb-87029

155. St044514

156. Ab1011529

157. Tr-037960

158. Ft-0630825

159. 1, 6-fluoro-1,4-dihydro- 4-oxo-7-piperazinyl

160. Ab00052328-09

161. A837996

162. 3b2-0115

163. Brd-k78113049-001-12-1

164. 1,8-naphthyridine-3-carboxylic Acid, 6-fluoro-1,4-dihydro- 4-oxo-7-piperazinyl

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

166. 1-ethyl-6-fluoranyl-4-oxo-7-piperazin-1-yl-1,8-naphthyridine-3-carboxylic Acid

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

168. 1-ethyl-6-fluoro-4-oxo-7-piperazinylhydropyridino[2,3-b]pyridine-3-carboxylic Acid

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 320.318883 g/mol
Molecular Formula C15H17FN4O3
XLogP3-0.2
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count8
Rotatable Bond Count3
Exact Mass320.128469 g/mol
Monoisotopic Mass320.128469 g/mol
Topological Polar Surface Area85.8 A^2
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 (&ge;18 years of age) with the following infections caused by susceptible strains of the designated microorganisms: (1) uncomplicated urethral or cervical gonorrhea due to <i>Neieria gonorrhoeae</i>, (2) uncomplicated urinary tract infections (cystitis) due to <i>Escherichia coli</i>, <i>Staphylococcus epidermidis</i>, or <i>Staphylococcus saprophyticus</i>, and (3) complicated urinary tract infections due to <i>Escherichia coli</i>, <i>Klebsiella pneumoniae</i>, <i>Proteus mirabilis</i>, <i>Pseudomonas aeruginosa</i>, <i>Staphylococcus epidermidis</i>, or <i>Enterobacter cloacae</i>.


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 reduce the growth or reproduction of BACTERIA.


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.


5.3 ATC Code

J01MA04 - Enoxacin < J01MA - Fluoroquinolones < J01M - Quinolone antibacterials < J01 - Antibacterials for systemic use < J - Antiinfectives for systemic use



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 eential bacterial enzyme DNA gyrase (DNA Topoisomerase II).