Enoxacin

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Enoxacin
File:Enoxacin.svg
Systematic (IUPAC) name
1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a601013
Routes of
administration		 Oral
Identifiers
CAS Number 74011-58-8 YesY
ATC code J01MA04 (WHO)
PubChem CID: 3229
DrugBank DB00467 YesY
ChemSpider 3116 YesY
UNII 325OGW249P YesY
KEGG D00310 YesY
ChEBI CHEBI:157175 YesY
ChEMBL CHEMBL826 YesY
Chemical data
Formula C15H17FN4O3
Molecular mass 320.319 g/mol
  • Fc1c(nc2c(c1)C(=O)C(\C(=O)O)=C/N2CC)N3CCNCC3
  • 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) YesY
  • Key:IDYZIJYBMGIQMJ-UHFFFAOYSA-N YesY
  (verify)

Enoxacin[note 1] is an oral broad-spectrum fluoroquinolone antibacterial agent used in the treatment of urinary tract infections and gonorrhea. Insomnia is a common adverse effect.[1][2] It is no longer available in the United States.

It has been shown recently that it may have cancer inhibiting effect.[3]

Mechanism of action

Quinolones and fluoroquinolones are bactericidal drugs, eradicating bacteria by interfering with DNA replication. Like other fluoroquinolones, enoxacin functions by inhibiting bacterial DNA gyrase and topoisomerase IV. The inhibition of these enzymes prevents bacterial DNA replication, transcription, repair and recombination.[4][5] Enoxacin is active against many Gram-positive bacteria.[note 2] The quinolone is also active against Gram-negative bacteria[note 3][6][7]

Pharmacokinetics

After oral administration enoxacin is rapidly and well absorbed from the gastrointestinal tract. The antibiotic is widely distributed throughout the body and in the different biological tissues. Tissue concentrations often exceed serum concentrations. The binding of enoxacin to serum proteins is 35 to 40%. The serum elimination half-life, in subjects with normal renal function, is approximately 6 hours. Approximately 60% of an orally administered dose is excreted in the urine as unchanged drug within 24 hours.[8][9] A small amount of a dose of drug administered is excreted in the bile.[10] High concentrations of the fluoroquinolone are reached in the urinary tract and this fact ensures an antibacterial effect continued over time, particularly in this district.

Medical uses

Enoxacin can be used to treat a wide variety of infections, particularly gastroenteritis including infectious diarrhea, respiratory tract infections, gonorrhea[11] and urinary tract infections.[12][13]

Adverse effects

Enoxacin, like other fluoroquinolones, is known to trigger seizures or lower the seizure threshold.[14] The compound should not be administered to patients with epilepsy or a personal history of previous convulsive attacks as may promote the onset of these disorders.[15]

Contraindications

Enoxacin is contraindicated in subjects with a history of hypersensitivity to the substance or any other member of the quinolone class, or any component of the medicine. Enoxacin, like other fluoroquinolones, can cause degenerative changes in weightbearing joints of young animals. The compound should only be used in children when the expected benefits are outweigh the risks.[16][17]

Interactions

  • Fenbufen: co-administration with some quinolones, including enoxacin may increase the risk of seizures. For this reason, concomitant administration of fenbufen and the quinolone should be avoided, as a precaution.[18][19][20][21]
  • Theophylline: in patients treated concurrently with theophylline and enoxacin, concentrations of the methylxanthine in plasma arise due to a reduced metabolic clearance of theophylline.[22][23][24][25]
  • Ranitidine, sucralfate, antacids containing magnesium or aluminum, supplements containing calcium, iron, or zinc: co-administration with these substances can lead to therapeutic failure of the antibiotic due to decreased absorbment by the intestinal tract. For example, magnesium or aluminum antacids turn enoxacin into insoluble salts that are not readily absorbed by the gastroenteric tract.[26][27][28]

Notes

  1. ↑ Enoxacin is sold under the following trade names: Almitil, Bactidan, Bactidron, Comprecin, Enoksetin, Enoxen, Enroxil, Enoxin, Enoxor, Flumark, Penetrex, Gyramid, Vinone.
  2. ↑ Examples of Gram-positive bacteria include: Klebsiella pneumoniae, Staphylococcus aureus, Staphylococcus epidermidis, Clostridium perfringens.
  3. ↑ Gram-negative bacteria include: Acinetobacter, Citrobacter, Campylobacter, Escherichia coli, Haemophilus influenzae, Moraxella catarrhalis, Serratia marcescens, Pseudomonas aeruginosa, Proteus mirabilis, Proteus vulgaris, Salmonella, Shigella flexneri.

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ http://www.pnas.org/content/early/2011/02/24/1014720108
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Flowerdew, A., E. Walker, and S. J. Karran. "Evaluation of biliary pharmacokinetics of oral enoxacin, a new quinolone antibiotic." 14th International Congress of Chemotherapy, Kyoto. 1985.
  11. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  14. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  15. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  16. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  17. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  18. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  19. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  20. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  21. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  22. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  23. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  24. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  25. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  26. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  27. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  28. ↑ Lua error in package.lua at line 80: module 'strict' not found.

Additional reading

  • Lua error in package.lua at line 80: module 'strict' not found..

External links

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