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Flumequine information


Flumequine
Clinical data
Other names9-Fluoro-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]-quinolizine-2-carboxylic acid
AHFS/Drugs.comInternational Drug Names
ATC code
  • J01MB07 (WHO)
Legal status
Legal status
  • removed from clinical use
Pharmacokinetic data
Excretionurine and feces
Identifiers
IUPAC name
  • 7-fluoro-12-methyl-4-oxo-1-azatricyclo[7.3.1.05,13]trideca-2,5,7,9(13)-tetraene-3-carboxylic acid
CAS Number
  • 42835-25-6 checkY
PubChem CID
  • 3374
DrugBank
  • DB08972 ☒N
ChemSpider
  • 3257 ☒N
UNII
  • UVG8VSP2SJ
KEGG
  • D02302 checkY
ChEBI
  • CHEBI:85267 ☒N
CompTox Dashboard (EPA)
  • DTXSID5045623 Edit this at Wikidata
ECHA InfoCard100.050.857 Edit this at Wikidata
Chemical and physical data
FormulaC14H12FNO3
Molar mass261.252 g·mol−1
3D model (JSmol)
  • Interactive image
Melting point253 to 255 °C (487 to 491 °F)
SMILES
  • Fc2cc1C(=O)/C(C(=O)O)=C\N3c1c(c2)CCC3C
InChI
  • InChI=1S/C14H12FNO3/c1-7-2-3-8-4-9(15)5-10-12(8)16(7)6-11(13(10)17)14(18)19/h4-7H,2-3H2,1H3,(H,18,19) ☒N
  • Key:DPSPPJIUMHPXMA-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Flumequine[1] is a synthetic fluoroquinolone antibiotic[2][3] used to treat bacterial infections. It is a first-generation fluoroquinolone antibacterial that has been removed from clinical use and is no longer being marketed.[4] The marketing authorization of flumequine has been suspended throughout the EU.[5] It kills bacteria by interfering with the enzymes that cause DNA to unwind and duplicate. Flumequine was used in veterinarian medicine for the treatment of enteric infections (all infections of the intestinal tract),[6] as well as to treat cattle, swine, chickens, and fish, but only in a limited number of countries.[4][7][8] It was occasionally used in France (and a few other European Countries) to treat urinary tract infections under the trade name Apurone.[4][9] However this was a limited indication[10] because only minimal serum levels were achieved.[11]

  1. ^ INN: Lomefloxacin Hydrochloride
  2. ^ Nelson JM, Chiller TM, Powers JH, Angulo FJ (April 2007). "Fluoroquinolone-resistant Campylobacter species and the withdrawal of fluoroquinolones from use in poultry: a public health success story". Clinical Infectious Diseases. 44 (7): 977–980. doi:10.1086/512369. PMID 17342653.
  3. ^ Kawahara S (December 1998). "[Chemotherapeutic agents under study]". Nihon Rinsho. Japanese Journal of Clinical Medicine (in Japanese). 56 (12): 3096–3099. PMID 9883617.
  4. ^ a b c "Quinolones and fluoroquinolones". Pharmacorama. Archived from the original on 2019-05-12. Retrieved 2010-04-04.
  5. ^ "Disabling and potentially permanent side effects lead to suspension or restrictions of quinolone and fluoroquinolone antibiotics". European Medicines Agency. 11 March 2019.
  6. ^ Francis PG, Wells RJ (1998). "Flumequine". Joint FAO/WHO Expert Committee on Food Additives. Residues of some veterinary drugs in animals and foods. Rome: Food and Agriculture Organization. ISBN 92-5-104128-8. OCLC 39798999.
  7. ^ Use of quinolones in food animals and potential impact on human health (PDF). WHO meeting. Geneva, Switzerland: World Health Organization. June 1998. Archived from the original (PDF) on 14 January 2010. Cattle only in Europe and Latin America. (Limited use in Latin America), Poultry only in Europe, Asia and Latin America, Fish only in Asia
  8. ^ Lavenberg DL. "IX4Q 4586, Brrytrit 3.23% Concentrate Solution for Use in Chicken Drinking Water, Genera. Correspondence, Published Literure" (PDF). Bayer. Archived from the original (PDF) on 5 October 2012 – via U.S. Food and Drug Administration. Quinalones are often used to treat severe cases of human infection with Campylobacter spp., and they are also used in veterinary medicine, especially for treating poultry.
  9. ^ Schena FP, Gesualdo L, Caracciolo G (January 1988). "A multicentre study of flumequine in the treatment of urinary tract infections". The Journal of Antimicrobial Chemotherapy. 21 (1): 101–106. doi:10.1093/jac/21.1.101. PMID 3356617.
  10. ^ The quinolones (Third Edition 2000) By Vincent T. Andriole Chapter I History and overview By Dr. Peter Ball (page 5)
  11. ^ King DE, Malone R, Lilley SH (May 2000). "New classification and update on the quinolone antibiotics". American Family Physician. 61 (9): 2741–2748. PMID 10821154.

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