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flumequine

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Flumequine is a synthetic fluoroquinolone antibiotic 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. The marketing authorization of flumequine has been suspended throughout the EU. 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), as well as to treat cattle, swine, chickens, and fish, but only in a limited number of

Key facts

Drug.Verifiedfields
changed
Drug.Watchedfields
changed
Drug.verifiedrevid
449624549
Drug.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
Drug.image
Flumequine.svg
Drug.image_class
skin-invert-image
Drug.legal_status
withdrawn
Drug.excretion
urine and feces
Drug.CAS_number
42835-25-6
Drug.ATC_prefix
J01
Drug.ATC_suffix
MB07
Drug.PubChem
3374
Drug.DrugBank
DB08972
Drug.ChEBI
85267
Drug.UNII
UVG8VSP2SJ
Drug.KEGG
D02302
Drug.ChemSpiderID
3257
Drug.smiles
Fc2cc1C(=O)/C(C(=O)O)=C\N3c1c(c2)CCC3C

via Wikipedia infobox

~7 min read

Encyclopedic overview

11 sections
Contents
  • History
  • Drug residue
  • Licensed uses
  • Availability
  • Mode of action
  • Adverse reactions
  • Drug interactions
  • Chemistry
  • Pharmacokinetics
  • See also
  • References

Flumequine is a synthetic fluoroquinolone antibiotic 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. The marketing authorization of flumequine has been suspended throughout the EU. 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), as well as to treat cattle, swine, chickens, and fish, but only in a limited number of countries. It was occasionally used in France (and a few other European Countries) to treat urinary tract infections under the trade name Apurone. However this was a limited indication because only minimal serum levels were achieved.

==History== The first quinolone used was nalidixic acid (was marketed in many countries as Negram) followed by the fluoroquinolone flumequine. The first-generation fluoroquinolone agents, such as flumequine, had poor distribution into the body tissues and limited activity. As such they were used mainly for treatment of urinary tract infections. Flumequine (benzo quinolizine) was first patented in 1973, (German Patent) by Rikker Labs. Flumequine is a known antimicrobial compound described and claimed in U.S. Pat. No. 3,896,131 (Example 3), July 22, 1975. Flumequine is the first quinolone compound with a fluorine atom at the C6-position of the related quinolone basic molecular structure. Even though this was the first fluoroquinolone, it is often overlooked when classifying the drugs within this class by generations and excluded from such a list.

Excerpted from Wikipedia’s “flumequine” article, available under the CC BY-SA 4.0 licence.