PART A: Medicine Description
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.
PART B: Medicine Functions
Flumequine is a member of the quinolone antibiotics family, which are active against both Gram-positive and Gram-negative bacteria. It functions by inhibiting DNA gyrase, a type II topoisomerase, and topoisomerase IV, enzymes necessary to separate bacterial DNA, thereby inhibiting cell division.
This mechanism can also affect mammalian cell replication. In particular, some congeners of this drug family (for example those that contain the C-8), display high activity not only against bacterial topoisomerases, but also against eukaryotic topoisomerases and are toxic to cultured mammalian cells and
in vivo
tumor models.
Recent studies have demonstrated a correlation between mammalian cell cytotoxicity of the quinolones and the induction of micronuclei.
As such, some fluoroquinolones may cause injury to the chromosome of eukaryotic cells.
There continues to be considerable debate as to whether or not this DNA damage is to be considered one of the mechanisms of action concerning the severe adverse reactions experienced by some patients following fluoroquinolone therapy.
Property Name
|
Property Value
|
Reference
|
Molecular Weight
|
261.25
|
Computed by PubChem 2.1 (PubChem release 2023.05.07)
|
XLogP3-AA
|
2.9
|
Computed by XLogP3 3.0 (PubChem release 2023.05.07)
|
Hydrogen Bond Donor Count
|
1
|
Computed by Cactvs 3.4.8.18 (PubChem release 2023.05.07)
|
Hydrogen Bond Acceptor Count
|
5
|
Computed by Cactvs 3.4.8.18 (PubChem release 2023.05.07)
|
Rotatable Bond Count
|
1
|
Computed by Cactvs 3.4.8.18 (PubChem release 2023.05.07)
|
Exact Mass
|
261.08012141
|
Computed by PubChem 2.1 (PubChem release 2023.05.07)
|
Monoisotopic Mass
|
261.08012141
|
Computed by PubChem 2.1 (PubChem release 2023.05.07)
|
Heavy Atom Count
|
19
|
Computed by PubChem
|
Complexity
|
462
|
Computed by Cactvs 3.4.8.18 (PubChem release 2023.05.07)
|
Isotope Atom Count
|
0
|
Computed by PubChem
|
Defined Atom Stereocenter Count
|
0
|
Computed by PubChem
|
Undefined Atom Stereocenter Count
|
1
|
Computed by PubChem
|
Defined Bond Stereocenter Count
|
0
|
Computed by PubChem
|
Undefined Bond Stereocenter Count
|
0
|
Computed by PubChem
|
Covalently-Bonded Unit Count
|
1
|
Computed by PubChem
|
Compound Is Canonicalized
|
Yes
|
Computed by PubChem (release 2023.05.07)
|
PART
D
:
Contact Information
Website: