| Stereochemistry | ACHIRAL |
| Molecular Formula | C9H6N2O3 |
| Molecular Weight | 190.1555 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC=C(C2=CC=CN=C12)[N+]([O-])=O
InChI
InChIKey=RJIWZDNTCBHXAL-UHFFFAOYSA-N
InChI=1S/C9H6N2O3/c12-8-4-3-7(11(13)14)6-2-1-5-10-9(6)8/h1-5,12H
| Molecular Formula | C9H6N2O3 |
| Molecular Weight | 190.1555 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Nitroxoline (8-hydroxy-5-nitroquinoline) has been used since 1962 in the treatment of urinary tract infections especially those due to gram negative bacilli (E. coli). Nitroxoline is active against
most Gram-negative and –positive uropathogenic bacteria, against mycoplasmas (M. hominis, Ureaplasma
urealyticum) and human pathogenic Candida spp. The mode of antibacterial and antifungal action is
based on the ability of nitroxoline to chelate with various
metallic bivalent cations. Nitroxoline is a fluorquinolone that is active against bacterial gyrases. This drug may also have antitumor activity by inhibition of type 2 methionine aminopeptidase (MetAP2) protein which is involved in angiogenesis. Nitroxoline induces apoptosis and inhibits glioma growth in vivo and in vitro. Due to the excellent anticancer activity and its well-known safety profile and pharmacokinetic properties, nitroxoline has been approved to enter into a phase II clinical trial in China for non-muscle invasive bladder cancer treatment
Originator
Approval Year
Doses
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
Drug as victim
Tox targets
PubMed
Sample Use Guides
Nitroxoline was mainly
administered for treatment of uncomplicated and complicated
UTI as well as for prophylaxis of recurrent UTI
with daily dosages mostly between 300 and 900 mg. The
treatment duration varied mainly between 3 and 10 days
depending on the indication.
Route of Administration:
Oral
The rate of susceptibility of E. coli
at a MIC of nitroxoline of ≤8 mg/l is practically
100% and has not changed over the years as shown by
a recent in vitro study with 499 strains from patients
with community acquired UTI showing MIC50- and
MIC90-values of 2 mg/l and 4 mg/l, respectively. For other uropathogens, such as K. pneumonia, P.
mirabilis. P. vulgaris, M. morganii, and S. saprophyticus
the MIC50- and MIC90-values were between 4–8/
4–8 mg/l with highest MIC of 8 mg/l.
|
|
ACTIVE MOIETY |
Proven to be very effective at combating biofilm infections.
|
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