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EntityQ304570· pop 12· linked from 54 articles

nitroxoline

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Also known as A-82, 8-Hydroxy-5-nitroquinoline, 5-Nitro-8-quinolinol, 5-Nitro-8-oxyquinoline, 5-Nitrox, 5-NOK, 5NOK, 5-Nitro-8-hydroxyquinoline

Nitroxoline is an antibiotic that has been in use in Europe for about fifty years, and has proven to be very effective at combating biofilm infections. Nitroxoline was shown to cause a decrease in the biofilm density of P. aeruginosa infections, which would allow access to the infection by the immune system in vivo. It was shown that nitroxoline functions by chelating Fe2+ and Zn2+ ions from the biofilm matrix; when Fe2+ and Zn2+ were reintroduced into the system, biofilm formation activity was restored. The biofilm degradation ability is comparable to EDTA derivatives, but this drug has a his

Key facts

Drug.Verifiedfields
changed
Drug.verifiedrevid
462262233
Drug.IUPAC_name
5-nitro-quinolin-8-ol
Drug.image
Nitroxolin.svg
Drug.image_class
skin-invert-image
Drug.width
120px
Drug.legal_US
IND
Drug.CAS_number
4008-48-4
Drug.ATC_prefix
J01
Drug.ATC_suffix
XX07
Drug.PubChem
19910
Drug.DrugBank
DB01422
Drug.ChemSpiderID
18756
Drug.UNII
A8M33244M6
Drug.KEGG
D07245
Drug.ChEMBL
1454910
Drug.C
9
Drug.H
6

via Wikipedia infobox

Wikidata facts

Mass
190.038
Show 5 more facts
chemical formula
C₉H₆N₂O₃
canonical SMILES
C1=CC2=C(C=CC(=C2N=C1)O)[N+](=O)[O-]
World Health Organisation international non-proprietary name
nitroxolinum
defined daily dose
1
melting point
180
Sources (6)

via Wikidata · CC0

~4 min read

Article

3 sections
Contents
  • Anticancer activity
  • ''Balamuthia'' infection
  • References

Nitroxoline is an antibiotic that has been in use in Europe for about fifty years, and has proven to be very effective at combating biofilm infections. Nitroxoline was shown to cause a decrease in the biofilm density of P. aeruginosa infections, which would allow access to the infection by the immune system in vivo. It was shown that nitroxoline functions by chelating Fe2+ and Zn2+ ions from the biofilm matrix; when Fe2+ and Zn2+ were reintroduced into the system, biofilm formation activity was restored. The biofilm degradation ability is comparable to EDTA derivatives, but this drug has a history of human use in clinical settings and therefore has a precedent with which to allow its use against “slimy” biofilm infections.

==Anticancer activity== The chelating activities of nitroxoline have also been used in an anticancer setting. Nitroxoline has been shown to be more cytotoxic to HL60, DHL-4, PANC-1, and cells lines than clioquinol and other 8-hydroxyquinoline derivatives. It also demonstrated an increase in reactive oxygen species (ROS) production over controls, especially when Cu2+ was added. The ROS levels reached over 350% of the controls with addition of CuCl2. The cytotoxicity production was markedly decreased with addition of ZnCl2, indicating, based on this model, that nitroxoline is not a zinc chelator. Because the zinc chelating action of clioquinol has been associated with subacute myelo-optic neuropathy, the use of nitroxoline as a cytotoxic drug in the treatment of cancers should not exhibit neurotoxic effects in humans, and in vivo trials on tumour xenografts in mice have not yielded any negative neurodegenerative effects.

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