Nitroxoline

Nitroxoline
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	J01XX07 (WHO) ;
Legal status
Legal status	US: IND;
Identifiers
	IUPAC name 5-nitro-quinolin-8-ol;
CAS Number	4008-48-4 ;
PubChem CID	19910;
DrugBank	DB01422 ;
ChemSpider	18756 ;
UNII	A8M33244M6;
KEGG	D07245 ;
ChEMBL	ChEMBL1454910 ;
CompTox Dashboard (EPA)	DTXSID4046284 ;
ECHA InfoCard	100.021.513
Chemical and physical data
Formula	C9H6N2O3
Molar mass	190.158 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES [O-][N+](=O)c1ccc(O)c2ncccc12;
	InChI InChI=1S/C9H6N2O3/c12-8-4-3-7(11(13)14)6-2-1-5-10-9(6)8/h1-5,12H ; Key:RJIWZDNTCBHXAL-UHFFFAOYSA-N ;
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Nitroxoline is an antibiotic^[1] 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.^[2] 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.

^ Pelletier C, Prognon P, Bourlioux P (March 1995). "Roles of divalent cations and pH in mechanism of action of nitroxoline against Escherichia coli strains". Antimicrobial Agents and Chemotherapy. 39 (3): 707–713. doi:10.1128/aac.39.3.707. PMC 162609. PMID 7793877.
^ Sobke A, Klinger M, Hermann B, Sachse S, Nietzsche S, Makarewicz O, et al. (November 2012). "The urinary antibiotic 5-nitro-8-hydroxyquinoline (Nitroxoline) reduces the formation and induces the dispersal of Pseudomonas aeruginosa biofilms by chelation of iron and zinc". Antimicrobial Agents and Chemotherapy. 56 (11): 6021–6025. doi:10.1128/aac.01484-12. PMC 3486607. PMID 22926564.

[pmid7793877-1] Pelletier C, Prognon P, Bourlioux P (March 1995). "Roles of divalent cations and pH in mechanism of action of nitroxoline against Escherichia coli strains". Antimicrobial Agents and Chemotherapy. 39 (3): 707–713. doi:10.1128/aac.39.3.707. PMC 162609. PMID 7793877.

[2] Sobke A, Klinger M, Hermann B, Sachse S, Nietzsche S, Makarewicz O, et al. (November 2012). "The urinary antibiotic 5-nitro-8-hydroxyquinoline (Nitroxoline) reduces the formation and induces the dispersal of Pseudomonas aeruginosa biofilms by chelation of iron and zinc". Antimicrobial Agents and Chemotherapy. 56 (11): 6021–6025. doi:10.1128/aac.01484-12. PMC 3486607. PMID 22926564.

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