Nitroxoline

Nitroxoline Basic information
Product Name:Nitroxoline
Synonyms:5-NITRO-8-HYDROXYQUINOLINE;5-NITRO-8-QUINOLINE;5-NITRO-8-QUINOLINOL;8-HYDROXY-5-NITROQUINOLINE;NOTROXOLINE;NITROXOLINE;5-Nitro-8-oxychinoline;5-Nitro-8-oxyquinoline
CAS:4008-48-4
MF:C9H6N2O3
MW:190.16
EINECS:223-662-4
Product Categories:ENTEROCOL;pesticide intermediates;Quinoline&Isoquinoline;Quinolines;Hydroxyquinolines;Nitroquinolines
Mol File:4008-48-4.mol
Nitroxoline Structure
Nitroxoline Chemical Properties
Melting point 181-183 °C(lit.)
Boiling point 325.64°C (rough estimate)
density 1.3907 (rough estimate)
refractive index 1.5570 (estimate)
storage temp. Keep in dark place,Inert atmosphere,Room temperature
solubility alcohol: very slightly soluble
pka2.55±0.10(Predicted)
form powder to crystal
color Light yellow to Brown to Dark green
Merck 14,6655
NIST Chemistry Reference8-Hydroxy-5-nitroquinoline(4008-48-4)
Safety Information
Hazard Codes T,Xi,Xn
Risk Statements 23/24/25-36/37/38-22/24/25-20/21/22
Safety Statements 26-36-45
RIDADR UN 2811 6.1/PG 3
WGK Germany 3
RTECS VC8225000
Hazard Note Toxic/Irritant
HazardClass 6.1
PackingGroup III
HS Code 29334900
ToxicityLD50 oral in rat: 510mg/kg
MSDS Information
ProviderLanguage
8-Hydroxy-5-nitroquinoline English
ACROS English
SigmaAldrich English
ALFA English
Nitroxoline Usage And Synthesis
DescriptionNitroxoline is an 8-hydroxyquinoline that has diverse biological activities, including antibacterial, antiproliferative, and bromodomain interaction-inhibiting properties. Nitroxoline is active against the bacteria E. coli, S. aureus, E. faecalis, K. pneumoniae, and P. mirabilis in vitro (MIC90s = 4, 4, 8, 8, and 8 mg/L, respectively). It also inhibits biofilm formation of certain strains of multidrug-resistant (MDR) A. baumannii and P. aeruginosa, as well as methicillin-resistant S. aureus (MRSA) and S. epidermidis (MRSE) with minimum biofilm eradication concentration (MBEC) values of 46.9, 1,500, 188, and 125 μM, respectively. Nitroxoline inhibits the growth of human U87 and U251 glioma, A549 lung, and PC3 prostate cancer cells (IC50s = 50, 6, 38, and 23 μg/ml, respectively). In vivo, it reduces tumor growth in a PTEN- and KRAS-driven glioma mouse model when administered at a dose of 80 mg/kg per day. Nitroxoline also inhibits the interaction between the first bromodomain of bromodomain-containing protein 4 (BRD4) with acetylated histone H4 with an IC50 value of 0.98 μM.
Chemical Propertiesochre-yellow to brownish crystalline powder
Usesantibacterial
Uses5-Nitro-8-hydroxyquinoline is an antimicrobial agent used for the treatment of urinary tract infection. 5-Nitro-8-hydroxyquinoline is also a potent and reversible inhibitor of cathepsin B. 5-Nitro-8-h ydroxyquinoline has been shown to have anti-cancer activity.
Uses8-Hydroxy-5-nitroquinoline was used in the synthesis of novel CO2-soluble 8-hydroxyquinoline chelating agents.
DefinitionChEBI: A monohydroxyquinoline in which the hydroxy group is positioned at C-8 with a nitro group trans to it at C-5.
Brand name5-nitrok;Dovenix;Entercol;Enterocol;Isinok;Nicene;Nikinol;Nikopet;Noxine;Trodax;Uro-coli.
World Health Organization (WHO)Nitroxoline, a urinary antiseptic, was introduced in the mid-1960s. By the early 1970s long-term animal studies revealed the development of cataracts in rats and, although no serious adverse effects had been reported in man, the drug was withdrawn in at least two countries. Preparations containing nitroxoline remain widely available.
Biochem/physiol Actions8-Hydroxy-5-nitroquinoline is an effective anti-microbial and anti-cancer agent. It is an effective drug for the treatment of urinary tract infections due to gram negative bacilli.
in vitrothe machnistic study showed that nitroxoline, in the treatment of acute or recurrent urinary tract infections caused by escherichia coli, could be decreased in the presence of mg2+ and mn2+ but not ca2+. moreover, with the divalent metal ions, a shift in the nitroxoline a448 indicated the formation of drug-ion complexes and a clear correlation was observed between the chelating property and antibacterial activity of nitroxolinet. in addition, it was found that the uptake was energy-independent and with biphasic kinetics: a rapid cell association phase and then a slower increase of cell- nitroxoline association [1].
in vivoprevious animal study showed that nitroxoline suspension with tween-80 in a could decrease the tone of the rat and guinea-pig ileum and diminish their peristalsis. moreover, when administered orally in a dose 50 mg/kg to rats, nitroxoline was able to inhibit the agar-, serotonin-, as well as carrageenin-induced edemas of the rat paws without affecting the response to subplantar histamine injection [2].
references[1] pelletier c,prognon p,bourlioux p. roles of divalent cations and ph in mechanism of action of nitroxoline against escherichia coli strains. antimicrob agents chemother.1995 mar;39(3):707-13.
[2] zaks as,zil'ber al,kapitonenko ta. spasmolytic and anti-inflammatory activity of 8-hydroxyquinolines. farmakol toksikol.1984 sep-oct;47(5):44-7.
[3] lambert-zechovsky n,lévêque b,bingen e,pillion g,chapelle j,mathieu h. clinical study and effect of nitroxoline on fecal flora in childrenpathol biol (paris).1987 may;35(5):669-72.
Isoquinoline NITROGEN DIOXIDE Nitromethane Quinclorac p-Nitrobenzoic acid 3-Nitroacetophenone 5-Nitroquinoline Ethoxyquin 5-([(5-NITRO-8-QUINOLINYL)OXY]METHYL)-2-FUROIC ACID Quinoline Yellow TRITON 8-Hydroxyquinaldine Chrysin Nitrobenzene 8-Hydroxyquinoline CHLOROPHOSPHONAZO III Quinhydrone Nitroxoline

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