Nitroxolin

Bezeichnung:Nitroxolin

CAS-Nr4008-48-4

Englisch Name:Nitroxoline

CBNumberCB9711910

SummenformelC9H6N2O3

Molgewicht190.16

MOL-Datei4008-48-4.mol

Synonyma

Nitroxolin

Nitroxolin physikalisch-chemischer Eigenschaften

Schmelzpunkt	181-183 °C(lit.)
Siedepunkt	325.64°C (rough estimate)
Dichte	1.3907 (rough estimate)
Brechungsindex	1.5570 (estimate)
storage temp.	Keep in dark place,Inert atmosphere,Room temperature
Löslichkeit	alcohol: very slightly soluble
pka	2.55±0.10(Predicted)
Aggregatzustand	powder to crystal
Farbe	Light yellow to Brown to Dark green
Merck	14,6655
NIST chemische Informationen	8-Hydroxy-5-nitroquinoline(4008-48-4)

Sicherheit

Kennzeichnung gefährlicher	T,Xi,Xn
R-Sätze:	23/24/25-36/37/38-22/24/25-20/21/22
S-Sätze:	26-36-45
RIDADR	UN 2811 6.1/PG 3
WGK Germany	3
RTECS-Nr.	VC8225000
Hazard Note	Toxic/Irritant
HazardClass	6.1
PackingGroup	III
HS Code	29334900
Toxizität	LD50 oral in rat: 510mg/kg

Gefahreninformationscode (GHS)

Nitroxoline Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R23/24/25:Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
Beschreibung
Nitroxoline 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.
Chemische Eigenschaften
ochre-yellow to brownish crystalline powder
Verwenden
8-Hydroxy-5-nitroquinoline was used in the synthesis of novel CO₂-soluble 8-hydroxyquinoline chelating agents.
Verwenden
antibacterial
Verwenden
5-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.
Definition
ChEBI: A monohydroxyquinoline in which the hydroxy group is positioned at C-8 with a nitro group trans to it at C-5.
Trademarks
5-nitrok;Dovenix;Entercol;Enterocol;Isinok;Nicene;Nikinol;Nikopet;Noxine;Trodax;Uro-coli.
Weltgesundheitsorganisation (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 Actions
8-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 vitro
the 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 vivo
previous 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].
Einzelnachweise
[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.

Nitroxoline Upstream-Materialien And Downstream Produkte

Nitroxolin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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