ChemicalBook CAS DataBase List 4008-48-4

4008-48-4

Name	Nitroxoline
CAS	4008-48-4
EINECS(EC#)	223-662-4
Molecular Formula	C9H6N2O3
MDL Number	MFCD00006791
Molecular Weight	190.16
MOL File	4008-48-4.mol

Chemical Properties

Appearance	ochre-yellow to brownish crystalline powder
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
form	powder to crystal
pka	2.55±0.10(Predicted)
color	Light yellow to Brown to Dark green
Merck	14,6655
InChI	InChI=1S/C9H6N2O3/c12-8-4-3-7(11(13)14)6-2-1-5-10-9(6)8/h1-5,12H
InChIKey	RJIWZDNTCBHXAL-UHFFFAOYSA-N
SMILES	N1C2C(=C([N+]([O-])=O)C=CC=2O)C=CC=1
NIST Chemistry Reference	8-Hydroxy-5-nitroquinoline(4008-48-4)

Safety Data

Symbol(GHS)	GHS06
Signal word	Danger
Hazard statements	H301+H311+H331-H315-H319-H335
Precautionary statements	P280-P301+P310+P330-P302+P352+P312-P304+P340+P311-P305+P351+P338
Hazard Codes	T,Xi,Xn
Risk Statements	23/24/25-36/37/38-22/24/25-20/21/22 less more
Safety Statements	26-36-45 less more
RIDADR	UN 2811 6.1/PG 3
WGK Germany	3
RTECS	VC8225000
Hazard Note	Toxic/Irritant
HazardClass	6.1
PackingGroup	III
HS Code	29334900
Storage Class	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Acute Tox. 3 Dermal Acute Tox. 3 Inhalation Acute Tox. 3 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3
Toxicity	LD50 oral in rat: 510mg/kg less more

Hazard Information

Chemical Properties

ochre-yellow to brownish crystalline powder

Uses

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.

Uses

antibacterial

Definition

ChEBI: A monohydroxyquinoline in which the hydroxy group is positioned at C-8 with a nitro group trans to it at C-5.

Description

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.

Brand name

5-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 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.

Synthesis

5-nitroso-8-hydroxyquinoline hydrochloride

63450-86-2

4008-48-4

8-Hydroxy-5-nitrosoquinoline (10) was oxidized to 8-hydroxy-5-nitroquinoline (11) according to the method of Petrow and Sturgeon. The procedure was as follows: finely ground 8-hydroxy-5-nitrosoquinoline hydrochloride (10) (15.0 g, 0.7 mmol) was slowly added to a 500 mL beaker containing concentrated nitric acid (45 mL) and water (30 mL) under ice bath conditions. The reaction mixture was kept continuously stirred at 17 °C for 85 min. Upon completion of the reaction, an equal volume of cold water was added and the mixture was cooled to 0°C. Subsequently, the pH was adjusted to 13.0 with cold concentrated potassium hydroxide solution to prepare the basic. The red potassium salt formed decomposed after neutralization with acetic acid and the precipitate was collected by diafiltration and washed with cold water. Finally, the residue was recrystallized from ethanol to give yellow crystals of 8-hydroxy-5-nitroquinoline. The yield was 14.10 g (90.1% yield) and the melting point was 179 °C (literature value: 179.5-181.5 °C).

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].

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.

Material Safety Data Sheet(MSDS)

Spectrum Detail

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