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140325

Sigma-Aldrich

8-Hydroxy-5-nitroquinoline

96%

Sinonimo/i:

5-Nitro-8-quinolinol

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About This Item

Formula empirica (notazione di Hill):
C9H6N2O3
Numero CAS:
4008-48-4
Peso molecolare:
190.16
Numero CE:
223-662-4
Numero MDL:
MFCD00006791
Codice UNSPSC:
12352100
ID PubChem:
24848465
NACRES:
NA.22

Livello qualitativo

100

Saggio

96%

Forma fisica

powder

Punto di fusione

181-183 °C (lit.)

Solubilità

alcohol: very slightly soluble
diethyl ether: very slightly soluble
hydrochloric acid: freely soluble (hot)

Gruppo funzionale

nitro

Stringa SMILE

Oc1ccc([N+]([O-])=O)c2cccnc12

InChI

1S/C9H6N2O3/c12-8-4-3-7(11(13)14)6-2-1-5-10-9(6)8/h1-5,12H
RJIWZDNTCBHXAL-UHFFFAOYSA-N

Categorie correlate

Applicazioni

8-Hydroxy-5-nitroquinoline was used in the synthesis of novel CO2-soluble 8-hydroxyquinoline chelating agents.

Azioni biochim/fisiol

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.

Pittogrammi

Skull and crossbones
GHS06

Avvertenze

Danger

Indicazioni di pericolo

H301 + H311 + H331,H315,H319,H335

Classi di pericolo

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificati d'analisi (COA)

Lot/Batch Number
STBG8313
S42156
S07423
10523KG
08418BG

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E Bergogne-Berezin et al.
Pathologie-biologie, 35(5 Pt 2), 873-878 (1987-06-01)
Nitroxoline (8-hydroxy-5-nitroquinoline) has been used since 1962 in the treatment of urinary tract infections especially those due to gram negative bacilli (E. coli). The current renewal of the drug is in relation to the recently shown activity of nitroxoline against
H Latrache et al.
Folia microbiologica, 45(6), 485-490 (2001-08-15)
Nitroxoline (5-nitro-8-quinolinol; NIQ) at subinhibitory concentrations (sub-MIC) decreased the adherence of uropathogenic Escherichia coli to catheter surface and significantly enhanced cell surface hydrophobicity. The surface hydrophobicity increased in the presence of sub-MIC of NIQ and also in an excess of
Shridhar Bhat et al.
Organic & biomolecular chemistry, 10(15), 2979-2992 (2012-03-07)
Two substituted oxines, nitroxoline (5) and 5-chloroquinolin-8-yl phenylcarbamate (22), were identified as hits in a high-throughput screen aimed at finding new anti-angiogenic agents. In a previous study, we have elucidated the molecular mechanism of antiproliferative activity of nitroxoline in endothelial
Novel mechanism of cathepsin B inhibition by antibiotic nitroxoline and related compounds.
Bojana Mirković et al.
ChemMedChem, 6(8), 1351-1356 (2011-05-21)
Joong Sup Shim et al.
Journal of the National Cancer Institute, 102(24), 1855-1873 (2010-11-20)
Angiogenesis plays an important role in tumor growth and metastasis; therefore, inhibition of angiogenesis is a promising strategy for developing new anticancer drugs. Type 2 methionine aminopeptidase (MetAP2) protein is likely a molecular target of angiogenesis inhibitors. Nitroxoline, an antibiotic
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