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140325

Sigma-Aldrich

8-Hydroxy-5-nitroquinoline

96%

Synonym(s):

5-Nitro-8-quinolinol

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About This Item

Empirical Formula (Hill Notation):
C9H6N2O3
CAS Number:
4008-48-4
Molecular Weight:
190.16
EC Number:
223-662-4
MDL number:
MFCD00006791
UNSPSC Code:
12352100
PubChem Substance ID:
24848465
NACRES:
NA.22

Assay

96%

form

powder

mp

181-183 °C (lit.)

solubility

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

SMILES string

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

InChI key

RJIWZDNTCBHXAL-UHFFFAOYSA-N

Related Categories

Application

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

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.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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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