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Merck
CN

140325

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
NACRES:
NA.22
PubChem Substance ID:
24848465
UNSPSC Code:
12352100
EC Number:
223-662-4
MDL number:
MFCD00006791
Assay:
96%
Form:
powder

Key Documents

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InChI key

RJIWZDNTCBHXAL-UHFFFAOYSA-N

InChI

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

SMILES string

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

assay

96%

form

powder

mp

181-183 °C (lit.)

solubility

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

functional group

nitro

Quality Level

100

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

signalword

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

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

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
STBG8313
S42156
S07423
10523KG
10210MR

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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
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
A Sobke et al.
Antimicrobial agents and chemotherapy, 56(11), 6021-6025 (2012-08-29)
Since cations have been reported as essential regulators of biofilm, we investigated the potential of the broad-spectrum antimicrobial and cation-chelator nitroxoline as an antibiofilm agent. Biofilm mass synthesis was reduced by up to 80% at sub-MIC nitroxoline concentrations in Pseudomonas
Novel mechanism of cathepsin B inhibition by antibiotic nitroxoline and related compounds.
Bojana Mirković et al.
ChemMedChem, 6(8), 1351-1356 (2011-05-21)
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