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Details

Stereochemistry ACHIRAL
Molecular Formula C9H6N2O3
Molecular Weight 190.1555
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NITROXOLINE

SMILES

OC1=C2N=CC=CC2=C(C=C1)[N+]([O-])=O

InChI

InChIKey=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

HIDE SMILES / InChI

Molecular Formula C9H6N2O3
Molecular Weight 190.1555
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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). Nitroxoline is active against most Gram-negative and –positive uropathogenic bacteria, against mycoplasmas (M. hominis, Ureaplasma urealyticum) and human pathogenic Candida spp. The mode of antibacterial and antifungal action is based on the ability of nitroxoline to chelate with various metallic bivalent cations. Nitroxoline is a fluorquinolone that is active against bacterial gyrases. This drug may also have antitumor activity by inhibition of type 2 methionine aminopeptidase (MetAP2) protein which is involved in angiogenesis. Nitroxoline induces apoptosis and inhibits glioma growth in vivo and in vitro. Due to the excellent anticancer activity and its well-known safety profile and pharmacokinetic properties, nitroxoline has been approved to enter into a phase II clinical trial in China for non-muscle invasive bladder cancer treatment

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.0 µM [Ki]
271.8 µM [Ki]
55.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Nibiol
Primary
PubMed

PubMed

TitleDatePubMed
In vitro activity of the chelating agents nitroxoline and oxine against Mycobacterium bovis BCG.
2001 Dec
Powder diffraction study of the hydrogen bonds in nitroxoline and its hydrochloride.
2002 Jan
[Is nitroxoline an allergen?].
2002 Mar-Apr
Effect of nitroxoline on angiogenesis and growth of human bladder cancer.
2010 Dec 15
Thermodynamic investigations of nitroxoline sublimation by simultaneous DSC-FTIR method and isothermal TG analysis.
2010 Jan
Evaluation of a Rapid Differentiation Test for Mycobacterium Tuberculosis from other Mycobacteria by Selective Inhibition with p-nitrobenzoic Acid using MGIT 960.
2010 Jul
[Species composition and antibiotic resistance of lactobacillus in infants].
2010 Nov-Dec
Novel mechanism of cathepsin B inhibition by antibiotic nitroxoline and related compounds.
2011 Aug 1
Patents

Sample Use Guides

In Vivo Use Guide
Nitroxoline was mainly administered for treatment of uncomplicated and complicated UTI as well as for prophylaxis of recurrent UTI with daily dosages mostly between 300 and 900 mg. The treatment duration varied mainly between 3 and 10 days depending on the indication.
Route of Administration: Oral
In Vitro Use Guide
The rate of susceptibility of E. coli at a MIC of nitroxoline of ≤8 mg/l is practically 100% and has not changed over the years as shown by a recent in vitro study with 499 strains from patients with community acquired UTI showing MIC50- and MIC90-values of 2 mg/l and 4 mg/l, respectively. For other uropathogens, such as K. pneumonia, P. mirabilis. P. vulgaris, M. morganii, and S. saprophyticus the MIC50- and MIC90-values were between 4–8/ 4–8 mg/l with highest MIC of 8 mg/l.
Substance Class Chemical
Created
by admin
on Tue Mar 06 11:27:41 UTC 2018
Edited
by admin
on Tue Mar 06 11:27:41 UTC 2018
Record UNII
A8M33244M6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NITROXOLINE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
NITROXOLINE [INN]
Common Name English
5-NITRO-8-QUINOLINOL
Systematic Name English
NITROXOLINE [MART.]
Common Name English
NSC-74947
Code English
NITROXOLINE [MI]
Common Name English
A-82
Code English
NITROXOLINE [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QJ01XX07
Created by admin on Tue Mar 06 11:27:41 UTC 2018 , Edited by admin on Tue Mar 06 11:27:41 UTC 2018
WHO-ATC J01XX07
Created by admin on Tue Mar 06 11:27:41 UTC 2018 , Edited by admin on Tue Mar 06 11:27:41 UTC 2018
Code System Code Type Description
DRUG BANK
DB01422
Created by admin on Tue Mar 06 11:27:41 UTC 2018 , Edited by admin on Tue Mar 06 11:27:41 UTC 2018
PRIMARY
EPA CompTox
4008-48-4
Created by admin on Tue Mar 06 11:27:41 UTC 2018 , Edited by admin on Tue Mar 06 11:27:41 UTC 2018
PRIMARY
PUBCHEM
19910
Created by admin on Tue Mar 06 11:27:41 UTC 2018 , Edited by admin on Tue Mar 06 11:27:41 UTC 2018
PRIMARY SWITZERF
WIKIPEDIA
NITROXOLINE
Created by admin on Tue Mar 06 11:27:41 UTC 2018 , Edited by admin on Tue Mar 06 11:27:41 UTC 2018
PRIMARY
MESH
C005308
Created by admin on Tue Mar 06 11:27:41 UTC 2018 , Edited by admin on Tue Mar 06 11:27:41 UTC 2018
PRIMARY
CAS
4008-48-4
Created by admin on Tue Mar 06 11:27:41 UTC 2018 , Edited by admin on Tue Mar 06 11:27:41 UTC 2018
PRIMARY
RXCUI
31901
Created by admin on Tue Mar 06 11:27:41 UTC 2018 , Edited by admin on Tue Mar 06 11:27:41 UTC 2018
PRIMARY RxNorm
MERCK INDEX
M8012
Created by admin on Tue Mar 06 11:27:41 UTC 2018 , Edited by admin on Tue Mar 06 11:27:41 UTC 2018
PRIMARY Merck Index
EVMPD
SUB09331MIG
Created by admin on Tue Mar 06 11:27:41 UTC 2018 , Edited by admin on Tue Mar 06 11:27:41 UTC 2018
PRIMARY
INN
1833
Created by admin on Tue Mar 06 11:27:41 UTC 2018 , Edited by admin on Tue Mar 06 11:27:41 UTC 2018
PRIMARY
ChEMBL
CHEMBL1454910
Created by admin on Tue Mar 06 11:27:41 UTC 2018 , Edited by admin on Tue Mar 06 11:27:41 UTC 2018
PRIMARY
ECHA (EC/EINECS)
223-662-4
Created by admin on Tue Mar 06 11:27:41 UTC 2018 , Edited by admin on Tue Mar 06 11:27:41 UTC 2018
PRIMARY
NCI_THESAURUS
C72634
Created by admin on Tue Mar 06 11:27:41 UTC 2018 , Edited by admin on Tue Mar 06 11:27:41 UTC 2018
PRIMARY
Related Record Type Details
ACTIVE MOIETY