Identification

Name
Nitroxoline
Accession Number
DB01422
Type
Small Molecule
Groups
Approved
Description

Nitroxoline is a urinary antibacterial agent active against susceptible gram-positive and gram-negative organisms commonly found in urinary tract infections. It is a fluorquinolone that is active against bacterial gyrases.

Structure
Thumb
Synonyms
  • 5-Nitro-8-hydroxyquinoline
  • 5-Nitro-8-oxyquinoline
  • 5-Nitro-8-quinolinol
  • 5-Nitrox
  • 5-NOK
  • 5NOK
  • 8-Hydroxy-5-nitroquinoline
  • Nitroxolina
  • Nitroxolinum
External IDs
A-82
International/Other Brands
Nitroxoline
Categories
UNII
A8M33244M6
CAS number
4008-48-4
Weight
Average: 190.1555
Monoisotopic: 190.037842068
Chemical Formula
C9H6N2O3
InChI Key
RJIWZDNTCBHXAL-UHFFFAOYSA-N
InChI
InChI=1S/C9H6N2O3/c12-8-4-3-7(11(13)14)6-2-1-5-10-9(6)8/h1-5,12H
IUPAC Name
5-nitroquinolin-8-ol
SMILES
OC1=C2N=CC=CC2=C(C=C1)[N+]([O-])=O

Pharmacology

Indication

Nitroxoline is an antibiotic agent.

Pharmacodynamics
Not Available
Mechanism of action

This drug may also have antitumor activity by inhibition of type 2 methionine aminopeptidase (MetAP2) protein which is involved in angiogenesis. Its antibacterial activity may stem from the metal ion complexation vital for bacterial growth.

TargetActionsOrganism
AMethionine aminopeptidase 2
inhibitor
Human
UMagnesium cation
chelator
Human
UManganese cation
chelator
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AgmatineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Agmatine.Experimental, Investigational
AmiodaroneThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Amiodarone.Approved, Investigational
AmlodipineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Amlodipine.Approved
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Nitroxoline.Approved, Investigational
AmrinoneThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Amrinone.Approved
AranidipineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Aranidipine.Approved, Investigational
AzelnidipineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Azelnidipine.Approved, Investigational
AzimilideThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Azimilide.Investigational
BarnidipineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Barnidipine.Approved
BencyclaneThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Bencyclane.Experimental
BenidipineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Benidipine.Approved, Investigational
BepridilThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Bepridil.Approved, Withdrawn
BioallethrinThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Bioallethrin.Approved, Experimental
BuspironeThe metabolism of Buspirone can be decreased when combined with Nitroxoline.Approved, Investigational
BusulfanThe serum concentration of Busulfan can be increased when it is combined with Nitroxoline.Approved, Investigational
CarboxyamidotriazoleThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Carboxyamidotriazole.Investigational
CaroverineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Caroverine.Experimental
CilnidipineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Cilnidipine.Approved, Investigational
CinnarizineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Cinnarizine.Approved, Investigational
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Nitroxoline.Approved, Investigational, Withdrawn
ClevidipineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Clevidipine.Approved, Investigational
CyclandelateThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Cyclandelate.Approved
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Nitroxoline.Approved, Investigational, Vet Approved
DarodipineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Darodipine.Experimental
DidanosineDidanosine can cause a decrease in the absorption of Nitroxoline resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
DiltiazemThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Diltiazem.Approved, Investigational
DocetaxelThe metabolism of Docetaxel can be decreased when combined with Nitroxoline.Approved, Investigational
DofetilideThe serum concentration of Dofetilide can be increased when it is combined with Nitroxoline.Approved, Investigational
DotarizineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Dotarizine.Investigational
EfonidipineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Efonidipine.Approved, Investigational
EperisoneThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Eperisone.Approved, Investigational
EthosuximideThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Ethosuximide.Approved
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Nitroxoline.Approved
FelodipineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Felodipine.Approved, Investigational
FendilineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Fendiline.Withdrawn
Fish oilThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Fish oil.Approved, Nutraceutical
FlunarizineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Flunarizine.Approved
FluspirileneThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Fluspirilene.Approved, Investigational
FosphenytoinThe serum concentration of Nitroxoline can be decreased when it is combined with Fosphenytoin.Approved, Investigational
GabapentinThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Gabapentin.Approved, Investigational
GallopamilThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Gallopamil.Investigational
IsradipineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Isradipine.Approved, Investigational
LacidipineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Lacidipine.Approved, Investigational
LamotrigineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Lamotrigine.Approved, Investigational
LercanidipineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Lercanidipine.Approved, Investigational
LevetiracetamThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Levetiracetam.Approved, Investigational
LidoflazineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Lidoflazine.Experimental
LoperamideThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Loperamide.Approved
LosartanThe metabolism of Losartan can be decreased when combined with Nitroxoline.Approved
Magnesium sulfateThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Magnesium sulfate.Approved, Investigational, Vet Approved
ManidipineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Manidipine.Approved, Investigational
MentholThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Menthol.Approved
MethsuximideThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Methsuximide.Approved
MibefradilThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Mibefradil.Investigational, Withdrawn
NaftopidilThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Naftopidil.Investigational
NicardipineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Nicardipine.Approved, Investigational
NifedipineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Nifedipine.Approved
NiguldipineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Niguldipine.Experimental
NiludipineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Niludipine.Experimental
NilvadipineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Nilvadipine.Approved, Investigational
NimesulideThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Nimesulide.Approved, Investigational, Withdrawn
NimodipineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Nimodipine.Approved, Investigational
NisoldipineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Nisoldipine.Approved
NitrendipineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Nitrendipine.Approved, Investigational
NylidrinThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Nylidrin.Approved
OtiloniumThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Otilonium.Experimental, Investigational
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Nitroxoline.Approved, Vet Approved
PinaveriumThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Pinaverium.Approved
PrenylamineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Prenylamine.Withdrawn
ProgesteroneThe absorption of Progesterone can be decreased when combined with Nitroxoline.Approved, Vet Approved
QuinidineThe serum concentration of Quinidine can be increased when it is combined with Nitroxoline.Approved, Investigational
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Nitroxoline.Approved, Investigational
RifabutinThe serum concentration of Rifabutin can be increased when it is combined with Nitroxoline.Approved, Investigational
RifampicinThe serum concentration of Rifampicin can be increased when it is combined with Nitroxoline.Approved
RifapentineThe serum concentration of Rifapentine can be increased when it is combined with Nitroxoline.Approved, Investigational
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Nitroxoline.Approved, Investigational
SeletracetamThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Seletracetam.Investigational
SolifenacinThe metabolism of Solifenacin can be decreased when combined with Nitroxoline.Approved
SucralfateSucralfate can cause a decrease in the absorption of Nitroxoline resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
SunitinibThe metabolism of Sunitinib can be decreased when combined with Nitroxoline.Approved, Investigational
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Nitroxoline.Approved, Investigational
TerodilineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Terodiline.Experimental
TetrahydropalmatineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Tetrahydropalmatine.Investigational
Tolfenamic AcidThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Tolfenamic Acid.Approved, Investigational
TranilastThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Tranilast.Approved, Investigational
TrimebutineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Trimebutine.Approved
TrimethadioneThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Trimethadione.Approved
VerapamilThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Verapamil.Approved
VinpocetineThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Vinpocetine.Investigational
WIN 55212-2The therapeutic efficacy of Nitroxoline can be increased when used in combination with WIN 55212-2.Experimental
ZiconotideThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Ziconotide.Approved
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Nitroxoline.Approved
ZonisamideThe therapeutic efficacy of Nitroxoline can be increased when used in combination with Zonisamide.Approved, Investigational
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0015491
PubChem Compound
19910
PubChem Substance
46505497
ChemSpider
18756
BindingDB
64987
ChEBI
67121
ChEMBL
CHEMBL1454910
PharmGKB
PA164754993
HET
HNQ
Wikipedia
Nitroxoline
ATC Codes
J01XX07 — Nitroxoline
PDB Entries
3ai8 / 5y1y

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)180 °CPhysProp
logP1.99HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility2.73 mg/mLALOGPS
logP1.9ALOGPS
logP1.77ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)6.88ChemAxon
pKa (Strongest Basic)2.08ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area78.94 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.28 m3·mol-1ChemAxon
Polarizability17.16 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9903
Blood Brain Barrier+0.8359
Caco-2 permeable+0.5318
P-glycoprotein substrateNon-substrate0.7501
P-glycoprotein inhibitor INon-inhibitor0.8255
P-glycoprotein inhibitor IINon-inhibitor0.7717
Renal organic cation transporterNon-inhibitor0.8555
CYP450 2C9 substrateNon-substrate0.7446
CYP450 2D6 substrateNon-substrate0.8236
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateInhibitor0.514
CYP450 2C9 inhibitorNon-inhibitor0.5166
CYP450 2D6 inhibitorNon-inhibitor0.7747
CYP450 2C19 inhibitorNon-inhibitor0.519
CYP450 3A4 inhibitorNon-inhibitor0.7765
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5604
Ames testAMES toxic0.9492
CarcinogenicityNon-carcinogens0.7562
BiodegradationNot ready biodegradable0.9907
Rat acute toxicity2.6189 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7788
hERG inhibition (predictor II)Non-inhibitor0.8267
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (8.15 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-002b-3900000000-cf44cf477f74a379b18a

Taxonomy

Description
This compound belongs to the class of organic compounds known as nitroquinolines and derivatives. These are compounds containing a nitro group attached to a quinoline moiety.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Nitroquinolines and derivatives
Direct Parent
Nitroquinolines and derivatives
Alternative Parents
8-hydroxyquinolines / Nitroaromatic compounds / 1-hydroxy-2-unsubstituted benzenoids / Pyridines and derivatives / Heteroaromatic compounds / Propargyl-type 1,3-dipolar organic compounds / Organic oxoazanium compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds
show 4 more
Substituents
Nitroquinoline / 8-hydroxyquinoline / Nitroaromatic compound / 1-hydroxy-2-unsubstituted benzenoid / Pyridine / Benzenoid / Heteroaromatic compound / C-nitro compound / Organic nitro compound / Organic oxoazanium
show 13 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
C-nitro compound, monohydroxyquinoline (CHEBI:67121)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Poly(a) rna binding
Specific Function
Cotranslationally removes the N-terminal methionine from nascent proteins. The N-terminal methionine is often cleaved when the second residue in the primary sequence is small and uncharged (Met-Ala...
Gene Name
METAP2
Uniprot ID
P50579
Uniprot Name
Methionine aminopeptidase 2
Molecular Weight
52891.145 Da
References
  1. Shim JS, Matsui Y, Bhat S, Nacev BA, Xu J, Bhang HE, Dhara S, Han KC, Chong CR, Pomper MG, So A, Liu JO: Effect of nitroxoline on angiogenesis and growth of human bladder cancer. J Natl Cancer Inst. 2010 Dec 15;102(24):1855-73. doi: 10.1093/jnci/djq457. Epub 2010 Nov 18. [PubMed:21088277]
2. Magnesium cation
Kind
Small molecule
Organism
Human
Pharmacological action
Unknown
Actions
Chelator
References
  1. Pelletier C, Prognon P, Latrache H, Villart L, Bourlioux P: [Microbiological consequences of chelation of bivalent metal cations by nitroxoline]. Pathol Biol (Paris). 1994 May;42(5):406-11. [PubMed:7824304]
  2. 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. [PubMed:7793877]
3. Manganese cation
Kind
Small molecule
Organism
Human
Pharmacological action
Unknown
Actions
Chelator
References
  1. Pelletier C, Prognon P, Latrache H, Villart L, Bourlioux P: [Microbiological consequences of chelation of bivalent metal cations by nitroxoline]. Pathol Biol (Paris). 1994 May;42(5):406-11. [PubMed:7824304]
  2. 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. [PubMed:7793877]

Drug created on July 24, 2007 05:15 / Updated on June 02, 2018 06:48