NAV

Nitroxoline

Identification

Generic Name
Nitroxoline
DrugBank Accession Number
DB01422
Background

Nitroxoline is a urinary antibacterial agent active against susceptible gram-positive and gram-negative organisms commonly found in urinary tract infections. It is a hydroxyquinoline derivative unrelated to other classes of drugs.1 Nitroxoline is active against bacterial gyrases.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 190.1555
Monoisotopic: 190.037842068
Chemical Formula
C9H6N2O3
Synonyms
  • 5-Nitro-8-hydroxyquinoline
  • 5-Nitro-8-oxyquinoline
  • 5-Nitro-8-quinolinol
  • 5-Nitrox
  • 5-NOK
  • 5NOK
  • 8-Hydroxy-5-nitroquinoline
  • Nitroxolina
  • Nitroxoline
  • Nitroxolinum
External IDs
  • A-82

Pharmacology

Indication

Nitroxoline is an antibiotic agent.

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Contraindications & Blackbox Warnings
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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
Humans
UMagnesium cation
chelator
Humans
UManganese cation
chelator
Humans
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be increased when used in combination with Nitroxoline.
DicoumarolThe therapeutic efficacy of Dicoumarol can be increased when used in combination with Nitroxoline.
FluindioneThe therapeutic efficacy of Fluindione can be increased when used in combination with Nitroxoline.
PhenindioneThe therapeutic efficacy of Phenindione can be increased when used in combination with Nitroxoline.
PhenprocoumonThe therapeutic efficacy of Phenprocoumon can be increased when used in combination with Nitroxoline.
WarfarinThe therapeutic efficacy of Warfarin can be increased when used in combination with Nitroxoline.
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Food Interactions
Not Available

Products

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International/Other Brands
Nitroxoline

Categories

ATC Codes
J01XX07 — Nitroxoline
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1-hydroxy-2-unsubstituted benzenoid / 8-hydroxyquinoline / Allyl-type 1,3-dipolar organic compound / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / C-nitro compound / Heteroaromatic compound / Hydrocarbon derivative / Nitroaromatic compound
show 13 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
C-nitro compound, monohydroxyquinoline (CHEBI:67121)
Affected organisms
Not Available

Chemical Identifiers

UNII
A8M33244M6
CAS number
4008-48-4
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

References

General References
  1. Wijma RA, Huttner A, Koch BCP, Mouton JW, Muller AE: Review of the pharmacokinetic properties of nitrofurantoin and nitroxoline. J Antimicrob Chemother. 2018 Nov 1;73(11):2916-2926. doi: 10.1093/jac/dky255. [Article]
Human Metabolome Database
HMDB0015491
PubChem Compound
19910
PubChem Substance
46505497
ChemSpider
18756
BindingDB
64987
RxNav
31901
ChEBI
67121
ChEMBL
CHEMBL1454910
ZINC
ZINC000015831592
PharmGKB
PA164754993
PDBe Ligand
HNQ
Wikipedia
Nitroxoline
PDB Entries
3ai8 / 5y1y

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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)6.89Chemaxon
pKa (Strongest Basic)1.92Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area76.26 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity48.28 m3·mol-1Chemaxon
Polarizability17.25 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

Targets

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Details1. Methionine aminopeptidase 2
Kind
Protein
Organism
Humans
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. [Article]
Details2. Magnesium cation
Kind
Small molecule
Organism
Humans
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. [Article]
  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. [Article]
Details3. Manganese cation
Kind
Small molecule
Organism
Humans
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. [Article]
  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. [Article]

Drug created at July 24, 2007 11:15 / Updated at February 21, 2021 18:51