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Identification
NameNitroxoline
Accession NumberDB01422
TypeSmall Molecule
GroupsApproved
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 Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
NitroxolineNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIA8M33244M6
CAS number4008-48-4
WeightAverage: 190.1555
Monoisotopic: 190.037842068
Chemical FormulaC9H6N2O3
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassNitroquinolines and derivatives
Direct ParentNitroquinolines and derivatives
Alternative Parents
Substituents
  • Nitroquinoline
  • 8-hydroxyquinoline
  • Hydroxyquinoline
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Organic nitro compound
  • Organic nitrite
  • C-nitro compound
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Organic zwitterion
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationNitroxoline is an antibiotic agent.
PharmacodynamicsNot Available
Mechanism of actionThis 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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point180 °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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.15 KB)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesJ01XX07
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

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-, Cys, Gly, Pro, Ser, Thr, or Val). The catalytic activity of human METAP2 toward Met-Val peptides is consistently two orders of magnitude higher than that of METAP1, suggesting that it is responsibl...
Gene Name:
METAP2
Uniprot ID:
P50579
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 ]
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Drug created on July 24, 2007 05:15 / Updated on August 17, 2016 12:23