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Identification
NameNitroxoline
Accession NumberDB01422
TypeSmall Molecule
GroupsApproved
DescriptionNitroxoline 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 KeyRJIWZDNTCBHXAL-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
IndicationNitroxoline is an antibiotic agent.
Structured Indications Not Available
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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Methionine aminopeptidase 2Proteinyes
inhibitor
HumanP50579 details
Magnesium cationSmall moleculeunknown
chelator
Humannot applicabledetails
Manganese cationSmall moleculeunknown
chelator
Humannot applicabledetails
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
Interactions
Drug Interactions
DrugInteractionDrug group
AmlodipineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Amlodipine.Approved
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Nitroxoline.Approved, Investigational
AmrinoneThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Amrinone.Approved
AzelnidipineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Azelnidipine.Approved
AzimilideThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Azimilide.Investigational
BarnidipineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Barnidipine.Approved
BenidipineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Benidipine.Approved
BepridilThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Bepridil.Approved, Withdrawn
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
CaiThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Cai.Investigational
CilnidipineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Cilnidipine.Approved
CinnarizineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Cinnarizine.Approved
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Nitroxoline.Approved, Investigational, Withdrawn
ClevidipineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Clevidipine.Approved
ConivaptanThe metabolism of Conivaptan can be decreased when combined with Nitroxoline.Approved, Investigational
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Nitroxoline.Approved, Investigational, Vet Approved
DarodipineThe risk or severity of adverse effects can be increased when Nitroxoline is combined 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 risk or severity of adverse effects can be increased when Nitroxoline is combined with Diltiazem.Approved
DocetaxelThe metabolism of Docetaxel can be decreased when combined with Nitroxoline.Approved, Investigational
DofetilideThe metabolism of Dofetilide can be decreased when combined with Nitroxoline.Approved
DotarizineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Dotarizine.Investigational
EfonidipineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Efonidipine.Approved
EperisoneThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Eperisone.Approved, Investigational
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Nitroxoline.Approved
FelodipineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Felodipine.Approved, Investigational
FendilineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Fendiline.Withdrawn
FlunarizineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Flunarizine.Approved
FosphenytoinThe serum concentration of Nitroxoline can be decreased when it is combined with Fosphenytoin.Approved
GabapentinThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Gabapentin.Approved, Investigational
GallopamilThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Gallopamil.Investigational
IsradipineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Isradipine.Approved
LacidipineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Lacidipine.Approved
LamotrigineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Lamotrigine.Approved, Investigational
LercanidipineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Lercanidipine.Approved, Investigational
LosartanThe metabolism of Losartan can be decreased when combined with Nitroxoline.Approved
Magnesium SulfateThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Magnesium Sulfate.Approved, Vet Approved
ManidipineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Manidipine.Approved
MibefradilThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Mibefradil.Withdrawn
NaftopidilThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Naftopidil.Investigational
NicardipineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Nicardipine.Approved
NifedipineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Nifedipine.Approved
NiguldipineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Niguldipine.Experimental
NiludipineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Niludipine.Experimental
NilvadipineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Nilvadipine.Approved
NimesulideThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Nimesulide.Approved, Withdrawn
NimodipineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Nimodipine.Approved
NisoldipineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Nisoldipine.Approved
NitrendipineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Nitrendipine.Approved
PerhexilineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Perhexiline.Approved
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Nitroxoline.Approved, Vet Approved
PimozideNitroxoline may increase the arrhythmogenic activities of Pimozide.Approved
PinaveriumThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Pinaverium.Approved
PregabalinThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Pregabalin.Approved, Illicit, Investigational
PrenylamineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Prenylamine.Withdrawn
ProgesteroneThe therapeutic efficacy of Progesterone can be decreased when used in combination with Nitroxoline.Approved, Vet Approved
QuinidineThe metabolism of Quinidine can be decreased when combined with Nitroxoline.Approved
RanolazineThe metabolism of Ranolazine can be decreased when combined with Nitroxoline.Approved, Investigational
RifabutinThe serum concentration of Rifabutin can be increased when it is combined with Nitroxoline.Approved
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
RisedronateThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Risedronate.Approved, 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
Tolfenamic AcidThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Tolfenamic Acid.Approved
TranilastThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Tranilast.Approved, Investigational
VerapamilThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Verapamil.Approved
VinpocetineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Vinpocetine.Investigational
XylometazolineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Xylometazoline.Approved
ZiconotideThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Ziconotide.Approved
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Nitroxoline.Approved
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesJ01XX07
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot 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
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

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