| Common Name |
Nitroxoline
| Description |
Nitroxoline is only found in individuals that have used or taken this drug. It 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.This drug may also have antitumor activity by inhibition of ype 2 methionine aminopeptidase (MetAP2) protein which is involved in angiogenesis. Its antibacterial activity may stem from the metal ion complexation vital for bacterial growth.
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
5-nitro-8-HydroxyquinolineChEBI
5-nitro-8-OxyquinolineChEBI
5-nitro-8-QuinolinolChEBI
5-NitroxChEBI
5-NOKChEBI
5NOKChEBI
8-Hydroxy-5-nitroquinolineChEBI
NitroxolinaChEBI
NitroxolinumChEBI
5-NitroksHMDB
5-NitroxineHMDB
cysto-Saar plusMeSH
Nitroxoline monofluorideMeSH
Nitroxoline, potassium saltMeSH
5-Nitroquinolin-8-olMeSH
NibiolMeSH
| Chemical Formlia |
C9H6N2O3
| Average Molecliar Weight |
190.1555
| Monoisotopic Molecliar Weight |
190.037842068
| IUPAC Name |
5-nitroquinolin-8-ol
| Traditional Name |
nitroxoline
| CAS Registry Number |
4008-48-4
| SMILES |
OC1=C2N=CC=CC2=C(C=C1)[N+]([O-])=O
| InChI Identifier |
InChI=1S/C9H6N2O3/c12-8-4-3-7(11(13)14)6-2-1-5-10-9(6)8/h1-5,12H
| InChI Key |
RJIWZDNTCBHXAL-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as nitroquinolines and derivatives. These are compounds containing a nitro group attached to a quinoline moiety.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organoheterocyclic compounds
| Sub Class |
Quinolines 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
Organonitrogen compounds
Organic zwitterions
Organic oxides
Hydrocarbon derivatives
| Substituents |
Nitroquinoline
8-hydroxyquinoline
Nitroaromatic compound
1-hydroxy-2-unsubstituted benzenoid
Pyridine
Benzenoid
Heteroaromatic compound
C-nitro compound
Organic nitro compound
Organic oxoazanium
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Hydrocarbon derivative
Organic zwitterion
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound
| Molecliar Framework |
Aromatic heteropolycyclic compounds
| External Descriptors |
C-nitro compound (CHEBI:67121 )
monohydroxyquinoline (CHEBI:67121 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Drug
| Biofunction |
Anti-Infective Agents, Urinary
Antifungal Agents
| Application |
Pharmaceutical
| Cellliar locations |
Cytoplasm
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point180 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.73e+00 g/LNot Available
LogP1.99HANSCH,C ET AL. (1995)
| Predicted Properties |
| Property |
Value |
Source |
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
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| LC-MS/MS |
LC-MS/MS Spectrum – , positivesplash10-002b-3900000000-cf44cf477f74a379b18aView in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01422
21059682
details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01422
21059682
details
|
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
DB01422
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
Not Available
| KNApSAcK ID |
Not Available
| Chemspider ID |
18756
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Nitroxoline
| NuGOwiki Link |
HMDB15491
| Metagene Link |
HMDB15491
| METLIN ID |
Not Available
| PubChem Compound |
19910
| PDB ID |
HNQ
| ChEBI ID |
67121
Product: Amrubicin (hydrochloride)
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
Not Available |
Enzymes
- General function:
- Involved in aminopeptidase activity
- Specific function:
- Removes the amino-terminal methionine from nascent proteins. Required for normal progression through the cell cycle
- Gene Name:
- METAP1
- Uniprot ID:
- P53582
- Molecular weight:
- 43214.9
References
- 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 ]
PMID: 21050755
