Explore a selection of our essential drug information below, or:
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
Structure for Nitroxoline (DB01422)
- 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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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.
Target Actions Organism AMethionine aminopeptidase 2 inhibitorHumans UMagnesium cation chelatorHumans UManganese cation chelatorHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcenocoumarol The therapeutic efficacy of Acenocoumarol can be increased when used in combination with Nitroxoline. Dicoumarol The therapeutic efficacy of Dicoumarol can be increased when used in combination with Nitroxoline. Fluindione The therapeutic efficacy of Fluindione can be increased when used in combination with Nitroxoline. Phenindione The therapeutic efficacy of Phenindione can be increased when used in combination with Nitroxoline. Phenprocoumon The therapeutic efficacy of Phenprocoumon can be increased when used in combination with Nitroxoline. - Food Interactions
- Not Available
Products
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- 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
- 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]
- External Links
- Human Metabolome Database
- HMDB0015491
- PubChem Compound
- 19910
- PubChem Substance
- 46505497
- ChemSpider
- 18756
- BindingDB
- 64987
- 31901
- ChEBI
- 67121
- ChEMBL
- CHEMBL1454910
- ZINC
- ZINC000015831592
- PharmGKB
- PA164754993
- PDBe Ligand
- HNQ
- Wikipedia
- Nitroxoline
- PDB Entries
- 3ai8 / 5y1y
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 180 °C PhysProp logP 1.99 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 2.73 mg/mL ALOGPS logP 1.9 ALOGPS logP 1.77 Chemaxon logS -1.8 ALOGPS pKa (Strongest Acidic) 6.89 Chemaxon pKa (Strongest Basic) 1.92 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 76.26 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 48.28 m3·mol-1 Chemaxon Polarizability 17.25 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9903 Blood Brain Barrier + 0.8359 Caco-2 permeable + 0.5318 P-glycoprotein substrate Non-substrate 0.7501 P-glycoprotein inhibitor I Non-inhibitor 0.8255 P-glycoprotein inhibitor II Non-inhibitor 0.7717 Renal organic cation transporter Non-inhibitor 0.8555 CYP450 2C9 substrate Non-substrate 0.7446 CYP450 2D6 substrate Non-substrate 0.8236 CYP450 3A4 substrate Non-substrate 0.5 CYP450 1A2 substrate Inhibitor 0.514 CYP450 2C9 inhibitor Non-inhibitor 0.5166 CYP450 2D6 inhibitor Non-inhibitor 0.7747 CYP450 2C19 inhibitor Non-inhibitor 0.519 CYP450 3A4 inhibitor Non-inhibitor 0.7765 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5604 Ames test AMES toxic 0.9492 Carcinogenicity Non-carcinogens 0.7562 Biodegradation Not ready biodegradable 0.9907 Rat acute toxicity 2.6189 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7788 hERG inhibition (predictor II) Non-inhibitor 0.8267
Spectra
- Mass Spec (NIST)
- Download (8.15 KB)
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-01r6-2900000000-0826262edf2cf93fa0a8 LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS splash10-002b-3900000000-cf44cf477f74a379b18a MS/MS Spectrum - , positive LC-MS/MS splash10-002b-3900000000-cf44cf477f74a379b18a Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 142.3416326 predictedDarkChem Lite v0.1.0 [M-H]- 142.5970326 predictedDarkChem Lite v0.1.0 [M-H]- 127.64041 predictedDeepCCS 1.0 (2019) [M+H]+ 143.0441326 predictedDarkChem Lite v0.1.0 [M+H]+ 143.1412326 predictedDarkChem Lite v0.1.0 [M+H]+ 130.8921 predictedDeepCCS 1.0 (2019) [M+Na]+ 142.6665326 predictedDarkChem Lite v0.1.0 [M+Na]+ 142.5520326 predictedDarkChem Lite v0.1.0 [M+Na]+ 139.254 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General 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 responsible for processing proteins containing N-terminal Met-Val and Met-Thr sequences in vivo
- Specific Function
- aminopeptidase activity
- Gene Name
- METAP2
- Uniprot ID
- P50579
- Uniprot Name
- Methionine aminopeptidase 2
- Molecular Weight
- 52891.145 Da
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. [Article]
Unknown
Chelator
References
- 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]
- 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]
Unknown
Chelator
References
- 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]
- 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