Nitroxoline

Synonyms :
5-Nitro-8-hydroxyquinoline, 5-Nitro-8-oxyquinoline, 5-Nitro-8-quinolinol, 5-Nitrox, 5-NOK, 5NOK, 8-Hydroxy-5-nitroquinoline, Nitroxolina, Nitroxolinum

Status : approved

Category

Antifungal Agents

Therapeutic Classification

OTHER ANTIBACTERIALS

ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
OTHER ANTIBACTERIALS
Anti-Infective Agents, Urinary

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.

Used

Nitroxoline is an antibiotic agent.

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.

Chemical Classification

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.

Nitroquinolines and derivatives

Organic compounds

Organoheterocyclic compounds

Quinolines and derivatives

Nitroquinolines and derivatives

Chemical Name

5-Nitro-8-hydroxyquinoline

Calculated Property

kind Value Source
logP 1.9 ALOGPS
logS -1.8 ALOGPS
Water Solubility 2.73e+00 g/l ALOGPS
logP 1.77 ChemAxon
IUPAC Name 5-nitroquinolin-8-ol ChemAxon
Traditional IUPAC Name nitroxoline ChemAxon
Molecular Weight 190.1555 ChemAxon
Monoisotopic Weight 190.037842068 ChemAxon
SMILES OC1=C2N=CC=CC2=C(C=C1)[N+]([O-])=O ChemAxon
Molecular Formula C9H6N2O3 ChemAxon
InChI InChI=1S/C9H6N2O3/c12-8-4-3-7(11(13)14)6-2-1-5-10-9(6)8/h1-5,12H ChemAxon
InChIKey InChIKey=RJIWZDNTCBHXAL-UHFFFAOYSA-N ChemAxon
Polar Surface Area (PSA) 78.94 ChemAxon
Refractivity 49.28 ChemAxon
Polarizability 17.16 ChemAxon
Rotatable Bond Count 1 ChemAxon
H Bond Acceptor Count 4 ChemAxon
H Bond Donor Count 1 ChemAxon
pKa (strongest acidic) 6.88 ChemAxon
pKa (strongest basic) 2.08 ChemAxon
Physiological Charge -1 ChemAxon
Number of Rings 2 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five 1 ChemAxon
Ghose Filter 1 ChemAxon
MDDR-Like Rule 0 ChemAxon

Target within organism

  • Methionine aminopeptidase 2 : in Human
  • Magnesium cation : in Human
  • Manganese cation : in Human