Compound: NITROXOLINE
SMILES: O=[N+]([O-])c1c2c(nccc2)c(O)cc1
InChIKey: RJIWZDNTCBHXAL-UHFFFAOYSA-N
Synonyms: NITROXOLINE, 5-nitroquinolin-8-ol, 4008-48-4, 8-Hydroxy-5-nitroquinoline, 5-Nitro-8-quinolinol, 5-Nitro-8-hydroxyquinoline, 5-Nitrox, 5-NOK, 5-Nitro-8-oxyquinoline, Nitroxolina, 5NOK, Nitroxolinum, DTXSID4046284, NSC-74947, A8M33244M6, DTXCID2026284, CHEBI:67121, Nicene, RefChem:166162, 223-662-4, Nitroxolin, Noxibiol, Nibiol, Noxin, 8-Quinolinol, 5-nitro-, 5-Nitroxine, 5-Nitroks, 5-Nitro-8-oxychinoline, Nitroxolinum [INN-Latin], Nitroxolina [INN-Spanish], A-82, BAS 58, NSC 74947, MLS000069750, MFCD00006791, SMR000059036, Galinok, Isinok, Nicene Forte, Nitroxoline (INN), NCGC00160664-01, NITROXOLINE [INN], Uro-Coli, CAS-4008-48-4, Nitroxoline [INN:BAN:DCF], EINECS 223-662-4, BRN 0166146, Nitroxlina, UNII-A8M33244M6, Nitroxoline (TN), HNQ, Nitroxoline (Standard), 3ai8, Opera_ID_204, 5-Nitro-quinolin-8-ol, NITROXOLINE [MI], 5-Nitro-8hydroxyquinoline, Quinolin-8-ol, 5-nitro-, NITROXOLINE [MART.], Oprea1_594857, 8-Hydroxy-5-nitro-chinoline, NITROXOLINE [WHO-DD], 5-21-03-00297 (Beilstein Handbook Reference), cid_19910, MLS001148594, SCHEMBL151248, REGID_for_CID_19910, orb1310648, WLN: T66 BNJ GNW JQ, CHEMBL1454910, SCHEMBL21816802, SCHEMBL29363027, BDBM64987, GTPL13964, HY-B1159R, APL1202, GLXC-20116, HMS2230I14, HMS3264C05, HMS3374D08, HMS5083J17, KUC105356N, Pharmakon1600-01506173, 8-Hydroxy-5-nitroquinoline, 96%, APL-1202, HY-B1159, MSK11425, NSC74947, Tox21_111969, EBC-03494, KSC-8-140, NSC760393, NSC832678, s4591, SBB037944, STK099582, AKOS001053242, Tox21_111969_1, AC-7828, CCG-213981, CS-4761, DB01422, FN35484, NSC-760393, NSC-832678, PS-5547, compound 10 [PMID: 30939017], NCGC00160664-03, ST086486, DB-049530, H0805, NS00004195, EN300-17364, D07245, 5-Nitro-8-quinolinol|5-Nitro-8-hydroxyquinoline, AB00572598_14, AG-205/04556035, F044621, Q304570, SR-01000721863, SR-01000721863-4, BRD-K97534525-001-23-5, BRD-K97534525-001-24-3, Z56922155, InChI=1/C9H6N2O3/c12-8-4-3-7(11(13)14)6-2-1-5-10-9(6)8/h1-5,12
Theoretical properties:
molecular_formula: C9H6N2O3
molecular_weight: 190.16 g/mol
exact_mass: 190.03784206 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 0
heavy_atom_count: 14
topological_polar_surface_area: 78.9 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
solubility: 2.73e+00 g/L
Descriptions:
pubchem: Nitroxoline is a monohydroxyquinoline in which the hydroxy group is positioned at C-8 with a nitro group trans to it at C-5. It has a role as an antimicrobial agent, an antiinfective agent, an antifungal agent and a renal agent. It is a C-nitro compound and a monohydroxyquinoline.
chebi: A monohydroxyquinoline in which the hydroxy group is positioned at C-8 with a nitro group <em>trans</em> to it at C-5.
chembl: NITROXOLINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Nitroxoline is an antibiotic that has been in use in Europe for about fifty years, and has proven to be very effective at combating biofilm infections.  Nitroxoline was shown to cause a decrease in the biofilm density of P. aeruginosa infections, which would allow access to the infection by the immune system in vivo. It was shown that nitroxoline functions by chelating Fe2+ and Zn2+ ions from the biofilm matrix; when Fe2+ and Zn2+ were reintroduced into the system, biofilm formation activity was restored.  The biofilm degradation ability is comparable to EDTA derivatives, but this drug has a history of human use in clinical settings and therefore has a precedent with which to allow its use against “slimy” biofilm infections.