Nitroxoline - CAS 4008-48-4
Catalog number:
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
Molecular Weight:
Nitroxoline is a urinary antibacterial agent had proven to be very effective at combating biofilm infections.
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Ochre-yellow to brownish crystalline powder
Soluble in DMSO
Store at 2-8 °C
An antibiotic
Quality Standard:
Enterprise Standard
Shelf Life:
As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
Boiling Point:
419ºC at 760mmHg
Melting Point:
181-183 ºC
Canonical SMILES:
1.The syntheses and structures of '3+2' and '2+2+1' oxorhenium mixed-ligand complexes employing 8-hydroxy-5-nitroquinoline as the bidentate N,O donor ligand.
Chen X1, Femia FJ, Babich JW, Zubieta J. Inorganica Chim Acta. 2000 Oct 20;308(1-2):80-90.
The syntheses and structural characterizations of a series of novel '3+2' and '2+2+1' mixed-ligand complexes carrying 8-hydroxy-5-nitroquinoline (HL) as the bidentate N,O donor atom system are reported. Thus one-pot reactions of [ReOCl(3)(PPh(3))(2)] with dianionic tridentate ligands H(2)L(n) (where H(2)L(1)=HOC(6)H(4)-2-CH=NC(6)H(4)-2-OH; H(2)L(2)=HOC(6)H(4)-2-CH=N-C(6)H(4)-2-SH; H(2)L(3)=HOC(6)H(4)-2-CH=NN=C(NHC(6)H(5))-SH; H(2)L(4)=2-CH(2)OH-C(5)H(3)N-6-CH(2)SH; and H(2)L(5)=2-CO(2)H-C(5)H(3)N-6-CO(2)H) and HL afforded a series of '3+2' oxorhenium complexes of the type [ReO(H(2)L(n))(L)] 2-6, which exhibit distorted octahedral geometries. Crystals of 1 are monoclinic space group C2/c, a=16.702(1), b=14.275(1), c=22.363(2) A, beta=108.083(1) degrees V=5068.2(7) A(beta) and Z=8; those of 2 are monoclinic space group P2(1)/n, a=8.5093(4) b=38.518(2), c=11.6092(5) A, beta=97.708(1) degrees , V=3770.7(3) A(3) and Z=8; those of 5 are triclinic, space group P1-, a=7.
2.Powder diffraction study of the hydrogen bonds in nitroxoline and its hydrochloride.
Yatsenko AV1, Paseshnichenko KA, Chernyshev VV, Schenk H. Acta Crystallogr C. 2002 Jan;58(Pt 1):o19-21. Epub 2001 Dec 14.
The crystal structures of 8-hydroxy-5-nitroquinoline, C9H6N2O3, (I), and 8-hydroxy-5-nitroquinolinium chloride, C9H7N2O3+*Cl-, (II), have been determined from X-ray powder data. In (I), the molecules are linked via moderately strong hydrogen bonds to form dimers. Such a packing motif is likely to be responsible for the low solubility of (I) in water. In (II), the inversion-related cations form stacks, and anions fill the interstack channels.
3.[Present status of nitroxoline].
Bergogne-Berezin E1, Berthelot G, Muller-Serieys C. Pathol Biol (Paris). 1987 Jun;35(5 Pt 2):873-8.
Nitroxoline (8-hydroxy-5-nitroquinoline) has been used since 1962 in the treatment of urinary tract infections especially those due to gram negative bacilli (E. coli). The current renewal of the drug is in relation to the recently shown activity of nitroxoline against fungi (Candida, Torulopsis), Mycoplasma and U. urealyticum, as well as Trichomonas. In order to update the knowledge of the drug, the aim of this study was a pharmacokinetic study in serum and urines collected after administration of one single dose (2 X 100 mg) and after multiple doses (200 mg X 3). Eight healthy volunteers were included in the study. The assays were carried out by means of the microbiological procedure and HPLC comparatively in the same samples. From the results several comments should be made: 1) In all subjects, serum levels were measurable 15 to 30 min. after administration, suggesting a rapid absorption. 2) Despite individual variations due to oral administration, pharmacokinetic parameters could be calculated: Tmax: 1.
4.Experimental and theoretical quantum chemical investigations of 8-hydroxy-5-nitroquinoline.
Arjunan V1, Balamourougane PS, Kalaivani M, Raj A, Mohan S. Spectrochim Acta A Mol Biomol Spectrosc. 2012 Oct;96:506-16. doi: 10.1016/j.saa.2012.05.080. Epub 2012 Jun 6.
The FT-IR and FT-Raman spectra of 8-hydroxy-5-nitroquinoline have been recorded in the regions 4000-400 and 4000-100 cm(-1), respectively. The spectra were interpreted in terms of fundamentals modes, combination and overtone bands. The normal coordinate analysis was carried out to confirm the precision of the assignments. The structure of the compound was optimised and the structural characteristics were determined by density functional theory (DFT) using B3LYP method with 6-31G(**), 6-311++G(**) and cc-pVDZ basis sets. The vibrational frequencies were calculated in all these methods and were compared with the experimental frequencies which yield good agreement between observed and calculated frequencies. The infrared and Raman spectra were also predicted from the calculated intensities. (1)H and (13)C NMR spectra were recorded and (1)H and (13)C nuclear magnetic resonance chemical shifts of the molecule were calculated using the gauge independent atomic orbital (GIAO) method.
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CAS 4008-48-4 Nitroxoline

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