5-nitroquinolin-8-ol

• ChemBase ID: 1230
• Molecular Formular: C9H6N2O3
• Molecular Mass: 190.15554
• Monoisotopic Mass: 190.03784206
• SMILES: Oc1c2ncccc2c([N+](=O)[O-])cc1
• Canonical SMILES: [O-][N+](=O)c1ccc(c2c1cccn2)O
• InChI: InChI=1S/C9H6N2O3/c12-8-4-3-7(11(13)14)6-2-1-5-10-9(6)8/h1-5,12H
• InChIKey: RJIWZDNTCBHXAL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-nitroquinolin-8-ol
• IUPAC Traditional name: nitroxoline
• Brand Name: Noxin; Noxibiol; Galinok; Isinok; Nicene forte
• Synonyms: 5-Nitrox; 5-Nitroxine; 5-NOK; Nitroxolina [inn-spanish]; Nitroxolinum [inn-latin]; 5-Nitroks; Nitroxoline; 5-Nitroquinolin-8-ol; 8-Hydroxy-5-nitroquinoline 97%; 5-Nitro-8-quinolinol; 8-Hydroxy-5-nitroquinoline; 5-NITRO-8-HYDROXYQUINOLINE; 5-(Hydroxyl[oxido]amino)-8-hydroxyquinoline; 5-Nitro-8-oxychinoline; 5-Nitro-8-oxyquinoline; 5NOK; 8-Hydroxy-5-nitroquinoline; A 82; BAS 58; NSC 74947; NSC 74948; Nibiol; Nitroxolin; Nitroxoline; Noxibiol; 5-硝基-8-羟基喹啉; 8-羟基-5-硝基喹啉

Database IDs

• CAS Number: 4008-48-4
• EC Number: 223-662-4
• MDL Number: MFCD00006791
• Merck Index: 146655
• PubChem SID: 46505497; 24848465; 160964690
• PubChem CID: 19910

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.8931537
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.7498512
• LogD (pH = 7.4): 1.1540734
• Log P: 1.7673193
• Molar Refractivity: 48.2807 cm^3
• Polarizability: 19.421053 Å^3
• Polar Surface Area: 76.26 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.9
• LOG S: -1.84
• Solubility (Water): 2.73e+00 g/l

PROPERTIES

Physical Property

• Melting Point: 177-182°C; 181-183 °C(lit.); 181-183°C
• Hydrophobicity(logP): 1.99 [HANSCH,C ET AL. (1995)]

Safety Information

• Storage Warning: Toxic/Harmful/Irritant/Light Sensitive/Air Sensitive/Store under Argon
• RTECS: VC8225000
• European Hazard Symbols: Toxic (T); X
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22-36/37/38; 23/24/25-36/37/38
• Safety Statements: 26-36/37; 26-36-45
• TSCA Listed: 否
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H315-H319-H331-H335; H302-H315-H319-H335
• GHS Precautionary statements: P261-P280-P301 + P310-P305 + P351 + P338-P311; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Product Information

• Purity: 96%
• Empirical Formula (Hill Notation): C9H6N2O3

DETAILS

MP Biomedicals - 02155883

(5-Nitro-8-quinolinol) Crystalline

DrugBank - DB01422

• Drug Groups: approved
• 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.
• Indication: Nitroxoline is an antibiotic agent.
• External Links: Wikipedia

Sigma Aldrich - 140325

Packaging
5 g in glass bottle

Toronto Research Chemicals - N496215

5-Nitro-8-hydroxyquinoline is an antimicrobial agent used for the treatment of urinary tract infection. 5-Nitro-8-hydroxyquinoline is also a potent and reversible inhibitor of cathepsin B. 5-Nitro-8-hydroxyquinoline has been shown to have anti-cancer acti

REFERENCES

• Mirkovic, B. et al.: ChemMedChem, 6, 1351 (2011): Jiang, H. et al.: Cancer Lett., 312, 11 (2011)
• Ghoneim, M.M. et al.: Bioelectrochemistry, 80, 162 (2011)