Nitroxolin
5-NITRO-8-HYDROXYQUINOLINE · Nitroxolin · Niroxoline · 5-Nitro-8-oxyquinoline · 8-HYDROXY-5-NITROQUINOLINE · 5nok · A-82 · 5-NOK
Identifikatoren & physikalische Daten
| CAS No. | 4008-48-4 |
|---|---|
| Summenformel | C9H6N2O3 |
| Durchschnittliche Molmasse | 190,16 g/mol |
| Monoisotopische Masse | 190,03784206 g/mol |
| SMILES | O=[N+]([O-])c1ccc(O)c2ncccc12 |
| InChIKey | RJIWZDNTCBHXAL-UHFFFAOYSA-N |
| PubChem CID | 19910 |
| ChEMBL | CHEMBL1454910 |
| ChEBI | CHEBI:67121 |
| EC No. | 223-662-4 |
| DTXSID | DTXSID4046284 |
| Lokaler Name | Nitroxolin |
Chemische & physikalische Eigenschaften
| XLogP | 2,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 78,9 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 14 |
| Formalladung | 0 |
| Komplexität | 229 |
| LogP (Verteilungskoeffizient) | 1.99 |
| Löslichkeit | 2.73e+00 g/L>28.5 [ug/mL] (The mean of the results at pH 7.4)alcohol: very slightly soluble |
| Schmelzpunkt | 180180 °C181-183 °C(lit.) |
| Physical Description | Solid |
| Siedepunkt | 325.64°C (rough estimate) |
| Dichte | 1.3907 (rough estimate) |
| Brechungsindex | 1.5570 (estimate) |
| Lagerbedingungen | Keep in dark place,Inert atmosphere,Room temperature |
| pKa (Säurekonstante) | 2.55±0.10(Predicted) |
| Aggregatzustand | powder to crystal |
| Farbe | Light yellow to Brown to Dark green |
| Merck | 14,6655 |
| Henry-Konstante | 2.7×103 mol/(m3Pa) at 25℃, Abraham and Jr. (2019) |
| 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 |
| SMILES | N1C2C(=C([N+]([O-])=O)C=CC=2O)C=CC=1 |
| NIST chemische Informationen | 8-Hydroxy-5-nitroquinoline(4008-48-4) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301 (87.3%): Toxic if swallowed [Danger Acute toxicity, oral]H302 (12.7%): Harmful if swallowed [Warning Acute toxicity, oral]H311 (87.3%): Toxic in contact with skin [Danger Acute toxicity, dermal]H315 (98.2%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (98.2%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H331 (87.3%): Toxic if inhaled [Danger Acute toxicity, inhalation]H335 (96.4%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 55 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Weitere Sicherheitsinformationen | IMAP assessments - 8-Quinolinol, 5-nitro-: Human health tier I assessmentIMAP assessments - 8-Quinolinol, 5-nitro-: Environment tier I assessment |
| Hazard Classes and Categories | Acute Tox. 3 (87.3%)Acute Tox. 4 (12.7%)Skin Irrit. 2 (98.2%)Eye Irrit. 2 (98.2%)STOT SE 3 (96.4%) |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | UN 2811 6.1/PG 3 |
| Zollcode | 29334900 |
| RTECS-Nr. | VC8225000 |
| R-Sätze (R) | 23/24/25-36/37/38-22/24/25-20/21/22 |
Anwendungen & Verwendung
Beschreibung
Nitroxoline is an 8-hydroxyquinoline that has diverse biological activities, including antibacterial, antiproliferative, and bromodomain interaction-inhibiting properties. Nitroxoline is active against the bacteria E. coli, S. aureus, E. faecalis, K. pneumoniae, and P. mirabilis in vitro (MIC90s = 4, 4, 8, 8, and 8 mg/L, respectively). It also inhibits biofilm formation of certain strains of multidrug-resistant (MDR) A. baumannii and P. aeruginosa, as well as methicillin-resistant S. aureus (MRSA) and S. epidermidis (MRSE) with minimum biofilm eradication concentration (MBEC) values of 46.9, 1,500, 188, and 125 μM, respectively. Nitroxoline inhibits the growth of human U87 and U251 glioma, A549 lung, and PC3 prostate cancer cells (IC50s = 50, 6, 38, and 23 μg/ml, respectively). In vivo, it reduces tumor growth in a PTEN- and KRAS-driven glioma mouse model when administered at a dose of 80 mg/kg per day. Nitroxoline also inhibits the interaction between the first bromodomain of bromodomain-containing protein 4 (BRD4) with acetylated histone H4 with an IC50 value of 0.98 μM.
Verwenden
antibacterial