Nitroxolin

Nitroxoline

HCID 19910
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Grundinformationen

CAS
4008-48-4
Standard-SMILES
O=[N+]([O-])c1ccc(O)c2ncccc12
InChIKey
RJIWZDNTCBHXAL-UHFFFAOYSA-N
Summenformel
C9H6N2O3
Durchschnittliche Molmasse
190,16 g/mol
Monoisotopische Masse
190,03784206

Namen und Bezeichner

Bevorzugter Name
Nitroxoline
IUPAC
5-nitroquinolin-8-ol
Lokaler Name
Nitroxolin
Englischer Name
Nitroxoline
Summenformel
C9H6N2O3
Molmasse
190.16

Namen und Synonyme

NITROXOLINE5-nitroquinolin-8-ol4008-48-48-Hydroxy-5-nitroquinoline5-Nitro-8-quinolinol5-Nitro-8-hydroxyquinoline5-Nitrox5-NOK5-Nitro-8-oxyquinolineNitroxolina5NOKNitroxolinum
Weitere Namen anzeigen
NitroxolinNiroxolineA-82bas58Noxin
DTXSID4046284NSC-74947A8M33244M6DTXCID2026284CHEBI:67121NiceneRefChem:166162223-662-4

Datenbank-Bezeichner

CAS
4008-48-4
PubChem CID
19910
DTXSID
DTXSID4046284
ChEMBL
CHEMBL1454910
ChEBI
CHEBI:67121
UNII
A8M33244M6
EC Number
223-662-4
Nikkaji
J3.716H

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2,1
Polarare Oberfläche (TPSA)
78,9 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
0
Schwere Atome
14

Experimentelle und physikochemische Eigenschaften

LogP · 2 Einträge

1.99

1.99

Solubility · 2 Einträge

2.73e+00 g/L

>28.5 [ug/mL] (The mean of the results at pH 7.4)

Melting Point · 2 Einträge

180

180 °C

Physical DescriptionSolid

Physikochemische Eigenschaften

Schmelzpunkt
181 · 181-183 °C(lit.)
Siedepunkt
325.64 °C · 325.64°C (rough estimate)
Dichte
1.3907 · 1.3907 (rough estimate)
Brechungsindex
1.557 · 1.5570 (estimate)
storage temp.
Keep in dark place,Inert atmosphere,Room temperature
Löslichkeit
alcohol: very slightly soluble

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

Danger

H301 (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 exposure; Respiratory 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.

Gefahrenhinweise

Other Safety InformationIMAP assessments - 8-Quinolinol, 5-nitro-: Human health tier I assessment；IMAP assessments - 8-Quinolinol, 5-nitro-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 3 (87.3%)；Acute Tox. 4 (12.7%)；Acute Tox. 3 (87.3%)；Skin Irrit. 2 (98.2%)；Eye Irrit. 2 (98.2%)；Acute Tox. 3 (87.3%)；STOT SE 3 (96.4%)

Sicherheitsdaten

wgk
3
ridadr
UN 2811 6.1/PG 3
hs_code
29334900
RTECS-Nr.
VC8225000
risk_code
23/24/25-36/37/38-22/24/25-20/21/22
Toxizität
LD50 oral in rat: 510mg/kg

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

J - Antiinfectives for systemic use；J01 - Antibacterials for systemic use；J01X - Other antibacterials；J01XX - Other antibacterials；J01XX07 - Nitroxoline

QJ - Antiinfectives for systemic use；QJ01 - Antibacterials for systemic use；QJ01X - Other antibacterials；QJ01XX - Other antibacterials；QJ01XX07 - Nitroxoline

Mechanism of ActionThis 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.
MeSH Pharmacological Classification · 2 Einträge

Substances capable of killing agents causing urinary tract infections or of preventing them from spreading.

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.

Cellular LocationsCytoplasm

Verwendung und Herstellung

Uses · 1 Eintrag

Use (kg; approx.) in Germany (2009): >1000；Use (kg; exact) in Germany (2009): 1197；Consumption (g per capita; approx.) in Germany (2009): 0.0122；Consumption (g per capita; exact) in Germany (2009): 0.0146；Excretion rate: 1；Calculated removal (%): 22.9

Anwendungen · 2 Einträge

BeschreibungNitroxoline 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.

Verwendenantibacterial

Vor- und nachgelagerte Produkte

Anbieter100 Anbieter

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
河北展药生物科技有限公司15369953316 +8615369953316 · [email protected]
科瑞迪化学400-821-5857 021-64326257 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: A monohydroxyquinoline in which the hydroxy group is positioned at C-8 with a nitro group trans to it at C-5.

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