Nitroxoline

HCID 19910
NotesReactions
Substructure searchFind similar structures

Basic information

CAS
4008-48-4
Standard SMILES
O=[N+]([O-])c1ccc(O)c2ncccc12
InChIKey
RJIWZDNTCBHXAL-UHFFFAOYSA-N
Molecular formula
C9H6N2O3
Average molar mass
190.16 g/mol
Monoisotopic mass
190.03784206

Names & identifiers

Preferred name
Nitroxoline
IUPAC
5-nitroquinolin-8-ol
English name
Nitroxoline
Molecular formula
C9H6N2O3
Molecular weight
190.16

Names & synonyms

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

Database identifiers

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

Properties

Computed structural properties

XLogP
2.1
Topological polar surface area
78.9 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
0
Heavy atoms
14

Experimental & physicochemical properties

LogP · 2 items

1.99

1.99

Solubility · 2 items

2.73e+00 g/L

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

Melting Point · 2 items

180

180 °C

Physical DescriptionSolid

Physicochemical properties

Melting point
181 · 181-183 °C(lit.)
Boiling point
325.64 °C · 325.64°C (rough estimate)
Density
1.3907 · 1.3907 (rough estimate)
refractive index
1.557 · 1.5570 (estimate)
storage temp.
Keep in dark place,Inert atmosphere,Room temperature
solubility
alcohol: very slightly soluble

Safety & regulation

GHS classification

GHS Classification · 5 items

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.

Hazard information

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%)

Safety data

PPE
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
wgk
3
rtecs
VC8225000
ridadr
UN 2811 6.1/PG 3
hs_code
29334900
Toxicity
LD50 oral in rat: 510mg/kg

Chemistry & industry

Pharmacology

ATC Code · 2 items

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 items

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

Uses & manufacturing

Uses · 1 item

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

Applications · 4 items

DescriptionNitroxoline 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.

Usesantibacterial

Uses5-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-h ydroxyquinoline has been shown to have anti-cancer activity.

Uses8-Hydroxy-5-nitroquinoline was used in the synthesis of novel CO2-soluble 8-hydroxyquinoline chelating agents.

Upstream & downstream products

Suppliers100 total

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]

Additional notes

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

Related reactions

7 records
New reaction record

Compound notes

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