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Nitroxoline

Nitroxoline structure

CAS No:
4008-48-4
Formula:
C9H6N2O3
Chemical Name:
Nitroxoline
Synonyms:
8-Quinolinol,5-nitro-;5-Nitro-8-quinolinol;8-Hydroxy-5-nitroquinoline;5-Nitro-8-hydroxyquinoline;Nitroxoline;Nibiol;Nitroxolin;5-Nitro-8-oxyquinoline;5-Nitro-8-oxychinoline;5NOK;Noxibiol;5-Nitroxine;BAS 58;5-Nitrox;A 82;NSC 74947;NSC 74948;5-(Hydroxyl[oxido]amino)-8-hydroxyquinoline;52440-95-6;64667-01-2
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

Description

Nitroxoline is an antibiotic that has proven to be very effective at combating biofilm infections. Nitroxoline functions by chelating Fe2+ and Zn2+ ions from the biofilm matrix.

Solid

Nitroxoline is a monohydroxyquinoline in which the hydroxy group is positioned at C-8 with a nitro group trans to it at C-5. It has a role as an antimicrobial agent, an antifungal agent, a renal agent and an antiinfective agent. It is a C-nitro compound and a monohydroxyquinoline.|Nitroxoline is a urinary antibacterial agent active against susceptible gram-positive and gram-negative organisms commonly found in urinary tract infections. It is a hydroxyquinoline derivative unrelated to other classes of drugs. Nitroxoline is active against bacterial gyrases.

Nitroxoline Basic Attributes

Molecular Weight：

190.16

Exact Mass：

190.16

EC Number：

223-662-4

UNII：

A8M33244M6

NSC Number：

760393|74947

DSSTox ID：

DTXSID4046284

ATC Code：

J - Antiinfectives for systemic use

HScode：

2933499090

Characteristics

PSA：

78.9

XLogP3：

2.1

Appearance：

Solid

Density：

1.5±0.1 g/cm3

Melting Point：

180 °C

Boiling Point：

419°C at 760 mmHg

Flash Point：

207.2±25.9 °C

Refractive Index：

1.728

Water Solubility：

alcohol: very slightly soluble

Storage Conditions：

Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

Vapor Pressure：

0mmHg at 25°C

Toxicity：

LD50 oral in rat: 510mg/kg

Safety Information

Packing level：

Ⅲ

Hazard category：

6.1

Transport codes：

UN 2811 6.1/PG 3

wgk germany：

hazard class code：

23/24/25-36/37/38-22/24/25-20/21/22

safety instructions：

26-36-45

RTECS Number：

VC8225000

Marks：

T,Xi,Xn

Hazard note：

Toxic/Irritant

Stability/Shelf Life：

Stable under normal temperatures and pressures.

Precautionary statement(s)：

P261-P280-P301 + P310-P305 + P351 + P338-P311

Hazard Statements：

H301 + H311 + H331-H315-H319-H335

GHS Classification：

|Danger|H301+H311+H331 (65.96%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]|P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P311, P312, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 141 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

Drug Indication：

Nitroxoline is an antibiotic agent.

MeSH：

Substances capable of killing agents causing urinary tract infections or of preventing them from spreading. (See all compounds classified as Anti-Infective Agents, Urinary.)|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. (See all compounds classified as Antifungal Agents.)

Mechanism of Action：

This 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 Entry Terms：

5-nitro-8-hydroxyquinoline

Nitroxoline Use and Manufacturing

Methods of Manufacturing

The oxidation of 8-hydroxy-5-nitrosoquinoline (10) to 8-hydroxy-5-nitroquinoline(11 ) was carried out according to the procedure ofPetrow and Sturgeon20. Finely grounded 8-hydroxy-5-nitrosoquinoline hydrochloride (10) (15.0 g, 0.7mmol) was added into a 500 mL beaker containingconcentrated nitric acid (45 mL) and water (30 mL)in an ice bath. The mixture was stirred for 85 min at17 °C. Equal volume of cold water was added andthe mixture cooled to 0 °C and alkaline was madewith cold concentrated potassium hydroxidesolution pH 13.0. The red potassium salt wasdecomposed on neutralization with acetic acid, filtered by suction and washed with water. Theresidue was recrystallized from ethanol to afford abright yellow crystal of 8-hydroxy-5-nitroquinoline.Yield 14.10 g (90.1percent), mp 179 °C (lit 179.5-181.5°C)20.

Uses

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 activity.

Computed Properties

Molecular Weight:190.16
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Exact Mass:190.03784206
Monoisotopic Mass:190.03784206
Topological Polar Surface Area:78.9
Heavy Atom Count:14
Complexity:229
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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