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| Other Sizes |
| Targets |
Nitroxoline targets bacterial enzymes involved in DNA replication, specifically DNA gyrase and topoisomerase IV. These enzymes are essential for bacterial DNA replication and transcription. By binding to these enzymes, Nitroxoline inhibits their activity, thereby blocking DNA and RNA synthesis and ultimately leading to bacterial cell death. Its mechanism is similar to that of other quinolone antibiotics. Additionally, Nitroxoline has been identified as a potent inhibitor of Cathepsin B, a cysteine protease involved in various cellular processes, including cancer progression.
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| ln Vitro |
Pseudomonas aeruginosa exhibits an 80% reduction in biofilm mass at doses of 0.25–16 μg/mL of nitroline, resulting in a mesh-like structure as opposed to a dense one. Nitroline (2.5–20 μM; 24 hours) efficiently prevents a 4-log decrease in the number of viable cells in small cell lung cancer (SCLC) cells in produced biofilms [1]. and MCL1), as well as increase the phospholipid protein Bim to cause SCLC cells to undergo apoptosis. Research has revealed that nitroxoline alters the expression of MDM2 by causing the destruction of phospholiposomes, which in turn increases the expression of the substrate protein p53 for MDM2 [2].
In vitro, Nitroxoline exhibits potent antibacterial and antifungal activity against a wide range of microorganisms. It is particularly effective against E. coli and other common urinary tract pathogens. It has also been shown to be very effective at combating biofilm infections. Its activity as a Cathepsin B inhibitor has been demonstrated in biochemical assays, with the compound showing potent inhibition of the enzyme. These diverse in vitro activities confirm its potential beyond its traditional use as an antibacterial agent. |
| ln Vivo |
In the C3H/He bladder subcutaneous model of bladder cancer, nitroxoline (15–60 mg/kg; intragastric gavage) can dramatically decrease tumor growth [3].
In vivo, Nitroxoline is used as a urinary antibacterial agent. It is effective against susceptible Gram-positive and Gram-negative bacteria commonly found in urinary tract infections. It has also shown nephroprotective and anti-infective properties. Its clinical use has been established for the treatment of urinary tract infections. Its activity against biofilms suggests potential for treating chronic or recurrent infections. |
| Enzyme Assay |
Non-cell-based in vitro assays for Nitroxoline include antibacterial susceptibility testing. The minimum inhibitory concentration (MIC) is determined using broth microdilution or agar dilution methods against various bacterial and fungal strains. Its mechanism of action is studied using DNA gyrase or topoisomerase IV inhibition assays, where the compound's ability to inhibit the enzymatic activity is measured. Cathepsin B inhibition assays are performed using purified enzyme and a fluorogenic substrate.
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| Cell Assay |
Cell Viability Assay[2]
Cell Types: H446, H1882, H1417 and H1688 Cell Tested Concentrations: 2.5 μM, 5 μM, 10 μM, 20 μM Incubation Duration: 24 hrs (hours) Experimental Results: Effectively inhibited the survival of small cell lung cancer (SCLC) cells. Western Blot Analysis[2] Cell Types: H446, H1882, H1417 Cell Tested Concentrations: 5 μM, 10 μM, 20 μM Incubation Duration: 24 hrs (hours) Experimental Results: Anti-apoptotic proteins (such as Bcl-2 and MCL1) are inhibited and pro-apoptotic The protein Bim is upregulated. Cellular assays for Nitroxoline involve treating bacterial cultures with the compound to determine its MIC. For its antiproliferative activity, cancer cell lines are treated with the compound, and cell viability is measured. The compound's effects on DNA synthesis and cell cycle progression are also studied. Its anti-biofilm activity is assessed using biofilm formation assays. |
| Animal Protocol |
Animal/Disease Models: C3H/He mice were injected with MBT-2 cells [3] into the bladder.
Doses: 15 mg/kg or 60 mg/kg. Route of Administration: po (oral gavage); five times a week, on days 1, 2, 4, and 5. , 7, 8, 10 and 11 days. Experimental Results: Dramatically inhibited tumor growth. In vivo animal models for Nitroxoline would typically involve models of urinary tract infection. Animals are infected with a pathogenic bacterium, and the compound is administered orally or intravenously. Efficacy is assessed by measuring bacterial burden in the urine and bladder, as well as by monitoring clinical signs of infection. Detailed protocols are not extensively provided in the referenced sources. |
| ADME/Pharmacokinetics |
Nitroxoline has a molecular weight of 190.16 g/mol and a molecular formula of C₉H₆N₂O₃. Its CAS number is 4008-48-4. The compound appears as yellow needles and has a melting point of 258°C. Purity is typically ≥98%. Storage conditions: 2-8°C, protected from light. The compound is supplied for research use only. Detailed pharmacokinetic parameters are not extensively reported.
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| Toxicity/Toxicokinetics |
Nitroxoline is generally well-tolerated. Detailed toxicological data are not extensively provided in the referenced sources. As a urinary antibacterial agent, it is considered safe for its intended use. The compound is for research use only and is not for human consumption. Standard laboratory safety precautions should be followed when handling the compound.
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| References |
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| Additional Infomation |
Nitrazoline is a monohydroxyquinoline compound with a hydroxyl group at the C-8 position and a trans nitro group at the C-5 position. It possesses antibacterial, antifungal, nephroprotective, and anti-infective properties. It is a C-nitro compound and also a monohydroxyquinoline compound. Nitrazoline is a urinary tract antibacterial agent, effective against both susceptible Gram-positive and Gram-negative bacteria commonly found in urinary tract infections. It is a hydroxyquinoline derivative and is unrelated to other drug classes. Nitrazoline has activity against bacterial DNA gyrase. Nitrazoline has been reported to exist in bovine animals (Bos taurus), and relevant data are available. Drug Indications Nitrazoline is an antibiotic. Mechanism of Action This drug may have antitumor activity by inhibiting the methionine aminopeptidase type 2 (MetAP2) protein involved in angiogenesis. Its antibacterial activity may derive from metal ion complexation, which is crucial for bacterial growth.
Nitroxoline is also known as 8-Hydroxy-5-nitroquinoline, 5-nitroquinolin-8-ol, and 5-Nitro-8-hydroxyquinoline. It is a urinary antibacterial agent active against Gram-positive and Gram-negative organisms. It is also a potent Cathepsin B inhibitor and has shown antiproliferative and bromodomain interaction-inhibiting properties. Its CAS number is 4008-48-4. |
| Molecular Formula |
C9H6N2O3
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| Molecular Weight |
190.1555
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| Exact Mass |
190.037
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| CAS # |
4008-48-4
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| Related CAS # |
Nitroxoline-d4
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| PubChem CID |
19910
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| Appearance |
Light yellow to green yellow solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
419.0±35.0 °C at 760 mmHg
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| Melting Point |
181-183ºC
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| Flash Point |
207.2±25.9 °C
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| Vapour Pressure |
0.0±1.0 mmHg at 25°C
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| Index of Refraction |
1.728
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| LogP |
2
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
14
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| Complexity |
229
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
RJIWZDNTCBHXAL-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H6N2O3/c12-8-4-3-7(11(13)14)6-2-1-5-10-9(6)8/h1-5,12H
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| Chemical Name |
5-nitroquinolin-8-ol
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~50 mg/mL (~262.94 mM)
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.2587 mL | 26.2936 mL | 52.5873 mL | |
| 5 mM | 1.0517 mL | 5.2587 mL | 10.5175 mL | |
| 10 mM | 0.5259 mL | 2.6294 mL | 5.2587 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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