Nitroxoline | CAS#4008-48-4

MedKoo Cat#: 318374 | Name: Nitroxoline

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Nitroxoline is an antibiotic that has been in use in Europe for about fifty years, and has proven to be very effective at combating biofilm infections. Nitroxoline was shown to cause a decrease in the biofilm density of P. aeruginosa infections, which would allow access to the infection by the immune system in vivo. It was shown that nitroxoline functions by chelating Fe2+ and Zn2+ ions from the biofilm matrix; when Fe2+ and Zn2+ were reintroduced into the system, biofilm formation was reconstituted. The activity of biofilm degradation is comparable to EDTA, but has a history of human use in clinical settings and therefore has a precedent with which to allow its use against “slimy” biofilm infections.

Chemical Structure

Nitroxoline

CAS#4008-48-4

Theoretical Analysis

MedKoo Cat#: 318374

Name: Nitroxoline

CAS#: 4008-48-4

Chemical Formula: C9H6N2O3

Exact Mass: 190.0378

Molecular Weight: 190.16

Elemental Analysis: C, 56.85; H, 3.18; N, 14.73; O, 25.24

Price and Availability

Size	Price	Availability	Quantity
2g	USD 350.00	2 Weeks
5g	USD 750.00	2 Weeks

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Synonym

Nitroxoline, 5-nitrox, 5-NOK, Cysto-saar plus, Nibiol

IUPAC/Chemical Name

5-nitroquinolin-8-ol

InChi Key

RJIWZDNTCBHXAL-UHFFFAOYSA-N

InChi Code

InChI=1S/C9H6N2O3/c12-8-4-3-7(11(13)14)6-2-1-5-10-9(6)8/h1-5,12H

SMILES Code

OC1=C2C(C=CC=N2)=C([N+]([O-])=O)C=C1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Nitroxoline is an antibiotic.

In vitro activity:

In this study, the effectiveness of nitroxoline to eradicate biofilms was determined using an in vitro [minimum biofilm eradication concentration (MBEC) = 46.9 µM against A. baumannii] and ex vivo porcine skin model (2-3 log reduction in viable biofilm cells). Nitroxoline was also found to eradicate methicillin-resistant S. aureus (MRSA) persister cells in non-biofilm (stationary) cultures, whereas vancomycin and daptomycin were found to be inactive. Reference: Int J Antimicrob Agents. 2017 Feb;49(2):247-251. https://pubmed.ncbi.nlm.nih.gov/28110918/

In vivo activity:

LPB fibrosarcoma cells were implanted in C57Bl/6 mice and nitroxoline (40 mg/kg) was administered in their drinking water for the entire duration of experiment or for 15 days only. Nitroxoline (Fig. 5A) as well as CA-074 (Fig. 5B) increased the time required for LPB tumors to reach a volume of 40 mm3 (Fig. 5C and 5D) and caused a delay in tumor growth (Fig. 5E and 5F). An orthotopic mouse breast cancer model was also employed in which primary MMTV-PyMT cells were injected into the left inguinal mammary gland of FVB/N congenic recipient mice. Nitroxoline (40 mg/kg) treatment of these mice reduced the growth of induced tumors (Fig. 6A). Reference: Oncotarget. 2015 Aug 7;6(22):19027-42. https://pubmed.ncbi.nlm.nih.gov/25848918/

	Solvent	mg/mL	mM
Solubility
	Ethanol	1.0	5.26
	PBS (pH 7.2)	0.5	2.63

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 190.16 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Hoffmann AM, Wolke M, Rybniker J, Plum G, Fuchs F. Activity of the old antimicrobial nitroxoline against Mycobacterium abscessus complex isolates. J Glob Antimicrob Resist. 2023 Feb 24;33:1-4. doi: 10.1016/j.jgar.2023.02.010. Epub ahead of print. PMID: 36842457. 2. Abouelhassan Y, Yang Q, Yousaf H, Nguyen MT, Rolfe M, Schultz GS, Huigens RW 3rd. Nitroxoline: a broad-spectrum biofilm-eradicating agent against pathogenic bacteria. Int J Antimicrob Agents. 2017 Feb;49(2):247-251. doi: 10.1016/j.ijantimicag.2016.10.017. Epub 2016 Dec 6. PMID: 28110918. 3. Lin W, Sun J, Sadahira T, Xu N, Wada K, Liu C, Araki M, Xu A, Watanabe M, Nasu Y, Huang P. Discovery and Validation of Nitroxoline as a Novel STAT3 Inhibitor in Drug-resistant Urothelial Bladder Cancer. Int J Biol Sci. 2021 Jul 25;17(12):3255-3267. doi: 10.7150/ijbs.63125. PMID: 34421363; PMCID: PMC8375225. 4. Mirković B, Markelc B, Butinar M, Mitrović A, Sosič I, Gobec S, Vasiljeva O, Turk B, Čemažar M, Serša G, Kos J. Nitroxoline impairs tumor progression in vitro and in vivo by regulating cathepsin B activity. Oncotarget. 2015 Aug 7;6(22):19027-42. doi: 10.18632/oncotarget.3699. PMID: 25848918; PMCID: PMC4662473.

In vitro protocol:

In vivo protocol:

1. Lin W, Sun J, Sadahira T, Xu N, Wada K, Liu C, Araki M, Xu A, Watanabe M, Nasu Y, Huang P. Discovery and Validation of Nitroxoline as a Novel STAT3 Inhibitor in Drug-resistant Urothelial Bladder Cancer. Int J Biol Sci. 2021 Jul 25;17(12):3255-3267. doi: 10.7150/ijbs.63125. PMID: 34421363; PMCID: PMC8375225. 2. Mirković B, Markelc B, Butinar M, Mitrović A, Sosič I, Gobec S, Vasiljeva O, Turk B, Čemažar M, Serša G, Kos J. Nitroxoline impairs tumor progression in vitro and in vivo by regulating cathepsin B activity. Oncotarget. 2015 Aug 7;6(22):19027-42. doi: 10.18632/oncotarget.3699. PMID: 25848918; PMCID: PMC4662473.

1: Zhang QI, Wang S, Yang D, Pan K, Li L, Yuan S. Preclinical pharmacodynamic evaluation of antibiotic nitroxoline for anticancer drug repurposing. Oncol Lett. 2016 May;11(5):3265-3272. Epub 2016 Mar 29. PubMed PMID: 27123101; PubMed Central PMCID: PMC4841112. 2: Brodnik H, Požgan F, Štefane B. Synthesis of 8-heteroaryl nitroxoline analogues via one-pot sequential Pd-catalyzed coupling reactions. Org Biomol Chem. 2016 Feb 2;14(6):1969-81. doi: 10.1039/c5ob02364e. PubMed PMID: 26754567. 3: Chang WL, Hsu LC, Leu WJ, Chen CS, Guh JH. Repurposing of nitroxoline as a potential anticancer agent against human prostate cancer: a crucial role on AMPK/mTOR signaling pathway and the interplay with Chk2 activation. Oncotarget. 2015 Nov 24;6(37):39806-20. doi: 10.18632/oncotarget.5655. PubMed PMID: 26447757; PubMed Central PMCID: PMC4741862. 4: Knez D, Brus B, Coquelle N, Sosič I, Šink R, Brazzolotto X, Mravljak J, Colletier JP, Gobec S. Structure-based development of nitroxoline derivatives as potential multifunctional anti-Alzheimer agents. Bioorg Med Chem. 2015 Aug 1;23(15):4442-52. doi: 10.1016/j.bmc.2015.06.010. Epub 2015 Jun 14. PubMed PMID: 26116179. 5: Mirković B, Markelc B, Butinar M, Mitrović A, Sosič I, Gobec S, Vasiljeva O, Turk B, Čemažar M, Serša G, Kos J. Nitroxoline impairs tumor progression in vitro and in vivo by regulating cathepsin B activity. Oncotarget. 2015 Aug 7;6(22):19027-42. PubMed PMID: 25848918; PubMed Central PMCID: PMC4662473. 6: Chan-On W, Huyen NT, Songtawee N, Suwanjang W, Prachayasittikul S, Prachayasittikul V. Quinoline-based clioquinol and nitroxoline exhibit anticancer activity inducing FoxM1 inhibition in cholangiocarcinoma cells. Drug Des Devel Ther. 2015 Apr 8;9:2033-47. doi: 10.2147/DDDT.S79313. eCollection 2015. PubMed PMID: 25897210; PubMed Central PMCID: PMC4396583. 7: Lazovic J, Guo L, Nakashima J, Mirsadraei L, Yong W, Kim HJ, Ellingson B, Wu H, Pope WB. Nitroxoline induces apoptosis and slows glioma growth in vivo. Neuro Oncol. 2015 Jan;17(1):53-62. doi: 10.1093/neuonc/nou139. Epub 2014 Jul 28. PubMed PMID: 25074541; PubMed Central PMCID: PMC4483047. 8: Naber KG, Niggemann H, Stein G, Stein G. Review of the literature and individual patients' data meta-analysis on efficacy and tolerance of nitroxoline in the treatment of uncomplicated urinary tract infections. BMC Infect Dis. 2014 Nov 27;14:628. doi: 10.1186/s12879-014-0628-7. Review. PubMed PMID: 25427651; PubMed Central PMCID: PMC4262220. 9: Kresken M, Körber-Irrgang B. In vitro activity of nitroxoline against Escherichia coli urine isolates from outpatient departments in Germany. Antimicrob Agents Chemother. 2014 Nov;58(11):7019-20. doi: 10.1128/AAC.03946-14. Epub 2014 Sep 2. PubMed PMID: 25182654; PubMed Central PMCID: PMC4249399. 10: Wagenlehner FM, Münch F, Pilatz A, Bärmann B, Weidner W, Wagenlehner CM, Straubinger M, Blenk H, Pfister W, Kresken M, Naber KG. Urinary concentrations and antibacterial activities of nitroxoline at 250 milligrams versus trimethoprim at 200 milligrams against uropathogens in healthy volunteers. Antimicrob Agents Chemother. 2014;58(2):713-21. doi: 10.1128/AAC.02147-13. Epub 2013 Nov 11. PubMed PMID: 24217699; PubMed Central PMCID: PMC3910821. 11: Sosič I, Mirković B, Arenz K, Stefane B, Kos J, Gobec S. Development of new cathepsin B inhibitors: combining bioisosteric replacements and structure-based design to explore the structure-activity relationships of nitroxoline derivatives. J Med Chem. 2013 Jan 24;56(2):521-33. doi: 10.1021/jm301544x. Epub 2013 Jan 4. PubMed PMID: 23252745. 12: Sobke A, Klinger M, Hermann B, Sachse S, Nietzsche S, Makarewicz O, Keller PM, Pfister W, Straube E. The urinary antibiotic 5-nitro-8-hydroxyquinoline (Nitroxoline) reduces the formation and induces the dispersal of Pseudomonas aeruginosa biofilms by chelation of iron and zinc. Antimicrob Agents Chemother. 2012 Nov;56(11):6021-5. doi: 10.1128/AAC.01484-12. Epub 2012 Aug 27. PubMed PMID: 22926564; PubMed Central PMCID: PMC3486607. 13: Jiang H, Taggart JE, Zhang X, Benbrook DM, Lind SE, Ding WQ. Nitroxoline (8-hydroxy-5-nitroquinoline) is more a potent anti-cancer agent than clioquinol (5-chloro-7-iodo-8-quinoline). Cancer Lett. 2011 Dec 15;312(1):11-7. doi: 10.1016/j.canlet.2011.06.032. Epub 2011 Jul 6. PubMed PMID: 21899946; PubMed Central PMCID: PMC3395224. 14: Mirković B, Renko M, Turk S, Sosič I, Jevnikar Z, Obermajer N, Turk D, Gobec S, Kos J. Novel mechanism of cathepsin B inhibition by antibiotic nitroxoline and related compounds. ChemMedChem. 2011 Aug 1;6(8):1351-6. doi: 10.1002/cmdc.201100098. Epub 2011 May 20. PubMed PMID: 21598397. 15: Ghoneim MM, El-Desoky HS, Abdel-Galeil MM. Electrochemistry of the antibacterial and antifungal drug nitroxoline and its determination in bulk form, pharmaceutical formulation and human blood. Bioelectrochemistry. 2011 Feb;80(2):162-8. doi: 10.1016/j.bioelechem.2010.08.003. Epub 2010 Aug 31. PubMed PMID: 20833114. 16: Shim JS, Matsui Y, Bhat S, Nacev BA, Xu J, Bhang HE, Dhara S, Han KC, Chong CR, Pomper MG, So A, Liu JO. Effect of nitroxoline on angiogenesis and growth of human bladder cancer. J Natl Cancer Inst. 2010 Dec 15;102(24):1855-73. doi: 10.1093/jnci/djq457. Epub 2010 Nov 18. Erratum in: J Natl Cancer Inst. 2011 Jul 6;103(13):1070. PubMed PMID: 21088277; PubMed Central PMCID: PMC3001967. 17: Gao GY, Lin SY. Thermodynamic investigations of nitroxoline sublimation by simultaneous DSC-FTIR method and isothermal TG analysis. J Pharm Sci. 2010 Jan;99(1):255-61. doi: 10.1002/jps.21826. PubMed PMID: 19530075. 18: Yatsenko AV, Paseshnichenko KA, Chernyshev VV, Schenk H. Powder diffraction study of the hydrogen bonds in nitroxoline and its hydrochloride. Acta Crystallogr C. 2002 Jan;58(Pt 1):o19-21. Epub 2001 Dec 14. PubMed PMID: 11781483. 19: Murugasu-Oei B, Dick T. In vitro activity of the chelating agents nitroxoline and oxine against Mycobacterium bovis BCG. Int J Antimicrob Agents. 2001 Dec;18(6):579-82. PubMed PMID: 11738349. 20: Pelletier C, Prognon P, Bourlioux P. Roles of divalent cations and pH in mechanism of action of nitroxoline against Escherichia coli strains. Antimicrob Agents Chemother. 1995 Mar;39(3):707-13. PubMed PMID: 7793877; PubMed Central PMCID: PMC162609.