Prulifloxacin | NM-441 | CAS#123447-62-1 | Bacterial DNA Gyrase Inhibitor

MedKoo Cat#: 328337 | Name: Prulifloxacin

Description:

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

Prulifloxacin, also known as NM-441, is an inhibitor of bacterial DNA gyrase used to treat urinary tract infections. Prulifloxacin is an oral fluoroquinolone with a broad in vitro activity spectrum against Gram positive and negative bacteria and among fluoroquinolones has the lowest power of inducing resistance. In vitro and in vivo studies have shown its clinical efficacy and pathogen eradication.

Chemical Structure

Prulifloxacin

CAS#123447-62-1

Theoretical Analysis

MedKoo Cat#: 328337

Name: Prulifloxacin

CAS#: 123447-62-1

Chemical Formula: C21H20FN3O6S

Exact Mass: 461.1057

Molecular Weight: 461.46

Elemental Analysis: C, 54.66; H, 4.37; F, 4.12; N, 9.11; O, 20.80; S, 6.95

Price and Availability

Size	Price	Availability
50mg	USD 150.00	Ready to ship
100mg	USD 250.00	Ready to ship
200mg	USD 425.00	Ready to ship
500mg	USD 750.00	Ready to ship
1g	USD 1,250.00	Ready to ship
2g	USD 1,950.00	Ready to ship
5g	USD 3,950.00	Ready to ship

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Related CAS #

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Synonym

Prulifloxacin; NM-441; NM 441; NM441

IUPAC/Chemical Name

6-fluoro-1-methyl-7-(4-((5-methyl-2-oxo-1,3-dioxol-4-yl)methyl)piperazin-1-yl)-4-oxo-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid

InChi Key

PWNMXPDKBYZCOO-UHFFFAOYSA-N

InChi Code

InChI=1S/C21H20FN3O6S/c1-10-16(31-21(29)30-10)9-23-3-5-24(6-4-23)15-8-14-12(7-13(15)22)18(26)17(20(27)28)19-25(14)11(2)32-19/h7-8,11H,3-6,9H2,1-2H3,(H,27,28)

SMILES Code

O=C(C1=C(SC2C)N2C3=C(C=C(F)C(N4CCN(CC5=C(C)OC(O5)=O)CC4)=C3)C1=O)O

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

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

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#A23M05B01

QC Data

View QC data: current batch, Lot#A23M05B01

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Prulifloxacin is a fluoroquinolone antibiotic with a broad spectrum of activity against Gram-positive and -negative bacteria.

In vitro activity:

In E. coli strains isolated from urinary tract infections, prulifloxacin exhibited superior potency compared to ciprofloxacin and levofloxacin with an impressive MIC(90). Prulifloxacin-resistant mutants displayed compromised growth rates, reduced fitness indices, impaired adherence capabilities to uroepithelial cells and urinary catheters, lower surface hydrophobicity, increased susceptibility to ultraviolet irradiation, resistance to colicins, and reduced plasmid transfer. Reference: Int J Antimicrob Agents. 2007 Jun;29(6):679-87. https://pubmed.ncbi.nlm.nih.gov/17363225/

In vivo activity:

Prulifloxacin was administered for 28-days in Wistar albino rats at 0, 100, 200, 400mg/kg/day followed by 14-days recovery period. It was concluded that long-term repeated dose of prulifloxacin may produce blood parameters abnormality, liver damage, stomach ulcers, joint damage, and dysfunction of lungs in rats. Reference: Environ Toxicol Pharmacol. 2012 Sep;34(2):588-607. https://pubmed.ncbi.nlm.nih.gov/22885677/

	Solvent	mg/mL	mM
Solubility
	DMSO:PBS (pH 7.2) (1:5)	0.2	0.35

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 461.46 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. Fritsche TR, Biedenbach DJ, Jones RN. Antimicrobial activity of prulifloxacin tested against a worldwide collection of gastroenteritis-producing pathogens, including those causing traveler's diarrhea. Antimicrob Agents Chemother. 2009 Mar;53(3):1221-4. doi: 10.1128/AAC.01260-08. Epub 2008 Dec 29. PMID: 19114678; PMCID: PMC2650572. 2. Gualco L, Schito AM, Schito GC, Marchese A. In vitro activity of prulifloxacin against Escherichia coli isolated from urinary tract infections and the biological cost of prulifloxacin resistance. Int J Antimicrob Agents. 2007 Jun;29(6):679-87. doi: 10.1016/j.ijantimicag.2007.01.009. Epub 2007 Mar 23. PMID: 17363225. 3. Giusti M, Blasi F, Iori I, Mazzone A, Sgambato F, Politi C, Colagrande P, Casali A, Valerio A, Gussoni G, Bonizzoni E, Campanini M. Prulifloxacin vs Levofloxacin for Exacerbation of COPD after Failure of Other Antibiotics. COPD. 2016 Oct;13(5):555-60. doi: 10.3109/15412555.2016.1152236. Epub 2016 Mar 30. PMID: 27027547. 4. Nandi U, Roy B, Das AK, Pal TK. Correlation among the toxicity profiling (28-days repeated oral dose toxicity), toxicokinetics and tissue distribution data of ulifloxacin, the active metabolite of prulifloxacin in Wistar albino rats. Environ Toxicol Pharmacol. 2012 Sep;34(2):588-607. doi: 10.1016/j.etap.2012.07.001. Epub 2012 Jul 14. PMID: 22885677.

In vitro protocol:

In vivo protocol:

1. Giusti M, Blasi F, Iori I, Mazzone A, Sgambato F, Politi C, Colagrande P, Casali A, Valerio A, Gussoni G, Bonizzoni E, Campanini M. Prulifloxacin vs Levofloxacin for Exacerbation of COPD after Failure of Other Antibiotics. COPD. 2016 Oct;13(5):555-60. doi: 10.3109/15412555.2016.1152236. Epub 2016 Mar 30. PMID: 27027547. 2. Nandi U, Roy B, Das AK, Pal TK. Correlation among the toxicity profiling (28-days repeated oral dose toxicity), toxicokinetics and tissue distribution data of ulifloxacin, the active metabolite of prulifloxacin in Wistar albino rats. Environ Toxicol Pharmacol. 2012 Sep;34(2):588-607. doi: 10.1016/j.etap.2012.07.001. Epub 2012 Jul 14. PMID: 22885677.

1: Chen J, Zhang L, Huang Y, Zhou Y, Yu Y, Li X. Quantitative study of ternary polycrystalline mixtures of prulifloxacin based on Raman spectra and Raman imaging maps. J Pharm Biomed Anal. 2024 Jan 20;238:115799. doi: 10.1016/j.jpba.2023.115799. Epub 2023 Oct 14. PMID: 37866080. 2: So-Ngern A, Jirajariyavej S, Thuncharoon H, Khunthupat N, Chantarojanasiri T, Montakantikul P. A randomized, controlled trial of prulifloxacin as conversion therapy after intravenous carbapenem in the treatment of acute pyelonephritis caused by third generation cephalosporin resistant pathogens: A pilot study. Clin Transl Sci. 2023 Dec;16(12):2709-2718. doi: 10.1111/cts.13665. Epub 2023 Oct 28. PMID: 37853952; PMCID: PMC10719478. 3: Cooper TE, Teng C, Howell M, Teixeira-Pinto A, Jaure A, Wong G. D-mannose for preventing and treating urinary tract infections. Cochrane Database Syst Rev. 2022 Aug 30;8(8):CD013608. doi: 10.1002/14651858.CD013608.pub2. PMID: 36041061; PMCID: PMC9427198. 4: Tulone G, Giannone S, Mannone P, Tognarelli A, Di Vico T, Giaimo R, Zucchi A, Rossanese M, Abrate A, Pavan N, Claps F, Ficarra V, Bartoletti R, Simonato A. Comparison of Fluoroquinolones and Other Antibiotic Prophylaxis Regimens for Preventing Complications in Patients Undergoing Transrectal Prostate Biopsy. Antibiotics (Basel). 2022 Mar 20;11(3):415. doi: 10.3390/antibiotics11030415. PMID: 35326878; PMCID: PMC8944856. 5: Sahoo BM, Bhattamisra SK, Das S, Tiwari A, Tiwari V, Kumar M, Singh S. Computational Approach to Combat COVID-19 Infection: Emerging Tools for Accelerating Drug Research. Curr Drug Discov Technol. 2022;19(3):e170122200314. doi: 10.2174/1570163819666220117161308. PMID: 35040405. 6: She P, Li S, Liu Y, Xu L, Zhou L, Zeng X, Li Y, Liu S, Li Z, Hussain Z, Wu Y. Repurposing Sitafloxacin, Prulifloxacin, Tosufloxacin, and Sisomicin as Antimicrobials Against Biofilm and Persister Cells of Pseudomonas aeruginosa. Curr Microbiol. 2021 Dec 14;79(1):12. doi: 10.1007/s00284-021-02729-w. PMID: 34905092. 7: Gupta P, Modgil V, Kant V, Kaur H, Narayan C, Mahindroo J, Verma R, Mohan B, Taneja N. Phenotypic and genotypic characterization of antimicrobial resistance in clinical isolates of Vibrio cholerae over a decade (2002-2016). Indian J Med Microbiol. 2022 Jan-Mar;40(1):24-29. doi: 10.1016/j.ijmmb.2021.11.008. Epub 2021 Dec 9. PMID: 34848326. 8: Hu Q, Chen S, Chen F. Determination of thiourea by terbium (III)/ prulifloxacin sensitized potassium permanganate-sulfite chemiluminescence with quenching method. Spectrochim Acta A Mol Biomol Spectrosc. 2022 Jan 5;264:120332. doi: 10.1016/j.saa.2021.120332. Epub 2021 Aug 28. PMID: 34488001. 9: Elder FCT, Proctor K, Barden R, Gaze WH, Snape J, Feil EJ, Kasprzyk-Hordern B. Spatiotemporal profiling of antibiotics and resistance genes in a river catchment: Human population as the main driver of antibiotic and antibiotic resistance gene presence in the environment. Water Res. 2021 Sep 15;203:117533. doi: 10.1016/j.watres.2021.117533. Epub 2021 Aug 8. PMID: 34416649. 10: Gourgoulianis K, Ruggieri A, Del Vecchio A, Calisti F, Comandini A, Esposito G, Di Loreto G, Tzanakis N. Prulifloxacin Effectiveness in Moderate-to-Severe Acute Exacerbations of Chronic Bronchitis: Α Noninterventional, Multicentre, Prospective Study in Real-Life Clinical Practice-The "AIOLOS" Study. Can Respir J. 2021 May 25;2021:6620585. doi: 10.1155/2021/6620585. PMID: 34122678; PMCID: PMC8172323. 11: Sahoo BM, Ravi Kumar BVV, Sruti J, Mahapatra MK, Banik BK, Borah P. Drug Repurposing Strategy (DRS): Emerging Approach to Identify Potential Therapeutics for Treatment of Novel Coronavirus Infection. Front Mol Biosci. 2021 Feb 26;8:628144. doi: 10.3389/fmolb.2021.628144. PMID: 33718434; PMCID: PMC7953054. 12: Samarinas M, Skriapas K, Mitsogiannis I, Gravas S, Karatzas A, Tzortzis V. Cefixime versus prulifloxacin as a prophylactic treatment for prostate biopsy: a randomized study. Cent European J Urol. 2020;73(4):544-550. doi: 10.5173/ceju.2020.0072. Epub 2020 Oct 10. PMID: 33552582; PMCID: PMC7848831. 13: Kousar K, Majeed A, Yasmin F, Hussain W, Rasool N. Phytochemicals from Selective Plants Have Promising Potential against SARS-CoV-2: Investigation and Corroboration through Molecular Docking, MD Simulations, and Quantum Computations. Biomed Res Int. 2020 Oct 13;2020:6237160. doi: 10.1155/2020/6237160. PMID: 33102585; PMCID: PMC7568149. 14: Castrignanò E, Kannan AM, Proctor K, Petrie B, Hodgen S, Feil EJ, Lewis SE, Lopardo L, Camacho-Muñoz D, Rice J, Cartwright N, Barden R, Kasprzyk-Hordern B. (Fluoro)quinolones and quinolone resistance genes in the aquatic environment: A river catchment perspective. Water Res. 2020 Sep 1;182:116015. doi: 10.1016/j.watres.2020.116015. Epub 2020 Jun 6. PMID: 32622132. 15: Castrignanò E, Yang Z, Feil EJ, Bade R, Castiglioni S, Causanilles A, Gracia-Lor E, Hernandez F, Plósz BG, Ramin P, Rousis NI, Ryu Y, Thomas KV, de Voogt P, Zuccato E, Kasprzyk-Hordern B. Enantiomeric profiling of quinolones and quinolones resistance gene qnrS in European wastewaters. Water Res. 2020 May 15;175:115653. doi: 10.1016/j.watres.2020.115653. Epub 2020 Mar 10. Erratum in: Water Res. 2020 Sep 1;182:116345. doi: 10.1016/j.watres.2020.116345. PMID: 32208173. 16: Maia AS, Paíga P, Delerue-Matos C, Castro PML, Tiritan ME. Quantification of fluoroquinolones in wastewaters by liquid chromatography-tandem mass spectrometry. Environ Pollut. 2020 Apr;259:113927. doi: 10.1016/j.envpol.2020.113927. Epub 2020 Jan 10. PMID: 32023795. 17: Barbieri MA, Cicala G, Cutroneo PM, Mocciaro E, Sottosanti L, Freni F, Galletti F, Arcoraci V, Spina E. Ototoxic Adverse Drug Reactions: A Disproportionality Analysis Using the Italian Spontaneous Reporting Database. Front Pharmacol. 2019 Oct 8;10:1161. doi: 10.3389/fphar.2019.01161. PMID: 31649536; PMCID: PMC6791930. 18: Poletajew S, Krajewski W, Adamowicz J, Radziszewski P. A systematic review of preventive and therapeutic options for symptoms of cystitis in patients with bladder cancer receiving intravesical bacillus Calmette-Guérin immunotherapy. Anticancer Drugs. 2019 Jun;30(5):517-522. doi: 10.1097/CAD.0000000000000775. PMID: 30870228. 19: Tellone V, Coppola P, Ammendola M, Di Loreto G, Picollo R, Del Vecchio A, Comandini A, Garofolo F, Tongiani S. New Insights on the Pharmacokinetics of Ulifloxacin After Administration of Prulifloxacin in Patients with Mild, Moderate and Severe Renal Impairment. Drugs R D. 2018 Sep;18(3):237-245. doi: 10.1007/s40268-018-0245-9. PMID: 30151791; PMCID: PMC6131124. 20: Castrignanò E, Kannan AM, Feil EJ, Kasprzyk-Hordern B. Enantioselective fractionation of fluoroquinolones in the aqueous environment using chiral liquid chromatography coupled with tandem mass spectrometry. Chemosphere. 2018 Sep;206:376-386. doi: 10.1016/j.chemosphere.2018.05.005. Epub 2018 May 4. PMID: 29754062. 1.